HappyFunPeople: Jon Evans

Adventures in the dot-com boom and bust, globetrotting thriller novels, and a healthy, skeptical optimism about the great crypto future

HappyFunPeople is a series where we talk with HFCers about their life experience, what motivates them, and what it’s like to work at HFC. Jon is a tech industry veteran, an award-winning thriller novelist, a journalist who has reported from Iraq, Haiti, Colombia, and the Congo, and was TechCrunch’s weekly opinion columnist for a decade. He’s currently HFC’s CTO.

Robb: I appreciate you being able to take time to do this. I was going back to emails for something and we were going back and forth on the pilot podcast, and that was when I was in Colorado, so that would have been October of last year.

Jon: Yeah, that’s right. I was in San Diego, so yeah.

Robb: I feel like that’s the last time we really had a recorded conversation.

This last year has been interesting: we’ve gotten to meet up — I’ve probably seen more of you than I have of people who actually live in New York. We just happened to bounce around? Like, going out to Mill Valley and getting lunch was really nice.

Jon: I think you may be the only person I’ve seen on both coasts in the last two years.

Robb: Yes! I should get some sort of prize for that.

So, for these talks, I tend to do a bit of chronological history and try to unpack individual pieces. I think for you there’s probably going to be so much, we couldn’t possibly get through it in the time we have — not that you’re so old, necessarily.

Jon: I am, though. I am.

Robb: “Little do you know.”

I think you’re just a very well-travelled person with a lot of experience, and I learn more about it the longer we work together, which has already been over eight years.

Maybe we can start at the beginning: a little bit about your upbringing and your experiences as a kid.

Jon: Sure. “In the beginning was the word and the word was made flesh, and a light came across the firmament” — or something like that; I always forget how it goes. [laughs]

So, I grew up in a university town in Southern Ontario: the same university I wound up going to, the University of Waterloo. I was born, raised, educated there.

Waterloo has this co-op program where you go to school for four months and then work for four months, school for four months and work for four months. I was in engineering, where the work part is actually paid and sufficiently lucrative, and tuition was low enough, at least back then, that after first year, I paid my own way through university. Obviously, engineering was better-paid than some of the other options, but it was still a manageable thing. I kind of resent for the sake of the world that that’s less the case nowadays: Waterloo’s tuition has gone way up and although engineering co-op salaries have as well, I don’t think that’s an option.

I mostly worked in Ottawa over that time, although I did have one surreal work term in New York City where I had a very good time, in a way? I also lived in bunk beds in the office of my employer and wrote a whistleblower article [about it] — the university newspaper Imprint was threatened with libel — so that was an interesting work experience. We worked and moved and then returned back to Waterloo for another four months of education. That was very itinerant and peripatetic to begin with, right? Every four months you’re moving. So I kind of got into the swing of that fairly early on.

Robb: How did you become so widely travelled? People may not know this; I don’t know what the current country count is?

Jon: I feel guilty about keeping a country count at all, but I do sort of have a map, and you just count it from there. It also depends on how you define “country” and “visited” both, which have a surprising number of edge cases. But it’s very low three-digits: 100-and-something, I think, right now.

Robb: What spurred that? I’m guessing your wanderlust probably was initiated in part by this co-op experience, kind of shifting around?

Jon: Yeah. I mean, there was a combination of being used to moving around and also going to college in the same town I grew up in. The co-op program was an extended one: between the work and study, it’s a five-year program. I think I may have overcompensated for feeling like I had been in the same place for too long when I was — what was I, 23 when I finally graduated? So then there was a decade, or I guess 13 years, of basically being itinerant. I’d stay in one place for eight months — but less than a year — pretty much everywhere I went; I would work for a while as an engineer, save up a bunch of money, and go travelling. That was the next seven years after I graduated.

Robb: Interesting. What kinds of gigs were you doing at that point?

Jon: The web was just taking off in 1996, 1997, so I worked in San Francisco implementing Netscape Server for the investment bank that took Netscape public, actually: Robertson Stephens and Company. That was classic object-oriented software, Netscape Server, and kind of the Internet 1.0 dot-com boom before it really got going.

Then in London, at a consulting company called Aspect Internet, doing largely financial web stuff, because the web was new and exciting and everyone wanted to put stuff on the web, and it was London, so: center of the finance universe. Then where did I go? Back to Toronto for a while, and then to New York City. Those were sort of the work stints that took me to the new millennium, I suppose.

Robb: Nice. I’m curious: I mean, you were around for the dot-com boom and bust. Are there any highlights from that period, maybe some lessons learned? I feel we’re — I don’t want to necessarily call it a bubble now….

Jon: Yes. I actually bailed out sort of by dumb luck before the bust, so I missed that part of it.

I was working for a company called Quidnunc in New York City from 1999 through 2000, and 2000 was of course when things began to collapse. Quidnunc was a British company; they were a consulting firm, and they went from like five people in 1996 to more than 100 people across four continents when I was working for them. And then I left to go write novels.

They called me in for a very serious conversation, because they were saying, “You have stock options, we’re going to go public soon, we’re like Sapient and Scient and Razorfish” — which were the other big, similar companies at the time. “You’re turning your back on hundreds of thousands, if not millions of dollars by doing this.” And I was already pretty certain that that was not the case, so I sort of nodded and smiled, but did feel a certain pang of what-if regret and so forth.

So I went off to Montreal to write novels, and about two months later the bottom fell out. And about six months after that, they were four or five people who were — you know, there’s a Simpsons episode where after the dot-com bust, they’re ripping the copper out of the walls to resell on the wholesale market. It was kind of like that: they went from 100 people to five people in less than a year, I believe. The guy who laid off most of those people I think never quite psychologically recovered from that.

Robb: Yeah, that’s got to be painful.

How long were you pursuing writing as a principal endeavor?

Jon: I guess I took six months off, maybe eight months off in Montreal in 2001. Montreal was very cheap at the time; it’s still pretty cheap. Great city, one of my all-time favorites. I love it to death, except for the winters. And then I realized I had no money and had to go back to work.

In early 2002, a friend who I had worked with before in Toronto found me some work and brought me out of that winter of discontent. I think I was completely off work for a year there: from early 2001 to early 2002.

Robb: Along with probably a lot of other people.

Jon: Yes, that is the case. [laughs]

So, I’ve got to say: the 2002 team, when I did get a job? That was a really excellent working experience, because all the chaff had been shaken out of the industry. Everyone working on that team was a consummate professional who really knew what they were doing, had a lot of experience, and was very intelligent, because it was just such a high-risk market at that time. There were so many people looking for work who were very capable, post-dot-com bust. I don’t think it’s a coincidence that a lot of companies that are big now got started or really accelerated at that time: Google really took off, Facebook was founded in 2005, et cetera. The early aughts were a good time to found things just because there was so much talent out there.

Robb: When did you actually meet Ben and Will?

Jon: That’s a good question. I knew Will socially for some time before we started working together. I’m not totally clear on when exactly that was; this is through an old mutual friend of ours who I’ve known since I was a teenager, so I think since roughly that era. Certainly by 2006 or 2007.

In 2008 Will and I happened to be in Paris at the same time: my then-girlfriend was a TV host and was shooting a show for The Travel Channel. Will was there as well, so we wound up bringing him to the Fireman’s Ball. That’s my most concrete and specific dated memory, but we’d known each other before then, sort of in passing.

Robb: That’s cool. It’s hard to top a fun getaway in Paris where you just happened to be there at the same time.

Jon: And because I was based with a TV crew, we had inside access to absolutely everything, so it was a fun trip.

Robb: I think most people at HFC know you as our CTO and maybe as the primary tough interviewer if they’re an engineer coming to work for us –

Jon: I actually make a point of not being a tough interviewer. Maybe the analysis may be tough, but only one of my interview questions actually has a right answer. The goal of the interview is really to give people space to talk about what they know, what they do, and what they like, and then assess on that.

There are a lot of psych studies showing that if you quiz people on specifics, then the quizzer seems more intelligent than the quizee, but it doesn’t actually indicate knowledge or ability one way or another. So the interview style is more to give people space to express what they do and what they know.

Robb: That’s fair. I’d sort of meant that as a joke because I think, for the most part, you’re a pretty warm, approachable person. [laughs]

In any case, many people know you as our CTO, but you also had a column with TechCrunch for a long time and have written several novels. I’m curious to hear a bit about how you think about your writing career and how you think about that alongside all this work that you do with HFC.

Jon: I mean, I was a full-time novelist for about six years. Growing up, I always wanted to be a writer, and then basically for my 30th birthday I got a pretty lucrative two-book deal. I was able to take years off and write based on that, which was an interesting experience: getting the thing you’ve kind of always wanted at age 30 is obviously a wonderful experience, but also kind of an enlightening and educational one. And four years later, I found myself writing for a perceived audience more than writing for the pleasure of it.

And that was — you know, it was great spending five years gallivanting around the world as a hip, cool full-time novelist, et cetera, et cetera. That was a wonderful period, but just in terms of, I don’t know, artistic expression, it was weird doing it as a living: trying to aim for particular commercial outcomes and so forth.

My book sales did not match my publishers’ aspirational hopes and dreams, so I returned to the warm and vastly more lucrative embrace of the tech industry. But I didn’t really regret that as much as people I think would have expected at the time. Like, it was a great run, but turning your, I don’t know, your metier, your dream into a job is a complicated and sometimes two-edged business.

Robb: And coming back into tech hasn’t stopped you writing.

Jon: No, no. I mean, I have a new book making the rounds now which I think is deeply weird — which I’m pleased with! And of course, the decade-long run at TechCrunch took up a lot of writing spoons as well. Being a journalist, by the way, is also pretty great in its way.

TechCrunch has this very weird niche of being, at least at the time — maybe less so now, private equity buyouts, et cetera, et cetera — kind of significant and important and also kind of declassé and you-can-do-whatever-the-hell-you-want. Dropping obscenities into stories or headlines is actually encouraged there. Again, less so now; it got a little more corporate and controlled over time, but it was sort of a free-for-all for the first few years I was writing there. I had no editorial oversight whatsoever, which is always fun as well.

It was not writing fiction, but it was doing a lot of writing on a weekly basis to a deadline and trying to get something coherent every week, so that was an interesting challenge as well.

Robb: I definitely miss that column. I know I get a little flavor of it when you do our engineering newsletter, but it’s something that I looked forward to, particularly earlier in HFC, before we worked together as much.

Jon: I mean, honestly, I think the column may have degraded over the years. It came to be a little bit of a chore. I wrote 500 columns, which is a lot — especially when you’re an opinion columnist, which I was. It does sort of add up, and you start repeating yourself. I feel like everyone who writes opinions for a living should take long sabbaticals every now and again, just to get new opinions, for one thing.

Robb: I’m excited for the new book. Anytime you describe something as deeply weird, I definitely lean forward a bit. I take that as a good sign.

I’m curious to walk through a bit of the journey with HFC, once you joined. You’d known Will for some time before you actually kind of jumped in with both feet.

Jon: Yeah, I mean HFC had just been born — within the previous six months, I’m guessing? I don’t actually know the entire origin story pre-my arrival.

They needed someone, and Will was vaguely aware that I was a tech person who was talking about getting back into things. He emailed me kind of out of the blue and said, “Hey, can you do this thing for us? It’s just the kind of thing that you do.” And I wrote back and said, “no,” but then I followed up with, “but it is the kind of thing I guess I could figure out how to do.” I think I charged them sort of half my price while I was figuring out the particular framework we were working with; the initial thing was actually a native macOS App.

That went reasonably well, so that was just — like many of our engineers are — a recurring contract for the first couple of years.

Robb: When did that really transition to having a more permanent role?

Jon: I moved from Canada to California in early 2012, so I switched to a full-time role because that made getting the visa substantially easier — and also health insurance and so forth. But I would say that some months before then, HFC became kind of the only person I was working for. Initially, in Winter 2011, I think, they were one of half a dozen clients I was contracting for, but the work was more interesting and the relationship was better, and the others sort of fell by the wayside.

Robb: I hear these themes where you’ve chosen to put time into places where you enjoy the people you’re working with and have degrees of freedom to kind of make your own way. Is that what attracted you to HFC at that point?

Jon: Yeah. Not to be all “and the moral of the story is — ” but I think that it continues to be the thing that affects people at HFC: the sense of agency people have, whether they’re working here on a recurring or permanent basis. I think people appreciate that they have more individual independence and influence than they would in a lot of places.

Robb: I think that’s something that we all care about, especially those of us who have been here for a while, where it doesn’t feel like you’re constrained. Which can be scary at times, but being willing to learn new things is kind of the name of the game.

I want to ask about specific projects or experiences — and they don’t necessarily have to be at HFC, but I always like to tap into learning experiences. You talked about becoming a full-time novelist and what you took from that, but I’m curious about the technology side: maybe a project or a stint working somewhere where you learned something really valuable, either about how companies are run or what can go wrong with technology. I can think of a few projects we’ve worked on together where I feel like I learned a lot, but I’m curious about your perspective.

Jon: One of my very early projects was Rexly, which was this music sharing site. They actually made a TechCrunch Disrupt appearance in 2011, while I was writing for TechCrunch and also writing the Rexly code — which sounds like a conflict of interest, but I didn’t actually have much to do with the rest of TechCrunch at the time. I was just sort of a name on email addresses and on the content management system to them.

That one was, I mean I was pretty — I think it was my first major Rails project and it had significant performance issues. So, on the one hand, it taught me the importance of scaling and thinking about performance down the road if this did become a big hit. And then it did not become a big hit, and it turned out the performance issues were not that big a deal because the important thing was whether people were going to adopt it and try to use it in the first place. You know, I don’t think the performance would have mattered one way or another for that one.

And it was a good idea: it was definitely an idea worth taking a shot at. It was kind of like, “share your Spotify playlist” at the time, except using iTunes; do that automatically, that kind of thing. It just was not something that people wound up adopting and I don’t think it was going to be. So the other educational thing was that a lot of things people are going to try in this era are totally valid ideas that are totally worth trying and — not going to work. Establishing whether they’re not going to work is perhaps more important than getting everything particularly optimized out of the box. You want to be architected to subsequently optimize, but fast prototyping is probably more important than perfect, seamless, ready- to-scale-to-a-million-people-immediately.

Robb: How do you think things have changed? Obviously, mobile has come and peaked, and I think it’s much less of a hot space right now. And also the technologies for prototyping and scaling have changed dramatically.

Jon: I mean, there is a hot experimental space right now, but it’s crypto, which I have many conflicting feelings and thoughts about. Certainly, in the web and mobile space, it feels like everything has grown up and corporatized, and there’s a lot less throwing stuff at the collective wall to see if anything sticks. You haven’t seen a service like Twitter, for instance, come along for a very long time.

Things grow up, technologies mature, we move through the deployment phase into the iteration phase of technology as a whole, and that’s a natural part of the cycle. There are still a lot of people moving some fairly basic business stuff to the web and so forth, but there is less of a sense of chaotic creation and collective discovery and “what the hell is going to happen next?”, I think, going on in the web and mobile world.

Robb: Yeah, it does feel like crypto is probably the hottest area where it is still kind of the Wild West and people are figuring things out. You said you had some conflicting feelings; I know you’ve written about some of them. I know it’s something that you’ve had an interest in for a while, but I’m curious how you see crypto entering the consumer space that we tend to operate in.

Jon: I think cryptocurrencies are basically a lot of interesting babies in an enormous sea of bathwater, and it’s easy for people to see the one and ignore the other in both cases. I think the notion of decentralized permissionless technologies in general is very important; I think the kind of get-rich-quick, my-money-is-more-valuable-than-your-money, pump-it-up, his-is-better-than-yours is questionable.

And I’ve been in the crypto space long enough that I’ve seen so many things rise and fall that it’s kind of hard to take the latest hot thing seriously. It’s like “oh, Solana is the new, EOS is the new” — I don’t know, master coin. Not really a great analogy there, but you know there has been a lot of rise and fall over the years. I guess the Basic Attention Token is the new et cetera, et cetera. You can see the rise and fall of the latest idea.

There have been ideas that I thought were really quite interesting and compelling, like Blockstack, which just never really took off or worked one way or another. And then of course you have the NFT craze, which is resulting in artists being paid, so I support it on that basis, but on a technical basis I find kind of appalling. So: Many conflicting thoughts, as I said.

I actually think NFTs in the future, when they grow up, will be quite cool and good and interesting, but I also think today’s NFTs are articles of faith more than they are technology, and I think that disjunct is going to eventually become apparent to everyone.

Robb: It’ll be interesting to see who actually solves some of these puzzles in a way that actually has some staying power. I always ask what makes you excited about the future, whether it’s a technology trend or verticals that are starting to emerge or mature in interesting ways. Would it be crypto for you, or are there other areas of the industry that have your attention now?

Jon: I mean, there are layers of excitement mixed with layers of appalled horror when it comes to crypto, so it’s sort of hard to say. It’s not boring, I’ll give the crypto space that, but there’s a lot to look very askance at the same time. So in the long run: maybe, we’ll see. I mean, I appreciate the entertainment value if nothing else, though. It’s certainly the most popcorn-heavy area of technology at the moment.

Robb: [laughs] That’s fair.

Jon: In terms of things I’m excited about, I’m actually excited about the developer experience improving. I’ve only played a tiny little bit with GitHub Copilot, for instance, and GitHub Codespaces. I know I’m technically a GitHubber — I have never been a GitHub employee technically, but I have been working for them on their archive program for the last couple of years — but I genuinely think those things are great. The ease of developers spinning up an entire end-to-end life cycle — and a mature one which includes a front end, the back end, testing, a managed database, and so forth, is so much vastly easier than it used to be. I think that is great — and increasingly the case on the mobile side as well, I would say.

I think the leverage that individual developers can have in terms of prototyping and building stuff out — I haven’t done that myself in about a year or so, but I wrote a couple of one-off little things last year. I was really impressed, without even using the new suite of tools and the environment, how much easier it’s gotten to build something out on your own.

So I’m excited for the tooling, which I realize is a boring answer, but it’s actually the space which seems to be making the greatest leaps and bounds at the moment.

Robb: I guess it’s only a boring answer if you’re not one of the people who really appreciates that, which I think many of us are. Always happy to geek out on tooling.

I always close with this question: Advice for someone who’s starting out at HFC today?

Jon: I guess my generic advice for people in technology is just play around with new things: not necessarily on a deep level, but take a few hours and play with things. I feel like reading about things doesn’t give you as much gut-level understanding as actually taking a couple hours to wire it up, regardless of what it is. So, I think that’s fairly generic advice.

For people at HFC: because it’s easy to be focused on your own project at HFC — you probably have a lot to do and things are a little chaotic, because sometimes they are — I think people sometimes neglect to interact with others, bounce questions and ideas and random engineering commentary and so forth, as much as they could, whether it be in Slack or standups. So, I guess: “be playful outside the stuff that you’re actually working on and just talk to people about the stuff you’re experimenting on” would be my advice.

Robb: I’m going to reinstitute the Slack water cooler.

Jon: Well, the engineering channel sort of is that.

Robb: That’s true.

Anything else that you’d want to talk about? Normally, I’d probe a lot more on, if not personal stuff, career development kinds of questions, which I don’t think are really appropriate for you.

Jon: I don’t really have a career in the traditional sense anyways, so.

Robb: Well, actually let me ask you one more thing: What do you think that we’re generally looking for? What do you think makes a successful developer at HFC?

Jon: I guess the flip side of authority is responsibility, and the flip side of agency is ownership. People who are willing to take ownership of their projects; not necessarily try to push everything through themselves in order to decide what’s going on or something, but to be a full partner in how the project is shaped, as opposed to people who will just be like, “Okay, drop me a Jira ticket. I will do the thing that is in the Jira ticket specifically as written, I will send it back, and I will wait for the next one to arrive in my inbox.” To have more of a holistic view of what the project is, how to push it forward, and what the overall goals are.

Robb: Yeah. I like that description. It’s actually that sense which the engineers I’ve worked at HFC successfully have all embodied. You’re not throwing things over the fence, you’re not waiting for someone to throw something over the fence. It’s much more collaborative.

Jon: I think a lot of people have been trained to or just want to have stuff thrown over the fence at them. Which you know, in a way it’s easier, but I myself would not want that; many people do not want that. My guess is that those people are generally a better fit.

Robb: What’s your pitch to engineers who are thinking about joining us?

Jon: I think I tell people when we’re interviewing them that we’re comfortable with various different forms of engagement. That might mean working 40 hours a week — we’re also comfortable with people working part-time regularly or what I like to call comet people: who come in for a bit, go off and do their own thing for a while.

We also have a lot of projects, a lot of types of things going on. Those seem to be adequate to attract people’s interest? And honestly, I don’t consider those particularly — maybe the first one is unusual? But I don’t feel I’m selling the company particularly hard when I say those things. I’m just being descriptive.

Robb: Any final thoughts to take us out?

Jon: I guess there is some sort of mildly pithy line in that before HFC, the longest I’d ever held a job was 8 months. So clearly, I like it.

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