I was born in Washington, D.C. Both of my parents migrated from the middle of the country to an urban center, because they had to escape their sort of tough rural backgrounds. My parents were working middle class people, educated through high school but aspiring for more, and in Washington they could have white collar jobs. I went to public schools in DC and I loved growing up there because I just got a great sense of history and news in the making – all that sort of thing. [Washington] was to a degree integrated [at that time], lots of international people were there, and obviously lots of African-Americans. Looking back I’m really glad I had that [experience growing up].

My first aware career aspiration was to be an artist [chuckles] – I meant like with a beret and a smock and palette, you know? I had no real career sense of anything about professional life, but my parents always said—because they were working class—”You have to work and support yourself, no matter what.” So that was a given. “We don’t care what else you do, but you’re going to work and have a job.”

I graduated from high school in 1969. In other words, I was a hippie. There were various cultures at my high school, but hippies were definitely a big contingent, and that was the easiest one for me, because I was not ever a girly girl, I was not ever into dating, so that was just the group that suited me and vice versa, I think. My parents were church-going people, and [they sent me to] a little Lutheran college in Ohio, which they strongly preferred. I thought of myself as an urban person, but I ended up actually loving my experience there. The school is called Wittenberg. It’s one of like 10,000 liberal arts schools in Ohio [chuckles]. And I made lifelong friends there, I had wonderful teachers. But, again, no big career plan. I studied what I wanted to study – all liberal arts. It was humanities all the way – lots of literature, lots of history, art history. My mom had insisted I learn typing in high school, so I had typing too, and that has been my life ever since, really.

My dad died when I was a senior in college. Without a clear plan, I moved back to my mom’s in the Maryland suburbs and got jobs in Washington for a couple years, and went to graduate school then, [once] again in American Studies. So I have two degrees in American Studies. I was in a Smithsonian program, studied material culture and folklore and things like that. I enjoyed that, and I also worked at the same time. That’s how I paid my tuition, by working at George Washington University.

I was now a young professional adult with young adult friends. Still didn’t have any particular plan, I held office jobs, and I was smart, and I could type, and I could read, and I just had a series of those kind of jobs. In graduate school, I studied oral history, and I happened to be at school at a time when a couple of local professors uncovered what had been missing for 40 years, the archives of the Federal Theatre Project, which was part of the WPA [Works Progress Administration]. There were just trunks and trunks of material that the Library Congress owned and had misplaced. These two found it, and got a big grant to catalog it all.

So thanks to my graduate work, I actually had a job in my field, which is to say I became the oral historian for their [FTP cataloging] project for two years. And that led me to do what you’re doing now, which is travel around the country and interview people who had worked for the WPA Theatre Project, when I was 25 or 26.

What a dream.

I loved that because I knew the material very well. The [interviewees] were all charming theater people, by and large. They included people like – these are names that may not mean anything to you – Joseph Cotten, Arlene Francis, people who later became big stars. And so that was fantastic. [This project] didn’t really lead anywhere, and I knew that. I remember [thinking] that I didn’t really feel like an academic career. Some of my graduate school friends pursued going further into the field of oral history and historical projects.

I felt like, I don’t want to get further away from the real world, because I was already so in my head. I didn’t want to get a PhD, I thought a master’s degree was plenty. Anyway, I enjoyed that period—it was couple of years—but the [FTP] grant money was coming to an end and the project was more or less done.

Again with no clear plan, I had met a guy and he didn’t have a big plan either, and Ronald Reagan had been elected, and was coming into office. This was 1979, and I said, “I cannot live in Washington under Ronald Reagan,” so we moved West – but we had no plan. We took four months to drive across the country. We did end up in San Francisco where we had friends, but when you’re in your late 20s, nobody has really a stable place to live for long-term visitors who come and hang out with you while they’re looking for jobs. We were a little intimidated at the time, and ended up going up to Oregon, where I had another friend. [Eventually] I did get a job in Portland, and and [ended up] stayed there five years. I worked on an oral history project that had to do with women shipyard workers [during World War II] in the Pacific Northwest. It paid like five cents. It was a side thing, but it was still interesting. I also had a job in a little non-profit, a membership group of independent filmmakers, because I was interested in media. This was basically like an office job, running a little membership organization, I think there were two and half people on the payroll [laughs], including me. As a result of doing that for a couple years, I met somebody at a conference who said, “There’s a job in San Francisco. You should apply for it. It’s a bigger organization.” And much as I loved the Northwest, Portland was extremely depressed in the 80s, had no real economy. It was a pretty run-down place, charming, but it wasn’t big enough [for me].

So, I did apply for this job and I got it. And it was [with] an organization called Media Alliance, which had a lot of progressive media types, and [also] people who were moving to the Bay Area looking for jobs. So, I took the job. It wasn’t that enjoyable [thin margins!], but on the board of directors of this organization was a guy named David Bunnell who started PC Magazine and then PC World magazine. Now, he was a quirky guy, kind of nerdy, kind of shy, a bit of a weird character. But he took a liking to me and talked to me very readily, where he didn’t talk to a lot of people. After about a year at Media Alliance, he said, “I want to hire you.” He was running a computer publishing company in this heyday of thousands of computer magazines. The beginning of personal computing. I said, “But I don’t know anything.” I used a K-Pro! But he felt comfortable with me, and I was going to be his conduit to the real world, is what I realized after I got there. Going there doubled my pay –  stability at last. And I loved the people. I remember thinking in 1985, “How is it that there’s a world with all this jargon, all this lingo, that a world of these magazines, I barely understood what they were talking about. These trade shows, like Comdex. How has this sprung up so quickly out of nowhere? Where did this come from?”

All the people in [computer publishing] at that time, nobody that I knew was really experienced at it. Everybody was new and young and getting into it – but we were really smart, bookish, funny people and so, I just loved it. I just loved learning about magazines, I loved putting them together, and having a regular schedule, and working with people who were funny and were making fun of technology as they were working on it. It just suited me perfectly. And that’s how I fell into technology.

I stayed there four years, and I was David’s right hand. We started a little R&D group. I worked a lot with the editors of the different magazines. Again, now I have life-long friends from that experience.

Eventually, he left because his contract ended. I, again, didn’t really have a plan, but by then, I knew people, and so, I got a contract for about a year to start a new technical journal for Addison Wesley, a book publisher. They’d never done a periodical, and I had a strange experience dealing with mathematician Steven Wolfram (the journal was about his program Mathematica). Once again, I just sort of felt my way. But now, I began to have a network of people who work here and there and who knows things about  publishing and who knew things about technical stuff. It just led to different—sometimes freelance—jobs. I think I had a freelance period there for a while where I was writing and editing.

We’re in the early ’90s now, and I had a job at an awful technology PR firm, one of the early ones. I didn’t like doing PR, but I liked the people that I worked with. That led to a job at a very hot startup called 3DO – and my first IPO. I had friends who’d already been through IPOs, and I was determined to be in one too. [3DO] was a big hit for 20 minutes. But again, I met good people there. That’s where I first met Omid Kordestani, was at 3DO. Again my network grew because everybody I knew was doing the same thing: You’d move here, you’d move there, you’d have a new job, you’d try something out, [you’d make friends along the way].

After 3DO, I had a couple more years of freelance work. By now my editorial friends were editors of different magazines. So as the web came online, I was invited to put together one of the first consumer guides to the web. It’s so antique now. I should show it to you. It has lots of spider and web puns in it, it’s just ridiculous [chuckles]. It came out in 1995. I didn’t get a lot of money for it, but it led to my editorial friends inviting me to review LOTS of websites for their publications.

So I did that for a couple of years, writing up consumery-type things for tech. I was never really particularly technical, but I knew how to explain the value to [consumer readers]. And then I joined this startup a friend of mine had got going called Planet Out. It was really the early gay portal. My friend [Tom Rielly] is a great character, and he had this vision of this web and AOL portal that would be news and information for the gay community. I was the executive editor, assigning stories and hiring writers. It was great. But it did not do well as a startup. I left and went back to the magazine side – [I became] the executive editor of Upside [a hot monthly mag then].

My whole mantra during this period was, I can work in these kind of corporate climates if I feel like I’m providing useful information, or it’s something that people can use. I can remember when I joined IDG,  the parent company of the first computer magazines, I remember thinking, “Well, it’s not Bechtel.” I mean, [IDG] has a public value. They have a usefulness to people. And that’s what I cared about. And that, I think, has been a guiding thing for me.

Upside was interesting, because it was about the business of technology, which has become a really interesting area. I liked having a big role at a magazine, where I worked with a lot of writers. I knew I was a good editor, and that made me a better editor, to be working with good writers, and to have back-and-forth conversations about what they were trying to do.

I stayed 18 months, but it was just a bad atmosphere, so I pivoted then. I thought, ” if the web is going to be a big thing, I love information and words and ideas, so how now, since we don’t have to be linear anymore, and we’re not limited by a page, the size of a book, the size of a magazine, how then to present information and make it discoverable?” There was a thing then called information design, which now has morphed into UX and content strategy. I had friends at an early web design firm [Studio Archetype] that were really getting into this in a deep way. They kept saying, “You should come over.” I did go, where I managed teams who did that, [and in the process, I gained an] understanding of business development; what is content strategy; how to take somebody’s corporate information, business information and make it useful online, chunk it up and all that sort of thing. Again, I loved the people there. Really fantastic group. It was a great company, but it wasn’t particularly financially successful, because there was a lot of overhead. So they ended up selling to a much bigger systems integrator [Sapient].

And that [integration] was fascinating to go through, because we were a little artsy design studio, and here came this much bigger [entity]. [Sapient] was a consulting business [which plugged people into long-term projects like this: “You’re an engineer with three years of C++, you’re going to Dallas for two months” or whatever it was. They couldn’t really figure out how to plug in the creative people. And the creative people mostly revolted, of course, but again, the process of going through an integration that didn’t work well was pretty great. And led me to understand why acquisitions often don’t work [laughter].

Somewhere in here, one of my old friends I had worked with at two companies, I kept in touch with her. In 1999 she said, “Hey, I’m taking a new job at this startup. It’s called Google, come visit some time.” So I kept in touch, I visited her a couple of times around 2000. The way I understood search [on the early web] was that one of my writing assignments was to compare search engines, and there were tons of them before Google. So, I had looked at them and tried different search terms and stuff. When it came to Google, it was instantly so much better than all the others. Many orders of magnitude better. It occurred to me a couple of times that I should call her, because I was still freelancing here and there. But I thought, that’s a long commute. Much to my regret!

The big tech crash happened in 2000. I was at a little startup that folded. It was tough then for, I don’t know, close to two years [because jobs dried up]. So I was freelancing, but my income had really dropped – and I had bought my first home. Eventually I called my friend at Google and said, “Hey, you have any freelance work?” She said, “Oh, we just hired a marketing writer, but I’ll keep you in mind.” And she called back, maybe a couple of months later, and said, “You know what, we’re really slammed, so come in to meet some people.” So I went down, and they were really nice. They said, “When can you start?” And I’m like, “Right away.”

So I started out as a marketing writer on contract to Google in 2002. Right away, I liked the people, and I believed in what they were doing. I [remember thinking], “This is in close alignment with my values. They’re helping people find information, it’s a service that is useful.” And of course, they had that great mission statement. So, I just started telling people there: I want to work here, I want to work here, I want to work here. By this time, I was enough of a utilitarian writer and editor – I could take copy and turn it into something good quickly, so I just made myself as indispensable as I could around the office. And I tried to be enough of a fixture that people would say, “She’s one of us,” It  took more than a year. Eventually, I did get hired on to be full-time. I was 50 or 51 when I got hired there. By then, I’d had this long, tough stretch where I was not earning enough, and so I just was so grateful to get in. I remember thinking, “Please, God, don’t let them have an IPO until after I get in!” And they didn’t. (It took another year after I joined.) I just made my way in the communications team… I knew enough about how PR worked, there was no confusing me with a flack, and everybody understood I had this different role. Google was small enough and young enough that there were lots of things that hadn’t been identified that just popped up. I think that formed a lot of my experience.

My view now is you just have to try things, and you can’t get hung up by the job description. You can’t get hung up by the title. You have to get in there and see what happens. In a place like Google at that time, that’s perfect, because it was not at all tamped down, it was kind of messy, and a lot of things needed doing. You were encouraged to try different things. I learned how to navigate.

Meanwhile, Google was growing up, getting bigger, but because I’d been there early enough, I became sort of part of the furniture and a little bit of an old hand, in all the best ways. The team grew up. What I did became more specialized, or I became known for a couple things. One was managing the original Google blog, which it turns out to have been an early company blog, at a time when companies didn’t do that very much. Google was different enough that it did. Then, all around Google, everybody wanted their own [blog] for their product and their country. So, I codified what the rules would be about how to do that – and then for a few years, people wanted me to talk about this, because they were fascinated by Google, but also wanted to publish company news on a blog. [Other places] were navigating complexity with lawyers, who didn’t want them to do this sort of thing. I had done it, and it worked pretty well. It worked pretty well because Google people had flexible minds about this sort of thing. They weren’t hidebound and that really helped.

In 2009 I had been watching Twitter. I knew the Twitter guys, and I thought, “Google has to be on Twitter.” I made a case for it internally, but initially people said, “we don’t need another channel for our news.” I said, “Twitter has attracted lots of techies, including reporters. We need to be there. I’ll do it.” They said, “that’s good, because we don’t have any headcount.” I said, “you don’t need headcount. I can do this.”

So I brought them around. [My thought was] this is a layer of an audience that you don’t get another way. I still believe that about Twitter. You raise your [visibility] and reach more people. So, I became known for bringing @Google onto @Twitter – which is ultimately what led me to getting a job at Twitter. Because at that time Twitter was like a younger company that had not codified this stuff. They hadn’t really thought it through. So I came in to do this and embroider lots of things related to it. There was an atmosphere of, “we’ve never really done that,” or, “We do it a different way,” or, “That sort of fell off the radar, so we don’t know.” Now I say, “Well I have an idea. Let’s try it and see.” I just think my lack of [having a plan ahead of time] has saved me a lot of ulcers. I tell people who are sometimes a lot younger, who get super hung up on the trappings, or what it says on the page about the thing, or what the original was: “Well, it can change. It can change. Just relax. If it’s not tenable, it’s not tenable. But let’s find out.” I think that’s just been my approach, “It can’t hurt you to find out.”

How have you seen tech evolve and change over the years?

It’s just so much easier to do things now, right? You used to have to have floppy disks. The idea of the amount of space they have for anything is just—everything was just bigger and slower.

I remember even when I was at IDG the computer magazine company, I had a contemporary Macintosh, but there were networking problems. And I guess we were all on just a local area network, I’m guessing, because it was before the internet really took off. And I remember I had my little phone address book and I had a post-it list, every day, a list of people I needed to call, and I would call people on my phone – which I don’t do anymore at all.

So in a certain way, it’s astonishing how much tech has changed in not very much time. I remember when I got into the Mathematica project. These were academics, right? And they were at universities like Princeton. And I remember talking to some of them about articles, and [at a time when] there were all kinds of weird publishing systems where you were submitting to ftp [sites] and all this stuff.

I remember [asking] this guy, what’s your email address and he said so and so at princeton.edu. I’m like, that doesn’t make any sense. What service are you on – MCI Mail, are you on CompuServe – you can’t just have an address. [laughter] What are you talking about? Of course, they had addresses, right, because [academic email] had come out of DARPA. They just had [email] addresses. That’s what we were all going to be getting [instead of subscribing to one closed service or another]. I didn’t understand that for a while. I had every account for the longest time.

At Macworld, we had an early project – we were trying to figure out how to put Macworld magazine online using GE’s AppleLink, and we were asking, is there a way to turn off the meter so people see the ads but they’re not being charged for the ads, because it was like 35 dollars an hour to have access over that kind of network. That was like 25 years ago. It’s not that long. It feels ancient but it’s really not. It’s kind of astonishing.

So it’s changed in a ton of ways. I’ve lived in my place for 16 years. When we moved in, we threaded CAT5 cable throughout the house, and there are Ethernet ports in every room. But I haven’t used Ethernet in five years or more. Now I have Nest thermostats and Nest smoke detectors, and things like that.

You can’t fathom it in a certain way, you can’t believe it’s happened that fast. Even though we’re in a bubble here, it doesn’t just touch an exclusive population in the Bay Area. [Internet access] has become ubiquitous and important for everybody; that’s the most fascinating thing.

When the Internet turned commercial and Wired magazine started, I still remember Louis Rossetto’s opening essay, “There’s this giant tsunami of technology information coming our way, in a good way. We welcome it.” He started a category of publishing that still exists today. [But] we don’t need the kind computer magazines we used to have, they’re all dead. Can’t even find them online in some cases. But you know what? It doesn’t matter. I have some paper copies, it doesn’t really matter. It’s more like having some understanding of how it’s all come along. And I laugh because I’m just as impatient as anybody else now — like I can’t get a signal, I can’t get wifi – I don’t stop and think, “This is so great to have it [at all].”

How does it feel to have such a depth of knowledge and experience, and be surrounded by so many young, enthusiastic folks who are super brilliant, but have no context for what they’re in?

I wish they cared more about how fast [technology development] has come up, and I wish they cared more about history. But they don’t. I think that’s more or less the nature of people. You don’t really care that much about the past. I like history and I like understanding the relationship between past and present, but I don’t think a lot of people do. Now people are completely tuned into the world of today. I do sometimes wish people understood how miraculous it all is in a certain way. But they don’t. We start from where we are.

I made friends at Google who were engineers, younger than me, but [of course] way more technical. It’s fun to see them and geek out with them about how things were [even in the early days of Google]. Honestly, even a few years ago—I mean I’m friendly with one of the early early early engineers at Google, who was like employee number eight. He and I used to print out like raw pages of the Google search index every month to figure out the original Google Zeitgeist – which we would publish monthly!  So we would take the printout—just search terms that people had put in, and we tried to come up with interesting patterns for music themes, or sports, or holidays, or whatever it was. I’d print out like 50 pages and we’d go through with a yellow highlighter. That is primitive, right? And that was not even 15 years ago. Anyway, it’s fun to think about. You just pick who you can [to remember] about that stuff who also has an appreciation of it.

What has become most important to you in your work over time? How does what you want in a job now differ from what you wanted earlier in your career?

I’m from a one step removed from blue collar background, speaking of my parents and how I grew up. People had [to work]. You didn’t think about quality of life [chuckles] or [larger] aspirations. My roots are in that. Obviously, over time I have cared [about quality of jobs], I have quit jobs I didn’t like and easily got other ones many times over the years.

So I have had more expectation about what I did want, and I guess the biggest driver for me, thinking back to our last conversation, is probably [paying attention to] what a company does. Right? What the business is or the industry, that does matter to me. That has become important, like thinking about working somewhere that provides educational information, useful information, that has sort of a public service to it. Which I think [both] Google and Twitter do. I’d have a harder time working in many industries…even in technology, it would be much more of a stretch for me to work for a company that made some piece of hardware that was a peripheral or something. I like being attached to something that has a public good and a public value. And frankly, that is world-changing. I think that has determined for me, maybe for the last 20 or 25 years, some aspect of what I’m doing for a living. It’s lucky that I landed in those places, in order to form that thought. I could have gone down other roads, and that part seems like happenstance. But, then once I got into this [technology] world, this is an important driver to me. I couldn’t go be the editorial director or creative director at Coca-Cola, or an insurance company, or something.

What are your biggest motivators? What drives you?

One is the mission, or the cause, behind the business. And, by the way, much to my surprise, like working for a for-profit business. I wouldn’t have expected that of myself. I had my earlier years were non-profit and educational institutions. I just feel like this is where stuff is being sorted out that affects so many more people.

I think besides the sort of mission of the business has, working with smart and creative people whose skills are varied, a mix of races and countries and backgrounds – a rich mix of people is a big motivator [for me]. I don’t think I’d like being somewhere where conformity was valued or where people had to really tow the party line. I just read an item today about how Time Inc. made a business-sized card now for Time Inc. employees to carry in their wallets about the mission of Time Inc. Right? Because Time has been through a lot of turmoil in the last few years – and that will continue – and it’s very funny that that’s how they want to have an incentive for people to care about what they’re doing. I don’t think that I’d go for that either. And not a big legacy business. I need the more modern, the more—things are changing right now kind of contemporary.

How have you seen Silicon Valley and its culture evolve and change since your earlier years in the industry?

Well, the biggest thing by far, by far, is just the influence of the idea of this place called Silicon Valley on the world. Where I came into it when it was about the power of the personal computer, and that certainly was a powerful thing, to get away from the priesthood of the mainframes and all that. Putting the power of publishing and ideas and creativity in people’s hands – that was the beginning. [Since then] we’ve taken giant leaps forward from the beige plastic thing on the desk. Technology is now so much more pervasive in everything in the developed world and even, frankly, in the developing world, in terms of mobile devices.

When Wired magazine launched, Louis Rossetto wrote this opening about how we’re in this era that’s equivalent to discovering fire. It was that dramatic. I understood it then, and he was right. But now I feel like you just can’t explain the world, a lot you can’t do or understand or explain without some part of this world of technology that has developed in Silicon Valley. And obviously not only physically here – this is a notional place. And I’m in the middle of it.

Over the years I’ve had to host any number of delegations and tour groups – I think I was mentioning this last time – from around the world, who want to see Google, they want to see Twitter, they go visit Facebook, they want to see Apple. They want to understand Stanford, they want to understand this place and what it looks like, what people are doing, and how they might have it where they live in some way. And they mean the physical spaces and the offices, but they also mean the intellectual heft and the money and the dynamism to build great new things and have the ability to fail and like all of that.

Mostly, in a certain way, they can’t. If it’s like a government ministry wants that, they really cannot do that [governments can’t mandate innovation]. Some of it is about a free market, some is demographics and education levels, and all these things. But they want it because it represents so much success and promise and all the wondrous things coming out of it. I admit I like being in it and not in a sort of pale version of it.

Anyway, I do feel like [what Silicon Valley has produced] has changed the world. Probably within the last 10 years, my totally non-technical friends, people who work for nonprofits, are social workers, teachers, completely not connected to this world or even actively disliked either business or technology – they all got mobile phones, and typically got on Facebook, have an iPad or use FaceTime, or maybe their office moved to the cloud or they use Amazon…. They look at me like, “You’re at the sharp end of this thing. You were there first, you know all this stuff; how did you know that this would turn out to be this way? We’re coming into it late.”  Of course I didn’t know, but ended up being in the swim early. Now it’s such a given that people are using devices and services, technologies that none of us dreamed of ten years ago, in a mass market.

I’m curious to know if you’ve had mentors or people you’ve looked up to for inspiration? Or even people who were really pivotal in your path to where you are today?

Well, the most direct one I can point to was the guy who hired me to work at IDG at PCWorld and Macworld magazines. He came, himself, from a publishing background, as in a small town newspaper in Nebraska. And he’d stumbled into these early computer magazines. His name is David Bunnell. He lives in Berkeley. And he was the guy who was my board member when I was at a non-profit who hired me away to come to IDG.

There couldn’t have been a more stark “I’m going to show you this new world and change your life,”  but that is what happened. That was a turn in the road. So he was a mentor in that he made me feel like I could fit in and learn all this stuff where it was a totally foreign world to me. He made it seem like, “It’s no big deal and I like you and have faith in you and you’re fitting in. It’s all going to be fine.” That was the kind of mentoring he did. “Come along for the ride with me.” That’s probably the biggest, clearest marker in my life.

Then another one for me would probably be my friend, Tom Rielly, who now is the director of the TED Fellows program for the TED conferences. He’s worked for TED for ten or more years in New York, but I’ve known him from my early days at the IDG magazines, simply because we had mutual friends, and eventually met, because of that. He was a nerdy young man, younger than I am. He was a classic early adopter. He worked for some of the early Macintosh companies as a marketer. He was always out in front of all that stuff, and I just watched him and hung around with him. It was so much a part of his nature and his style. He’s a natural marketer, and he’s a very infectious person. He’s smart, and he’s funny, and you want to go along wherever he  is going. That was almost 25 years ago. He had a circle of friends, almost all of them were younger than me. But again, there was no sense of, “You can’t be here. You can’t come in.” I think that it was fun. It was fun to geek out, to get the latest thing and wait in line at Macworld or the Apple Store when the that eventually came along. Now looking back, it reminds me when I was a young teenager I was early into the Beatles. We would go to the record store on Tuesdays when the new shipment of records came in and I was among the first to get the albums. [chuckles] It’s not that different from waiting in line at the Apple Store or to put in your order which I’ve done at 12:01 am when something new is available.

Did you have have support networks in place early in your career, and where do you find them now?

Not in any formal, professional way. No, I really didn’t. I just had friends. Now I know I’m a natural networker and connector. And I think I just had friends here and there that I liked wherever I worked and so on. There were older businesswomen, but they weren’t like me. I was a misfit to a certain extent, and I’m a bit of an outsider. So I didn’t see myself having sort of a straight job where I could go to the next level in the marketing organization or something like that. So no, I had an informal network, which is very important – we were all sort of making our way here and there in kind of roughly parallel paths. The fact is I was older than a lot of them, it turned out, in the technology world. That didn’t matter as much as over time, I found that I had among my friends people I looked on as a brain trust – who I could get advice from about office politics, or which companies were better, or the way to cast my own role or something like that. But it was just kind of a situational grid of people more than any kind of model or mentor.

Did you work alongside many women earlier in your career? Where have you seen them go?

I have worked alongside women since my time in San Francisco began, which is now 31 years, yes. Typically again we’ve been in sort of parallel-ish roles because the higher you go the fewer women executives there are, that’s certainly still true in technology with a few exceptions. I’m in an odd position because of what I’ve always been interested in doing – not business side operations meaning sales, or finance, or that sort of thing. And I’m not technical, but neither am I HR, or PR strictly speaking which would have been traditionally women’s roles. Right? I’ve been in in-between positions. But I’ve always had women friends certainly, and women colleagues scattered throughout in related roles. At Twitter, for example, I have a good friend in consumer marketing, a different team, but, we certainly are each other’s support system and are professionally aligned even though our work is different.

What are some of the things that you’ve seen yourself and people close to you, women close to you in the industry experience over time?

Age plays a positive factor for me, because the fact that I’ve been older all along through this period. There’s a whole world [now] of women in engineering and technical jobs that’s growing and getting a lot of attention, which is great. There are other women, often in sales and marketing, other functions. And there’s a little bit looser aspirational [efforts there]. I drop in on them – they want to know how to negotiate better for a salary, or how to be the only woman in a group of men, or something like that. They want to know how to be taken seriously. And I am taken seriously. Whether or not I have a lot of clout is a whole other story, but people don’t dismiss me as an airhead or a little girl, so that’s an advantage of age [chuckles]. I can play the age card to my advantage to a certain extent. And I think [these younger women] are finding they want to make their mark, want to figure out the politics and how to self-promote because that’s not a normal thing [for women]. And I do understand all those things, though I don’t feel like they’re my fights [at this point]. And by the way, I’m single and I don’t have kids. So, I didn’t have to worry about that either, and these are very real things that people go through. Some of my women friends at work who are moms or have young kids or take maternity leave develop bonds and connections for support that are great, and I’m not really part of that. I’m glad they are doing that. Some of it like I say is age related, where I don’t have to worry about some of the same things that they’re [dealing with now].

So you come from a blue-collar background. How do your friends and family feel about your life in Silicon Valley and how far you’ve come?

Well, my parents are gone now. My mom lived a long time, and she came to visit me at Google once. She lived to be 92, and the fact that her life spanned including going to the Google campus was kind of amazing. I don’t think she ever really understood what I did there other than work in technology, and it had to do with writing and editing and whatnot, but she knew I was successful. That was satisfying to her for sure, that I’d grown up and I bought a house. That was kind of the extent of it, honestly. I did once buy her a Mac. Interestingly, she had to learn how to use a mouse because she spent many, many, many years typing on a typewriter, so this weird extra thing that is this object, and that’s how you touch the screen. She got it, but it was a bit of a struggle.

Anyway [to family and friends] I think I’m considered interesting. It goes with the things I was saying earlier: People with absolutely no connections to this world, know a word like “Google” or know the word “Twitter” or know Silicon Valley or San Francisco or the Bay Area. They don’t know necessarily what I do, to them all of that symbolizes success. “You’ve made something of yourself, that sounds important, we’ve heard the company names.” Right? Even my friends from college, for example, who are more sophisticated than that, but to virtually all of them, I’m the one who ended up in business. Funny, because we were all hippies. And I turned this corner, not with a plan to do so.

You mentioned that a lot of people come to you for advice on how to get into tech.

I wrote that post on Medium about getting into tech for a couple reasons. One is I’ve known a lot of journalists over the years; I love journalism and reporting. I’m a big newshound and I just like the field, even though I didn’t really do it myself. I’ve gotten to be friendly with a lot of reporters and editors, especially from the tech world. They knew me as someone who was not a flack working in PR, and someone who appreciated their world. As the tide started to turn for the news industry, say in the last five, six, seven years in particular. Magazines were the first to go. Newspapers are in trouble. So some would reach out to me and ask, What am I going to do? You don’t seem to have sold out to the dark side, and you have a corporate job that is successful – like how do I that? Should I do that? At Google especially I got a lot of, “Should I apply for this job at Google? What’s it like?” Because they knew I’d had some journalism in my background, I’d been a freelance writer, and I wasn’t a spin doctor type, and neither were my Google PR friends, so they’d ask, what it would be like if I were to turn the switch.

And then, more recently, I would just get a lot of referrals: People would say, “Hey, my friend is moving from New York, and they had an old media job, they were an old media executive, now they’re coming to Silicon Valley, what’s that like? And here you are, you live in that world.” So it was the combination of those two that led me to feel like I could codify some of this for people. If they’ve been executives and they expected a lot of traditional executive treatment, they weren’t going to get that in these younger companies and startups. If they were reporters who prided themselves on being kind of lone wolves and getting the byline, that would be over. You have to be more collaborative. I thought I’d put it together in a post. As to why I get referred to people, I think it’s just that I’m pretty approachable – people have always said, “Hey, you are a nice person can I introduce you to someone who would benefit?” I’m interested in hearing people’s stories and what they’re thinking. I really like connecting them, “You need to talk to someone over here who had a similar experience.” It’s like pay it forward a little bit and spread it on.

I’d love to know your thoughts around diversity and retention in tech.

I think I just love—I’m a technology optimist, and I’ve just seen so much incredible change in my world anyway, and the developed world again, in the last x number of years. I wouldn’t want to not be in something that is that fast-paced, but I do hear from friends sometimes a quality of life thing, sometimes cheaper place to live than the Bay Area, which I understand. Sometimes sort of like, you know what I had breakfast today with a colleague of mine who’s maybe closer to my age than some, and he said, “I feel like I’ve put in my 20 years here working at different companies, and I think I’m interested in commercial real estate, or something completely different, as another thing to do, that I’m thinking about.” I do hear all these things– I feel like there’s waves of people continue to  technology, Silicon Valley, the Bay area, take your pick of any of these. Because of all the mystique and there’s still a huge draw for people coming in. The question is, are there enough sort of hold overs and veterans to mix with them to make it interesting and valuable, as some other people leave. And some of them don’t leave, by the way. I’ve known very successful people who really get into philanthropy and social causes and social entrepreneurship and that sort of thing as well. That may be more of a function of having been in this business and being successful enough that they’d want to do that. But, it’s not wholesale either way. It’s not like people are leaving tech in droves. It’s more, I think some of it is situational and geographical, and some of it is, yeah sure. I remember in the, what, it probably would have been the, maybe early 90s. I remember the phrase then was Microsoft Millionaires, because after they went public, whenever that was, probably in the 80s, I remember reading about people would make like, $2 million, and they’d quit their job at Microsoft and open– they create a non-profit. I think the guy behind Room to Read was somebody like this. And now, it’s interesting. It’s possible to do, probably you’d have another zero attached or you’d want more money before you did that presumably, because the cost of everything has gone up. But, I don’t know, even the TED Conference is an interesting place to look where there’s a world of people who come there and I’ve gone for so many years. I see there are true entrepreneurs, there are true start-up people and technologists who may be successful, but who believe in the power of technology. It’s interesting, by the way, to see the number of very successful—mostly guys from Google who have taken their money and put it into something like a health thing [laughter]. very cute, very nice. You know, they move from like search technology into something they didn’t know anything about that has to do with the genome or something like that. And so, I don’t know, I’m often [crosstalk].

Where do you see yourself in 5 or 10 years?

I still want to be doing the kinds of thing I’m doing [now], just more for myself. I’m on a couple of non-profit boards, and there have been interesting learning situations there. I think what I continue to like is the variety, the interesting mix of people, the mix of ideas and conversation, some high culture, some low culture, some in between. I like the intellectual stimulation. I’m a humanities person at heart. I’m not going to go to a generic startup, but I don’t mind helping some [of them] with the notion of what’s their culture, how they communicate with each other, and other things that I can do for them, because there’s just a world of interesting ideas and new ways to do things. I’m still too much of a generalist, and too much of a humanities person, and [have] hippie views about not wanting to commit to one thing. Because that was always sort of a credo of being a hippie: “I have all my options open, everything is available to me.” It’s not true when you get old, it turns out, but there’s some part of that spirit that I like still.

What lessons, from a high level, have been most important to you over this time, that you would share with folks hoping to either join tech or stay in tech long-term?

It’s really great to have an appreciation of where things have been, and where they are now. To have a sense of history and trajectory about things, because I think you enjoy more knowing. With my older friends, we can geek out about remembering when fax machines seemed like a good idea, when they came in, or when we used to have, I don’t know, a Syquest drive for backing up stuff. Whatever it is, something that seems so absurd now, and is only from the last 20 years. It’s really fun to be able to marvel and appreciate this incredible arc that is within a lifetime. Within even a portion of a lifetime. It’s amazing, to be swept along, whatever your company, or your business, or technology reference is. That to me is worth it.

But you really only get that sense of appreciation over time. Another notion is that so many of these things have a big impact around the world, even if it’s something really simple. Like when Twitter started, it was designed around the small text message limitation. That was on  purpose, to be able to do it in places where you only had SMS. That sort of thing is compelling for people who are in, or  want to be in, these kinds of world-changing businesses. Like a Google search, that search quality is so good, and continues to improve, and no one’s work is done. You want to keep on and look the impact this thing has had. I think, that’s a draw for people, as well as [giving] purpose and meaning. Another draw would  be the kind of pace you get to see, and live with, in the technology world. I could not live without a draw like that. Don’t take that away from me!

It’s complicated… I am an American citizen. I was born in New Orleans, but we started moving around when I was two years old. In 1967, when I was 5, my dad went as a civilian to Vietnam, doing international development, which means they had this strange idea that, if you “developed” Vietnam economically, they wouldn’t want to be communists and the war would be over. We can see how that worked out. Meanwhile, my mother and I lived in Bangkok. So that’s really what I remember first in my life. After two years, my dad was posted to Bangkok. My little brother was born there.

When I was 9, my parents divorced. My brother stayed with my mother in Bangkok and I came back to the States with my dad. He eventually remarried, and he, my stepmother, and I lived in Pittsburgh, and then Connecticut. Then he started his overseas career again, and we went to Bangladesh. I had just started eighth grade, and when we got to Bangladesh, there wasn’t an American school I could go to. I did eighth grade all by myself via correspondence.

After a year of that, I was happy to go Woodstock School (nothing to do with the concert!), an international boarding school in the Indian Himalayas. I stayed there for all of high school. By that time I had already attended 14 different schools, so Woodstock provided stability and a community that saved my life in a lot of ways. Today it’s my point of reference: the people I went to school with are essentially my family. This year we’re celebrating the 35th anniversary of our graduation; a bunch of us will be meeting in India for that.

I visited the US once in those years, but I’d never felt particularly at home in the US even when I lived there. It wasn’t until years later that I learned to define myself as a third culture kid. This is what happens when you’re born in one culture and you’re raised in one or more other cultures:  you become something else entirely. I’m certainly not Indian, I’m not Thai – but I’m not really American either. Now that I live in the US again, I’m a “hidden immigrant,” which has sometimes caused me problems, both personally and professionally.

I came back to the US for college in 1981. I did my first year at UC Santa Cruz, then my dad realized he couldn’t afford out of state tuition in California. I was an out-of-state student no matter where I went – we didn’t have residency [for tuition purposes] in any state. That made me feel even more alienated: I could be generically “American,” but no state would treat me as a native! And I wanted so much to fit in and feel at home in my supposed native country.

I transferred to the University of Texas, which in those days was very cheap, even for out-of-state. I ended up doing a degree in Asian studies and languages, with all my tuition paid by the US government because I was studying exotic Indian languages. They hoped that I would go work for the CIA or something. [chuckles] I spent my final college year back in India on a study abroad program.

I had just returned from that, had been back in the US for less than a week. I was visiting a friend in Connecticut and she said: “Well, we have to go on this picnic with this Italian guy because I told him I would, and I think he likes me, but I don’t like him, at least not that way.”

I basically took one look at him and thought: “You don’t want him? I’ll take him!”

We ended up a few years later married, with a kid.

He was doing his PhD in Mathematics at Yale, but, when you marry an Italian, it’s pretty much a given that you’re going live in Italy. And we did.

Italy is a lovely country and there’s a lot to like about it. I lived there for seventeen years – way longer than I’ve lived anywhere else in my life.

Meanwhile, I had accidentally started a career in tech before I even knew such a thing was possible. Here’s how it happened:

When I left college, I had no idea what I was going to do with myself. I had had various part-time jobs during college just to help support myself, and those always seemed to end up being around early electronic technology. It all started from the fact that I was a fast typist: I’d taken typing class in high school, and I preferred typing because my handwriting was so bad. So I’d get hired for anything involving a keyboard.

Around 1983 I took a job doing electronic typesetting, which at that time meant learning a markup language, although I didn’t know to call it that. I also did word processing on a Philips word processor. In a later job, I worked on a Wang word processing system. I simply thought of myself as a secretary who knew how to use equipment.

So, out of college, I ended up working as a secretary for a lobbying firm in Washington, which was just completely random. I had moved to DC because I didn’t know where else to be. It was sort of close to Enrico, whom I’d just met, and my dad had a friend near DC that I could go stay with for a while.

This was in the days of WordPerfect, and because I was always curious and willing to learn, and I wasn’t intimidated by technology, I became the person in the office who knew how to handle WordPerfect and make it do stuff. I still didn’t think of this as being a particular skill.

Then a friend of my dad’s decided that he wanted to get into being a small systems integrator. This was just at the end of the time you could still make money doing that. He wanted to offer desktop publishing as a service, along with teaching people how to do desktop publishing. This was a brand new thing then – we’re talking 1987 or ‘88. This is so long ago that Windows 1.something or 2.something was the sexy new operating system!

At that time, just knowing what a font was – was unusual. With the experience I had from my previous jobs, I figured out desktop publishing and I started A) doing it as a service and B) training other people. I was designing the courses and writing the training materials myself. I didn’t have any background in training, but people liked the courses, and they definitely learned. My approach was to have them bring in work they actually needed to get done, and apply what they were learning to something they would naturally do in their jobs.

My boss had also been in international development – that’s how my dad knew him – so all of his contacts were in international development organizations. So, weirdly, I ended up doing two jobs for the World Bank in Africa. I went to Cameroon with 12 boxes of equipment, installed it, and taught people how to use it. Which was really fun.

As part of training for that trip, I took a class in how to take apart and put back together desktop PCs. I was the only woman in the class, and all the other trainees were very surprised, like, “Oh, you actually know how to take out a motherboard?” I was like, “Yeah, it’s not that hard.” [chuckles]

I ended up giving up that job in 1989 because I married Enrico and moved to New Haven, and then I was home with a baby. So when we moved to Italy I had been out of work for over a year taking care of my daughter, and I didn’t know how to go about looking for a job in Italy.  I just did the American thing of mailing out resumés to anything that looked promising, but I didn’t hear back from anybody. I had people literally laugh at me when I walked into their offices and said, “I’m looking for work.” That is just not how it’s done in Italy.

But eventually this guy called me and said, “Hey, I got your resumé a while back and you’ve got some interesting skills. I have a software company, we’re doing an OCR software. Do you think you could write a manual about it?”

“Well, I’ve never done that before, but I could probably manage.” Having written my own training materials for the desktop publishing courses, I didn’t think a software manual could be all that hard.

And so, I ended up doing this project for him and, after that was over, he said, “Well, I really like the way you work but I don’t have any more work for you right now.”

I’d also started to write articles for Italian computer magazines (in Italian!), so I was thinking, “Well, maybe I should try to write a book.” And about that time, Fabrizio called me back and said, “Hey, do you want to write a book?”

He was working on one of the first Windows software packages for recording CDs. This was back when CD recording was just becoming something that consumers would be able to do. The first desktop CD recorders had just been announced – before that, a CD recorder was a $100,000 piece of equipment the size of a mini-fridge, with really awful command-line driven software. Blank CDs cost $25 or $50 – screwing them up was expensive!

Fabrizio was producing CDs as a service for other people, and he saw the need for consumer software that would be easy for anybody to use, to go with the new low-priced recorders that were coming. I’m amused to see that Easy CD, the software we created, is still available – it’s in version 12 or something now. Even at the time, almost nobody knew that it was originally an Italian product.

Fabrizio was a Silicon Valley style entrepreneur, but in Italy, which is a really hard thing to be. So we wrote the book, published in 1993, called “Publish Yourself on CD-ROM,” partly as  marketing for the software. By the time we finished that, he hired me full time to do documentation, translation, marketing, and a bunch of other stuff.

There’s a piece on my website about how I had been communicating online since 1982, when I got into Compuserve. So in ’93 when the book was published, we were using Compuserve to hear from people who were reading the book. Then Compuserve invited me to actually run a forum about CD recording. That was the beginning of my experience in communicating with customers and supporting a product online.

Fabrizio took his company to Silicon Valley, moved all the Italian engineers here, and hired American marketing and so on. I started travelling back and forth a lot because I was working closely with the engineers. And after eighteen months, he sold it for 48 million dollars, which was a lot of money in 1995. The company that bought us was Adaptec, and I ended up working as a contractor for them for six years. They wouldn’t hire me as permanent staff because, “Well, that’s weird, you’re sitting in Italy, we can’t hire you there.” But it was fine, they paid me a lot of money.

That went on through the dot com boom. By late 2000, I was making a second attempt to move my family to the Bay Area. I’d been trying for years to persuade my husband to move to the US with me so I could pursue my career. I said, “Let me get to VP level and we will never have to worry again.” Because even back then I recognized that executives are a protected class.

I felt increasingly vulnerable as a remote employee – it was a very unusual thing to be in those days, people just didn’t know or care how to work with me at a distance. Some seemed to think that I was pampered, working from Italy, and that my job was just a hobby to me. I started an MBA to try to prove that I was serious about my career!

A few years after acquiring us, Adaptec spun us off again as an independent software company. I again asked my family to move to California with me while I pursued this great opportunity in a brand-new company with a big job. At first my husband agreed to try it for a year or two, “but not this year.” I was traveling back and forth like crazy between California and Italy, overseeing the launch of a new website for the new company, and starting to organize moving my husband and child to the US, trying find a place to live and a school and so on.

I was working 14 hours a day, and I thought that doing great work would be enough to get me recognition and advancement. I was wrong about that, and I was really bad at company politics. Someone else, who spent her time schmoozing the executives, and (as I later learned) taking credit for my work, was promoted over me – she got my job and became my boss. It was utterly disheartening. And I was coming “home” to a hotel room every night and arguing with my husband over the phone about whether he would move to the US to join me. I finally said: “I can’t fight on both fronts anymore.” I told the company I was not going to move to the US after all, and I went back to Italy with my tail between my legs.

This was in March 2001. I kind of saw the dot com crash coming. I certainly knew I was in a vulnerable position with the company, because the woman who had been promoted over me was threatened by me. When cuts began to happen, I would be one of the first to go.

Then that July my mother-in-law got breast cancer, so I said, “Well, I cannot deal with major family stress and hating my job every day,” so I quit. My husband never got over that. From the Italian point of view, walking away from a salary – no matter how much you hate the job – makes no sense. But I’d have been laid off a few months later, so I really didn’t give up much.

After that I was decreasingly employed. For a while I got contract work from former colleagues. But Italy also entered a slump that it has never really come out of. There are just no jobs, especially not jobs in tech for a middle-aged foreign woman with opinions.

By 2007 I was getting desperate, I was running out my of dot-com savings. I had put away what seemed like a lot of money to me at the time, but I hadn’t made it big on any stock or anything, it was just savings from six years of good earnings. But from 2001 I earned less and less every year, and was increasingly dependent on my husband (again), which I hated. I really don’t like being dependent on anyone. I worked for Fabrizio again in his new startup, but he was paying me exploitative wages (less that I might have earned as a supermarket cashier!), and the commute to Milan from where we now lived on Lake Como was two hours each way – it was terrible and exhausting, but I couldn’t see any alternative.

In 2007, I got in touch with Dan Maslowski, an old friend from Adaptec days, who had ended up working at Sun Microsystems. He created a contract job for me to work on content and community at Sun. I started traveling to the US for that. It paid well, and it was exciting work, with great colleagues.

In the meantime, my daughter had gotten fed up with the Italian school system and had gone off to Woodstock School in India for her senior year. We knew that leaving the Italian education system probably meant that she would not be able to attend university in Italy and would have to do that in the US. She had effectively left home for good, which is very unusual for an 18-year-old Italian.

And all of a sudden, it was like somebody had flipped a switch in my head. I just woke up one day in Italy and thought: “What am I doing here? I’m not happy.”

In March of 2008, Sun Microsystems offered me a “permanent” job, but they said, “We can’t hire you in Italy, so pick a US office.” I didn’t even ask my husband that time. I just said, “Yes, I’m going.” I came back to the US, to Colorado initially. I figured I would eventually end up in the Bay Area because this is where everything is happening, but I didn’t want to deal right away with the expense and traffic.

Almost immediately after I moved to the US, acquisition rumors started about Sun. A couple of months later, we knew we were going to be acquired by Oracle, and everything was frozen: no promotions, no transfers. There went my chance to be transferred to California. If I’d done that with Sun, I would have gotten a cost of living raise and everything would have been easier, but now I was stuck in Colorado long past when I was ready to leave there.

My job was working with the OpenSolaris community. I was still doing a lot of content — some writing, blog management, and I had started to do a lot of video. I had very strong ideas about using video.

Even before the acquisition was completed, Oracle said: “You people who work on community, we don’t do community that way, so now you’re in marketing.” And the marketing director was like, “Well, your little videos are nice, but go write white papers.” I had been saying for years that white papers were just not popular anymore. And then the first white paper I wrote pissed off a VP, which in retrospect is amusing – I need to have words with him about that, now that we have both moved on to other things.

I could go on for hours about the Oracle acquisition (I’ve written about it), but basically it was not a good place to be. By summer of 2010 I was looking for a new job but I was also very sick with sinus infections. After two sinus surgeries and some medical leave, I quit Oracle the Monday after Thanksgiving.  And as it turned out, my boss’ boss – that same marketing director — quit the same day. I was trying to message my boss that morning. I’m IM’ing saying “I need to talk to you, I need to talk to you.” She’s like, “Yes, I know, but Dan just quit.” I ended up driving down to Santa Clara to be in a meeting at which Dan’s resignation was announced, and eventually mine, and his boss actually spoke to me — for the first time ever — to thank me for my work. And I was thinking, “Gee, if you’d ever bothered to say a kind word to me before, I might have felt differently about this job.”

So then I started at Joyent, which had been one of the pioneering cloud computing companies. I followed some Sun engineering friends into it, and I was hired by one of the founders, Jason Hoffman. I ended up working there for 4 years, in a bunch of different roles, as is typical for startups and small companies. I was the Director of Training, and then I was the Community Architect for the new SmartOS open source community, and then they gave training back to me again as well – and I turned that into a money-making business for the company. Things were starting to look really interesting and good there. In 2013 I was reporting directly to Jason, the cofounder and CTO — and then he left the company. And, you know, when your executive ally leaves, all his projects tend to get canned, so I was, all of a sudden, in a very bad position. And that’s another whole realm of stories, but basically it was clear that I should move on as quickly as I could. In the event, it took a while.

One of the things I would mention, if people were asking me for career advice, is the need for a sponsor. I’ve never really had a mentor in my life but Jason stepped up for me as a sponsor and he got me into Ericsson. And apparently he really had to fight for me because I was being seen as a training person, and some of the Ericsson people who were supposed to make this decision were saying, “Well we don’t need any more training people.” But, I later heard, he really argued for me and got me the job, and even got me a hefty raise. Since then I’ve proved myself and my value to the company, but that first step really took some effort on his part. And I’ll always be grateful for that.

I’m so curious to hear what it was like pioneering some of those earliest concepts of community.

When I started, nobody knew to call it “community.” On the Internet Archive you can find the website I did for Roxio, the spin-off company, when it launched in 2001. I actually use the term “community” there to refer to our users – I was surprised to be reminded of that, years later.

I was a pioneer, but I didn’t realize it at the time – it all seemed to happen organically. First I was on the CompuServe forums, answering questions and interacting with people. An interesting side note is I did get harassed there, but only once [laughter].

Then people started saying, “You should be checking out the Usenet because people are talking about your products there.” I wasn’t even sure what it was, but I needed to be wherever people were talking about us, so I went and learned about the Usenet. It used to be possible to search all those old Usenet groups on Google, and you could find my name there going back many years.

Unfortunately, some of the most prominent posts were from this serial harasser who tried to bug me for years, calling me a liar and so on (none of which was true). In those days ISPs had terms of service that you weren’t allowed to use their services to harass people. I never did or said anything to the guy, but other people in the groups would get pissed off at the way he treated me and report him to his ISP. He kept getting thrown off his ISPs [laughter]. Which of course made him madder and he blamed me.

So I had started interacting with people on the Usenet and then some people said, ‘We don’t like dealing with the atmosphere of the Usenet [which was starting to become toxic with trolls], so why don’t you start a mailing list?”  

So I started a discussion list for users of our software. I moderated it only to the extent necessary to keep people polite to each other. I didn’t care if they said negative things about the product or the company – I mean, I cared, but I allowed it, and tried to answer criticism rather than pretend it didn’t exist. If anything, the other users would have liked heavier moderation than I was doing.

So that was our foundational community, and people cared a lot about it as a community as well as a source of information about CD recording. At some point the company needed beta testers, so I chose the 10 or 12 most active and useful members of the discussion list to be beta testers. It was a very varied little elite group – we had everything from a literal rocket scientist to a pioneer in audio technology to a monk who lived next door to the Vatican – but was also a huge Star Trek fan and had been a DJ! [I was the only woman in it, come to think of it – and I created that group!]

Some people said, “Well, this discussion list is too active – I can’t handle this much email. Can we just have something in a newsletter form?” So I started newsletters as well. By the time I left the company, we had something like 160,000 subscribers. If I can get those numbers in my current job [chuckles], I’ll be doing really well.

I really enjoyed interacting with people – and to me everybody had an interesting story. Like what you said earlier, I just find people fascinating.

The marketing side of the company and the CEO wanted to market to the cool, hip crowd. To get photos to use on the new website, they went out in the street in San Francisco and hired six random attractive young people to be the faces of our website. I kept saying, “Yeah, but the customers who are actually buying our software, as opposed to pirating it, are grandmas who want to burn photos of their grandkids onto CD to save them.” The CEO did not want to hear that. But, sure enough, the first email I ever got to the webmaster at Roxio address was somebody saying, “Your site is very appealing and looks great, but I’m a 65-year-old grandma. What do you have for me [chuckles]?” Damn it. I knew it [chuckles]. I solved that by interviewing active community members [of all ages] and featuring them on the site – that’s where I explicitly identified them as members of a community. It may have been a first for a company website.

Over the course of your career what has been the most exciting parts of your work for you? What really activates you?

In much of my career I have worked remotely, without much day-to-day interaction with my peers. But I was always part of a team, and that’s what I really enjoy: not just doing cool stuff, but doing it together with great people. During the dot com boom I had the opportunity to build and run a team, then really haven’t had that again until now. And I’m loving it. I really enjoy finding the right people, putting them together, smoothing the path for us all to get things done together. Managing people is hard work, but I’m finding it very rewarding.

What I’m doing for Ericsson now seems to be pulling together of lot different threads in my life. Next Monday [Feb 22nd] we’re about to launch a new website — I’m the project lead on this. Part of what I bring to the project is knowing enough about the technical content (cloud) to be able to say something useful as a managing editor. But I also bring knowing how websites work, the basics of SEO, and all of the other components to go into making a big site work. All the experience I’ve gained over the years is coming together.

It’s also an opportunity to apply the philosophies I’ve developed over years of communicating with people online – things that were radical when I started doing them, like sounding human instead of corporate, and being aware that what happens online is a conversation, not a broadcast. It’s interesting to finally get a chance to bring all that to fruition.

What have been some of your biggest struggles throughout your time in tech?

When I was young I didn’t realize this stuff was happening to me. Keep in mind that I started my working life as a secretary at a K Street lobbying firm in Washington in 1986 – in those days an executive would pat you on the ass and no one thought anything of it!

Now when I look back on things, I go, “Holy shit! That was pretty damn sexist.” I was just young and naive and I also do have my share of geeky obliviousness, so there are things I just don’t notice or don’t think about. I never consciously tried to “be one of the boys,” but I have a salty sense of humor. I don’t mind dirty jokes, so that kind of thing never bothered me and I never thought of it as sexist (maybe sometimes I should have).

The most egregious sexism I ever experienced (I’ve written a long piece about this on my website) was when my Italian boss, Fabrizio, moved his startup to Silicon Valley. He took all the engineers (who were men) with him, so what was left of the company in Milan was mostly women.

Fabrizio felt like he had to leave someone in charge in Milan. And he went and chose the sales guy because he was the only guy left, which was just a joke. He was a good salesman, but he literally had only a fifth grade education and was just not very smart or experienced in anything except sales. Not surprisingly, he didn’t do well at managing the company. Fabrizio then hired a consultant to buck him up and make a man of him. That man was the most flaming, overt chauvinist I have ever met. The story on my blog is actually pretty funny because we ran rings around him, but all that happened because Fabrizio would not trust any of us women to run the company.

So, stuff like that happened. I did notice early on that I’d go to conferences where I was essentially the booth babe, and people would be astonished that I actually knew anything…the kind of stuff that happens to most women in tech, and has been happening for a long time.

You mentioned in your pre-interview that you wish you had been better at self-marketing in the beginning, because you’ve pioneered a lot of these very early concepts, and that narrative got taken away from you.

It’s a classic, “If I’d known then what I know now.” Because, years later, I would see people like Seth Godin talking about these things that seemed very obvious to me. It was like, “Yeah I’ve been doing that for years.”  For our new website we’re implementing an inbound marketing tool. Our boss said, “Everybody has to do the certification.” I was really resenting having to take the six hours to do it, and then was irritated by a lot of the content of the training. I realized that this  was because almost every piece of this “inbound methodology” they describe I’ve been doing for 20 years, and it may be fair to say that I invented some of these ideas. I just didn’t know what to call it at the time. (Ironically but not surprisingly, I made 95% on the certification exam.)

I wonder now: maybe if years ago I had had a better sense of marketing myself and my skills as a business, or had a mentor to advise me, I would have done what some of these “web gurus” were doing. There are people who’ve made a lot of money being “experts” with far less hands-on experience than I had. But – oh, well.

I’m curious to know how you’ve seen tech change culturally through different tech cycles, different booms and busts.

I don’t think it really has. A lot of the same people or same kinds of people are in power as before. As I was saying earlier, I figured out a long time ago that if you get to executive level, you’re in a protected class and you’ll never have to worry again. There’s not that many people who get there, and they mostly started out pretty privileged.

I wish I could say tech culture has improved in the 30 years I’ve been working in it, but I’m not seeing it. You still get half-naked women as “entertainment” at tech conferences, and that’s just one of the overt signs of how the industry generally thinks of women. People of color are hardly visible at all. Perhaps now there is hope for improvement because at least some people are beginning to agree that diversity is needed.

What do you look for in a job now, versus when you started?

I have very rarely really looked for a job, which sounds exactly opposite of the way I mean it. I mean I have rarely had the luxury of choice. My life has been buffeted along by other people’s decisions. I ended up in Italy because I married an Italian, and I was constrained by whatever I could find to do there. It wasn’t really until I decided to leave Oracle in 2010 that I had some choices. I didn’t really evaluate choices then, though, because I decided to follow my friends and went to Joyent, where I already knew people. Had I done a real job hunt then, I don’t know how it might have gone.

The first time in my life I’ve done interviewing in any serious way was January of 2013, when I started trying to leave Joyent. It was an interesting process, but didn’t work very well for me, I think partly because my resume is just all over the place and it’s hard to define who I am and what I do. Standard titles and job descriptions never quite fit, and many hiring managers are just not interested in someone where they have to think about “How do I fit her in?”

I did ask for help on that. Steve O’Grady of RedMonk knew me a bit, especially since I had spoken at Monktoberfest the year before on Marketing Your Tech Talent. I asked him for advice and he said, “Well, it seems to me that what you’re doing is developer community management.” He and his business partner, James Governor, helped me get some interviews and were very supportive. It meant a lot to know that they thought well enough of me to want to help.

But some weird things happened during that job search, a few things that made me think, “No, I don’t think I want to work for that company after all.”

Like what?

At one company I had a pleasant in-person interview where they asked me “What would you need to do in the first three months of the job to build up our community?” I said, “I need to look at this information that you have about your customers and people who are already signed up,” and so on —  basically outlining how the job needed to be done.

So I left with a good feeling and was waiting for a call back. A week or two later I wrote to the person who had set up the appointment, and she said, “Well, as part of the interview process, can you do all this?” — and it was basically what I had told them would be the first three months of the job! It would have been at least three weeks of solid work just to draft a project, and it wasn’t even really possible to do without access to all their internal information. Why would I do this for no pay?

I said, “This seems like a lot to ask for as part of an interview process — this is part of the actual job.” She wrote me back and said, “Oh, well, it’s just as well you didn’t put any time into this because we found somebody else for the position.” Really? The whole thing left a very bad taste in my mouth in regards to this company.

I’ve heard from others that this idea that people should work for free as part of the interview process seems to be a growing problem. I’ve got a friend who’s a really talented UI designer and she’s had the same thing happen, it’s like people basically asking her to do work for free, and claiming it’s part of the interview process. No.

How do you feel about the state of tech in 2016? Like what really excites you? What frustrates you?

There’s always a lot that’s exciting. I love tech — I always have, that’s why I stuck so hard with it even when it would have been easier to go do something else, or at least take my technical skills to some other industry. But in tech there’s always new and exciting things happening, and I really do believe that we can solve the world’s problems by good use of technology. But I don’t think that solving the problems of the person sitting next to us at a coffee shop in San Francisco is going to help. I wish people would get out more and get more experience of the world.

I’ve heard one fairly young person speak, someone who is quite wealthy because of previous jobs he’s had (deservedly so – he’s also brilliant and kind) and can do pretty much what he likes. He gave a talk in which he seemed to be groping towards these concepts that, I realized, have always been part of my vocabulary and thought process because I grew up with my dad working in international development. I grew up thinking about how do you help people help themselves, and with the core value that we should all be trying to help others.

People who have only experienced the US and the tech industry, even when their hearts are in the right place, they just may not have the experience or the vocabulary to express what they’re trying to do.

One of the things I like about working for Ericsson is that it’s got a very different perspective from any other company that I’ve seen. At some point I may have the chance to bring together even more threads of my life, not just my working life, but the way I was raised and things that I think are important in the context of the world.

Walk me through when health became a focus in your life and how that changed everything for you.

This is the first time I’m going to put this out there plainly: Even before cancer, my health has rarely been great. If I had been born in Victorian times, I would have been called “sickly.” My dad was actually told this about himself as a child – the family doctor said to his mother, “He’ll never be healthy.”  I’ve had respiratory problems and sinus infections all my life, and about five years ago I was finally diagnosed as having IgA deficiency. This is a very common inherited immune deficiency – about 1 in 500 Caucasian people have it – which means that the immune defenses of your mucous membranes are weak. Lots of people with this deficiency never even know they have it. In my case, it has meant I’ve gotten respiratory infections, sinus infections, ear infections all my life.

My dad probably had the same thing (and it probably contributed to his death), but it was not never diagnosed and, even when you know, there’s not anything you can really do about it. All I could do was say: “Okay, I just have to deal with the fact that I get sinus infections and what have you.” A lot of the time people don’t even know I’m sick. I just keep going. I may be feeling like absolute shit but I don’t want to let it dominate my life, so I just do stuff. I probably overdo sometimes [chuckles].

The IgA deficiency means that I can’t just hope that infections will go away. “Just use the neti pot” doesn’t work for me – it has to be antibiotics, sometimes over and over again. I’ve become very attuned to my body and I have a good sense of when something’s wrong.

In 2010, after the Oracle acquisition of Sun Microsystems, I really needed to leave that job and the stress was very unhealthy for me. I had a series of sinus infections that nothing was working on, and ended up having two sinus surgeries and a lot of other horrific things done to me before it was finally cleared out.

I should have taken medical leave at the first surgery, but my manager was confused about our status – the acquisition was so recent that I didn’t have six months as an Oracle employee, and she said, “You’re not eligible to take paid leave.”

I couldn’t afford to take unpaid leave, and I was afraid I would lose my job and my health insurance, so I had to power on and pretend I was okay while I was really sick and taking an antibiotic that had horrible side effects.

When it came to the second surgery in October, I was that much sicker from stress and having tried to keep working. The doctor said, “Normally I would say, ‘Take a couple weeks and you’ll be fine.’ But you are in such bad shape at this point that you need to take six weeks off.” By then I had been an Oracle employee for 8 months, so I was definitely eligible for partially paid leave. I ended up taking five weeks.

After that surgery, the sinus situation was under control for a while, and now recurring sinus infections are just something I live with. But in the spring of 2014, when I was looking for a new job and the situation I was stuck in was (again) extremely stressful, I could feel that it was starting to hurt my body. I remember feeling one day like my body was burning, and thinking: “I’m going to get really sick if I don’t get out of this.”

I finally got to where I was waiting for the new job to come through and I was doing this juggling act of “Well, If I resign now, then I have to pay for COBRA, how much is COBRA going to cost?” Previously, when I had been in that situation, COBRA was going to be $800 a month. “How long can I afford that?” I finally managed to work it so that I resigned, I then had the remainder of a month of coverage and was okay until the new job began. I knew that as long as I kept hanging on at the old job, it was taking its toll on me physically.

I’ve done a little bit of research since then. As far as I can tell, there’s no evidence that stress quote-unquote “causes cancer.” There may be some evidence that being under stress can cause tumors to grow more quickly. You have to wonder, because I had a clean mammogram in April of 2014, and by the end of October I had a two and a half centimeter tumor in my breast. Something happened there. I’d been working for Ericsson since June. I had the stress of going into a new job and new situation, you’re the new kid on the block and so forth. That’s a good kind of stress, relatively, and I was happy. Maybe it was the earlier bad stress that caused it. There’s no genetic factor and little history of cancer in my family, so… just bad luck?

I had started to travel a lot (which I love doing) for Ericsson. I had been to Sweden three times, then I went to Paris for the OpenStack Summit in early November and I had just had the biopsy October 31st. I was thinking, I’m doing this conference. I’m seeing a lot of people I know. I’m attending sessions, working the booth, talking to people. And all the time I’ve got these biopsy wounds that are hurting and reminding me that I’ve got something I should maybe be worried about. It was very weird, you know? Here we are in Paris and it’s so beautiful and I’m having a good time with my colleagues. An old friend came to visit me, so I had some support –  I told her what was going on. Then she had to leave the night before I did. So that final night I’m in the hotel room alone, looking out over the lights of Paris, and I finally get hold of the doctor who got the biopsy results. She goes, “Yeah, you have a little tumor,” [chuckles]. “But don’t worry. It’s small. We’ll take care of it. Here’s the name of the surgeon.”

Of course, you’re in shock when you hear something like that. I was meeting some colleagues for dinner and they were late. I’m standing outside the restaurant talking to this surgeon in California, making an appointment to get the initial pre-surgery stuff done, and it was just weird. They were still running late so I’m sitting in this restaurant. I started– “Give me something to drink, right now.” So finally these three colleagues turned up. Two of them are people I work closely with and knew well and the other one was someone completely new to me and I was like, “Hey, I have cancer!” [chuckles]. They were great about it. It was just very strange.

I had scheduled my trip such that I was going back through London to visit my stepmother. I took the train from Paris to London, spent the weekend with her, then I came back to California and just started dealing with having cancer. I’ve written a lot about it on my blog. The synopsis is: it’s no fun.

I’d had one or two scares before. My doctors made me start mammograms at age 35 because I have very dense breast tissue. I didn’t understand this at the time, partly because I didn’t get the nuances of what the Italian doctor said to me, but now I know that having really dense breast tissue makes you more likely to get cancer. So, with all those mammograms, of course a couple of times they had said, “Oh, there’s something here we don’t like, we need to do more tests.” So I’d been through scares before, and I’d always thought, “Anything but chemo. I don’t want to do chemo.”

I had the surgery [a lumpectomy] on the Tuesday before Thanksgiving. I chose to have it then because I didn’t have plans for Thanksgiving – I could use  that time to recover.

They took out the tumor and a couple of lymph nodes, and there was no evidence of any spread. Which was the best possible news considering how big the tumor was. Then they sent the tumor off for genetic analysis and that took a few weeks. By the time the analysis finally came through, we were on vacation in Australia (I had started arranging that at the end of October, before all of this stuff started happening). When we arrived in Sydney, I was still waiting to hear the results of this test. So while driving out of Sydney airport I called the doctor, and the doctor’s assistant said, “Oh, I have the results, was about to fax them over to the oncologist and yeah, you need chemo.”

So, we had the month in Australia, and we figured we should have as much fun as possible because the next year was going to be hell. We went to Uluru  (Ayers Rock), the big monolith in the middle of Australia. That was just amazing and magical. Went snorkeling on the Great Barrier Reef, and things like that. Had a really good time.

Then came back in mid-January and had to have a port put into my chest because, of the three chemo drugs they were giving me, one of them, if it gets on your skin, it burns you, so they have to administer the drug directly into a vein. The port sits under your skin and there’s a little catheter that runs into one of the big veins that goes from the heart. So that was another piece of surgery.

So, I went through all of that. I’ve written a blog post for the Ericsson Careers blog about this because the company was really good about it. I later learned that, in a way, they don’t have a choice. I think it’s part of the Americans with Disabilities Act. Companies that have federal contracts have to have a certain percentage of– their employees have to be people with disabilities. Just about the time I was starting to think, “Okay. I’m going to need to actually take a leave because I’m just feeling too horrible,” by coincidence, this email came around from Ericsson HR saying, “Voluntarily, please fill in this form about disabilities.”

I found an article in The Wall Street Journal from the year before saying Americans are suspicious about filling out forms like this, and it’s true – because you always fear that information about a disability or health condition might be used against you. We’ve all heard horror stories about companies finding excuses to get rid of people who have health problems and so on. This article said, “Here’s why that form exists and here’s why it’s a good thing to fill it out.” Then I actually went and looked at the form, and was amused that the very first thing listed [as a disability] was cancer.  I was like, “Oh, okay, I’m officially disabled. They can’t fire me!”

Wow.

So, it was partly that they couldn’t. But also, just the way everybody [at Ericsson] was being about it, I didn’t think they would’ve anyway. It’s a different kind of company with a different kind of attitude. While I was under treatment all the stories were coming out about [a certain big company] and how awful it was to work there. There was one story from a woman who’s like, “I got pregnant, I got cancer, I got fired.”

It took me a while to reach the point that I felt enough trust in the company that I thought they were going to do the right thing, and, when I did, it was a huge relief. I was definitely not at that point right away, because I’d only been with the company for a few months when I got the diagnosis. Jason [Hoffman] had gotten me hired, but he was only one person, no matter how well positioned. So, it was just a huge relief and, as other people have said since, it says a lot about the company that they did the right thing.

I was in chemo from the end of January until mid-June, and I only officially went on leave about a week before chemo ended, then I took off only five weeks. Because that was all I wanted to take off.

People [at work] were being very accommodating, letting me stay involved — I wanted to because I would have been incredibly depressed, bored, and lonely if I had just been sitting here at home with nothing to do. Feeling engaged and useful was so important to my mental health.

After chemo I had a month break from treatment, then radiation every weekday for six weeks. I was scared about radiation, too, because reactions are extremely unpredictable. They told me that I would probably have a worse time because I’m fair-skinned and I’d just done chemo – I could end up having blistering wounds, and this does happen, but fortunately, none of it happened to me. It was mostly just the hassle of having to drive there every day while I was still tired from the chemo.

I was just about finished with that in late August, when Ericsson was participating in a big way in the IDF conference in San Francisco. All of my teammates were coming in from all over the world for it, and I went to San Francisco for that. That was my reemergence into tech society. I had actually just completed a project to amp up some of the web content around our cloud, in record time for Ericsson — while recovering from chemo while everybody else was on vacation! I had hired as a contractor an old friend from Sun to help out with this. That went so well, that’s part of the reason that we were able to do this big web project that we just launched last week [Feb 22nd]. Not only did Ericsson not fire me — they gave me more responsibilities, and that just keeps growing.

When I was in Stockholm this January, we had a big meeting with the extended team of about 30 people and my boss showed a slide about “how are we going to organize around this big project.” And at the top was a box that said “Leadership,” and mine was one of four names in it. I almost cried, because it’s taken so damn long to be there.

So that’s where we are. Trying to keep everything together and do all these big new things and hire people. I’m just drafting a series of tweets about interns I need to hire.

How has that whole experience affected what you look for in a job or in your work?

Ericsson is very different from any other company that I’ve worked for. They really invest in employees, seem to expect that you are going to be with the company for the rest of your life – the company is about the people, which is really amazing. You can do all different kinds of roles and you could possibly live in different countries. Once people get in there they tend not to want to leave. There’s a good chance I will be with Ericsson for the rest of my career. I won’t always be doing [exactly what I’m doing now]. They’ve given me opportunities and responsibilities that I’m not sure I would have gotten anywhere else.

That’s really amazing and ties in really well to the next thing I want to talk to you about because so many folks in tech feel that their career is in danger after they hit approximately 35. Ageism is strong in tech right now. I’m curious from your perspective, in what ways has that affected you or people you know.

I became aware of ageism in tech in my first tech job. We were hiring. We brought in this guy who was maybe fifty, fifty-five, who mentioned that it was hard to get tech jobs because he was older. And I remember, even at my own young age, thinking, “That seems really stupid. He’s got experience, why wouldn’t we want him?”

So, ageism in tech goes back quite a ways, which is interesting and sad. All the evidence is that it’s a very real thing. I don’t know, in my own job search in 2014, how much my age was a factor. Probably it was. I only actually face-to-face interviewed with three or four companies. The one where I mostly had that impression was [big famous company]. I just had a general feeling when I walked on the campus, it felt like a slightly over-age college campus, a bunch of 30 year olds. They don’t really seem to have a place for somebody who’s 50 (unless, of course, you’re an executive). I’ve talked with friends in their 40s and 50s who have also felt that way when interviewing at some companies, especially startups. They may not blatantly say that you’re unwelcome, but the whole atmosphere can feel like there’s no place for you.

So ageism is definitely there and one way especially you see it come out is if you deal with social media. People just assume that “digital natives” are the only people who can do social media. No, actually experience helps there, too. If you didn’t keep hiring 20 year old interns to do your social media, you wouldn’t have these social media disasters that we always hear about in the press!

We’ve been interviewing people lately for our team at Ericsson, and I’ve actually been really pleased that our recruiter has brought in people who have not been afraid to say on their resume “20 years of experience.” It’s like—“Yes, experience! I like experience. This is good.” I’m happy to bring on young people and work with them and train them, but it’s also nice to have people I don’t have to train.

Yeah. It never occurred to me until this moment that someone would be afraid to put 20 years of experience on a resume here.

The received wisdom when you’re doing a resume is, “Don’t put your experience too far back, because that dates you. Don’t say what year you got your college degree, because if it’s pre-2000, you’re too old.” People are trying to find ways to fudge how old they actually are. I gave up trying to hide my age a while ago, because it’s pretty clear. I had things on my website about turning 50, so anybody who does a minimum of research is going to figure that one out.

I did draw the line at getting bifocals. My optometrist said, “You would be much better off for seeing and reading if you got bifocals.” I’m like, “I’m in tech. I cannot be walking around with bifocals.” Or gray hair.

I’m also curious about forms of sexism that you mentioned you’ve experienced in the workplace.

I’ve got that geeky oblivious thing, there’s probably been a lot of stuff over the years that I just haven’t noticed, or haven’t picked up on.

There have been times that I’ve worn makeup and skirts and heels. Lately I’ve had to give up makeup, partly because I have such bad seasonal allergies that my eyes get irritated really easily, plus one of the fun side effects of chemo is it makes your eyes really sensitive. Even now, every time I go outside my eyes start watering. There is just no makeup that’s going to survive that. But people don’t know that, and no doubt there are some who think that I’m making some sort of statement by refusing to wear makeup.

Clothing is always a huge problem. As Deborah Tannen says, there is no “unmarked” look for women. It’s very hard to know how to dress for work. For a while I was wearing low-cut tops and showing cleavage, until I realized that it was just distracting for people. I think it’s just biological. It’s like, if there’s breasts out there, we all look at them (women, too). Maybe it’s a survival thing: as babies, we had to be focused on the breast.

I was having a conversation once with a colleague. We’re having a perfectly sane, rational conversation and right in the middle of it, he stops and he’s doing this [staring at my chest]. I’m like, “Okay, I just can’t do this to these guys. It’s not fair [chuckles].” Since then I’m not exposing so much. [laughter]

Let’s go into another kind of form of isolation that we talked about earlier in your interview, about not being technical.

Being technical? As in, having a technical degree?

Yep, and the importance given to that and how it has affected your career.

My college degree was in Asian Studies and Languages partly because, back in the 80s when Reagan was cutting education funding, the US government paid me to study “exotic” languages, in hopes that I would go work for the CIA (I didn’t).

The things I do now for my job didn’t even exist when I was in college, so I could not have studied them. But many of the skills I use now I learned in the jobs I did then to earn pocket money. I was always interested in technology and I’m a fast learner. I have been a writer since childhood, and that helps in any job.

I took one programming course, my freshman year, but it went very badly. I’m now not sure if that was because I sucked at it, or the course or the professor just weren’t that good. I never considered any further technical courses. No one ever suggested it to me, either.

I never learned to code (unless you count HTML), but I am good at figuring out and using and explaining technology. Whether for jobs or for myself, I am constantly learning. In 2001, I paid for lynda dot com to learn how to use Dreamweaver, the best website production software available at the time. I started my own website to have a place to put my writing, but I also used it to learn about how to build a site, how to analyze and improve web traffic, etc.

There are lots of people out there who code without having computer science degrees. Should we really emphasize the CS degree that much? Yeah, there’s a lot basic engineering that you can learn in a CS degree, but it’s also a field that changes rapidly. Ironically, I have known engineers who insist on the value of a CS degree, while despising people who are academic computer scientists: “They don’t have real world experience.”

CS degrees are valuable, but they’re not the only things that are valuable. I particularly find it distressing that companies looking to hire new grads keep talking to the same universities. This tends to reinforce biases: the majority of people who are coming out of most CS programs at the moment are white men. So we just keep that cycle going where somebody who’s graduated from Brown says: ” I really want to talk to candidates from Brown,” and he hires candidates from Brown, and they’re going to be more white men. And so it goes on.

So I think it would help diversity if we thought harder about diversity of qualifications. A lot of companies are putting money into building the STEM pipeline. “Let’s get girls into STEM careers starting from middle school, and let’s help fund women to do CS degrees at university level.” That’s nice (and great PR), but it’s something a company will never be able to measure. There is almost never going to be somebody that you can say, “We paid for this program at some middle school, and this person ended up working for us.”

The emphasis on building the pipeline also takes away attention from the very real problems for the people who are already in the job market and in the jobs. What’s making it hard to retain them? We as minorities and disadvantaged people keep telling companies [what’s wrong] – or we try to. And yet the problems keep happening.

How did all this affect your personal life?

It’s hard to talk about this without getting into stuff that is too personal and potentially hurtful for others for me to be very specific right now. So I’ll try to distill it down.

It’s very, very hard to be a two-career couple, especially when you have kids. It’s rare that you can both be doing exactly what you want, where you want, when you want, and still maintain a life together. There have to be compromises. For most heterosexual couples, given the cultural assumptions about family roles and work, it’s the woman who does the compromising. I do know a few couples where the woman’s career has taken precedence, and the man’s career takes a backseat or he even becomes a stay-at-home father. It works fine for them, but we notice it precisely because it’s rare.

Even with couples who say they believe in sharing housework and childcare equally, women end up doing the lion’s share of it – we know this from research as well as personal experience. All the assumptions and habits we all grew up with are stacked against us. Maybe women just care more about having clean houses.

The only solution I ever found to arguments and resentments over housework was to pay someone else to do it! I came to that conclusion 20 years ago when I was working as a consultant and my hourly rate was far higher than the hourly cost of paying someone to clean my home – it made no economic sense for me spend those hours cleaning.

The best piece of wisdom I could give anyone about any relationship is: be with someone who values the same things in you that you value in yourself.

If your career is important to you, you need to be with someone who values that, who respects your right and need to do something in the world and supports you in that. Again, this usually requires compromise. And historically it’s been very hard for a woman to find a man who would even temporarily bend his own career trajectory to suit hers.

Many men (and women) of my generation grew up with stay-at-home moms, or moms whose careers were secondary to their husbands’. I grew up with feminism and being told that women’s needs and careers were equally important, but I didn’t see this demonstrated in my daily life. So for a long time I accepted that my husband’s career was more important than mine. When I began to really want to pursue my career, that caused tremendous friction in our relationship.

It eventually came to the point that no further compromise was possible: his job was in Italy, but I could no longer find work there commensurate with my experience, skills, and interests (nor can most Italians!). I accepted a job back in the US in 2008, and we finally broke up 18 months later.

I have some hope that there is a generational change going on. Many younger men and women have now grown up with mothers (increasingly, single mothers) who have important jobs. They understand instinctively that, yes, Mom works, and her career matters at least as much as Dad’s does. There’s still a lot of cultural pressure about how a woman is supposed to put her relationships and family first, but maybe younger men will be more supportive of their women’s careers. Maybe!

My last question for you if you have the time would be, what is some of the advice that you could share to folks, a woman just starting out. What do you wish you’d known in the beginning in your career?

There’s a bunch of standard advice people give that is absolutely true, for example: learning to negotiate for yourself is vitally important. My failures to negotiate salary earlier in life have scary consequences for my future retirement funds.

You need a sponsor as well as mentors. As a wise person has said: “Mentors help you skill up, whereas sponsors help you move up.” I haven’t had mentors, but I have had sponsors at two critical points in my career who have been almost literally lifesavers.

“Networking” sounds like a cynical term, but there’s nothing wrong with knowing a lot of people and using those connections – as long as you also pay it back, pay it forward, and help others wherever you can. We do need to help each other. Most people deserve it and it’s a good thing to do, but especially we need to help each other as women and as other under-represented people. Because it’s so hard for us to get into tech and stay without that support and help.

Anything you say ends up sounding sort of cliché, but believing in yourself and standing up for yourself… those are important, too. If I could go back, I would probably be less inclined to let some things go that I let go before, such as other people taking credit for my work. Of course, there were times when I stood up for myself and it did absolutely no good!

But, if you don’t try, you’ll definitely get nowhere.

I’m from New York. I was born in Brooklyn, and lived there until grade school then my parents moved to the suburbs. I grew up in a suburb called Great Neck, which is a predominantly jewish suburb.  Lots of doctors, lawyers and business people – the proverbial golden ghetto. I went to a good high school, and my family really focused on academics. Music was a big part of my life—I studied music very seriously and thought about going to a conservatory but I didn’t love it enough to only do music. I’m the oldest of four children. Both my parents are doctors. Interestingly my mother always worked, as did my mother-in-law, actually, my grandmother also worked outside the home as a teacher.

I went to Dartmouth and majored in Government. My career goal was to be a diplomat or work for the World Bank or IMF.  After Dartmouth I got my master’s at Georgetown in International Relations and took the Foreign Service Exam, so I was on that path. I worked for the Agency for International Development when I was at Georgetown and realized that I wasn’t suited towards working for the government so I switched gears and went to get my MBA.

Backtracking bit on the personal side, my husband and I both went to Dartmouth. We met on a Government department foreign study program. We got married right when we graduated from college which I suppose is a little bit unusual. In fact I was 20 when we got married. Steve worked in DC while I went to Georgetown and then we both went to Harvard Business School together. My oldest son was born while I was at Georgetown, also a little unusual for my generation. I always knew I wanted to have children and I didn’t particularly want to wait, and just assumed I’d work while I had my children so we started our family young. My oldest son went to Harvard Business School daycare and I got pregnant with my second son when we were in business school.  We decided after graduating from business school that we’d come to the bay area because he was from California and I wanted to work in tech so we moved out to the bay area in ’88. I’ve been working in Silicon Valley since then.

My first job was at Informix—a database company—competitor to Oracle. I was there six years—four years in marketing, then two years in Latin American sales. I’ll come back to that as it’s—probably one of the more interesting things I did. Then I worked for another database company called Gupta, then consulted for a little while and then joined Netscape post-IPO, that was 97. I was at Netscape for six years, ended up running the browser division for the last two years there. I joined before the AOL merger and stayed through the AOL and Time Warner merger craziness. When AOL decided to get out of the browser business, I left. That was ‘03.

I went to Yahoo where I ran Yahoo Mail, was at Yahoo for a year—and Yahoo was getting very big and bureaucratic.  I thought I want to try a startup and I went to this little company called Metalincs that did e-mail analytics. I was their VP of marketing, launched the product and we got bought by Seagate.  I went to work at Check Point where I ran their consumer business and was VP of marketing. Check Point is one of the major security technology companies.  I realized that I’ve run businesses several times and was actually ready to run a company.  

I joined SugarSync at the end of 2008—right when the market was collapsing. SugarSync was really a great concept and the founders had tremendous vision, but the company at that point was in crisis – the debt holders had taken over and they had run out of money.  I came in and did a restart. The company had had no revenue at that point and was down to 13 people.  I grew the business from there about 75 people and a 20-million-dollar run rate over 4 years.  We had millions of users and terrific reviews.  We had multiple offers to buy it up to nine figures.  The board didn’t want to sell so we agreed to disagree and I left.  Later in 2013 I joined a company called Catch.com as CEO.  I later sold that company to Apple.  I had twice joined existing start-ups and thought if I’m going to do this start-up thing again, it would be better to start my own. I started researching some different start-up ideas I was interested in, did a little bit of consulting—I needed the right product and the right people, and those two things came together about a year-and-a-half ago and we started Context Engines.  We’re now beginning to test our product with the earliest users, and hopefully we’ll launch it in a couple months.

Back to the personal side, I have three other children that were born here in California. I was pregnant with my second son in business school, but he was born at Stanford. My kids are 20 through 30. My oldest son lives nearby, they have a three-year-old and they’re expecting a baby girl in March. It’s coming full circle and I’m so enjoying being a grandmother.

I mean, gosh, you’ve walked me through a very extensive impressive career really quickly, but kind of digging into that specifically, of all the things that you’ve accomplished, between is saving companies, building companies, selling companies, what have been the proudest accomplishments of your career?

Well, I’m very proud of what I built at SugarSync. I took a company that was on the brink and built a pretty substantial business. Unfortunately, I didn’t get to exit it so while I’m proud of what I did these things are evaluated by the end outcome and the CEO after me was not able to grow the business and sold for a modest amount. I’m extremely proud of the work I did at Catch—I achieved a really excellent outcome for the investors in just six months.  On the product side I’m very proud of the work I did at Netscape. I was promoted to VP right after Netscape 6.0 shipped. Netscape 6.0 was a pretty bad product—I pulled the team together over the following six months and shipped Netscape 6.1 which was a good product. I look back over a lot of different products I’ve worked on that I’m proud Netscape 4.5,  6.1 and 7, Yahoo Mail, Metalincs. And then I’m very proud of the teams I’ve built. I’m fundamentally a people person, so I really love that part of the role.

I’d love to hear how fundraising and building a business was while raising multiple children.

Let’s see. Where do I start? When I interviewed for the SugarSync CEO role, my youngest son was 12. I didn’t have babies at home. And in fact when I interviewed for the position, one of the board members actually asked me, “how are you going to do this job while you have children?”  I’m not sure how it would have worked to do the startup CEO role when my children were small. I had very big jobs while I had babies—I had a VP job at Netscape managing a team of 220 people, but I didn’t have the stress of being CEO. But I have always felt like having the experiences of being a parent gave me confidence. It gave me a sense of maturity, a way to deal with people. I do believe fundraising can be tricky for women.  I think actually the irony is a lot of the investors want to be open to women CEO’s– they don’t want to be biased. They think of themselves of liberal, even-handed people yet they’re just not used to women CEOs. When they do the classic pattern-matching, women don’t fit the pattern. So I do think it is challenging for women. That being said, it comes down to having a compelling business, having a compelling story and pounding the pavement. Bottom line I was able to raise money—multiple rounds. I see other women raising money despite the extra challenge.

What are some of the other challenges that you faced?

Well, child care was always a challenge. Generally I was not conflicted about, “Do I want to work?” I liked working. I wanted to work, but if our nanny quit, I was the one typically who would stress out. My husband somehow rolled with it—it didn’t get to him as much. I think with those things women tend to be the ones who are where the rubber meets the road. Childcare is really hard. It’s expensive. When you’re early on in your career, the expenses is pretty significant, and finding someone that you can trust—we definitely had some bumps there, and if you have to travel it makes it even harder. I did a fair amount of travel in my career. I was lucky that my mother-in-law lives about 90 minutes away in Stockton, and so while it was too far to do the day to day stuff, if my husband and I were both out of town (which we tried hard to avoid) she typically would come. I was lucky to have family support otherwise I don’t know what we would’ve done. We would’ve figured it out but business travel makes it challenging.

I just have a cat, and I feel the burden of traveling a lot [chuckles].

We have a cat too.

Oh yeah?

I’ve never been a pet person, however, when we moved in 2003, the kids made us feel so guilty that we were ruining their lives by moving and making them switch schools that in a moment of weakness I agreed to a cat. And now my kids are off in college and I still have their cat.

How dare they.

And she’s not even a good mouser.

Well what’s the use of that?

She’s cute. She’s a cute cat.

You as a sum of all of your life experience and your background and your four kids—how do you feel like that affects the way you approach your work and kind of what you bring to the table?

One of the biggest lessons you learn in parenting is to separate the behavior from the person. All kids misbehave, and parents need to guide them to behave appropriately. But you need to separate out I love you from I don’t love the fact that you wrote on the wall or didn’t obey the curfew etc. Fundamentally a lot of managers in the business world aren’t good at that. They do a poor job of giving feedback because they don’t make that separation.   “Hey, you’re smart, you are a really good employee, but next time you do a project like that here’s how you need to do it differently.” I think that’s hard for a lot of people yet it’s one of the more fundamental parts of management. I also believe just having my children kept me grounded and balanced. What I notice now that my kids are out of the house, where—typically I don’t have my kids around in the evening I no longer have a forcing function for me to shut off work.  I recognize how much my kids helped me keep a more reasonable balance—it  was a good thing. Now I have to develop alternative mechanisms.  For years when my kids were little I tried to shut work off from 6:30 to when my kids went to bed—I would try to be pretty vigilant unless it was an absolute work emergency to focus on the kids. People talk about work-life balance and I think that it’s healthier. For me, I can easily get overfocused on work—I’m the type that I would get more consumed with my work, probably to an unhealthy degree when I’m passionate about what I’m working on, so it’s healthy for me and my family to be not so one-sided.

I can relate in a different way. Just starting this year, to learn of the value of taking little breaks. I had to do it through meditation, but it is a life changer, honestly.

It’s funny you mention meditation, but I started when I was CEO of SugarSync.  SugarSync was exciting, but it was very stressful.  A couple of times we had very little money in the bank account when I was fundraising, and so there’s definitely a lot of stress there so I did this mindfulness-based stress reduction class. I don’t know if you’ve ever heard of the MBSR, it’s basically meditation class. I found it to be very helpful. I should meditate more often, my life right now isn’t quite as crazy, but I think it’s a really great tool.

What other disciplines, or life practices did you discover over the course of your career that made it possible for you accomplish all that you have?

At that same time at SugarSync, I started working out more regularly in the early morning. And actually, I can send you a link. There was an article on the Wall Street Journal about me doing this morning hike routine with some girlfriends, and it was a two-fer because I’d get the exercise which would clear my head. And frankly, I’ve always found outdoor exercise to really be much more of a stress reliever, head clearer. If I can’t do it outside, I’ll go to the gym and that’s helpful, but when I can, my favorite thing to do is to hike outside. Ideally with friends, and so it’s social, but if that doesn’t work out schedule-wise, I’ll listen to a podcast or listen to music, or just enjoy nature. And that’s one nice thing living here, one minute from just beautiful places to walk.  It’s amazing.

And I’ve always kept up my friendships, my girlfriends. I have more time now for that then I did with young kids at home—we hike with them or try to meet for lunch or coffee.

You were lucky to learn early on that other things matter. And taking care of yourself matters. And things other than the product, like exercise, friendships, the people in your life. I think a lot of folks take a lot longer to learn that here. I learned after I worked in tech.

I think because of having kids from the beginning of my career always had a life outside of work. And I think I’ve always been a social person. The exercise piece for me, it took ‘til about I’d say my mid-thirties for me to enjoy exercise. But now I love it, like I said, especially if I’m outside. And now I’ve gone back to my music and that’s something that with kids at home there was just no room in the schedule.  I didn’t play violin literally for about 28 years, and I’ve picked that back up about a year and a half ago. I’m enjoying that very much. I’m not as good as I use to be but I’ve made peace with that fact and am improving with practice.  I also enjoy the social since I do chamber music, that’s been fun.

That’s really neat, it’s nice that it’s all coming full circle.

Yes, the violin thing was something I had a mental block on, and I actually just wrote a blog post about that a few weeks ago.  I kept on putting it off because I didn’t like how I would play. I had set this standard for myself and then wasn’t playing because I knew I wouldn’t be above that standard. And then I finally realized, well it’s not going to get any better and I’m just missing out. When my youngest son went to college I realized if I don’t do it now I’m probably not going to ever. And so I got over that hump.

I grew up playing classical piano, competitively. I’m sure you can relate, practicing like four hours a day and it’s your life and I quit when I went to college, and wasn’t competing anymore so I didn’t see the point.

Okay. So then, you totally understand.

I have the same issue where I can’t even touch a piano, because just the pain of knowing that I can’t produce the perfect thing that I use to produce, so what’s the point.

I did those competition things with violin. We had this thing in New York called New York State’s School Music Association, where you’d go and play for a jury—chose a piece, and it would be at a certain level, and you’d get graded. So the highest level of pieces, I think was six or seven, and I was playing at that level when I was a junior and senior in high school. So, the piece I was playing when I picked it back up, and not playing easily, I think was a four or five. I don’t know if your music teacher did this, but you’d work on a piece of music and then they’d put the date, and say like, “For next week’s lesson, learn this movement or learn up to this repeat,” so I realized last spring, I was working on something I had worked on in seventh grade. I regressed a lot but I have some things I feel like I do better but the technique is not the same.

Yeah.

But, you know, I just decided to get over it.

It’s what you have to do.

I’m curious now, because I know how growing up with that discipline has affected me in good and bad ways in my tech career, which in so many ways is the opposite discipline of classically trained music. So, I’m curious to know how that upbringing—a rigid, strict, music upbringing (with perfectionist aspirations, because that’s built into it) affected your approach to your work, for good and for bad.

I’d say on the good side, it makes you appreciate diligence and working on things, especially things that sometimes come slowly. Even if you have a lot of talent, learning pieces, perfecting it, it’s sort of a day-by-day, little-by-little process. So just I think having that self-discipline and diligence is what I got out of it. But the perfectionism is dangerous, and I sometimes suffer from that. [chuckles]

The technique that my husband has tried to get me to use is, “Okay, you’re not satisfied with this. That’s fine. You have your own standard. But, if you were looking at this as a third party, how would you view it? What grade would you give yourself on a 1 – 10?” And if I really put myself in that outside shoe, I think I’m actually fair. I’ll say, “Okay, it’s a seven. It’s an eight. Whatever it is. This marketing campaign, you know what, it was pretty good,” But because, for me, when it’s not a 10, I can be very hard on myself. But I wonder if that was caused by the music or if people like you and I gravitate towards classical music, or survive through the years of classical music, because we have that. And the people who are just always going to say, “Oh, seven or eight’s pretty good. Those are the people who quit, because a lot of people quit classical music. The cause and effect of this whole topic I’m not clear on.

Yeah, it’s a big question.

I would suspect that is part of your current work too. That you go the extra effort to get the lighting and the setting, to get it all perfect—it’s like that extra diligence.

For sure. I love that we’re having this conversation.

You’ve seen tech through a couple of cycles and I’m curious to know your thoughts on where it is now, what excites you about tech, and what frustrates you about tech.

What really excites me is with the modern tools how quickly we can build interesting, useful things. My current startup, we’re two engineers—my two co-founders—and myself. Of course I wish we were going faster and that we shipped last but we’re able to leverage all these great tools in technology and build a lot quickly. That’s very exciting and satisfying to me, just the technical progress that we’ve made and the experiences we can offer. That really excites me.

What else? It has this—and I’m not talking like the unicorns and stuff—there’s a little bit of the gold rush mentality, where I feel like because tech has gotten so exciting, people who really aren’t truly passionate about it, it’s the hot thing to do. Just like when I finished business school in ’88, not that many of us came into technology. You had to be really, really interested. Most people were doing investment banking or consulting out of Harvard Business School. By the way, some of them loved finance and loved management consulting and were great at it, and some people were just the, “Well I’m going with what’s the hot, popular thing.” We’re getting a lot of people in tech here in the Bay Area who I think are doing the hot, popular thing. That is distracting. It makes for some junky stuff in the system. Even so it’s still, to me, just very exciting. What we’re able to build.

I wish we had made more progress on things like diversity. I’ve been here long enough to see that, no, we actually haven’t. It’s the same, or it may be slightly worse. That shouldn’t be. Other fields have made progress. When I graduated from college in ’85, med schools were 75-25, they’re 50-50 now. Our industry’s poor diversity is frustrating to me. I’m trying to do my part on that. Not just on the gender front, too. I read this article about Howard University—that they’re having trouble getting the Silicon Valley firms to recruit there, at their CS department. There’s no excuse for that. They claim they want to hire more people of color, then go there. I’m sure there are great students. I wish we were making more progress.

For me, technology is still just super exciting. One of the things I’ve always loved is how much variety I’ve had in my job. Most of the people in my family are doctors, and medicine is a great career, but I think what you do doesn’t change as much. It’s very important work, and I think it’s satisfying, but for me I like the fact that there’s been just so much change over, you know, what I do. For instance, in 1988—my first job was was as product manager in Informix, we did all these trade shows and seminars and data sheets and sales calls, and I just think about how the marketing discipline has changed, how technology has changed… it’s very exciting. So I think I would have been bored elsewhere. It’s never boring here.

Yeah, I agree. What sort of advice would you have for women in tech, or women entrepreneurs, or even mothers in tech based on what you’ve learned?

Good question. One piece of advice I’ve given people is, I wish I had gone to the startup world sooner. I think I perceived it as being very risky, but there’s risk anywhere. You could be at Yahoo now and chances are you’re worried about getting laid-off. You might as well be in a startup where you have more control over your destiny, there’s more transparency. Nothing wrong with big companies, I worked for big companies for 20 years, but I’ve enjoyed the startup world more.

Also, if I’m asked I always tell women not to wait to have kids. You never know. There will always be jobs but biology doesn’t wait. I’ve just had friends with a lot of disappointments and struggles. Those decisions are harder to change or undo. You can always find a different job. If you’re confident, you’re hard-working, I think that will work out.

Most importantly, If you’re planning to work and have kids, you need to really make sure your partner is committed to that. I’m very fortunate my husband and I feel like really we’ve partnered over the years, on the kids and the household stuff, and we’ve supported each other. We have different things we have done for the family, but I really felt like it was a shared enterprise.

Take the longer view—actually Sheryl Sandberg writes about this pretty clearly in her book. Let’s say you’re in your late twenties, so you’re relatively early on in your career, and you have a toddler and a baby. Childcare is going to be expensive, and because you’re early on in your career, maybe you don’t make that much more than what the childcare costs. It’s easy to look at that as, well then maybe I might as well stay home. But you’re looking at current income and current expense, and you really need to look at it with let’s say a 20 year future view. And your current childcare expense is an investment in your ability to earn income 10 years down the line. And I think when your kids are that age and you’re not sleeping, and you have maybe an annoying boss and whatever else is going on, you feel like it’s always going to be that way, but kids actually don’t stay babies for very long. It seems like when you’re in that sleepless state it’s going to go on forever. Let’s say you have two kids and they’re three years apart, after eight years everyone’s in school full-time. Maybe after three years kids are in school part-time, and it starts to be more manageable. I think it’s important to sort of step back and take the longer view. I had a lot of friends who dropped out of their careers at the baby stage and now they’re not quite sure what to do with themselves. When your kids leave for college I think it’s a tough stage and it’s really tough if you don’t have either a career or some kind of intense volunteer interest.

Yeah.

That being said, everyone has to do what’s right for them. I try to be careful not to be too judging—I mean, it’s a personal choice right?

I was born in Chico, California. My dad was the head of the chemistry department at California State University at Chico. As I got into primary school, my mother started running for elected seats like the school board, and ultimately she became Vice Mayor of Chico. But then, my father passed away when I was in fourth grade.  My mom, almost as soon as he passed away, started aggressively pursuing her career in politics, which took us down to Oakland. Her intention was to go to law school in San Francisco, but then she started working on people’s campaigns and got really involved in the State’s Democratic Party. Ultimately, by the time I was in high school, she was Treasurer and Chair of the California Democratic Party working with people like Nancy Pelosi and Jess Unruh. There were so many great characters I was exposed to and they all had incredibly strong belief systems. I had this highly active childhood with my mom, filled with democratic politics, but I was conflicted because my father’s parents, who were still a big part of my life, were staunch Republicans. So politics for me were very uncomfortable and I thought “Ah! Politics are horrible, and you shouldn’t talk about them because all people do is fight.” [chuckles]

I wanted everybody to get along and I just wanted to be normal with a normal family. It seems I never got to be that way though – I had this big curly hair that kids at school made fun of- calling me names like tumbleweed and bushy. So in high school I wore it up in a ponytail braid really tight all the time. I was really self-conscious of it and tried to make it go away.

Eventually as I was applying to college, I realized that my curly hair and my strange upbringing with just my sister and my mother, and all the characters in politics as well as my knowledge about it, was really making me different and it was becoming really fun.  When I got to college I picked a major that only had 13 people in it and was only offered at two schools in the nation at the time. I just liked doing these things that stood out or somehow made me stand out from the crowd even if just slightly.

The major was cognitive science, which I got interested in because I was leaning toward computer science at the time, but thought the comp sci majors were boring and introverted. Cognitive science was neuroscience, philosophy, computer science, a lot of linguistics at the school that I was at, and cognitive psychology. There were people doing all kinds of research and studies of stroke victims, babies developing language, the brain, and psychology so the group seemed really alive and gregarious. We studied language in the human brain and how it’s organized – human language is the one thing that sets us apart from animals, so understanding its constructs and processing in the brain when applied to computer processing, helps to make computers smarter. It was the early days of artificial intelligence, and we had philosophy in order to contemplate if developments were limited or unlimited and the implications of the work. Now this multidisciplinary program exists at many schools and ironically CogSci is a big feeder to product roles in tech – it took me 20 years out of school to migrate into a role like that, though!

When I got out of school I really just wanted to work and have stability, because I felt like my life had had a lot of instability. My mom’s political activities exposed me to a lot of hotels and their ballrooms for fundraisers, and I thought the hotel business looked like a lot of fun, so I went and worked for hotels – I know, funny choice for a Cognitive Science major. Hotels, though, gave me this intense appreciation for problem solving with people. In hotels, you’re working face to face with guests, and in the service industry it’s all about your guest and being an advocate for your customer – figuring out what they need before they need it. It was a nice way to start out my career, and customer advocacy is something I’ve taken with me to every role since.  

In particular in tech when I got there, it was so far from customer empathy because everybody was just trying to figure out the coding of our web site and back end systems. All the mind-share went to the complexity of the technology and it was very common for everybody to disregard the customer. Really, when we did take the time to think about the customer in the early days of tech, or at least in my early days, it was just this revolutionary thing that impressed people[chuckles]. Meanwhile, hospitality and  the retail world had been doing it for years so it was fun to bring that to tech.

So walk me through your early years in tech and some of the foundation you helped lay for e-commerce.

I would say I was a part of it, but I don’t ever feel like I made things happen on my own across eCommerce. It’s so funny when you get out of the Bay Area and look at the industry from the outside. It really does look revolutionary, but when you’re in the middle of it you feel like you’re just part of a big team, or part of a company that’s doing new things (sometimes in really messy ways), but you don’t realize how new they are, but then they become the norm everywhere else down the road.  eCommerce has been like that for me.

The first startup that I did was an online drugstore (more.com – more than a drugstore, just a click away…), and we were competing with PlanetRX and Drugstore.com. It was the early days of the dotcom bubble and we were heavily funded, which gave us a lot of money to acquire customers and we did just that.  Customers back then were unsure of the world wide web, let alone buying from it, but we had a fair share of early adopters. I was responsible for customer operations and on my first day my boss said to me “Oh, we have this typical merchandising success situation on our hands where we’ve launched the store and the customers are responding very positively, but  we’re out of inventory so we’re not able to fulfill the orders.” In other words, we had customers ready to buy, but we didn’t have the product to ship. Having come from the catalogue business, where my boss and I had worked together I said, “Well, let’s find a way to delight the customers and make sure that they’ll give us another chance and come back.” For this group of customers, and I don’t remember how many it was, and this was not a sustainable solution at all, we sent them an apology letter with a crisp $10 bill. We sent this little bribe to every single customer who didn’t get their order. In typical dot.com fashion, the idea was to get their attention, delight or surprise, then let them know that we cared about them. It is kind of appalling now, if you think about sending cash in the mail to your customer, but at the time, we wanted to make a big impact so he/she would remember who we were and get some cash to boot so they could get the product they needed that we couldn’t provide.  Customers loved it and held out to order from us again. It was very scrappy and a low-tech way to respond to a real customer problem without requiring technology, which would have taken too much time.  We needed to lay the foundation so that commerce on the web could be trusted and there were people behind the technology who would take care of their customer – this gesture helped.   

After all the dot-coms went out of business, I was a little shaken, and wondering if I really wanted to do start ups again – I had a family of four I was supporting after all.  I went to BabyCenter, which was a great set up, because they had been a startup that got acquired by Johnson & Johnson. J&J is really a very hands-off corporation in all the right ways. They expect you to run your business very independently and do what you need to do to make your business work. It was like being in with this great, big parent company behind you and supporting you while we took a second shot at an eCommerce business.  So, that was really where we got serious about making e-commerce work for the long run and we couldn’t pull tactics like sending ten dollar bills to your customers to take care of the mistake that you made. We focused on building a strong vendor community (they were still afraid to do business on the web), building strong and reliable customer operations, using the technology to our advantage, and getting to profitability. Are you familiar with Baby Center at all?

Not at all. [laughter]

Okay – BabyCenter’s secret sauce is when you come to their website for the first time they ask for the mother’s due date and that sets off a relationship with the site and the mom based on the stage of pregnancy and age of the baby. We had 8,000 articles about the health of the baby and pregnancy. We would send a weekly email about the development of the baby that got it right every single time. Moms would ask how we knew this was what was going on for her or her baby. I came on just as we were launching a new ecommerce business because their old one had gone down with the previous owner. In the store we leveraged the stage of the mom and the age of the baby with how we merchandised.

In terms of laying the foundations of eCommerce… the previous BabyCenter store had customer comments, which we brought back — I think it was originally just them and Amazon during the dotcom era. The thing about customer comments was they were so new our vendor community was really afraid of them – the thought of customers publicly sharing their view of a product was appalling to some manufacturers – of course now it’s completely the norm.

Three years into my tenure at BabyCenter, I became VP of the store, and I remember going with our fabulous merchandise buyers to do a dog and pony show around the country to our top vendors with the goal of building their trust or winning over vendors who refused to sell online at all.  We had to constantly reinforce that we were a legitimate store because they were afraid of online.  They fearfully thought we would undercut pricing or ruin their brand with crazy promotions funded by tech investments. BabyCenter, though, had this editorially objective health site with a critical mass of pregnant moms that really legitimized us. J&J too as a parent company legitimized us. So we got a lot of vendors, but they were still very nervous about the customer comments.  Eventually a few of the vendors started to figure out that the comments helped them design their products because they could listen to the customer to make improvements.  Our merchants were all over these types of stories when the next nervous merchant would complain so slowly the community started to understand the benefits of the wide open web.

The other thing that was great about the early time in eCommerce was we were all asking each other for help. Companies like A&E, HBO, Bluefly, Travelocity, NY Met Museum Store, the Smithsonian, Amazon, eBay, and anybody in the industry who was building a commerce site for the first time  would talk with each other and we’d help each other with our questions. We’d reinforce for each other what we knew was right – like helping customers by allowing customer comments  – even though our vendors threatened to pull their products.  We’d float a lot of site questions like should navs be on top or on the left, should we use tabs like Amazon, etc.   Shop.org and the Customer Experience Councils run by what is now called Collaborative Gain were big facilitators of those conversations. We all built strong networks of peers who were growing and scaling their businesses online and also growing in their careers and they’ve all become great friends over the years, which is so special to me. There is an intensity to these relationships because we were all very vulnerable and humble since the industry was so new.  

So true.

To give you a sense for how small and fledgling a community we were, the first Shop.org conference I went to had about 60 people in a meeting room at the Hyatt in New York.  It was amazing to meet everyone and realize they all had the same challenges and questions and that we could literally all help each other.  The last time I attended shop.org in 2007 there was something like 7 or 8 thousand people at a big convention hotel in Las Vegas – and it still goes on. It was really great to see that community grow and it was both vendors and stores. I loved the vendor aspect of the community because there were so many new types of technologies that your store could take advantage of but that we wouldn’t want to build for ourselves – tools like analytics, search, and the shopping sites that were lead gen for your store. The conferences were all about learning and connecting.

A lot of us were very vocal and I think participatory in asking for help, which is how I got involved in the Cyber Monday conversation. The Executive Director of Shop.org got a group of us together on the phone and floated the idea of this term “Cyber Monday.” We had all been talking about promotion trends for the holidays, and we knew that Black Friday was the big promotional day for bricks and mortar, but we also all knew that the following Monday, when everybody got back to work from Thanksgiving, our online orders spiked. We wanted online to own a part of the holiday season in the mind of customers and thought we could lean into the spiking of the orders on that Monday. We all agreed Cyber Monday was a great term and then a few of us were interviewed by the Wall Street Journal and they quoted me on the front page, which was something I never expected to happen and was exciting! We continued to collaborate over the holidays because there were such consistent patterns in the shopping across all of our sites. I don’t know that this happens anymore in eCommerce, where people communicate and share the dynamics of the season that they’re experiencing, but back then, we were looking at things like the final day to ship in time for Christmas, the Cyber Monday promotions, and tactics for extending out your window of shopping as long as possible. The fourth quarter was and still is the biggest quarter for most of these sites and the stakes are high for the merchant to get the orders right for the customer – we had good years and bad ones in terms of delivery accuracy across the industry and we worked collaboratively to reflect on the bad and improve. I’m completely confident now placing orders that have to arrive by a deadline and that is the result of all of our hard work in early eCommerce.  

It’s just amazing to think about E-Commerce being small enough to be a community.

Yeah and back then, I think we were excited about it approaching 2% of retail and maybe someday like in 5 years it would get to 4% of total retail sales. Now its approaching 8 and 9% of total retail sales and mobile has taken off.

For sure.

What other things – when it was a small community, and you all were just experimenting with different things, and showing ideas, and sharing dynamics with each other – what other concepts did you guys see and introduce for the first time that are just omnipresent now?

Shipping! The catalog industry for years had made money on their shipping charges, and when e-commerce came along, we wanted to remove any barriers to buying and conversion in check out. Many of the sites just had free shipping to combat any reason a customer wouldn’t try online. Shipping and lack of trust were the biggest reasons customers gave for not buying online. We wanted to build the customer trust and help them try the BabyCenter store so had a $5.99 flat shipping fee no matter what you purchased – so a pacifier would cost $5.99, a bed the same, if you bought the two together they’d ship separately but the customer still only paid $5.99.  We and all the other sites were losing our shirts with shipping costs. We weren’t even building the loss from the shipping cost into our retail price, because customers could compare prices with other sites and we had to be competitive on price.

Instead of talking to the online community for help, I talked with old catalogers.  If you talked to e-commerce people, they would say, “No, you absolutely can’t charge for shipping- the customers just won’t shop with you.” But the catalog industry was much more realistic. They ran the numbers very, very carefully to know how to charge and how to make money on it. The thing that the catalog business couldn’t do was have a calculator that a customer could use when doing mail order and adding up the charges themselves. Catalogs charged based on the value of the order for simple calculations. You paid the most for a high-value order. The problem was, a silk scarf might cost $450 and you have to pay the highest shipping cost even though it’s the lightest thing to ship. So the advantage that our e-commerce store had was we could build a calculator into our checkout that used the weight and footprint of the product. We shipped pregnancy pillows, which are these great big light things, but they’re actually expensive to ship because the footprint of the box is really big. We started to build in that kind of intelligence into our shipping calculators, and the idea was to charge the customer what was realistic and understandable in terms of the shipping charge.  This early move on the part of our store massively changed the bottom-line of the store and we had no customer rebellion because the charges could be explained and they made common sense. That was a really satisfying thing – We got to use the technology to its advantage, make some money for the store, give something realistic to the customer that they could understand, and the store’s P&L started to make a lot more sense.

It’s amazing. Did you expect at all that your experience in hospitality [laughter] and the catalog industry would be so valuable to you?

No I don’t think I was all that calculating when I was making choices for my career with catalog and hotels (I was calculating though when I went to that first start up because tech was so important to the Bay Area’s economy it seemed a shame not to tap into as a career choice) Before that though, I was really trying to go by what was going to make me happy, be the most engaging and developmental for me.

In hindsight, the other skill that hospitality and the catalogue business gave me was great analytical skills because I was doing a lot of forecasting and managing large labor & vendor costs. I knew when I got into tech I appreciated that real world experience that required us to make money and manage costs. In tech when you’re so focused on solving technical problems and proving new models to your customers or the business community it’s easy to lose sight of building good businesses that fulfill on their promise to the customer or share holder. I like that common sense business perspective that I’ve contributed to my businesses.

Absolutely. Tell me more about what it was like being a woman coming into tech from a totally different industry and having two babies when you started. What is that like? Were you the only mom around at that point?

Yes, at the startup I was the only one with kids (they were 18 months and 2.5 years old) except for the CFO who started toward the end and she had a middle schooler.  I found out long after we were done working with each other that she didn’t even know that I had babies during that time.   I think I kind of hid it there and came up with my own solutions. — Instead of working late into the night when everybody else did, I would get up at 4am to miss traffic and get to the office as early as 5 or 6am.  I’d have a few hours of quiet time where I could get a lot of work done and then be home in time for dinner and see my kids in the evening. I did have to push back on people calling for 6pm or 7pm meetings and then I do remember explaining I had small kids to get home to knowing it might hurt my influence somehow.  

With one start up I interviewed with after the dot.com bubble burst, I opted out altogether because the founders had dropped out of college to start the company so they weren’t exactly at the life stage I was at with small kids. Tellingly to their late night, late morning schedules my interviews were at 8pm in the evening. I couldn’t imagine they had any idea what it was like to have babies at home so I declined the opportunity – years later they ended up making it really big and I potentially could have made millions.  I remember thinking about that at the time and looking back on all the things my kids had gone through while I would have been out of the house killing myself for that business (the kids were learning to read, do math, dance, socialization, all normal kid stuff plus my daughter also had some learning differences we managed with some specialists, which took time and commitment to her) – no way would I change that decision to opt out of the start up. The kids needed me during that time and I’m so glad I had jobs that allowed me to be home at nights and on weekends. Maybe I worked just as hard at the companies that never made a killing, maybe I was actually afraid of taking the plunge into a completely new disruptive model, but in my mind I designed a career that didn’t remove me completely from my family life.  At least with one choice the monetary result of that decision wasn’t as positive – again though it was right for me and my family.

I think I struggled more at home though as a woman in tech than I did at the office.  When faced with the opportunity to go to the start up I did join, my husband and I spent a lot of time evaluating if this was really what we wanted.  We had decided my career would be primary and with tech I had the opportunity to thrive in my career vs. just survive juggling a nothing special job and being a mom. Earning a living started to fall onto my shoulders and care giving for our kids fell to my husband because my jobs demanded a lot of time and ultimately a lot of travel.  We had no role models and even the other working moms that I knew tended to have a husband who was also working. Those moms were balancing their career with being the heavy lifter at home, whereas I was putting everything that I had into my career, trying to be a good mom at the same time, but with a husband who was a really strong supporter at home. Without the role models, though, it was really hard for both of us to keep a balance in those roles, and I think ultimately, what happened to us was we kind of lost ourselves. I like to say “I leaned in so hard I fell over” ha ha.  For a variety of reasons, our marriage failed, but we would both say that we managed to raise two really great kids who have had the benefit of growing up with an involved working mom and a really involved dad. Ultimately, I wanted a bigger role with my kids, which I got as a single mom after the divorce and sharing custody.

Another unique aspect of my career, which was also true the years I’ve been in Tech, was that for whatever reason, I was in companies that had strong female leaders.  At BabyCenter, where I became part of the exec team for the first time, we had a female CEO and we had a majority of female exec’s.  Hotwire too had a majority women on our Exec team and Mulberry Neckwear had a female founder again with majority female leaders in senior leadership.  It really wasn’t until I was 35 that I noticed, or even realized how being a woman brought a different style to a team. It wasn’t until I was on an exec team that had a majority of men that I started to wake up to, “Oh, there are big differences between men and women and how they lead and manage people.”

I think the turning point for me was when I had a boss who was the CEO tell me that one of my female managers, who happened to be our best product person in the company, was too emotional.  He wanted me to work on that with her.  The conversation obviously raised some flags for me, and I wasn’t quite sure if it was ok or not. I walked away thinking, I don’t know what that means so I talked to a friend of mine, who is an amazing gender discrimination lawyer. I confided with her that I thought I needed to learn more about gender issues in the workplace.  As much as I had grown up with a feminist mother and maybe because she was a single mom, I didn’t know what sexism looked like and it had never felt like a factor in my work – my experience was if you deliver you’ll get recognized. My friend’s advice was to read ‘Men Are From Mars, Women are from Venus’ so I could understand gender differences a little better.  It opened up this whole new world for me because I was raised with my sister by a single mother and didn’t have strong male role models in our house. I had no idea what men were sensitive about and even that they are sensitive! I thought all men were strong and made of Teflon.   To apply the book’s content in the workplace was really eye opening and I hope my work on my own lack of sensitivity to men’s orientation served to bring me closer to the men I work with.  I never did address the quote emotional issue with my employee and instead continued to support her with her results, which she definitely was recognized for.

Silicon Valley is talking a lot these days about the obvious sexism when it occurs. What strikes me is that the men aren’t present in these dialogues after the fact.  Almost every company I join now has a women’s group or a women’s summit that works to develop us or support us. These groups are great – women mentor each other and focus on creating great results for their businesses. Consistently, though, the men aren’t present. What I would find really interesting is what the men think and experience. How do we learn that the conversation is just different when it involves women and men – it’s not about men changing or women changing, but instead about a dynamic that is completely different when we’re all equals at the table. We all have to realize it’s going to be uncomfortable and we’ll feel unease, but the benefit is huge because the diversity of styles and ideas will create better ideas and solutions. I’m not sure women and men are talking together about the fact that we need to do the hard work and feel that discomfort in order to move forward in creating diversity in the industry. It’s not comfortable when the people on your team don’t all look and act alike – the industry hasn’t figured out that the benefit of that discomfort is great results.

Let’s keep going with that. In your time in tech – you’ve been in 17 years, whether it’s related to being female, whether it’s related to something not having much to do with you – how have you seen tech change through these multiple cycles? How has it changed and how is it the same, for better or for worse?

I was going to say it seems like it’s getting younger!  That is just because I’ve aged though – we were young during the dotcom times ha ha.

For sure.

I certainly feel like I have a very strong set of peers who are the same age as me and we are all actively engaged with each other and involved in the tech community.  I’m not sure the tech world has learned that diversity of all types (including age) helps results though because you still find us in packs that all look alike.  

I think one clear change is that the female/male conversation is getting really loud. That was not present for me at all in the beginning or I was unaware of it if it was. I’m amazed at how loud the conversation is getting with the tweets, anecdotes, books, and media attention it’s getting. I still feel like it’s a lot of talk and there’s not a lot of actions going on that are truly changing the statistics of women in leadership roles at C-levels or on boards.

Another interesting change over time is that lot of the small companies have gotten extremely large, and they look like the large companies that we were all running from when we went to work for small companies. It’s amazing to me how these small companies start out so   nimble, and flexible, and then very consistently grow into pretty big operations with their own fair share of bureaucracy.

Maybe the tech world has more awareness of diversity and is more diverse as a result of these large sizes. The big companies I’ve worked for seemed more supportive of diversity efforts than the small ones I work with.  When you’re small it seems you surround yourself with people that look like you or act like you, but in the big companies, all types of people exist. I see them represented with groups. There’s LGBT groups, there’s minority groups, there’s any group that really wants to form, and the company is supportive of it. So versus the rest of the world, I see the big companies making an effort to embrace the diverse communities that they have within them. But again, it is at the lower levels of the company and when you get into the executive branch it’s very homogenous still. Which is where I think the work is to be done.

You mentioned in your pre-interview that your kids don’t find tech very desirable after seeing the experiences you’ve been through. Can you expand on that?

I think for them– they live with me and they know my highs and lows, and —they see you have to be pretty resilient in tech. They’ve seen my jobs come and go and the companies come and go. So some of that is just their personal experience with their mom, I think.

I’m really thankful for the opportunities because they’ve allowed me to provide a lot for my kids. They have a great start in life, but they’ve also gone to schools with people that have massive amounts of money as a result of tech. I think they’re very sensitive to the privilege that they’ve grown up with, and they have this suspicion that the tech community isn’t aware of its own privilege.. So they’re going into very creative careers, most likely in the arts or somehow connected to the arts. Right or wrong, and they haven’t experienced it with all the color that I have, they think about it in terms of sitting in a cubicle all day, commuting out of the city on one of the buses, and working for a big company vs. a start up. My daughter is a studio art major, and I always say, “Go into web design. It’s   the most competitive job in the valley right now.”and she’s like, “Yeah, yeah, whatever. I don’t want to sit in a cubicle.” They’re still young. I think there’s a chance they’ll end up connected to the industry, but they think a lot about privilege, and how that privilege creates distance with different communities in our country, and they’re sensitive to that.

Yeah, that makes sense. Kind of bouncing off of that, I’m thinking about risk.  Things turned out really well for you, and I’m curious to know if you got bit by a bug that prevented you from feeling risk or if your risk aversion was high from childhood?  I’m just curious leaving established industries and going into tech or a start up it’s super risky. I’m curious, as a mom, what was your relationship with risk or did you just know you would make it work, no matter what?

I feel like I’m really risk averse [chuckles]. Ironically, I was always looking for security and stability and work/family balance, but I think I knew that tech with its risks had a better chance of a high growth career than others.  Deep down I must have always known that I’m smart and can figure out jobs and I have a very strong network of people that trust me and that I trust – That I think is the insurance policy to the risks that I might take.

I think I learned with that first start-up, that feeling scared and nervous and like I may have made a mistake is the exact moment that you’re probably going to make a really big difference or learn something completely new. When I was working on a project that could either go really well or dramatically badly, and we tried to mitigate risks as best we could, there was always a point where we had to go with our best judgment. Those were the times that I was really nervous and afraid, but I learned it was because those were the projects that made the biggest difference for the businesses that I was in vs. ones that were tweaks and forgettable. Now I’m sort of at the point where if I’m not feeling that nervousness and being slightly scared I start to question if this is really where I should be focusing my efforts. If you’re just in a routine day in and day out you’re probably not making a big impact, which isn’t very fulfilling so you have to take risks.

Yeah. What are your goals for this year? What are you working on right now, either for your career or for yourself?

Well, my son is about to graduate from high school, so after this I’m an empty nester.

Wow. That’s exciting. Scary.

My goal this year is giving and contribution – I want to give more to my friendships and contribute in meaningful ways to their lives, I want to make strong and meaningful contributions to the company I work for. I’m not working currently and am in a job search, but I wouldn’t say it’s highly active yet because I’m trying to assess what I want the next stage of my career to be. I’m doing a lot of reflection and the foundation work to set myself up for being an empty nester who is having a lot of fun and is fulfilled from my contributions. I hope it means a lot of fun with my career and  a lot of fun with my personal life.

Amazing. Based on the reflection that you’ve done so far, what is important to you in a job now?

I think a strong sense of customer advocacy. A business that focuses on their customer experience so that their product is really great. The last two years I’ve been commuting to Cincinnati, helping a company in the midwest transform and become more technology-focused. I’m back in Silicon Valley now. It’s so interesting to see the, I guess, acceptance of experimentation and building for the long term that Silicon Valley has. I’m invigorated to go to a company that’s highly experimental and excited to test new directions. And then, maybe on the side or as an educational project for myself, I really want to learn about or start developing some programs to help companies get more diversity up in the executive levels because I think what we’re doing now isn’t quite enough. It’s not just about developing the women. I’d like to do some projects exploring what the men & women think of these conversations about the elephant in the room, what they’re aware of or not aware of, helping to bring awareness to everyone about what equality looks like. That’s another direction that I’m interested in going likely more as an interest than an actual job.

Yeah. Just, based on your experiences or experiences of your friends, what are the biggest gaping issues that you’d like to address sooner than later?

That is really easy:  unconscious bias amongst men and women.  Women and men are different – the differences add up to strengths that lead to better results when working as a team.  We’ve got to learn to embrace these differences rather than judge them. Men are very focused on results – which is good and we need that – and women are focused on broad contexts. They look at the full picture to understand all the dynamics that might be creating the results or preventing results from happening. And it’s a little bit of a slower process than just zeroing in on, “What are the results,” and “What did we do right,” or “What did we do wrong?” So you can see this spectrum where men operate at one end and women at another (I’m totally generalizing here).  Business leaders don’t know what operating in between those two ends looks like. I hope we can somehow start to identify what a gender neutral approach is or engage together and learn that neither way is wrong, so we accept both. This kind of operating amongst senior leaders does require going slow, it does require having very open and honest and messy conversations with people – some who might by nature not be very open and certainly not open to messy- I don’t think you can approach it with an agile methodology or something that can be easily blue-printed or replicated. As companies start to succeed in the area of diversity and equality we need to learn from them.  We need to hear about what exec team conversations look like when it is a truly diverse group, or what it looked like when they stumbled, and the things that the men struggled with, or that the women struggled with. This requires a ton of transparency.  The more those conversations can happen in a setting where both men and women are present, the better. It’s hard to get the men present for those right now and I’m not sure that we even ask vs. jumping in with a “women’s summit”

What advice would you have, based on your experiences in tech– what advice would you have for those folk just starting out? Like what do you wish you had known in the beginning?

What advice would I have? I think this can apply to most careers, I would advise to get experience managing people and working with customers early if they can. So much happens based on people’s ability to work with people. Learn analytics and business models, because that positions you for decision making roles. Move around in companies. Don’t go for a career where you stay in one place for 20 years, because the moving around of companies serves to build a pretty diverse skill set. Even move in industries if you can, or at least verticals within tech. It gives you a really strong foundation of diverse skills. The MBA may not be so important.  Stay close to yourself and design a life that allows you to be true to yourself inside and outside of work.

So, I was born on the East Coast and we moved around a great deal. It’s probably—may not be relevant that my dad was previously trying to be a computer programmer because of my mom who had been a math teacher, and then went into—became a systems analyst, and later like a manager up to vice president of systems groups, so more in sort of hardware and software selection than in the actual programing.

But they split up and I grew up with my mom, and she worked in computers and—I have a story more than a memory that when I was like six she took me into the office with her, and she was working at Macy’s at the time, and so I went into the machine room with all the programmers, and for whatever reason one of them taught me to count in Hex which I didn’t even get until much later in math when we were doing different bases, and I was like, “Wow, I remember that from…”

She actually did not think being in computers was a good thing. It was a good career for her because she was a manager and telling people what to do. She had the math background and understood things very well. In fact, she’s still doing that. She’s 76 now and she’s still working as a manager of computer projects like selecting the machinery and selecting the software and setting up a group, that kind of thing. I used to say “she’s a system analyst” when I was a kid and I had no idea what that was. No clue at all [laughter].

When I went to college I still actually didn’t know what I wanted to do. I was fairly young. I graduated high school when I was 15, so I wasn’t that aware of what was going on in the world, even though I was pretty sure I knew everything of course [chuckles]. I took her advice of what college to go to and on what to study to some degree, but I went to an expensive college back east, so I had to do work study. The options for work study were work in the computer lab, work in the administration office, or work in food service. I was like, “Well, the computer lab sounds best to me.”

At that point I hadn’t had a lot of connection to computers Some of my friends in high school had had an Apple 2 of their own, but my high school did not have a computer lab. My high school in Virginia did, but then we moved to California, and what with prop 13 and all, my high school in California had nothing. I didn’t really get into them very much, except to play with my friend’s computer a few times. A couple times my mom would bring something home from work, though she didn’t do much work at home, so I didn’t really see a lot of it.

I get to college and I’m like, “I want to work in the computer lab, but I don’t really know much about computers, so I’ll take a Basic programming class, the intro programming class.” That was so much fun, and I started to spend all my time online, writing extra programs and playing the games that they had at the time, which were fairly primitive. Adventure, that kind of thing. I got very into it, so I took another computer class and another computer class. I switched colleges to San Francisco State out here, and I started working in the computer lab there and just taking more and more classes both in what at the time was called the information Science department, which was business computing. Stuff like Cobol, accounting, statistical packages, that kind of thing. Also in the Computer—well, what was the Math department then and became the Computer Science department before I graduated. That was a fairly common evolution at that time, for the classes to start in the math department.

About halfway through college I went to the ACM programming contest with some friends of mine from the computer lab, and then the computer science department—which was still pretty new—was like, “why aren’t you a computer science student if you’re going to the programming contest to represent our school?”. I’m like, “oh, okay, sure, I’ll study computers”. Then I actually signed up for the degree program and got a degree in computer science. For the longest time I was honestly just doing it because it was fun and that’s what my friends did because we were all hanging out at the lab. I wasn’t really planning on a career; it was just the thing I enjoyed most in college was being in the computer lab, working on the computers, helping people get their stuff done, and it just kind of evolved.

I graduated college in ‘87 and at that point it was mostly defense contractors. There weren’t a lot of startups. Banks and big companies and that kind of thing. I interviewed at Lockheed and I interviewed at a small company in Berkeley that was doing natural language processing. It was a start-up before there were start-ups all over the place. I didn’t like the idea of working on spy satellite software, even though I’m sure it would have been fascinating as a problem. So I went to work with the start-up in Berkeley.

I was there for seven years and then it was time to move on. I thought, “I’m doing the same thing here over and over. I want to do something different.” It wasn’t as common then for people to change jobs every two years. I didn’t, at that time, really think of changing as a thing, until I was so tired of doing the same thing all the time and so stressed by the small company thing.

Then I went to work for a larger company, a database company. One of my friends was working there and I had just been saying on my friends mailing list, “I’d really like a new job.” and she was like, “come work with me.” I went to work there and after that, I took a short break and did web contracting, because the web was suddenly a thing and I was a little burnt out on working. That was in the mid 90’s. I wasn’t that good. I’m not a designer at all. I’m terrible with graphics and all  all that. So HTML was easy to learn, but it’s hard to really do something good with it without having a sense for design and user interface. That was all pretty new at the time, web design. So all the sites were just awful. I was not much worse than anyone else, but these days they would be absolutely terrible. And yet people were willing to pay me for it because nobody was doing it then.

And then when I went back into a full-time job, it was the dot-com era. I got a job and I was like, ”Wow. It’s a job in San Francisco.” Because I’ve been living in San Francisco since we moved here when I was in high school. But I was commuting down the Peninsula and over to Berkeley because that’s where the companies were. Then I got a job with an e-commerce company in  San Francisco. I was like, ”This is great. I can commute to work on the MUNI.” Which was still not dreadful at the time.

So I started working there, and I worked there for four years, and finally, it was kind of the same thing. The work became pretty much the same, and it was still a startup with no real income even after four years. I got a little tired of “every time you walk in you have to something to save the company because it’s going to go under.” I’m like, “If it’s going to go under unless I mobilize and stress out every day, I don’t really want to be involved in that.” I was getting more sensible by then. I still spent then and spend now almost all my time online. If something went wrong, I’d be there. I’d be there to help out at 2:00 in the morning or whatever. I don’t mind that, but I do mind the expectation that everyone will do that. Like I’m there because I happen to be there. I happen to be doing my own thing. I don’t want to be working literally from the moment I wake up to the moment I sleep anymore—although when I was younger, that was fine. I really didn’t mind. I really love what I do.

Not that I feel like I have to work that much, but I’m always interested and you can’t really turn it off. Like you’re working on something and you go home, and it’s still in your head. Even in the early days we still had dial-ups or we still had the source code on our machines that we could move around. You can keep working as much as you want to keep working and if you really like what you do, it’s hard to stop. It’s hard for anything to not be part of it. So I worked there for four years and then it was a series of dotcoms that went under—at that time, they were all going under.

Eventually I went to work for—I was like, “I’m so tired of companies dying out from under me. Get me a job at something that’s not going to die.” So one of my friends was working at Wells Fargo, and she said, “Come work here, it’ll never go under.” After I was there for about six months, another one of my friends from another of the startups that had died, we were having dinner and he—and we’re talking about I’m ranting or about my job and he says, “They’re destroying your soul. Come work with me [laughter].” I said, “Yeah. You’re probably right.”

And so I went to work with him at a Dotcom 2.0, a company called Shopping.com. That was wonderful. They were great. I was there for about three years but they got purchased by Ebay and became really, really, really boring. A lot of people I worked with there, I have worked with again since then because it just was another of those atmospheres that was really amazing. The first dotcom, I was the second engineer I guess, so I just hired all my friends. As we needed more people, I’d be like, “Well, I got a friend who could help us out.” It was good then. After I’ve been in the business for like 10, 15 years, it starts to get harder to get your friends to come work with you because they’re very happy where they are. They’ve found a nice place and so instead you go work where your friends are when you decide you need something new.

Since then, I’ve been working for a number of companies, mostly smaller ones. I really, on the whole, prefer start-ups or relatively small companies where I can understand all of what’s going on. But after my last start-up got bought by Facebook, one of my friends from Shopping.com was working at Twitter and he said, “You should come work at Twitter.” So I went down there and it was really nice. They were in their new building and the food was excellent. I had really liked working with him before and his team was very nice, so I went to work there. That was the largest company I’ve been at since Wells Fargo and one of the largest companies I’ve ever been at and it was growing like crazy while I was there. When I interviewed, I think they had about 1,200 people and by the time I was actually starting work, they had over 1,500. Then by the time I left they had about 3,000. That was two and half years later.

I did not like the bigness. I did not like the bureaucracy. I did not like the corporate-ness of it all. So I was like, “All right, this time I’m going to try to find something in between because I don’t want to be stressed out with a start-up that’s going to die everyday, but I also don’t want to be working at a big company where I just have no idea what’s going on.” Like, all I know is my little area and the communication is not great and all. That’s just natural to big organizations. Now I’m working at Instacart with another of the people I used to work with at Shopping.com and actually, one of my friends from Twitter came to work here as well. It’s a nice size. It’s got under a hundred engineers so you could squeeze all the engineers into the cafeteria and have us all talk to each other at once, which is pretty good. So that’s a very long-winded summary but nonetheless brief because I’ve actually worked for—I think I’ve counted 12 companies in, what is it now, 29 years. So, there’s more [laughter]. Those are the highlights.

What about your work really, really excites you in actually true to the core?

Basically, it’s puzzles. I love puzzles. I’m a gamer of all sorts: jigsaw puzzles, other kinds of puzzles, card games, board games, role playing games, video games, all of it. I used to play video games in the arcades when I was in high school and college and I didn’t have a console until much later. I still think of video games as standing up with the machine, even though now I sit on the couch and play with the controller. My favorites are always the puzzle solving ones. I think of most problems in software as being solving a puzzle because making a computer do what you want to do, in itself, is a simple but interesting puzzle. Even more so when something goes wrong. Then you have to envision the whole system and figure out where the problem came in and what you can do to correct it without breaking everything else around it. To me that’s very jigsaw puzzle-ish in conception because you have a lot of pieces that perhaps look a lot like or could be parts of almost anything and we have to be careful how we put it together. That’s a very strange analogy but still it’s how it feels when working on it.

What are your biggest motivators? What drives you?

Oddly, I feel like it’s the people. Both the people that I’m making the software for and the people I’m making the software with.  Day to day I can come in and not speak to my team all day. We might chat on Slack or something but it’s not really the same, although I do think of it very much the same. I’ve been chatting online since I was 16 and I had a lot of just social chats and social email lists, and then it was newsgroups and forums and so on. I see working with computers as extremely social. To me it has always been an interactive thing.

When I was in high school, the one contact I had with computers was going over to hang out at friend’s house who had a computer. When I was in college I was always in the computer lab with my friends who were also in that lab or who were in other labs and we’d be chatting online and talking about all sorts of things, not just technical work, but certainly that was part of what we talked about. Writing programs for each other, sharing code, pretty “open source” before that was a thing. You would even hand other people a print-out and they’d type it in; whatever it took but you always shared.

A lot of what makes me stop liking a job is when I don’t feel a good sense of being a team with the other people I’m working with. When I start to feel isolated in some way, whatever it may be, it can be from the company standpoint when I feel like the company doesn’t consider the programmers or it could be from the developer standpoint where I feel like I have a lot of disagreements or disconnects with the other developers when our style or our sense of what’s right is not the same. But, as long as I have that good feeling that I’m part of something, I’m happy, and similarly I love web development and tools development because I feel a lot closer to the customers that way.

When I was doing package software back in the early days, my first company I actually did customer support, so they would send me to a customer to find out what their problems were at a technical level. I’d actually sit down with their database and their software and dig into whatever their product domain was, whatever their business domain was, and try to help customize our software for them. Then I’d bring problems back to the office and sit with the other developers and we’d try to work out ways to deal with these unusual problems that I might encounter out in the wild. And then when I worked with the database company, it was really disappointing because I had no connection to the user or how they were using the software, and then when I got on the web, websites had a more direct sense of interaction with people because they’re built for people, rather than being built for computers. Even more so, these days, I do a lot of internal tools work, because then, not only am I a part of “the team” from a company standpoint, but I’m helping another part of the team and I can get direct feedback from them if something is not helping or something goes wrong. So yes, it’s very, very social and it’s very, very much about people.

Let’s flip to the dark side for a second. What have been some of your biggest struggles and roadblocks over the course of your career?

[chuckles] At Wells Fargo—I mean, mostly I’ve been really happy. At Wells Fargo, I was frustrated as a developer and the reason my friend said they were destroying my soul, I said to him, “Well, they’re forcing me to do a bad work on an evil product” [laughter]. Although really, the product wasn’t evil, it was just telephone banking, but the process that they had was to develop a product spec of like hundreds of pages, and then get it signed off by dozens of people, and then essentially, it’s thrown over the wall to the programmers, and we would try to implement it and then we’d come back, and we’d be like, “Well this is impossible. Literally, not physically possible.” And they’d be like, “Well, we can’t change the spec.” So then you’re like [chuckles], “Why are you not rational? Why don’t you understand that a computer simply cannot do this. So you have to change the spec.” “We cannot change the spec. It’s been signed off.” Then you’re like, “This is insane world. I can’t live in this world. I need a world that is more rational.”

That’s the worst example, but of course, there’s always examples like that. You always have things which are being decided by product people and then brought to the engineers later, and then you have to deal with people’s idea of what it is that you can do. Often, I find, it’s even worse when they’re trying to be nice to you. So they’ll say, “Well, we want this.” And if you go back and you say, “Why do you want that?” they’re like, “I thought it was easier. What I really want is this.” And then you’re like “Oh, what you really want is much easier than what you asked for [chuckles].”

I think during the early days, though, there was a lot more disconnect. These days, I’m working at companies where the product managers are much more technical, much more involved, and frequently embedded with the actual group that they’re supporting, so they know what’s going on day to day. So that’s gotten a lot better. But it was definitely frustrating and difficult in the earlier days.

Then, at Twitter I ran into a very different problem which I had never encountered before, which was being female, [chuckles] and I never—I was always mostly at small companies and I might be the one woman on a team of ten. But, I never really felt it. We were just all the developers. Then other times like at eGreetings, where I got a bunch of my friends hired, it was about half and half, actually—not precisely half and half, but certainly pretty close to it— and I didn’t really feel it there either. I didn’t feel it one way or the other. Although we did used to joke there that all the people in marketing were almost the same attractive blonde woman, I think because the guy who ran marketing might have had a little bit of a preference, but I think also just there always has tended to be more women in marketing and more men in software engineering.

Also, at eGreetings since it was the early dot-com days, practically anybody who could pick up a book on HTML would become a web developer. And so we also had an extensive team of people who did the web site things—the HTML—and they were also mostly female, so that also contributed, I think, to the feeling there that it was very evenly distributed. Other places—it’s back and forth, but I never really felt it until I went to Twitter. I went to Twitter, and I could, literally, go all day without seeing another woman. Every meeting I went to, all the people I worked with, all the people on my team—If I didn’t look up from my computer, and I just went to meetings, I’m the only one there. And somehow I started to feel it in a way that I had not felt it previously. I don’t know, really, what the situation is there—in terms of what the management thinks—but I do know that I went and counted, and there was only like seven percent women, as far as engineers go, and they were all at the lower levels. So, at the higher levels it was men. The management chain—you looked at anybody’s management chain and it was almost certainly six men. There might be one woman in there. I just started to feel really different. I’d never felt different before, I  was always—I won’t say one of the guys because it wasn’t like that. They were—I dated lots of them. They didn’t think of me as a guy, but I was one of the engineers and not “the female engineer” on the team. You know what I mean? And at Twitter you’ll be like—There were three of us who got together once in awhile, and one of us was invited to every interview, to every interview panel, to prove that Twitter had female engineers or something. I don’t know. It was really bad. Because it—Like, “Why am I interviewing for some team that, not only am I not on but I don’t even know what they do.” And they still put me on the interview panel because the team didn’t have any women [laughter].

I had been really interested in feminism and feminist issues back in college, as you do, and I posted a lot on soc.feminism, and I eventually became a moderator there, and I talked about all these issues at length, and then I just kind of forgot about it for 20 years. Not because I felt the problem was solved, I know the problem wasn’t solved, but it wasn’t really bothering me and wasn’t really bothering my friends and—Even though every once in awhile, I’d say something in a group discussion or somebody would talk to me as “the female engineer”, it just wasn’t a thing from day to day, until at Twitter it became a thing where I was really, really feeling it. So, I started getting involved in discussions there about the level of diversity, and arguments, and so on.

The other thing that I felt was my age—not that people commented on that—but that everyone there was so inexperienced in comparison. In fact, when I was hired they were arguing with me about my pay. They’re like, “Well, you’re going to make more than anyone else on your team.” I’m like, “I’ve got 20 years more experience than anyone else on my team.” So, I’m not going to take a pay cut. [laughter] There were so many times when—they’re these very, very bright people, but they just were not practical. They had not had experience putting things into production. So, they do a great job developing, but the sense of ownership, of maintaining it, of consideration for other developers—the person who would come next—how are they going to deal with your code? When you’ve done this really, really clever thing, but you haven’t explained it or tested it, or anything, how is that going to work when someone has to maintain it? Nobody wants to fix bugs. Everybody wants to be developing exciting new features. It’s all the shiny new object. and I was just like, “Believe me. My experience tells me that what you’re doing is a bad idea,” and they just don’t get it.

Even the people in management, they’re only a couple of years older. They’ve had no experience. And so I kept running into conflict with people because I was like, “No. I’m really, really, really sure that this is true,” that we need to do maintenance, that we need to have people who are focused on keeping the old stuff clean and working, and we have to every once in awhile clean up the platform. And everybody just had this really short-term point of view. “Everybody” is an exaggeration, with a thousand engineers of course there are people of all sorts of viewpoints, but just so frequently I would be meeting with people and trying to convince them that after 20 years of experience, I actually knew what I was talking about, and I couldn’t do it. And I was just like, “What’s going on here,” because again, I’ve never had that problem before. People had always had a similar point of view and even when it wasn’t similar, it was close enough they’d get what I was saying. And suddenly it was like being in a foreign country and I think I’m speaking the language, but I’m just not.

So I have no idea what  how that happened, but my sense is that—and from also looking into a lot more things about diversity, bias, and all of that—they started with a core of people who were very similar, and then in order to, quote, not lower the bar, which they literally said, hired more and more people who were precisely like the people they already had, until they just ended up with this great homogeneity of person and thought, which was really hard to pierce, because—I mean, you see this, when talking about political things too, where people are presented with contrary evidence to their political view it oddly actually reinforces them in their original incorrect view, rather than them learning. And in part that is because everyone else they know agrees with them. So the more you’re in an environment where everyone agrees, if you are the person who doesn’t agree, if you are the person who’s different, you can’t get through that, because everyone’s backing them up. “Yes, you’re right, you’re the same as me, we agree, we understand”.

That sense of being different was really odd to me, really, really odd, because I had never had that sense. And it was very difficult to work, because I felt constantly on the outside of everything; in some sense not wanted, right? Nobody wants to hear it. Nobody wants to be challenged. Nobody wants to hear that they’re doing it wrong or at least you think they’re doing it wrong. So, I was “too aggressive” and eventually—yeah, I know. And I’m like, well I mean, in a way I am, nobody would describe me as retiring in a work sense. I’m actually reasonably shy with new people in a social sense. But, at work certainly I’ve never been one to just shut up and let things go. But again, my experience in developers has been that they welcome better ideas and to have people just shut off any different ideas, forget better, right, like obviously I think it’s better, but, it’s “different”, and one of the things I love actually about the job is that discussion and that argument and that debate to try to find the best possible solution.

One of the things that attracted me to the field in the first place was that it was so much more logical and so much more deterministic than people are—software, it either works or it doesn’t and it works faster or it doesn’t work faster and it works better or it doesn’t work better. And so, while there are certainly still things that are subjective, there are a lot of objective measurements and a lot of ways to be able to determine “Yes this is right or at least this is not wrong.” Even when we’ve gotten into the most contentious arguments, I just enjoy that. I enjoy that we’re arguing to get better and not arguing because you have one what I would call religious view and I have a different religious view. Vi vs. emacs, you’ll never settle that, but you recognize that it’s a matter, if you will, of faith or belief and not a matter of fact. Eventually you just stop arguing about that one and you do your own thing.

For questions like, “Should we upgrade to the latest version of Ruby?” I don’t think that’s a matter of opinion or religion. I think that it’s a matter of fact that you have to keep your tools up to date. I’ve seen over and over again that when we don’t do that things go wrong. Then people are saying, “Well, it’s too much trouble to do that.” I’m like, “It’s too much trouble not to do that.” I’m good at compromise but I’m not good at letting things which are wrong go by. If I believe it’s my own feeling I’m perfectly happy to compromise, but if I think that it’s really truly wrong, then I just plant my feet. And that’s I guess not so good [chuckles]. I’m not going to stop, but it certainly can cause trouble.

Yeah, but it’s interesting that you’ve had so much perspective in that it was okay and it worked for a long time.

Well, at my new job it works a lot better. Even though again, I’m probably one of the oldest people here, and there’s only a fraction of people who I think have even ten years experience. I feel like the people here are much more open and much more of my viewpoint. So that’s another reason I think it’s not so much the industry, it’s the fact of when you collect a sort of critical mass of people who have the same viewpoint, and it makes it hard to be different. But as long as you have a community where everybody’s not from the same background and the same approximate age and social and everything, then it’s not so hard to disagree with people. That’s one of the things. I’m on the diversity committee here and to me, the important thing is not like specific characteristics of the person, but  the fact that they aren’t like everyone else. That we get that difference in viewpoint which allows people to continue to perceive that different viewpoints are valuable and okay. That’s the best environment to really learn in, too. So, I think it’s better for all the engineers, even if they don’t personally care.

Did that experience immediately affect what you were looking for in your next job?

Absolutely. But it’s hard to define, right? I mean, how do you say, “I want a really open-minded team that’s open to different ideas.” Of course everybody is going to say, “Of course we are.” But in reality, people just aren’t even maybe aware of how much of a little bubble they’re in. Until they get hit in the face with it a few times [laughter].

Where have you found your support networks, traditionally. Where did you find them early on and where do you find them now?

In college, it was the other people in the computer lab and the people that I talked to online. There was a program called Talk and it was like a sort of a mini IRC, so like a small channel plus personal chatting, across the State University system. We all had access to it, although most people didn’t know about it, but the sort of hardcore computer geeks did. So I had friends all over California from the State University system and then after I started working there were people I had met both at school and there was a dinner group over at Berkeley that I used to go to and, again, it was computer people who just socialized once a week.

So I just had a lot of friends from those kind of groups. They were founded on being engineers to a great degree, but they were also social groups. And over time, you introduce those friends to other friends, you introduce people that you work with and they bring in people they work with, and so the group expands and certain people you have more in common with and you get to be personal friends, and other people you just kind of hang with in the group, you know? So when there are group events then they’re all there.

I met people on Usenet. I met people occasionally through other interests, like I started going to board game conventions, so I’ve made friends there. As the industry has expanded, more and more of those people have turned out to be engineers, anyway.

So my circle of friends is still primarily engineers with, strangely, a bunch of lawyers who somehow crept in there. They seem to be big board gamers as well [laughter]. And then a few people from other areas. And then over time as I’ve been doing online gaming I’ve met people on there. And that’s actually where I get the most diverse group of friends is from online gaming because you get people from all over who—A lot of them it’s when they’re in college or if they’re unemployed or something. But a lot of people just keep at it for years and so I’ve met people from all over the world, people of all different ages and backgrounds.

I even for a while was playing a game in China. It was hosted on servers in China and it was all Chinese people. And then there were a few of us who had gone there to play because they had the game before it was released in the US. And they were super nice. They’d find somebody who could speak English if they wanted me to join their group, and you I didn’t really get to be friends with many people because the language barrier was such that beyond the gaming it was really difficult. But they were friendly, you know? I’d say most of my friends I’ve probably met online or if I haven’t met them online, I’ve maintained the relationship online, and then college and jobs.

I’m curious to know—going back to your earlier experiences—has that made you more drawn to finding and connecting with women in the workplace? I’m curious.

Only in the sense that I’m more open to it than I was. When I went to Twitter, they had a Women in Engineering group that invited me to like a lunch or something as an employee. I was just like, “Eh. Whatever.” That had never been a thing for me, so I just didn’t bother. Of my friends, some of them are women, but the vast majority are men. I’m just generally more used to hanging out with them, which is another reason why it was so weird, feeling different from the other engineers. I’ve been in groups of men all the time. I never felt like it. So I didn’t go there, but when I came to Instacart, the female engineers were like, “Hey, let’s you know, get together for a drink. I’m like, “Sure, let’s do it,” because I was like, “Alright. Maybe there’s a problem here that I should be involved in in helping solve.” As far as personally, apart from the issues that I’d like to see things improve in tech generally, no. In general my friends are men and they always have been.

Let’s go macro for a second. How do you feel about the overall state of tech in 2016? What excites you, what frustrates you, what would you like to see change?

I like the speed at this point of everything. Network connections, you know? I started out with a 300 baud modem. I like how fast everything is and I like how fast everything’s changing. It’s part of what keeps the job interesting. I’m essentially in school every day, learning new things and having to keep my brain working and not just repeating the same patterns. As I said earlier, I will often leave a job when I feel like I’m just doing the same thing over and over again. It’s actually to me somewhat more stressful. You think it’d be stressful learning new things, and it is. There’s always that feeling of, “I should be better at this,” but it’s more stressful to feel like you’re just grinding away on the same thing indefinitely. The way that the world keeps changing is wonderful to me because I’ll never get bored. I might get bored on a particular teams, on a particular task, at a particular company, but there will always be something new and interesting out there, hopefully at the same company because I don’t really like changing jobs. If not, then certainly at another one. I think it’s unfortunate that some of the things that are really nice—It used to be we were kind of looked down on as engineers. We were weird, we were not socially apt, we worked with computers, which were scary, or at best, really irritating to people. The IBM at the office where everything’s always crashing and it’s blue screen of death all the time, and people hated computers. The web came out and people started to use it. Suddenly, everybody’s using computers. I’m like, “Okay, this is cool. This is what I wanted to see.” I felt like that from the very beginning. Actually my very first class was back east at Wellesley and the instructor was a guy from Stanford who was a visiting instructor there. The first thing that I remember him showing us was, he logged into his account at Stanford and showed us the weather in California. Of course that made me horribly homesick.  because it was freezing in Massachusetts already and it was really delightful in California. But I was also like “Oh my God, you’re in California. You’re standing here in Massachusetts but you’re in California. That is so cool.” And that’s always how I thought about computers, you know, was as a way to communicate and a way to draw people together in some sense, to take away the distance. And that was maybe more of an issue for me because we moved so much and I always lost touch with people because, you know, you’d go away and I mean, especially if you’re a kid, you don’t travel back to see somebody who lives in another state the way you might when you’re out of college and you have friends or whatever. So I’d just lose touch with people all the time. This was a way to talk to people all over the world, to get different viewpoints, to talk about anything for people who felt—one of the cool things about Usenet was that people who’d felt really alone and different in their little community could find people in the larger world.

So now another, I guess it’s—wow, 20 years down the line since the web came out. Everybody’s seen that, right? Everybody’s feeling that. So the way I felt about computers when I was 16, now everybody feels that way and everybody is able to communicate with different people, keep in touch with people and find things out, look things up. That’s how I  always felt since the day I touched a computer till now. And now, everybody is that way. I remember [chuckles] when i was 16. People thought I was really weird, rushing home to read my emails all the time. Now, everybody is reading their emails at all moments, or their chats, or whatever is equivalent. So you see, I was not that weird. I was just ahead of my time [chuckles].

The things I don’t like—now we’re ridiculously spoiled. It used to be, we were paid decently but not amazingly. We were treated much less well than the sales people. The salespeople made the company money and we didn’t. They got all the nice stuff and we were stuc in our cubicles. There was not a great deal of respect. Like there was respect definitely, but it was sort of you’re just another professional. Now, it’s insane. Everybody is pinging you and telling you how great you are, it’s just silly.

Actually  that was another thing that was kind of discordant. Before Twitter I was used to a lot of positive feedback. The culture there is more of a culture of negative feedback. You don’t get a lot of people saying, “That was really great. Thank you.” But you do get complaints whenever anything goes wrong. That kind of brings you down. Right? I don’t expect everybody to constantly tell me how great I am, but I’d at least like to get general positive feedback of: you’re doing a good job, I like what you’re doing, keep it up. It just wasn’t the culture there and that’s uncommon. Most places I know engineering managers are pretty good. I think that they realize that we are slightly fragile and need some reassurance that we’re doing the right thing day to day, however big our egos may be [laughter]. But, unfortunately now, the egos are getting pretty big. Right? I used to say jokingly, “I don’t see why they’re so down on us. They do know we run the world.” Well now they do know we run the world. Unfortunately, that leads to a lot of engineers who have a lot of big egos and expect a lot of really excessive things in the ways of benefits and treatment and perks and everything. I’m like—in the end we’re still just another set of professionals doing a job that these days is very popular. But, I remember the days when we were much more negatively viewed.

Many of the stereotypes are still there. “Silicon Valley” is one of my favorite shows. It has all the terrible stereotypes and some people, they’re like, well, I don’t like it because it goes too far. I’m like, no, I know all of those guys. I know them. Sure, they exaggerate it a bit for the humor value, but it’s not unusual to meet people like that still. But they are also not the only people. There’re plenty of people who have lots of outside interests and can get dates and be social and all, you know? We aren’t so bewildered by the world as that show depicts computer people, which is nice. It does, however, make it hard to be the old-style engineer who is not so social, not athletic, not interested in sports, not interested in much of anything besides computers and in my case, board games and science fiction, that kind of thing. It used to be practically everybody I met was like that. And now I am more different than I was. The group is less homogenous and that makes it possible also to have pockets of greater homogeneity, which are very different from who I am and that is weird. It’s probably better on the whole, I just I miss the old days sometimes.

Totally.  My last question for you would be, what are some of the biggest lessons you’ve learned over your time in tech that you would give as advice to folks who are just starting out now?

Well, from a career standpoint, it’s most important to have friends. I’ve gotten almost all my jobs through friends. If I haven’t gotten the job, that way, I’ve either made friends, real-life friends with people at work or I’ve hired my friends at the job. Again partially it’s the people who are the best part of it, but also if you want to know that the place you’re going to is good, get a reference from somebody who works there. If you want to find a new job, but you don’t know where to go, ask your friends to refer you. If you don’t have any friends, well, or any friends in the industry, then you’re kind of out of luck.

And then, as far as while doing work, I think people really need to realize that the housekeeping and maintenance tasks are just as valuable. And if you’re the one doing them, then you should stick up for yourself and say, this is just as much needed as flashy new feature development. If you’re not the one doing them you should recognize that you would be a lot more unhappy if someone wasn’t taking care of all those things for you, and so respect those people. I mean I suppose to get into the gender stereotypes, again, it’s like mom at home and dad at work in these sort of faux-ideal—because I don’t think it was ever ideal—but this ideal that people had of someone being home taking care of all those housekeeping tasks—making you food, and cleaning, and laundry, and all of the things that just make your life run more smoothly—is just as important as the person who’s bringing in wads of money and paying for things.

And I think that engineering has a lot of housekeeping to be done, like a ton, and it’s not very glamorous. And you can’t be the one to point and say, “Oh, yeah, I developed this thing.” You would just be like, “Well, you know, I fixed a dozen bugs last weekend so the site kept running, so that was good.” But people don’t really appreciate that, and I think—One of the things that I try to do is make sure that people do appreciate that. And then finally, the other thing I think is really important is as people become more senior they should be teaching more and developing less. It’s a constant educational effort to stay good at what you’re doing, but it’s not just you educating yourself, but you helping the people around you. Which again, I guess is a little bit of a housekeeping thing. But if you’re not making your team better then in some sense, what good are you because nobody will miss you. You could be plugged in with another coder the next day, and nobody will care. You’re going to need to contribute more than just the code.

My dad was in the Air Force from 1960 to 1962-ish, something like that. He was stationed overseas in England. RAF Lakenheath was where I was born. Height of the Cold War. They literally started building the Berlin Wall the day that I was born, so it was just completely crazy to be out there. Then moved back here. His people and my mom’s people are both from the Bay Area, so I grew up in Sunnyvale from 1963 on.

I got a chance to see Silicon Valley happening kind of all around us. It was literally apricot orchards when we moved in, and they were tearing down some of them behind us to build another house behind us and all that. Fast-forward all the way to where we are now, and I’ve seen—I don’t know—six generations of Silicon Valley happening around me. It’s been really fun.

How did you first get interested in tech?

Well, growing up in suburban Sunnyvale, basically everybody’s dad worked for Lockheed or Martin, or one of the other missiles-and-space contractors. When I was a kid, my dad did not. He was a psych major and he was a writer. And he had a hobby store and a bunch of other stuff. He went into tech writing when the hobby shop went belly-up, and he was really talented.

He was able to look at what people wanted to say in writing such that other engineers – and later on – end users could actually understand what it was. He wrote the basic programming manual for a bunch of the early microcomputers – first generation things that people grew up with. So I think he wrote Beneath Apple Pascal for Apple, one of the early TRS-80 books for Tandy, and the Atari 400/800 BASIC programming guide.

I was the kid that they got to type in all of the program listings for the Atari 400/800 programming book.  So I got one of the early prototypes and the draft of the manual. And I got to type it all in and make sure it worked.

I had things to say about the text, and they actually listened to me and put it in. At that point it was kind of like, “Okay, this is what I want to do.” And I’m– I don’t know. This is 1978-ish, so I might have been 16 at that point. At 16, you don’t know what you want to do. And having something like this just kind of fall into my lap was really amazing.

So I just kept working on tiny computers.  In 1984 I was the guy who swept the floor and took out the garbage for a small software company. In those days we manufactured floppy disks. We copied the disks, stick on the label, put the disks in the envelop, put the envelope in the shrink wrap, put the shrink wrap on the manual, get the manual out the door … that kind of software production.

And then their phone system crapped out, and I was put in charge of finding a new phone system. And along with the new phone system came a T1 line, and along with the T1 line came the Internet. And I got email working for everybody, and a Gopher server, which let us save a ton of money by downloading files instead of using Federal Express.

And let’s see, 94-ish, this thing called Netscape suddenly appears about a mile down the road from us in Mountain View, and we put up a Web server and I had half a T1 to just monkey around with.

Again, I was super lucky, but I guess ready to be lucky at the same time.  So I learned how to work on the internet and build Web sites. I don’t know, I had an affinity for it and I really enjoyed it and I enjoyed talking to people about it.

I’ve got no computer science degree—I have no degree of any sort.  I’ve got absolutely nothing on paper that says “you should be an engineer.” I spent almost 19 years at this tiny company that later on turned out to be a big piece of WebMD. And then I took a year, tried to go back to college, and it didn’t work out, but then Yahoo called. And I took it, because I had always loved Yahoo.

I was at Yahoo for 5 years, and I really think of it as the college experience I’d never had. I helped them open up a bunch of APIs, and we invented Hack Day while I was there, plus most of the concepts everybody now thinks of as “front-end engineering.” Along with a bunch of other people, at Yahoo I went from a webdev to an engineer.

And then after Yahoo I went to Netflix for about two years.  There I worked on the first iPhone and Android apps. Again, lucky. And in the right place at the right time, with the right kind of ignorance about how impossible it was to build Netflix on a tiny Web browser, so they let me run with it.

After Netflix a tiny startup, which was later acquired by Yahoo, and after that, Pinterest.  The recruiter called my home phone and I wasn’t really looking for work, but my stepdaughter heard me say “Pinterest,” and she started waving at me like crazy from across the room.  “Pinterest! Yes! Pinterest is awesome! You! Want! To! Work! At! Pinterest!” And they were in town so I walked down and interviewed, and got the job, first person hired to work as a full-time front-end engineer there.

And, you know– I don’t want to minimize the work. There’s a lot of work, but there’s also a lot of, I guess, just listening and being available and being open to things.        

Anyway, so I’m here. It’s a long story.

In the scope of your career what accomplishments are you the proudest of?

It’s always the thing you’re working on right now.  When I was at Yahoo, I got to work on the front page at yahoo.com which (if you were to total up the page views) was at that point the single artifact that more human beings had read since the beginning of time, the Bible included. And leaving there, I thought “I’ve peaked, that’s it. Nothing I do will ever be that big and that important, and seen by more people.”  But then you go to Netflix and oh my God, everybody loves Netflix so much. And then you go to Pinterest and oh my God everybody loves Pinterest so much.

It’s the thing that you’re working on right now, really. I love working on a product that real actual people know about. I don’t like the business-to-business stuff so much. I think that’s kind of boring. I like to work on a thing that I can show to my mom.

My mom’s 76 years old and I can say to her, “Okay, see, I made this thing that makes the words “Pin it!” appear on the New York Times website, and when you click it you’re running my code, and I’m helping you share what you found with your friends.”

Yeah, I love that. As someone who’s from a small town, no one really understands what I do now – or what I did when I was a tech – that’s nice to kind of have those brief moments where you work on something that people from home recognize.

It’s super hard to explain what you’re doing to build Web sites to people who don’t also build Web sites. And it’s really important to understand that because we live surrounded by that stuff, it’s “the industry.”  If you live in Hollywood everybody knows what you’re talking about when you say “the industry.”  And the same goes for Silicon Valley this is “the industry.” But “the industry” is a tiny little dot on the surface of a really huge planet.

Yeah. Let’s go back to the first Hack Day. What was that like?

So there’s this genius named Bradley Horowitz who is currently VP of everything social at Google.  But he was hired at Yahoo — I want to say 2004-ish, something like that — and he was in charge of the part of Yahoo Search — yes, don’t laugh, Yahoo used to have its own search, and it was groundbreaking — that found images and music and video.  And he hired this other guy Chad Dickerson (now CEO of Etsy) to come in and do this thing called Hack Day. (Chad had other duties of course, but the important thing as far as Bradley was concerned was to do Hack Day.)

Nobody had thought about what Hack Day really meant. It was totally internal, not a visible outside thing. And the first one was the sales and marketing group hack day.  Although I didn’t work in SMG, my manager at the time said “This is something you should get in on,”  because I had this  habit of making something during the week and showing it to an internal mailing list every Friday. And he said, “You should go do this thing.”

So I stole a day and I went over to Santa Clara, which is where Search used to be.  And I participated in it and I won an award and I have that award on my desk to this day. It’s a little gold bowling trophy made by Leonard Lin, with the day hack logo on it.

It’s one of the most important things that ever happened to me.  I won an award for using APIs. It’s a dumb little technical nerdy thing but– there are audiences and there are audiences. Showing something that you built in an 8 hour period with everybody else around you sweating away and working on it– that was out of this world. That was a bit more than 10 years ago, that was early December 2005. We did a quarterly Hack Day and special editions 20 or 30 times while I was there, and during that time in 2006, we did an open one on the Yahoo campus for everyone who wanted, and one later in London. Beck came to Sunnyvale, and played for maybe a thousand people, right there on the lawn.

If there’s one thing I’ve participated in that actually matters it’s the idea that making a computer program should be something that is applauded, and recognized, and shown in public. And that’s an amazing thing, it’s an art form that didn’t exist before. And we made that. Well, Bradley made that, and Chad made that.

That’s amazing. Etsy Chad?

Yes! Chad’s now the CEO of Etsy. We went out to London for the first international Hack Day in 2007 and it was just amazing walking around with him– and I must have been up fifty hours straight at that point. Didn’t sleep on the plane and got in there, and got lost, and finally found the hotel and just as I was going to fall in to bed, phone rings and it’s Chad. He’s like, “Okay we’re here, we’re going out, let’s go!” And we actually went out, and we were out for half a day more, stomping around Camden Yard and those places.  Chad’s a good guy. I wish he was having an easier time of it at Etsy, but that’s life in the big leagues.

I feel like you’re a treasure trove of stories from the earlier dot coms.

I try not to be too old and boring, and the guy who’s always talking about his stuff, but it’s important.

People have to understand that everything I did was already done before, and everything they’re doing was already done before. Things progress in a cycle.

Everybody feels like they got it first. No one’s ever had to deal with this before but you know, yeah, they have. My parents in the ’60s, when the Berlin Wall was going up, they were dealing with stressy things too.

I’m curious how that affects your work—there are young folks now who are building things that they believe that they’re building for the first time, when there was literally the same start-up with a different name, 10 or 15 years ago. That died at some point, and I’m curious just to know what it’s like, to be surrounded by that young optimism and enthusiasm, and to know that things come and go.

I love the youth and energy. I feed off it, I’m an energy vampire. It keeps me young working for these guys. I don’t know. If they suddenly said to me, “Okay, here’s a group of your fellow 55-year-olds. You have to go work with them from now on,” I don’t think I could do it. I really enjoy working with people who have fresh perspectives. It reminds me every day that I need to keep my own perspective fresh, you know?

I do my best not to teach, not to lecture. A lot of this stuff can’t be taught, only learned. If people have questions, if people want help, I like to think I can help.

I’ve seen amazing repetition. A long time ago, I want to say five, six years ago, I went and got an internet domain called Local Fu. And the idea was I was just going to build a Twitter mashup so people could tweet something important about a local venue, like “Okay, here’s how to park in Palo Alto during the day,” that kind of thing.

And like so many of my other internet domains, I got it, and I went and got the @localfu account on Twitter and I kind of messed around with it and got busy and forgot about it and let it go. The domain went out of registration.  And the day after the domain went back into the pool somebody else bought it, and they were immediately doing the exact same thing that I was going to build. And first thing I did is I went and I looked at their Twitter account, and their Twitter account was like @getLocalFu or @myLocalFu or something like that, and one of the first messages was “If anybody knows who owns the @localfu Twitter account, can you please have them reach out,” so I just gave it to them.

The other thing that – I’m hesitant to talk about it, there are a lot of people, fine up-and-coming young white boys who just got out of Stanford or Berkeley and they have bright ideas and they attract a lot of VC funding.  They have a disproportionate amount of power in the real universe because they have all this money and they have the attention of power brokers and kingmakers, and they do these really dumb things, like, did you see the billboards that AirBnB bought during the election?

Mm-hmm.

I don’t know, that particular group of people should not have that much access to power in the real world. They build a lot of the wrong things. There’s a lot of apps being built—specifically in San Francisco—and they’re catering to people who are also building apps in San Francisco.  I remember seeing a parody about an app where they would literally come to your house and put the food in your mouth. It’s like early retirement for hipsters.

Yesterday, I think, somebody published an article saying “We can fix the whole prison overcrowding and funding thing. We can take Soylent – this product that’s just all your nutrition in a bottle, so you never have to cook – we can just feed the prisoners Soylent, give them virtual-reality headsets, and pack ’em in like sardines. I don’t know if you saw that, it was this hilarious thing.

Soylent for prisoners?

Yeah. And it’s how we’re going to streamline the whole prison thing, and not question the whole idea that this many people should be in prison, or that there should be private prisons, or that prisons should actually make a profit.  None of those questions get asked; these are givens.  It’s the one thing I worry–I worry about the younger generation. You kids today. [chuckle]

Yeah. I feel similarly. And I’m, at this point, just a twenty-eight year old photographer.

Don’t get me wrong, tech is a blast. I could never do anything else. I could potentially get a job building fences, but tech is the only thing I can really do that’s worth anything. It’s the way that everybody can have maximum impact on the largest amount of people’s lives. Build something amazing that lets people communicate with each other. Let’s people find things they didn’t even know existed. It’s one of the reasons why I’m at Pinterest. (I’ve totally drunk the Pinterest Kool-Aid, by the way. I think we’re the closest thing there is to a way to easily find something you didn’t actually know you were looking for in the first place.)

I agree.

That used to be Google. And Google is not nearly accessible enough to people who don’t want to learn how to speak Googlish. We don’t want to learn how to think like a computer.

Yeah. In your experience, I love that you’re enthusiastic about what you’re working on, and I’m curious to know, as someone who’s seen so many cycles of tech, what is exciting to you in this batch?

We’ve dropped the cost of entry to nothing. If you were building Yahoo many, many years ago, you had to go to Fry’s and buy some computers and wire them together and stick in a rack, and then call up AT&T and have them plug all the stuff in. And all of that is gone now.

Now, a 13-year-old can do it. You can talk to Amazon or Heroku or whoever’s running your cloud, and pull it together and have something up and running in the space of a Hack Day.

The cost of failing used to be 100,000 dollars. The cost of failing is now under a buck. You can fail for free. You can fail as much as you want. I think the lower the cost of failure goes, the easier it will be for people who have no business doing this – people like me – to actually give it a shot. I think that’s the chief difference: this batch of tech can be made by anybody.

I love that. Slight segue: You’re one of several folks I know in tech who don’t have college degrees at all, and you’ve done really well for yourself. How has that affected your career over the years, for good and for bad?

I got laid off from WebMD after almost 19 years. We basically took over WebMD, and we gradually shut down the entire Santa Clara operation. There were 5,000 people working there when we first started talking to them. And gradually we merged and purged, and then everything got shut down. We were the last little bit left in Santa Clara.

I’d started as the guy who ran shipping and receiving and stuffed floppies into envelopes to where I was the person running the entire Web-facing front end of the practice management division of WebMD.  Going from that into “okay, now go find another job” in an industry that won’t talk to you at all if you don’t have a CS degree– that was a bath of cold water.

I looked and looked and nobody wanted to talk to me. I’m 42 years old, at the time, and at that point, in 2003, at that point the age discrimination thing hadn’t really reared its head. It didn’t really work that way at all. That’s a thing that started in about 2007, courtesy of Mark Zuckerberg, and I can go into lots of detail on that later if you want.

Yes.

What entered into it is, I was not qualified on paper to write C++, which is what people were hiring for at the time. The Web languages — HTML, CSS and JavaScript — that was not considered programming at all. That was certainly not considered computer science, and to this day there are lingering questions.

So I went back to school. I went back to school because the stuff that I worked on wasn’t considered engineering, and that didn’t happen until I was at Yahoo. (There was a small group of people that actually made the concept of front end engineering out of nothing at Yahoo. That’s another great thing that came out of Yahoo.)

And I looked, and I looked, and I looked, and I’m like, “Wow, I can sit down and write this stuff, but I didn’t qualify.” I seriously would not have been able to convince an engineering recruiting type department that I was someone that they would want to hire. Google was not existent at this point. There really wasn’t a thing called Google when I was looking. I mean, it was there, but it was four or five guys trying to do something.

So I was at San Jose State, trying to finish up a very old bachelors in psychology, and I noticed that there wasn’t a really good way to study for this stuff. They had put me into a bunch of low-level undergrad courses, you know, Psych I and statistics and things like that. I wrote a thing purely for my own benefit to help me study online, and I opened it up to some of the other people in my classes, and it’s a commuter college so there are older people in the college, and I ran into some 30, 40 year old people who were in there basically doing the same thing I was.

I said, “Hey, I made this thing to help me quiz and get ready for this stuff, so if you want to try it out, you can try it out,” and I gave it to them. What it was, was a collaborative way of generating practice tests. We would just grab questions that had been on various pop quizzes, put them together with three wrong answers and one right answer.

Then everybody would re-take these quizzes until they were getting perfect scores.  It took the questions that people were missing, and sorted them up to the top.

And what we discovered was when we got to mid-term time, the questions that had sorted up to the top over the course of the semester were all on the mid-term, and we knew all the answers.

I ran this thing for three semesters and left San Jose State with a 5.2 grade point average. It was crazy. I got As and A-plusses in everything, and everybody else who had used this thing also got a bunch of As. To the point where, I had the dean of the psych department and some professors gather me into an office and say, “We have to talk about this thing that you’ve put online, because it really feels like you might be cheating.”

I showed them exactly what it was, and they got to the end of it and they were scratching their heads, and said, “Well, you’re obviously not cheating. You’re doing very well, but everybody else who is using it is also doing really well, and it’s kind of breaking the curve for everyone else in the class who isn’t using it.  Can you do us one favor and take it down at the end of the semester?”  And I did that.

But when Yahoo called, I  actually had something to show them.  Now, keep in mind they were paying $70,000 a year or something like that, which was approximately half of what I made the last year at WebMD. But it was like, “Sure. Absolutely. I’ll jump in and do it.”

So, I think in a very real sense not having the college degree actually got me the job. Because I wouldn’t have been doing what I was doing, and I wouldn’t have something verifiably useful to show them. Does that make sense? That’s very roundabout and weird.

Yeah, no. It reminds me– I actually want to pull it up. There was a quote that I saw on Twitter that stuck with me recently. It said, “My career only makes sense in hindsight.'”

Yes. Yes, that’s exactly right.

Me, I have a career because people wrote books. I have a career because there’s a thing called O’Reilly books. They make books for people who make websites. I had a career because of the Perl Book and the PHP book, and the Javascript book. I have a career because of Douglas Crockford, who worked at Yahoo. He was there when I was there, and he wrote a book called Javascript: The Good Parts. I looked at that, and it finally started to click and make sense for me. Up until then, I was a Web monkey. I was doing what they told me to do, and I would type in the tags and see if it works. It was all very guess-and-check. I wasn’t doing original programming, at least not using Web tech, until then. It’s all those guys. It’s those guys, and it’s getting lucky, and it’s working hard, and it’s being ready for things.

I am so intrigued by the fact that you can identify the moment when ageism became the thing.

That’s easy. Ageism began when Mark Zuckerburg said the famous words, “Young people are just smarter.”  It was a large plenary lecture for a bunch of people at Stanford, plus the Y Combinator people. If you look at the people who were in the audience, there were eight companies at Y Combinator, and I believe seven of which are still in business and several of which are now public.

You can see a direct correlation between what Zuckerberg says and how they do things at companies like Dropbox. Dropbox is famous for the bro culture, and “you need to be 22, and you need to drink, and you need to be white, and you need to go, go, go, go, go, and there’s no life outside of work, and you need to live right there and you need to come drinking with them every night, and for God’s sake don’t be a woman, you won’t fit in.”

All of that stuff comes right out of that one silly lecture that he did.

And the goofy thing is, Zuckerberg (now at the ripe old age of 31) still has yet to retract it. I have never seen where he has actually said, “hey, you know, I was 22 when I said that, and maybe I didn’t have all the perspective I could have possibly had, and you know, upon reflection, I no longer believe that young people are ‘just smarter.'”

I mean, he’s massively successful. He was a 22 year old billionaire, and of course, he’s going to stand up and say what he says, but look at that.  “Young people are just smarter.” If you were to substitute the word “white” for “young” you would get rocks thrown at you, and for good reason.

Yeah. So how have you felt the ripples?

I have personally never run into ageism in the workplace, but that’s because I think I have a talent for jumping out before they’re tired of me. I have these little mini-careers. I’ll have a nine-month career. At Yahoo I had five different careers. I was always looking for something I could lateral into that might potentially get me some more money at Yahoo. At Netflix I had a couple of major things.

At Pinterest I’ve basically been doing the same sorts of things since the day that I was hired, but I think it was because we were such a tiny company, and you could basically pick out what you wanted to do and work on it. I’ve just kept working on it for the entire time that I’ve been here.

But I know lots of people who can’t get hired. If you work on Linux and Apache and MySQL and PHP, you may be labeling yourself as a dinosaur.  If you don’t have a pretty solid looking GitHub profile, if you’re not actively contributing to open source, if you’re not making something new that other people are actually working on, working with and using, that’s the kiss of death.

They’re going to find somebody who is younger and cheaper. They’re going to find somebody who does not know that he should not be working those 14, 16, 18 hour days.

I mean, you already know you shouldn’t do that, it’s terrible for you. It’s eventually terrible for the company. These guys who are 22, they’ve just been handed millions of dollars by the VCs, they’re going to find some 21-year-olds, you know, who can be counted on to just work and work and work  until the money runs out or there’s a pivot.

How do you feel that, aside from sheer experience, how your time in tech and your perspective brings something to the table in your work?

I think as we get older we become much better pattern recognizers. Your brain cells die off as you get older but the connections between the brain cells become more and more complex. Your executive function is generally more in charge and what I’ve noticed with experienced people– are you familiar with Malcolm Gladwell’s theory of Ten Thousand Hours of Practice?

Yep.

That’s actually a really good way of thinking about it. People who are experienced, especially in software, especially running big projects in software, you can explain what you want to people like this and they can immediately give you a quick yes or no, and tell you whether something like this is a good idea to even try.

The key is, you have to phrase the question in the right way to actually get an explanation that makes sense. You don’t really want a yes or no. What you want is a, “Yes and here’s how we’re going to do it.” The flat “no” is never useful, you never give a flat “no.” People hate that.

What I think older and more experienced people are better at is immediately saying, “Okay, if you insist on doing it this way, here are the pitfalls your architecture is likely to fall into.” And when you pick somebody up who’s got that kind of experience it’s exactly as if you’ve handed the problem to someone who has no experience, they’ve worked on it for six months, they’ve made all the mistakes, learned all the learnings and then they’ve gone backwards in time to the instant when you ask them to do the product and then say “here are the things we’ve learned.” You get that free with someone who actually has the experience. Does that make sense?

If you look back on the span of your career, are there any major lessons learned that just really stand out to you?

Very few regrets. I would not be sitting in this chair having this conversation with you if anything had gone differently. I like to think that I could have listened harder, been more aware that things were going bad at various points in the career. I mean making that sideways dodge into this-or-that mini-career a little bit sooner in a couple places might have been better smarter.

But I certainly don’t regret not going to college and grinding my way through a computer science degree in 1983 which would have been totally useless for anything I’m doing right now.  I’ve no regrets on that.

I don’t know.  I do wish that I had listened harder to some well-meaning people that have talked to me throughout my entire career. People have offered me great advice and I’ve just been too stupid, too busy, too old, too set in my ways to actually listen to it. I wish I had listened more.

And lastly, what advice would you give to folks who are hoping to get into tech?

First of all, be aware of what’s already happening around you—what you can do without money or a college degree. Don’t listen to anybody who says, “If you spend $10,000, I will give you the equivalent of the college degree or golden ticket,” or whatever it is. You could probably just jump in, jump in and start running at yourself.

Find the change you want to see in the world. It’s old advice, it’s the same advice. Find something that’s busted, that makes you angry, that you want to fix. Go fix it, go make it better.

Listen to people, listen up. But I guess if you want to fix ageism in technology, ageism– I don’t know, I thought for a while I was going to be the poster boy for ageism in tech– in, actually, electronic stuff, and I don’t want to do that to my personal brands. I don’t think ageism is a fixable problem, but I do think that basic diversity in tech is a fixable problem. We can easily get more women in tech. We need more women senior engineers, more women founders, more women money, more women CTAs, and underrepresented minorities as well. All of those people need better representation, and if we can fix those problems – which are fixable problems – you can hire 22-year old women, you can hire 22-year old men, and people from underrepresented segments.

This advice is especially important for people who want to build consumer products. If you’re not building a thing that 100% of the population of the world will eventually use and love, you are aiming too low.  And if the people who build your product don’t genuinely represent that population, you will never be able to reach them and your product will inevitably fail.  If your founding team is a bunch of 22-year-old white male Americans, you’re already at a huge disadvantage and you must take immediate steps to overcome it.

Yeah. I want to dig deeper in that for a second. Just based on your experience, having worked with many different teams and seeing how teams change over time, what have been the benefits that you see of incorporating diverse employees into product work, into the company?

I do the same talk at every Hack Day that I’m invited to present at.  The talk is always “How to Win at Hack Day,” and I’m usually speaking to younger people, people who are in middle school, high school, maybe college age. I give them the same piece of advice, and the advice is, “No matter what you do about the thing that you’re working on, be sure that you have women on your team. And not one. Have at least two. You’re going to work together for 8 hours, or 24 hours, or maybe 36, and you need to stay on task. You need good modeling for listening and communication, and it will be magically better if you have women on your team.”

But all I can really say is “It will be magically better.” It always gets a round of applause from the women in the room, and it works really well.  I say, “I will tell you this right now. The winning team will have at least two women on it.”  And 24 hours later, guess what?  The winning team stands up – it’s got at least two women. Every time I predict it, it happens. It’s magic.

]]> /kent-brewster/feed/ 0