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

Have you explored with him, with you in a Coaching/Mentoring role, where he sees himself heading; who he sees himself being; what effects he sees himself making over the next year / 2 years / 5 years / at retirement?

Once you have the answers to those (and he may not have fully considered these things himself, to that degree of clarity and detail), you can then work together to see if any options exist where you both get what you want.

1) Chance for a life changing payday, that could free you from the burden of working (if that were desirable - I have a theory that working is more fun when it isn't required).

2) Ability to control how the game is played. You don't want to lose because you were forced to follow someone else's direction - if you lose it should be your own damn fault.

If you can create these two things in a big company, let me know :)

Yeah, you've missed everything. It's a nice idea to try and give an employee what he's looking for from a startup within your corporate environment, but it's just not possible. Corporate employees exist to build wealth for someone else. That's just the reality of the situation. There are a lot of benefits that come with corporate life, primarily stability, but if he wants freedom, he won't get it working for someone else. When I was an employee, I had to remind myself that every benefit and incentive was an addicting trap, designed to keep me from leaving. A steady paycheck will erode an entrepreneur's soul over time, because you come to rely on it and striking out on your own is that much harder.

To be clear, I think it's commendable that you're trying to provide a great environment for your employees, but I think the best case scenario here is that you'll work hard to keep him, and you might succeed, but something inside him will die a little and he'll always wonder if he made the right choice. Why not just let him go give it a shot? I think it'll cost you more in the long run to fight it than it would to just get a new employee.

And I know we don't want to get sidetracked on this, but entrepreneurs do not "quit their boss". They absolutely do quit their jobs because they long for the freedom and rush of creating something on their own, no matter how awesome their boss is. If you disagree, perhaps that indicates more about the difference between a corporate and entrepreneurial mindset than anything else.

In the meantime, I'm honing my programming skills. I've been programming for a while now, I'd say that I'm intermediate. I know Pascal, C, Python, and bits of Java, C# and Lisp (I'll look deeper into this one though). My main objective now is to design and code larger apps.