Okay, so let’s start from the beginning. Tell me a bit about your early years and where you come from.

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.