Founders at Work: Stories of Startups’ Early Days, Jessica Livingston (2007, Apress)
A Heartbreaking Work of Staggering Genius, Dave Eggers (2000, Simon & Schuster)

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In the 90s and early 2000s I was in school and toiling away for obscure startups in Switzerland, far away from the Silicon Valley-New England nexus of the dotcom boom. I still felt that I was witnessing it first hand, thanks to the distance-obliterating Web and the writing of figures such as Ev Williams (of Blogger, later of Twitter & Medium), Joel Spolsky (of Fog Creek, later of StackOverflow) and David Heinemeier Hansson (of 37 Signals, Ruby on Rails), all of whom influence me to this day.

So it was with undeniable nostalgia that I read Jessica Livingston’s Founders at Work, comprised of interviews with these three and many more founders about their startups’ journey from early days to some form of success.

The book was published in 2007, the interviews presumably recorded by Livingston in the 1 to 2 years leading up to that, and they are looking back at events from a few years to a few decades prior. Enough time passed and at least three paradigm shifts (mobile, cloud, AI) happened since to lend the book the patina of a historical record, an oral history of a certain type of American entrepreneurship at the turn of the millennium. The cross section of founders is excellent. If you can think of a successful or at least influential tech company founded in the 90s or early 2000s, it’s probably represented here. (As notable gaps I would call out Google, Amazon, Netscape – all only indirectly referenced in the book.)

Livingston also includes key businesses that came up in the pre-Web era, such as Lotus, Adobe and Apple. In fact, one of the interviews that resonated with me the most is with Mitch Kapor of Lotus, the creators of the genre-defining spreadsheet app of the 80s (Lotus 1-2-3). He seems more self-aware than most, candid about his blind spots and about instances of sheer luck that contributed to his success. He’s more of a product manager than an engineer:

Livingston: You guys grew to 1,000 employees before you went public. Did you know you were going to go public when you started?

Kapor: I didn’t know when, but this is what I’d learned from my time in Silicon Valley. To be honest, here’s what I was driven by: I wanted to do really a great product. Almost from day one I understood that I was passionate about the applications themselves, that they’d be integrated, easier to use and be powerful. They’d help make people more productive and I cared a lot about that. The other thing I wanted was financial independence. I had an enormous desire not to be dependent on other people, or to have a job. I wanted to dictate the terms. So I knew if you had an IPO, then you had a liquid currency and you had the ability to cash in and get that.

So I actually pushed for an early IPO, which we did successfully. But that brought all the usual problems. […]

Kapor embodies one founder archetype – he’s motivated by the full agency that his own business affords him. The flip side is crushing responsibility. Lotus outgrew him and he ended up stepping down as CEO in 1986, just 5-ish years into it (“I felt overwhelmed by what I had created, did not know how to step up to it, put enough brakes on it, hire the right people”).

The nature of the interview format means that the book is all anecdote and, certainly on the part of some of the founders, myth making. But then the formation of new companies has always been fuelled by myths. Without them nobody would be so out of their mind as to face the odds and put themselves through the startup wringer. The founders’ stories diverge significantly but anecdotes recur about near-fatal blows, sleepless nights and perseverance. With a few battle scars of my own, the anecdotal messiness is actually comforting. It complements the streamlined advice that you can get today as a VC-backed startup, exemplified by another book that I would recommend, Elad Gil’s High Growth Handbook.

What struck me as the most profound long-term trend that is well traced by the book is the commodification of hardware from the 70s through the early 2000s. Across multiple interviews you can piece together the progression from mainframes to minicomputers to microcomputers to commodity PCs as servers, and what that meant for a young business. All of the early Web startups in the 90s had to worry about physical server infrastructure from the jump, building and administrating of which was a required skill and expense that acted as a barrier to entry.

Hardware commodification culminated in the pretty much perfect virtualisation of servers we’ve achieved 10 years or so ago, a result of the rise of cloud providers plus modern containerization. For a while now, it’s been fantastically easy to ship and scale up software with almost no awareness of hardware. After all, it’s software that was eating the world. Given a basic competence with software, would-be founders as of late were constrained mainly by their own imagination, product sense and business acumen.

This is where it gets interesting. With ongoing AI advancements we may be on track to commodify software as well. I and the rest of the world are trying to figure out how this will impact individual engineers, teams, startups. Almost certainly it shifts the weight of critical skills even more towards Kaporian product instinct. I’ve had this mantra for a while and have consciously strived to build software and teams honoring it: code is easy, product is hard. Good judgment for what to build and how to bring it to the market becomes the key lever if how to build it gets ever easier. The business of technology may increasingly look just like … business.

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The coverage of Founders at Work stops where my personal history with US tech companies starts. I was preparing for my first stint as an intern in Silicon Valley in 2006 when I read somewhere that Dave Eggers’ A Heartbreaking Work of Staggering Genius captured “what it feels like to be young in San Francisco”. Naturally, I had to pick it up, and since already then I practiced a sort of method reading, bringing a subject into focus through a cluster of books, I read Kafka’s Amerika and Brett Easton Ellis’ American Psycho around the same time (unsubtle, I know).

Dave Eggers was in his early twenties when both of his parents died of cancer within five weeks. He gained custody of his brother Toph, only 8 years old at the time, and they moved to the San Francisco Bay Area. He pursued various creative enterprises and founded Might, a magazine for the affected and disaffected youth, all while figuring out how to be an orphan parent.

So much for the facts. A Heartbreaking Work is Eggers’ memoiristic novel or maybe novelistic memoir about those pivotal years of his life. He insists in the introduction that he chronicles events faithfully but undermines this with so much jokey banter as to leave a lot of room for doubt. Similar to Ocean Vuong (see last blog post), he blurs the boundaries between Eggers-the-memoirist and Eggers-the-character. The introduction also has a one-page “incomplete guide to symbols and metaphors” which maps “sky → emancipation” and “ocean → mortality”. The book is full of these kinds of self-conscious metafictional bits, which adds to its charm but runs counter to expectations of a memoir.

When I first read it back then, as an impressionable, somewhat timid young person about to set out for SF myself, I was an instant fan, blown away by the book’s combination of immediacy and playfulness. I was steeped in a dour Germanic tradition of novel writing. In the 90s and early 2000s practically the only permissible topics for German novelists were the events constituting the holy trinity of German trauma: the Holocaust, the Cold War and Reunification. (Austrian and Swiss writers were given more leeway but also frequently latched onto the trinity because they were selling to the same audience.) The so-called German “pop literature” was emerging, but none of those writers (Kracht, Stuckrad-Barre, Goetz et al.) had the range or seriousness of Eggers. I didn’t know one could unironically write about young people in the unmediated now in a way that felt this meaningful and was also fun.

Rereading the novel today, I am more ambivalent about it. It’s incredibly kinetic, everyone constantly hurtling around, jostling, throwing a frisbee or something. Sentiment is blotted out by action or semi-mindless dialogue – ok, perhaps this is what it feels like to be young to somebody more extroverted than me. Or perhaps I’m too old now.

I get that sublimation is at least partly the point, that I am supposed to sense the grief beneath all this furious activity. Maybe this does reflect Eggers’ own dealing with the loss of his parents but I found it odd that other characters at least weren’t afforded more varied responses to tragedy. Shalini, an office mate of the Might staff, spends several months in a coma after falling from a collapsing deck in the hills of SF. None of the friends and family who hold vigil over her seem capable of expressing grief at all. None of them break down in despair or even shed a tear, or if they do it must be off-camera.

My real motivation for this reread was that I thought I remembered descriptions of some of the early SF startup scene. Eggers-the-character and friends do intersect with the scene, and we get this one great rhapsody on South Park, location of the first Might office and center of the universe:

The warehouse, as luck would have it, is in San Francisco’s South Park neighborhood, an area of maybe six blocks which, if the newspapers are right, is itself about to explode, because this is where Wired makes its home, as do a handful of other magazines, mostly computer rags, but also SF Weekly, The Nose (humor) and FutureSex (“cybererotica” (naked people wearing virtual reality gear))—not to mention countless start-up software companies, Web developers, Internet providers—and this is 1993, when this stuff is new—graphic designers, architects, all surrounding or very close to a small oval of green called South Park (no relation)—bordered by small Victorians and bisected by an active playground – within which sits, on its perfect lush green grass, and incredibly dense concentration of sophisticated and gorgeous youth—a green oval teeming with the vernal and progressive and new and beautiful. They have tattoos before everyone has tattoos. They ride motorcycles, and their leather is amazing. They practice (or claim to practice) Wicca. They are the luminous young daughter of Charles Bronson, who interns at Wired, where the ratio of attractive young women to interns and assistants is 1:1, they being one and the same. There are bike messengers who also write socialist tracts, and bike messengers who are 200 lb transvestites, and writers who prefer to surf, and raves are still attracting crowds, and the young creative elite of San Francisco are here and only here, do not want to be elsewhere, because technology-wise, New York is ten or twelve years behind—you can’t even e-mail anyone there yet—and style-wise L.A. is so ’80s, because here, in stark contrast, there is no money, no one is allowed to make money, or spend money, or look like you’ve spent money, money is suspect, the having more than, say $17,000 a year—is archaic, is high school, is completely beside the point.

[…]

And there is no prestige like the prestige in working for Wired, wearing one of those new black shoulder bags they just had made, or having been at the party thrown by the people from Survival Research Laboratories, who make giant robots and have them fight each other—and though the material rewards are a joke, and the apartment rents are already starting to get silly, we say nothing and complain little because when the cherubic bald anchorman on the news says that this is the “best place on Earth” we cringe but then kind of even believe it, in a way, believe that we have to work eighteen hours a day, whether for ourselves or one of these tech start-ups or whatever, because we’re in a certain place, are lucky, feel lucky, feel lucky even though it’s been only a few years since the hills burned, since the highways collapsed— But so we are gathered here, each and every perfect warm-but-not-too-warm day, each day lathered in sun and possibility, probability, and while everyone drinks their lattes and eats their burritos, pretending not to be checking each other out—there is a feeling that we are, at least at this point in time, with our friends, on this lush grass, at the very red molten-hot core of everything, that something is happening here, that, switching metaphors, that we are riding a wave, a big wave—of course, not one that’s too big, not like one of those huge Hawaii kinds that kill people on the coral—

Note the Eggerisms on full display here: nested parentheses, creative italicization (“probability”), a cascade of em dashes—

Beyond this section though, Eggers-the-character and friends barely acknowledge the Internet revolution swirling around them, which is strange and not what I remembered. I’m sure in a close parallel universe Eggers-the-person, with his considerable entrepreneurial spirit, makes an appearance in Founders at Work because he struck it big as a founder during the first dotcom boom. But he’s a writer at heart, and so we got his influential literary ventures instead, after Might the much more durable McSweeney’s magazine and publishing house, as well as the 826 Valencia non-profit.