Framework
The founder 'sweet spot': sold once, but not for enough to get lazy
Shaan's heuristic for backing a second-time founder: a prior exit big enough to prove competence, but small enough that they're still hungry. Said about Adam Spector, who'd sold his prior company to Twitter.
“You know, you did just enough that I don't think you're an idiot, but you didn't get rich enough where, uh, where I, I'm worried that you're going to be, you know, some lazy wannabe Steve Jobs visionary type for your next thing. It's like you're, you're hungrier than you were the first time and you're smarter than you were the first time too.”
Steal thisBack second-time founders whose first exit was solid but not life-changing - proven, still hungry.
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