One massive win can offset many failures. A single correct bet dominates a portfolio's returns, which is why investors favor founders who have already failed once. The founder of Squad, a 2015 dating app, says you only need to be right once to achieve outsized success.
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I forget who it was, but they were like, here's everything I've done. It's like failure, failure, failure, win, failure, failure, failure. It's like if you can bat.200, you could be a multibillionaire.
I mean, that's the whole thing about investing, right? It's the power law. You only have to be right once. One thing I learned from all the angel investments, working for a non-first-time founder is a huge advantage. I know for Squad, which is the failed dating app startup that I had back in 2015, I would do roughly 1 million things different if I started that company today. Just go in and do it and see what happens. You only have to be right once.