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SD Sameer Dholakia On The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

“Oh, Harry, you have no idea. According to Byron, he said it was the lowest voted deal in the history of the firm of the time he had been there. But the fact that we were both there and had conviction… they're like, dude, that's where alpha comes from. If you guys really believe, go do it.”

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · Startups & Venture · October 2026

“Oh, Harry, you have no idea. According to Byron, he said it was the lowest voted deal in the history of the firm of the time he had been there. But the fact that we were both there and had conviction… they're like, dude, that's where alpha comes from. If you guys really believe, go do it.” — Sameer Dholakia, The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Harry Stebbings asked whether Bessemer's investment in Anthropic was controversial inside the firm. Dholakia says the deal got the weakest internal vote anyone could remember, and went ahead only because the partners leading it had conviction.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 2026-10-19 Listen to the episode → More from Sameer Dholakia → More Startups & Venture quotes →

Transcript

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch Around 07:15 into the episode
Speaker 4

it

Harry Stebbings

controversial in Bessemer?

Sameer Dholakia

Oh, Harry, you have no idea. According to Byron, he said it was the lowest voted deal in the history of the firm of the time he had been there. But the fact that we were both there and had conviction, and one of the things I love about Bessemer is empowerment is one of the values of the place. And they're like, dude, that's where Alpha comes from. If you guys really believe, go do it.

Speaker 4

What did you not see that you wish you had seen?

Sameer Dholakia

I wish I had the ability to convince us all to do a bigger check that round. I feel like we saw it. We knew it, but there are so many risks at that stage of the company. But we knew that the AWS relationship was pivotal, that it would provide both the compute for the training critically. And that…

Speaker 4

When we look at concerns today, one concern is the cost of intelligence shifts to open source because it's simply too expensive in Frontier models. And we see that in a lot of data that's being produced by Vercell and Guillermo, who publishes it. We're both big investors in fireworks. And so we…

Speaker names from our own diarization · position estimated from where the line sits in the episode

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