I went down the rabbit hole with the Kelly Criterion recently, last time I thought about venture capitalism. Starting with a scenario of a repeated bet where you have a 10% chance of a 50:1 upside, Kelly says to bet a percentage of your bankroll each time, while someone of a more conservative bent might want to have a 95% chance of not going below a certain drawdown.

With those stats, you have to bet 28-29 times to have a 95% chance of winning your 50x upside. So depending on your maximum drawdown, you have to make a much smaller bet than what Kelly Criterion counsels.

In fact that seems to be a general thing - Kelly Criterion is generally about maximizing geometric returns, but the volatility will kill you - it takes lot of betting to have high odds of being close to those theoretical returns.

I'm not really experienced enough with the math to find strategies that maximize your expected growth when subjected to a certain drawdown restriction, but that's what people need when they are at lower net worth levels.