That's a terrible analogy. Good analogies should provide an honest insight into a complex situation using a simple imaginary construction. In this case, there's no reason to assume that anyone's objection to founding a startup has anything to do with short-term versus long-term goals, and even if there was, the analogy of the "hill problem" doesn't address that objection at all.

I think it's much more reasonable to guess that this guy's reluctance to do the startup dance is the result of more complex considerations. His current job is safe; not glamorous, sure, but safe. He's probably making good money, and even if he doesn't really enjoy it, he's just found out that other people actually want him. That can be a powerful motivator by itself.

The startup thing is risky. Talking about it is all well and good, and we can make startups sound really sexy because they're what we prefer or need to do, but that doesn't mean that they're really for everyone. People might like the idea of startups, but when it comes to the actual risk, guesswork, and extreme hard work associated with them -- not so much.

I mean, hell, I'm working on my second one now, and I couldn't imagine working for anyone else ever again (or sitting in a cubicle). On the other hand, there are definitely days that I would love to not have to worry about whether or not I'll find enough business to pay the rent a couple of months from now. I haven't had a real get-away vacation in I-don't-know-how-long, and my average work day is probably around 11 hours long. I honestly don't know how my girlfriend puts up with it. And, I'm constantly thinking about one business or the other; it's not like I can just "punch out" at 5 or 6 o'clock each day and not think about work until the next morning.

So, yeah. Startups aren't all roses, and maybe some people are smart enough to figure that out before they jump into them.