Ask HN: What keeps you from beginning your Start Up?

Be the first to fund his startup.

This is one mistake employers do. Do not try to retain him. If he wants it enough (and in this case he does) he will sooner or later find a way to make it happen.

Join him. Give him office space. You can still use his brain while he is around.

EDIT: Entrepreneurs should also not be afraid to share their ambitions with their boss. That is only if your boss started his own business. You may find a new partner in your boss. Remember that those who made it always want to help others make it as well. They will see themselves in you and noone can resist that.

I don't think startup people are "quitting their boss" (i.e. running FROM something), but they are rather running TO something that is magical and not entirely rationale. Statistically/financially, it's a dumb decision to start a startup-- but it doesn't matter. You can sit down, run the numbers, make pro/con lists-- but it doesn't matter. You've already lost. Here's what you can't match:

1) The big win. You can heap stock options on him, but your board will block you from giving a dev more than 1% or so, I presume.

2) His baby. His own company. A sense of TRUE ownership.

3) A clean slate. New companies/new products are more fun than existing ones for a lot of people.

4) Having ANY boss. Everyone rolls their eyes at even the best boss SOMETIMES. The irony is that, if he succeeds, he'll be that boss. But it's a great feeling to NO MATTER what, be able to fix something that organizationally broken if you think it's important. To be where the buck stops.

5) Fame/notoriety. Some people are motivated by this. If your startup wins, he'll be an unnamed dev in a winning startup. If his startup wins, he'll be the guy the led it there. Either way, it feels WAY cooler to say "I own my own company" when someone says, "so what do you do?".

Doing a startup isn't a sensible CAREER decision... It's a largely emotional lifestyle decision.

Risk. I'm risk-averse (as most people who objectively have it pretty good are). I have shit to loose.

Bureaucracy. I hate that I can't just do something. Ironically, the level of bureaucracy might be less at my job than if I worked for myself because if I work for myself I have to do lots of crap like dealing with laws that govern companies. I could hire a lawyer/accountant, but that gets back to Risk.

Sites like this. They make you think too much about scaling and building for a billion users. Databases don't scale. None of them. You do have to turn to a dumber object store at some point and loose a lot of query power. I'm moving past this mental roadblock.

Winner-take-all economies. A lot of what I would like to create isn't likely to result in money. This isn't because they don't have value. It's because they aren't good without lots of users. This is the most aggravating. Once users are using one thing, even if you're better, they just use that one thing for the same reason that more data trumps better algorithms.

I'm still in high school, but this summer i had a chance of getting a job. I didn't get one, instead i decided that i need to learn to program better and learn a few new languages. I also learned to draw, and I've been working on my writing style and my English. I also learned a lot of otter stuff(how to meditate for example). I don't know if I'll ever get a "real job", but I'll avoid it if i can. I probably will get one eventually, money is not useless. We like adventure more, and don't like having a boss in general(or any other authority figure for that matter). We are not afraid of failure, if we fail, big deal, we can take it(job security is for people who are afraid of change). I don't know how many hackers are like this, but from what I read on HN, there are a lot of them. You should ask your hacker about his plan, he may have good reasons.

20% to do whatever you want (as long as it makes things better), kept me in the corporate environment ...