Nov 8, 2023Liked by Ben Yoskovitz

"sometimes that chip is so big it’s overwhelming. Sometimes a founder is just angry at the world. That’s not healthy." Good point, but the balance could be very delicate. A founder who is "changing quickly and requires a level of grit and perseverance that’s completely off the charts" won't quit till the very end of imaginable human capacity, does everything right and yet fails at the end, is indeed risking to wear himself almost surely into that "chip is so big it's overwhelming" situation. Getting there is my real nightmare. How do you reconcile the perseverance and the second-timer wish points? It seems to me that they are mutually exclusive ...

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I agree that there is a tricky balance here. You want founders that are absolute bulldogs with absurd determination. But if after all that they fail, you don't want them to be bitter and angry, b/c you hope with all the lessons learned that they try again.

Second-timers know what it takes. And hopefully they recover from the first time to recommit themselves, and can avoid some of the mistakes and speed bumps that make the first-time even more challenging. Can they go a bit faster? Can they be a bit smarter about it? You hope so.

But second-timers that won really big the first-time? They're probably over-confident in their abilities and don't always have the same fire in their bellies. And that's a big problem despite the fact that they've already won (which is a good thing).

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