Ask HN: What bad deals have you made / opportunities have you missed? - andrewstuart
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throwaway598674
Missed opportunities in roughly chronological order as I remember:

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.

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ggm
I graduated in 1982 and didn't go to the hiring fare. Microsoft was hiring,
MS-DOS had just hit and they were looking to bulk up.

