Two investors debate whether failure teaches anything without wins to balance it. One argues a 10-1 success ratio matters more than the lesson; the other says most deal-makers lie about their losses. Both agree that naming the risks upfront, not hiding them, is what builds trust.
You only learn more from your failures than your successes if you also have successes. If someone's 0-9, they haven't learned anything from their failures. Someone's 10-1, they've probably learned a lot from their failures.
Usually when you talk to people, they're like, "God, you know, never lost. I've never lost a deal," or "I never lost investor capital." It's all sunshine and roses, but I know that that's just not the case. Losses happen a lot, and people have lost investor capital.
I think it's really important to understand when you go into a deal, there's the "how do we make money" side of the equation, but there's also "what can go wrong." And I think when people say they've never lost, they're not humble in facing things that can inevitably go wrong in a transaction. And I think if you're objective about looking at that, you're a lot more sort of calm. And investors or prospects or partners ask about a deal, you're very transparent about: here's why we like it, here's the things that maybe keep us up at night or concern us, and then here's our plan for mitigating those risks. But you can never get it to zero, right?