“Venture is an asymmetric game. You lose the dollars you invest, but you can make 10x if you're right. And that asymmetry means that the sins of omissions are way higher than the sins of commissions. … You only see the deals we do, right? You don't see the deals we pass. But the most expensive mistakes venture capitalists make are the deals they passed, not the deals they did.”
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · Startups & Venture · October 2026
The host was pressing Ganesan on whether investors like him have stopped being disciplined about price. This was his explanation of why venture firms pay up to get into deals.
Transcript
differentness out there, we definitely pay up. So definitely call us.
Yeah, you do. And every time I'm like, man, look paying up. And you prove me wrong. Like you you're right and I'm proved wrong when I'm like God They're not disciplined on price and so I guess I'm questioning Does Ownership just need to completely reshape how we think about TAMs and market sizing?
Let's think about when people pay up people just sometimes pay up to be able to win the deal I think some sometimes people pay up because they're able to see a bigger TAM than the other investor and in those cases you're not actually paying a higher market price you're able to see that the opportunity is bigger and therefore you're willing to see that possibility. Now sometimes you're going to be right, sometimes you're going to be wrong. So to me, I don't necessarily think it's just price. Sometimes you don't see the TAM, you're just trying to win the deal and that's what the price it takes. Then you're just a clear price taker. And that happens too. The problem is venture is an asymmetric game. You lose the dollars you invest, but you can make 10x if you're right. And that asymmetry means that the sins of omissions are way higher than the sins of commissions. What do I mean by this? You only see the deals we do, right? You don't see the deals we pass. But the most expensive mistakes venture capitalists make are the deals they passed, not the deals they did.
When you say that, what's the most memorable past that haunts you? What
is it? My most memorable past was that I was a young board member at a company called Plaxo, which had an incredible board. Mike Moritz, Ram Sri Ram, Tim Kugel from Yahoo, and Little Unknown Me, and Sean Parker, and Todd Massanis, and was the founder and Cameron Ren. Sean had some challenges on that board and was asked to leave that board because I was the only person within 10 years of his age in that group. He was telling me he was going to Boston and he's going to work with his college dropout. And he's like, you should get involved. And I'm like, Sean, you just got booted out of this board and I have no idea what I'm doing. And I didn't even take that meeting. And I probably had the opportunity to write a $50,000 check. And those seed rounds were different. They were million dollar seed rounds.
That's a tough one. What was Sean like back then?
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