Karen Wickre
  • Years in Tech


  • Current Role

    Editorial Director , Twitter

  • Place of Origin

  • Interview Date

    February 2, 2016

I have worked in technology (chiefly publishing or business side) since 1985. I have worked for tech publishers, at startup companies, for content sites, and at big brand platforms (Google and Twitter).

So, I would love to start with the beginning. Tell me a bit about your earliest years and where you come from.

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!