In many ways, the year 2007 was a crossroad in tech, and this has much more to do than just the introduction of the iPhone (although, by all means, that was quite a watershed moment). 2007 was the last moment in time our software workmanship operated without Git or GitHub. Without the Go programming language. Without Y Combinator. Without Stack Overflow. Without Android. Without new JavaScript frameworks every weekend. Without Twitter. Without DevOps. Without Palantir. Without Instagrams influencers. Without Docker containers or Kubernetes. Without Claude Code. Such was l’air du temps captured in the pages of one of our Library choices for this month: “Founders at Work: Stories of Startups’ Early Days” by Jessica Livingston.
Well, to be honest Y Combinator did exist already at the time of its publication, but it had not yet reached the level of relevance that it would end up having today. Just to give you an idea, Sam Altman, the very founder of OpenAI, quickstarted his own career with a “geosocial networking” website called Loopt in 2005 (those with enough memory will surely remember) following a seed investment by Y Combinator. And 20 years later, here we are.
It is hard to speak about famous software startups today without mentioning Y Combinator. The list of startups funded in one way or another by it is too long to mention here. Suffice to throw some names like Dropbox, Heroku, Justin.tv (later known as Twitch), Reddit, Quora, Stripe, Scribd, Bitnami, DoorDash, GitLab, Zapier… You get the idea.
The connection between Y Combinator and “Founders at Work” is simple: the author of the latter, Jessica Livingston, is one of the co-founders of the former, and incidentally the wife of Paul Graham, of Viaweb and “On Lisp” fame… whose interview also appears in the book on page 205.
For rather obvious timing reasons, this book does not dive into the anecdotes of Y Combinator’s own founders, but rather represents quite a large scan across various famous companies who all started in some proverbial garage with some crazy idea behind. The names of Apple, Research in Motion, Lotus, Adobe, and Software Arts (of VisiCalc fame) appear in these pages, through the words of their own founders.
The message behind the book was strong and clear: start your own company, no matter what. Y Combinator found a simple formula: provide enough founding for a startup to become, following Paul Graham’s own words, “ramen profitable”, and grow from there. Of course this formula applies particularly well to a certain demographic: young people.
Ramen profitability is the other extreme: a startup that becomes profitable after 2 months, even though its revenues are only $3000 a month, because the only employees are a couple 25 year old founders who can live on practically nothing.
Too bad if you are older than that, or if you have kids that, you know, need something else in their diet than ramen, which is usually the case. In those cases you had better stay at your corporate job, thankyousomuch.
Of course I am being cynical here. Mr. Graham describes, however, a couple of interesting aspects about “ramen profitability”, in particular this one, often overlooked by most founders:
Raising money is terribly distracting. You’re lucky if your productivity is a third of what it was before. And it can last for months.
This is also one of the reasons having a minimalistic team of at least 2 founders is also helpful, with at least one of them taking care of money, and the other(s) taking care of tech. Again, Paul Graham had something to say about these mechanics:
Ideally you want between two and four founders. It would be hard to start with just one.
“Founder duo” pattern notwithstanding, the myth of the sole founder prevails in history books and popular culture; “Founders at Work” features interviews with just one founder for each hallmark startup in her book. (A nice touch, however, is that it is Woz, and not Steve Jobs, who got to talk about Apple; although I can only imagine that Jobs was quite busy with the impending launch of the iPhone at the time of the preparation of this book, and promptly declined the request.)
It is time for a mandatory caveat lector: this book could have also been named “Mostly White Male Founders at Work”. There are just three female founders in the pages therein, out of… 32 interviews. We are talking about Caterina Fake, founder of Flickr; Ann Winblad of Hummer Winblad Venture Partners; and Mena Trott, co-founder of Six Apart. Also, all of them are either of American, Canadian, or European origin, except Sabeer Bhatia, the founder of Hotmail.
Despite this lack of diversity, “Founders at Work” is a delightfully crafted collection of anecdotes from the trenches, war stories told by the generals that triumphed. It is, like any history book, biased: we only get the winners to tell their story. But many of those winners almost did not make it, and it in those cases that the book shines.
Suffice to mention the shenanigans of launching a blogging business during the dot-com bubble crash, as told in page 120 by Evan Williams, a man who would later launch Medium, and who was, precisely at the time of his interview, bootstrapping a new Ruby on Rails site called Twitter, which you might have heard about.
That was a really bad time. Actually the day that everyone told me they were leaving… I told everyone they were laid off and said, “Work with me if you can.” And at the time, everyone had already missed one paycheck, and they’d had it.
Ouch. So, just like the previous quote, the core idea of the book is anecdotes. Launch day issues. Growing pains. Marketing blunders. Lost financing. Coins dropping too late. There are so many learnings to get, it is hard to pinpoint the most representative. Let us try, anyway; spoiler alert: it ain’t pretty.
It’s hard to under-promise and over-deliver when everyone’s promising things for you. We’re trying not to hype up what we’re doing until we’ve got something people can use. People expect the world, so if you hype up what you are doing, you have to deliver, and it’s not easy.
(Blake Ross, co-creator of the Firefox browser, on page 398.)
I could not sleep well for 4 years. If you are in charge of technology at a really fast-growing company that gets lots of publicity, there’s always something that worries you. In early 2000, it was scalability.
(Max Levchin, co-founder of PayPal, on page 12)
You never know anything. The hardest part in a startup is that you wake up one morning, and you feel great about the day, and you think, “We’re kicking ass.” And then you wake up the next morning, and you think “We’re dead.” And literally nothing’s changed.
(Joe Kraus, co-founder of Excite, which admittedly depending on your age you might not have heard about until today, page 67.)
It all sounds very charming. Let us throw this assertion by Ms Livingston herself in the mix, found in the introduction:
Innovations seem inevitable in retrospect, but at the time it’s an uphill battle.
There are two parting thoughts I would like to add before closing this article.
The first one is that, if you are in the process of starting your own technology startup, please receive our most sincere wishes of success and strength, and our recommendation of reading “Founders at Work” in your (little) free time. But we would also have you keep in mind that being an entrepreneur is not for everyone, and pivoting, or simply closing your business, might be the right answer at the right moment depending on your own circumstances. Do not trade your mental health (nor that of your colleagues, co-founders, and employees) for the cover of Forbes. From the vantage point of the big scheme of things, it is simply not worth it.
The second thought is that, in the current times of Gödel’s Loophole being proven real, Switzerland (and, in general, Western Europe) have a one-in-a-lifetime opportunity to snatch some talent from the other side of the Atlantic; and certainly, local organizations like startupticker.ch, the EPFL, or ETH Zurich are doing all they can (sometimes, sadly, with little or no support from authorities) to make sure those minds find a location where to think in peace, launch, grow, and maybe IPO the next unicorn. This book, and even more important, the founding model imagined by Y Combinator, should be inspirations for the Swiss community to increase the attractiveness of the local startup scene.
Cover photo by the author.