I Fell In Love With The World Of Startups

The best things in my life happened by chance.

Most people don’t know that what got me hooked on startups was working on my book, Founders at Work. Writing that book inspired me to help early stage startups — and ultimately to want to start Y Combinator.

Eleven years ago, I was the VP of marketing at an investment bank. I was bored with the work and tired of doing stuff like writing press releases for things I didn’t care about. One night, I ended up at a party where I didn’t know a soul. I’d gone with the plan of meeting a friend there — only to be told upon arrival that he was in Arkansas, having just joined Wesley Clark’s presidential campaign. I wanted to turn around and go home then. I almost did. But at the last minute decided to stick around for a while.

I wound up talking to Paul Graham, the host of the party. He was a programmer — he’d developed Viaweb, a company that allowed users to build and host their own online stores. It was the very first web-based application. We hit it off and started dating.

Paul and his friends introduced me to the world of startups. I’d never had much exposure to them and certainly didn’t understand the concepts behind them or what made them successful early on. I became so intrigued that I decided to pursue a side-project — a book, I’d hoped — about this crazy world. I wanted to help people better understand how successful startup founders did it. I decided to call it Founders at Work, based on the Paris Review series “Writers at Work,” and I interviewed startup founders about their early days.

I ended up speaking to people like Steve Wozniak (Apple), Craig Newmark (Craigslist), and Max Levchin (PayPal). I learned so much while working on the book. Among other things:

1. That there was another way of doing things outside of the business world that I took for granted from Wall Street — almost a parallel existence in startups.
2. That this new world was not only more exciting but also more intellectually rewarding.
3. That while many people knew, for example, that Apple had started in a garage and gone on to become a big, successful company, they didn’t really understand everything that had gone wrong in the beginning. And that those lessons were actually critical to the success of the company as we know it today.
4. Finally, that most startups start by accident, not just with an initial big idea and lots of funding.

The information I was digging up in these interviews was so interesting and surprising that I knew after just a few that I was onto something big. Initially, I just wanted the book to inspire people to launch their own startups, and to make the early-stage challenges much more transparent.

What I didn’t realize is that I would also be personally inspired by these stories, and that I would go on to launch my own startup-like company. I didn’t know then that helping founders with their own ideas would give my life a huge sense of purpose, and that some of these ideas would actually go on to become very successful. (Paul and I had started Y Combinator with Trevor [Blackwell] and Robert [Morris] as a fun project to try to help give founders a more standardized option for seed funding. But we weren’t sure that it would actually work.)

There were plenty of other “accidents” along the way. For example, when we started Y Combinator in 2005, we did a “Summer Founders Program” with eight startups. We decided to fund a batch of startups at the same time because neither Paul nor I knew anything about angel investing and we thought this was the best way to learn.The original plan was to go back to funding companies one at a time soon after the summer. But we soon realized that it was actually more powerful to fund startups in batches — to bring groups of people together in what might otherwise be a very lonely and isolating endeavor. This was really critical to forming a supportive community, and we’ve been funding in batches ever since.

Everyone from Bill Gates to Larry Page and Sergey Brin started small. When they first got going, people didn’t believe in their ideas; they faced rejection; they struggled. But they had the determination to keep going when so many others might not have. Through Founders at Work, I wanted to help people who felt alienated from the regular business world; I wanted to lend hope to those who faced constant rejection and teach them how startups worked early on. I knew that if I could help them I might help bring more innovation into the world.

Incidentally, Paul and I are also now married. I’m very glad I went to that party.

As told to Adrienne Day

Cover GIF shot on a Samsung Galaxy S6 edge by Peter McCollough
Illustrations by Thoka Maer

Brought to you by the Samsung Galaxy S6 edge, The Moment is a series of personal essays from some of the best-known influencers of our time, each talking about a brief instance in time that changed the course of their lives.