Venture investor Jason Lemkin's rule: if you're 100% certain a deal will return 5x, invest it. The math works even on smaller ownership stakes. A 5x win can mean millions in personal carry, which beats worrying about fund returns.
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But I think any deal where you have 100% conviction you'll 5x, 100% conviction you'll 5x, you should do it irrespective of ownership or valuation just to do it. If you've already met with the founders, you already believe in it, you're not thinking you can make money, but you're like, I am 100% sure I'll 5x it, you'll always like to get an extra 5x out of X millions in your fund. It may not return the fund, but you'll never look back when you're in carry mode and say, you know what, if that 5 had become 25, that's an extra $5 million in my pocket. You'll never regret the sure thing 5x. I know it sounds silly, but this is where I started investing. And I lost track of it going to this. This is my rule, and this is my rule today. Again, if I'm 100% sure I'm gonna make 5x, then I'll do it, period.