It doesn't. I semi-retired at 33 and then spent the time since then doing 20+ different startup ideas. Still no success. Bank account is bigger now than when I retired, but startup dreams are effectively dead.

Bottleneck is that the market moves on in the time you spend pivoting, and eventually your inside information about what's hot and what's worth building gets stale, along with your technical skills. I know a number of other entrepreneur/retirees in the same boat - 5+ years working on various ideas, often after having a previous exit - and it never seems to result in a big company.