How much of a risk is it to not follow a career that you don't like (he's says he wasn't passionate about football in his comments)? I'd say that was the appropriate decision, not risky.

"5. Put in every dime I owned into Less Everything so Steve and I could change our piece of the internet."

OK, maybe, but answer the following questions and then we can ascertain the amount of risk taken:

1. approximately how much money?

2. how old were you?

3. did you have a mortgage

4. were you married at the time

5. did you have children?

I applaud his success, but we’re not really talking “Sell your parent’s farm for a 1 in a million chance” level of risk here, are we?