Github, early hire I was heavily involved in the Ruby on Rails community circa 2004 - 2007, with a popular Rails blog, a bunch of open source plugins, and as a contributor to the framework itself. I got to know the founders of many startups built on Rails. I was friends with the early founders of Github, and could have easily been the 6th or 7th hire. But didn’t think git was 10x better than svn for it to take off. I completely missed the social potential of Github.
Airbnb, first hire The founders of Airbnb ran a co-working space called Jelly back in 2008-09. I used to work out of there and got to know Joe. Since Airbnb was built on Rails, he asked me to work on it. I rejected since I didn’t think it could compete against Couchsurfing. Recently I found an email from Brian Chesky in 2009 looking for a Rails developer, which I ignored. So I missed TWO chances of being their first hire / engineer.
Groupon, early Groupon was a pivot of an early crowdfunding platform called The Point. I was at The Point and could have been one of the first employees at Groupon if I didn’t quit to pursue iOS development in early 2008.
Smule, acquisition One of my apps was doing really well in the App Store and got the attention of Smule’s investors. They reached out to me for a potential acquihire. I turned them down because I didn’t want a “real job”, and my app was doing amazingly well. Around this time some music labels wanted to license my iOS sound engine for their own apps. I rejected these deals because I didn’t want their apps competing with my own.
Facebook, early mobile hire A designer friend got a job at FB right around the time they were looking to build a mobile team. I was a offered a free flight to meet Zuck and interview. Turned it down because my own apps were doing better than I could make with a normal FB salary. I also vehemently didn't want to work for a company with an ad-based revenue model.
Square, early hire One of my friends was the co-founder of Square. He tried to hire me as their second engineer (he was the first, in addition to being a co-founder). I refused since I didn’t find mobile payments that exciting at the time. RIP Tristan.
Calm, CTO Alex reached out to me to be Calm’s CTO. I turned it down because I didn’t believe people would use an app to meditate.
There’s possibly others I’m forgetting, and more hidden in my inbox.