Why ‘At Bats Per Home Run’ Beats Batting Average in Venture Success

In venture capital, success rarely comes from steady, predictable wins. Instead, it’s the few, transformative ‘home runs’—businesses that go from almost nothing to global impact—that move the needle. Picture a baseball slugger: she might strike out most of the time, but if she nails enough home runs, her team wins. This flies in the face of usual business logic, where steady, safe performance is prized.

Top investors and entrepreneurs don’t obsess over failing less. They structure their decision-making so that they’re in position when a rare, outsized opportunity presents itself—even if it means more frequent ‘strikeouts’ along the way. The key is not to get every bet right, but to ensure that your biggest bets, when right, pay for all the misses and more.

This approach isn’t comfortable. Family, colleagues, and even your inner critic often question why you took on a risky project that didn’t pay off, ignoring the fact that a single ‘hit’ could change everything. The temptation to play it safe lurks.

Probability theory and asymmetric payoff logic from behavioral finance are at the heart of this strategy: what matters most is not how often you win, but the size of your wins relative to losses. The power-law distribution—where a tiny percent of actions account for the vast majority of results—is a proven pattern, not an accident.

To shift your focus from a string of small, safe wins to the possibility of bigger, transformative outcomes, start by honestly tracking both your failures and your home runs, learning from every outcome. Intentionally allocate some energy to pursuing bold ideas that have a real chance of making a big impact, even if it means you’ll strike out more often. Then, build in time to review which opportunities you let pass by and challenge yourself to understand why. By doing this, you’ll recalibrate your risk tolerance and raise your chances of catching that rare home run. Give yourself permission to go for it this month.