It seems to me that investing in the markets (which is what I assume you're question is about) means playing in a domain with stacked power laws. When markets are normal, you can spread your investments across many startups and win, but when a crash occurs in the overall market(s), you lose. So timing is everything, but every investment advisor will tell you that you cannot win by trying to time your trades. Obviously the flash traders feel differently, but they're still subject to the overall crash, no matter how well they are hedged.

Your word choice, e.g. "bets", implies that your mental model for life is gambling.

While very popular today, it's a losing game that you are playing.

Read/study about better, more empowering mental models, for instance, check the writings of Shane Parrish.