[poulsbohemian]

My first internships were early-stage / startup type businesses, and the last decade+ of my tech career were at similar companies or businesses of my own. They gave me a wider array of experiences and a greater sense of personal control, but there's no doubt I would have made a lot more money elsewhere.

I wish in the early part of my career I would have not been so eager to get into startup / entrepreneurship land and had instead tried to get a few more "name brands" on my resume, for the experiences and contacts. That would have helped down the road.

I would actually spin this question back around on you: Now that you are in a later stage of your career, what's stopping you from starting something now? Don't ask if you will regret not doing it, figure out your plan and do it.