[hugs]

There's yet another kind of startup founder, who merely starts a successful company that makes millions of dollars per year and is still in business almost a decade later. The company doesn't fail, but it doesn't have a huge blow-out liquidity event, either. The founder remains heads-down, in the trenches, with no interest in going the VC route. Regardless, they're in a boring B2B niche, so you'll never read about them.

[nibs]

So much more likely to succeed and so much less likely to make $100M. Definitely the surest path to $5-10M near the end of your career. If you only want <$5M perhaps being a corporate VP would be more optimal risk adjusted. This is my strong preference, I just wish there were more of a culture of that here. It could be the fact that this is a start-up forum but sustainable B2B niche business is really interesting and provides good opportunities to create wealth and do impactful work. It is merely less interesting to investors with large overhead and expectations. So it makes sense investors go big.

[drzaiusapelord]

The problem with that approach is that getting a high level VP position at a non-trivial sized company is pretty competitive and there are only so many open slots to go around. It also requires a strict career plan and the ability to play office politics very well, which I think most techies struggle with.

Being the guy who sells a small app, service, or utility on the side and clearing $150k a year, or more, via mostly passive income is a much easier trick to pull off. Also this approach can come with a sweetheart acquisition deal from a larger company that wants your product and can run in the millions, on top of what you've earned already.