How I Turned Down $300,000 from Microsoft to go Full-Time on GitHub

18 Oct 2008 – San Francisco

2008 is a leap year. That means that three hundred and sixty six days ago, almost to the minute, I was sitting alone in a booth at Zeke’s Sports Bar and Grill on 3rd Street in San Francisco. I wouldn’t normally hang out at a sports bar, let alone a sports bar in SOMA, but back then Thursday was “I Can Has Ruby” night. I guess back then “I can has _______” was also a reasonable moniker to attach to pretty much anything. ICHR was a semi-private meeting of like minded Ruby Hackers that generally and willingly devolved into late night drinking sessions. Normally these nights would fade away like my hangover the next morning, but this night was different. This was the night that GitHub was born.

I think I was sitting at the booth alone because I’d just ordered a fresh Fat Tire and needed a short break from the socializing that was happening over at the long tables in the dimly lit aft portion of the bar. On the fifth or sixth sip, Chris Wanstrath walked in. I have trouble remembering now if I’d even classify Chris and I as “friends” at the time. We knew each other through Ruby meetups and conferences, but only casually. Like a mutual “hey, I think your code is awesome” kind of thing. I’m not sure what made me do it, but I gestured him over to the booth and said “dude, check this out.” About a week earlier I’d started work on a project called Grit that allowed me to access Git repositories in an object oriented manner via Ruby code. Chris was one of only a handful of Rubyists at the time that was starting to become serious about Git. He sat down and I started showing him what I had. It wasn’t much, but it was enough to see that it had sparked something in Chris. Sensing this, I launched into my half-baked idea for some sort of website that acted as hub for coders to share their Git repositories. I even had a name: GitHub. I may be paraphrasing, but his response was along the lines of a very emphatic “I’m in. Let’s do it!”

The next night, Friday, October 19, 2007 at 10:24pm Chris made the first commit to the GitHub repository and sealed in digital stone the beginning of our joint venture. There were, so far, no agreements of any kind regarding how things would proceed. Just two guys that decided to hack together on something that sounded cool.

Remember those amazing few minutes in Karate Kid where Daniel is training to become a martial arts expert? Remember the music? Well, you should probably go buy and listen to You’re The Best by Joe Esposito in iTunes because I’m about to hit you with a montage.

For the next three months Chris and I spent ridiculous hours planning and coding GitHub. I kept going with Grit and designed the UI. Chris built out the Rails app. We met in person every Saturday to make design decisions and try to figure out what the hell our pricing plan would look like. I remember one very rainy day we talked for a good two hours about various pricing strategies over some of the best Vietnamese egg rolls in the city. All of this we did while holding other engagements. I, for one, was employed full time at Powerset as a tools developer for the Ranking and Relevance team.

In mid January, after three months of nights and weekends, we launched into private beta mode, sending invites to our friends. In mid February PJ Hyett joined in and made us three-strong. We publicly launched the site on April 10th. TechCrunch was not invited. At this point it was still just three 20-somethings without a single penny of outside investment.

I was still working full time at Powerset on July 1, 2008 when we learned that Powerset had just been acquired by Microsoft for around $100 million. This was interesting timing. With the acquisition, I was going to be faced with a choice sooner than I had anticipated. I could either sign on as a Microsoft employee or quit and go GitHub full time. At 29 years old, I was the oldest of the three GitHubbers, and had accumulated a proportionally larger amount of debt and monthly expenditure. I was used to my six digit lifestyle. Further confounding the issue was the imminent return of my wife, Theresa, from her PhD fieldwork in Costa Rica. I would soon be transitioning from make-believe bachelor back to married man.

To muddy the waters of decision even more, the Microsoft employment offer was juicy. Salary + $300k over three years juicy. That’s enough money to make anybody think twice about anything. So I was faced with this: a safe job with lots of guaranteed money as a Microsoft man –or– a risky job with unknown amounts of money as an entrepreneur. I knew things with the other GitHub guys would become extremely strained if I stayed on at Powerset much longer. Having saved up some money and become freelancers some time ago, they had both started dedicating full time effort to GitHub. It was do or die time. Either pick GitHub and go for it, or make the safe choice and quit GitHub to make wheelbarrows full of cash at Microsoft.

If you want a recipe for restless sleep, I can give you one. Add one part “what will my wife think” with 3,000 parts Benjamin Franklin; stir in a “beer anytime you damn well please” and top with a chance at financial independence.

I’ve become pretty good at giving my employers the bad news that I’m leaving the company to go do something cooler. I broke the news to my boss at Powerset on the day the employment offer was due. I told him I was quitting to go work full time on GitHub. Like any great boss, he was bummed, but understanding. He didn’t try to tempt me with a bigger bonus or anything. I think deep down he knew I was going to leave. I may have even received a larger incentive to stay than others, on account of my being a flight risk. Those Microsoft managers are crafty, I tell you. They’ve got retention bonuses down to a science. Well, except when you throw an entrepreneur, the singularity of the business world, into the mix. Everything goes wacky when you’ve got one of those around.

In the end, just as Indiana Jones could never turn down the opportunity to search for the Holy Grail, I could no less turn down the chance to work for myself on something I truly love, no matter how safe the alternative might be. When I’m old and dying, I plan to look back on my life and say “wow, that was an adventure,” not “wow, I sure felt safe.”