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Brian Gracely

Things Brian Says on Podcasts

Where to Find Them

Brian Gracely hosts The Enterprise AI Show .

Recently: “AI & Cloud News - End of October 2026” on The Enterprise AI Show (November 2026); “OpenClaw Enterprise: Making AI Agents Safe for the Enterprise” on The Enterprise AI Show (October 2026); “Confidence or Con? The Psychology of Tech’s Boldest Leaders” on The Enterprise AI Show (October 2026); “AI News - Mid-October 2026” on The Enterprise AI Show (October 2026); “Agents Are Identities Too: Identity Security After CyberArk with Amy Blackshaw” on The Enterprise AI Show (October 2026); “AI News for End of September 2026” on The Enterprise AI Show (October 2026).

What They Said

“This is probably the first major IPO in history that has absolutely no regulation, but has an entire section that says, oh yeah, and we could destroy the world or be massively damaging to all sorts of things. People are just like, oh yeah, okay, that's a checkbox.” — Brian Gracely, The Enterprise AI Show

Brian was picking through Anthropic's S-1, contrasting its extraordinary growth with its lack of profits. Here he points to the risk-factor language as an oddity for a listing in an unregulated industry.

The Enterprise AI Show · 2026-11-01 Permalink → Listen →
The Enterprise AI Show Around 29:55 into the episode
Brian Gracely

it. All right. Maybe we should get to the main event. Again, there are dozens and dozens of things in the AI and Cloud News of the Month stuff that you can folks can go dig through. Do you want to give your two cents on the $2 trillion potential S1 IPO from the folks at Anthropic?

Brandon Whichard

…where they go into like all these weird, you know, finance geek terms about revenue growth and SaaS and retention and net margin. And it's all that matters, man. All that really comes down to it is demand. So that's where I come down. What do you think? You've thought about a lot of this as well.

Brian Gracely

Yeah, no, I've had it thrown at me. And again, these days, like nobody, nobody really just does the like straight down the middle. This is what the numbers look like. And this is, this is what it would like. You hear very few just like finance professors or economists just go down through it and be like, it's always somebody who's like, hey, this is a bubble. They've got Ed Zittron on, and Ed's, of course, pitching his book of like the world's going to end and these guys are all, they're all frauds and blah, blah, blah. And then, of course, you'll have the all-in podcast or you'll have some Silicon Valley driven thing that's like, hey, you guys just don't even understand how big AI is going to be and it's going to, it's going to be 50 times as big as it is. And, but yeah, like it is one of these things where, and again, this is by no means financial advice. And by the way, for 99.99% of you that don't have a dad who's like works in private equity or something, like you're not going to get access to these shares anytime soon until maybe your like…

Brandon Whichard

a bullet point, too. It's just what a video. It's like, what do you mean? All right. So I like where you come from, but I think one of the things I've been thinking a lot about, and I heard this somewhere else, I'm ceiling it, but it's just how bad human beings are at exponential growth. And I'll…

Speaker 4

Is it Thomas

Brian Gracely

Watson? I think it's Thomas Watson, the founder of IBM, was like, we can't see a market for more than five computers in the world. So, yeah.

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.