All the time I was trying to find an idea for a startup. I still had the lawyer bit flipped on so lots of things I tried had a legal/regulatory bent. That was definitely a blind spot that held me back for a while.
The fun YC-related story on the founding of Cloudflare is that, before YC, Paul Graham used to host a conference called the “MIT Anti-Spam Conference.” He invited me the second year of the conference (2003, I think) to give a talk on how to write effective anti-spam laws. The very technical crowd was polite to the lawyer. I met a ton of interesting people, many of whom played outsized roles in machine learning over the next few years, including John Graham-Cumming, now Cloudflare’s CTO. Paul invited me back the following year saying I should do something similar.
I was pretty sure the audience wouldn’t tolerate the lawyer giving another talk about regulation, so I went to a young engineer on the team of the (bad) startup I was working on and suggested we build a system to track how spammers scrape your email addresses. He agreed to build the backend if I built the front end (which I largely stole from the hot startup of the time: LinkedIn). That turned into Project Honey Pot, which I gave a talk on at Paul’s conference. Project Honey Pot gave the initial seed of an idea that turned into Cloudflare. And the young engineer was Lee Holloway who cofounded Cloudflare with me and Michelle Zatlyn.
Lesson to me has always been even in times where you don’t feel like you’re making forward progress in your life and career, find ways to stay involved with interesting people and projects and chances are they’ll pay dividends in ways you don’t expect later in life.
I clearly remember walking back to Paul’s house in Cambridge after the 2004 conference where I’d presented Project Honey Pot. I believe he and Jessica had relatively recently started dating. They were talking about startups and how people didn’t understand how they worked. Paul suggested they should teach a class at MIT. And that, of course, is what later turned into YC.
There were other dramatic events that evening in Cambridge that I think sharpened all our minds and made us appreciate there’s no time like the present, but I’ll leave that story for another day.
I can't resist ...
> There were other dramatic events that evening in Cambridge that I think sharpened all our minds and made us appreciate there’s no time like the present, but I’ll leave that story for another day.
> ... appreciate there’s no time like the present ...
The present is now! Some of us are dying to hear the story.
Took me a bit to figure it out too