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The a16z Show

Cheeky Pint: Marc Andreessen, John Collison & Charlie Songhurst on Tech’s Big Questions

The a16z Show

a16z

Science, Innovation, Business, Entrepreneurship, Culture, Disruption, Software Eating The World, Technology

4.41.1K Ratings

🗓️ 1 October 2025

⏱️ 129 minutes

🧾️ Download transcript

Summary

Today we’re sharing a feed drop from Cheeky Pint, where Stripe cofounder and president John Collison chats with legends in technology over a pint of Guinness. In this episode, John is joined by a16z cofounder Marc Andreessen and tech investor Charlie Songhurst for a candid conversation about bubbles, downturns, and the psychology of markets. They discuss what makes Silicon Valley so hard to replace, the deep history of the Valley’s ecosystem, and the future of media. From the lessons of the dot-com crash to the future of venture capital and startups, this is an inside look at how big cycles shape innovation and what it takes to build on the frontier.

Transcript

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0:00.0

Today we're sharing a feed drop from Shiki Pint, the show where Stripe co-founder John Collison talks with builders and leaders over a pint.

0:08.7

In this episode, John sits down with A16Z co-founder Mark Andreessen and investor Charlie Songhurst to talk bubbles, downturns, risk-taking in Silicon Valley, and how AI might be the next great platform shift.

0:22.9

Let's get into it.

0:26.4

Do you mind if I start with a couple of questions?

0:29.8

I mean, sure.

0:31.7

Cheeky means what, exactly?

0:33.2

Okay.

0:33.8

In the context of a cheeky pint, it is a pint you're not really meant to be having. And when it becomes established, it starts to attract establishment people. The social network problem. Right, exactly. And in that sense, the downturns, as much of a pain in the butt as they are, are probably helpful. You go back to banking, you go back to consulting. Yes. Sorry, why is there more risk taking on the West Coast versus the East Coast? Because like... Ah, the frontier.

1:16.1

Because FOMO leads to high trust. That sort of has a cynical truth to it. Category 2 errors are much, much worse. By the way, they torture you for fucking decades. Right, because you read about the success cases that you've screwed up all the way up. And so you just learn the hard way. Like, you have to be extremely open-minded. I have found people willing to tolerate any level of chronic pain in order to avoid acute pain.

1:20.9

People would much rather lose slowly over five years than have the conversation that involves a dramatic change to stop losing. All right. All right. All right. Anyone need anything else?

1:26.0

Finally, a legitimately Irish bartender. I have a scheduling issue with these because 5pm, clearly after work clients, acceptable. 4pm, I don't know, after work if you're a banker or whatever. 3.30 p.m. like now I'm just drinking at the office. Mark Andresen has been around the internet since the very beginning, really. He co-founded Netscape, he invented the image tag. He was there at the beginning. And later he co-founded the venture capital giant and Driesen Harwoods. So I'll be speaking to him, along with our mutual friend, Charlie Songhurst. Cheers! Cheers to see you guys. Do you mind if I start with a couple of questions? I mean, sure.

2:02.6

Well, there's just a couple of things.

2:04.6

As a Midwestern American boy, there's just a couple of things.

2:07.6

This is not my natural habitat.

2:08.6

Cheeky means what, exactly?

2:10.6

Okay.

2:11.6

In the context of a cheeky pint, it is a pint you're not really meant to be having. And so if you were meant to be going home right after work,

2:21.2

and instead you stole away with a few co-workers,

2:25.2

you know, just off the books,

2:27.2

aren't meant to be at the pub right now.

2:28.8

That would be a cheeky pint.

2:29.7

And then pint, the thing about pints is just really puzzling

...

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