One problem with Kelly Criterion is that the swings are wild if you apply it. For example if your winning percentage is 55% on a double or nothing bet and you bet according to Kelly 1000 times you are practically guaranteed to have a drawdown of 50% at some point. If you bet 1/2 Kelly the odds of that are about 86% and if you bet 1/4 Kelly they are below 10%.

I've written quick Python script to show the results (1000 bets, 55% winning percentage, starting bankroll 1000, 10000 simulations each).

    Full Kelly:
    Average: 14174823.8 Median: 149660.0 drawdown50: 1.000 drawdown75: 0.939
    1/2 Kelly:
    Average: 145075.3 Median: 42632.0 drawdown50: 0.862 drawdown75: 0.135
    1/3 Kelly:
    Average: 27929.5 Median: 16098.0 drawdown50: 0.330 drawdown75: 0.009
    1/4 Kelly:
    Average: 12146.9 Median: 8916.0 drawdown50: 0.086 drawdown75: 0.000

drawdown50 is a probability of losing 50% of your bankroll at some point and drawdown75 is a probability of losing 75% of your bankroll at some point.

It's a wild ride either way but maybe consider that your utility of money function flattens out much faster than logarithmic one. You may not be able to get 1000 bets in and maybe you don't need 1000x or even 100x your starting capital to get all the money you could ever need.