Gokul Rajaram

speaker

1,839 appearances 2 recordings 2 series first heard Jan 2026 last heard 16 Mar

Gokul Rajaram’s voice in public audio — every appearance, attributed to the second.

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recordings per month · last 12 months

Recordings per month over the last 12 months — 2 in all, peaking in Mar 2026 with 1.

Appearances

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The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · 16 Mar 2026 podcast

I think they've gotten to $500 million in revenue.

But guess what?

They're still at $4 billion.

And so basically, they will not make 1x the capital they invested.

And so that's a challenge, I think.

But guess what?

Even in WeWork, Benchmark made money.

Benchmark made money at WeWork.

because they invested early enough.

So I think at sub-100 million, maybe that's an arbitrary number, you can, if the company is good, you'll make money regardless.

I don't think an A investor can do, there are two kinds of deals that A investors have to do.

One is, I think, where there is less legibility on the company, where you're betting on there is some early product market fit, there's not three million revenue, there's half a million revenue, and that's like you said, when you get it basically for 50 or sub-hundred million, a million or so.

But then as soon as it gets to three or four, it gets, maybe you can do a couple of deals like that, but I don't think you can build a series A fund doing deals at three or 400 million, because it's not gonna be enough ownership, some of these are going to fail, et cetera.

So I don't think, I think you can probably,

All of us, you know, I think even Benchmark, I think on your pod or one of the pods, I think Chetan mentioned this, where they've done a few of those deals where they have single digit ownership percentages in high valuation companies like Mercor or something like that.

But most deals, I think you've got to have double digit ownership.

You've got to invest slightly earlier.

It's a tough game, but you've got to be patient.

I think the good news is concentration is your friend in some ways.

It can be your enemy, it's also your friend.

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