Jason M. Lemkin presents a concise investment rule: if he is 100% convinced a venture deal will produce a 5x return, he will make the investment regardless of ownership dilution or fund-level return calculations. He frames this as a long-standing personal rule rooted in early investing experience and carry incentives—preferring a sure 5x that yields personal upside over forgoing the deal.
I think any deal where you have 100% conviction, you'll 5x 100% conviction to 5x. You should do it irrespective of ownership revaluation just to do it. If you've already met with the founders, you already believe that you're not thinking you can make money, but you're like I am 100% sure I'll 5 exit. 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 bucks 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 going to make 5x, then I'll do it. Period.
