Yes, but was he really risking bankruptcy? What was the worst case outcome of his decision? If GitHub eventually failed, I highly doubt he would go bankrupt. He would just have to find a new job, which for someone offered $300k from Microsoft would presumably not be difficult. In fact, he could probably walk right over to Microsoft and ask for a job.
A lot of these "life changing" decisions are portrayed as "risking bankruptcy" vs. job security. But for a talented developer, job security is not a fleeting opportunity. He could always choose to find a job later. He only had one chance to go with GitHub. When you think about the decision like that, the choice is obvious.
Maybe I'm overestimating how bad it really is when your startup attempt fails.
Here's what I'm imagining:
Working on a startup full-time without a job, before it starts earning money on its own, you're losing money constantly to bills and food. If your startup doesn't start getting profit soon enough, your stored money runs out, and you either have to live with a friend/family, or worst-case, become homeless unless you found a new job before the startup went totally under (you might not get any interviews in this time or get to the interviews and not get the job). Getting a job after running out of money living with friends/family, it'll have to either be remote or somewhere you can ride a bicycle/walk to, unless your friend/family lends you money or drives you around (less likely). I wouldn't feel safe having to use a bicycle as my primary transportation -- if my legs get tired I've gotta walk or find a bus. Showing up to your job interviews sweaty and exhausted probably doesn't leave a good impression. If you're homeless, I guess it might be possible by some stretch to remote from public libraries? More realistically, I guess you'd have to get a job at a supermarket or something along those lines and soon after that be able to sustain living at a low-rent apartment somewhere (if you live somewhere with reasonably-priced housing available, which you probably don't if you're in the startup hub of San Francisco). In the mean time you could shower and keep your clothes in a gym; I've heard lots of homeless people do that. Getting a job now and going through an interview at that point would probably be harder than before due to more stress, less good sleep, and so on. Hopefully you wouldn't lose all your possessions in the meantime.
Maybe I'm just too inclined to think pessimistically. The average outcome of a startup failure probably isn't that bad. If one option is a 9/10 chance something will turn out amazingly but a 1/10 it'll be a long-term disaster, and the other option is a 100% chance things won't be /amazing/ but they'll still be pretty great, I'll almost definitely go with the second one. I guess I'm just not the type for this kind of thing.
Presumably you would seek other income opportunities before you're so destitute as to be homeless. And that doesn't always mean quitting your startup, either. Many people or startups take on consulting projects while they're getting off the ground to make ends meet. There are many opportunities out there for people who have a demonstrable history of making real things happen.
Also, in big cities where startups usually are, it's not usually that hard to get by without a car.
Right, I'd just be afraid the other income opportunities might not come along, but apparently that fear isn't too rationally founded and programmers are in a pretty decent demand, according to what I've seen.
>There are many opportunities out there for people who have a demonstrable history of making real things happen.
Even if it was a failure?
>Also, in big cities where startups usually are, it's not usually that hard to get by without a car.
I used to get a bit tired just walking around my high school. I've never lived in a city, though. I'd probably adjust well enough eventually.
A lot of these "life changing" decisions are portrayed as "risking bankruptcy" vs. job security. But for a talented developer, job security is not a fleeting opportunity. He could always choose to find a job later. He only had one chance to go with GitHub. When you think about the decision like that, the choice is obvious.