Whenever you’re falling you want to fall the shortest distance possible, so it doesn’t hurt that much. When you go for a wave, you have to be prepared for what happens if you fall. This is true for waves of all sizes. Anyone who is successfully riding a wave has probably also wiped out on a wave of similar size.
In business, you should bet only what you can afford to lose, and you should start small. If you have two business ideas and one requires $1,000 to start and the other requires $100,000 to start, then pick the smaller one. It will hurt less if you fall.