**Rory O'Driscoll** (0:00)
As it's becoming painfully clear now, no one in America, other than us here in California, likes the AI trend. We have people who are brilliant scientists, who politically are utter morons. And the people who are utter morons at AI, but brilliant at politics, are going to have us for lunch. At least when MEDA was busy destroying the world, they were smart enough to pretend it was all about bringing friends together and not destroying democracy.
**Jason Lemkin** (0:22)
We're going to have to reflate and hire thousands and thousands of people per tech leader to avoid social unrest. We see no signs that there's a short-term crash coming.
**Harry Stebbings** (0:32)
This is 20VC with me, Harry Stebbings. It's my favorite show of the week. Rory O'Driscoll, Jason Lemkin, analyzing the biggest news in tech. Starting off, Andre Karpathy joins Anthropic, an Anthropic Eye, a $900 billion evaluation for their latest fundraise. Then we dig into the public markets. Data Dog up 31%, Figma up 12%.
What happens from here? Next, we have Cerebras IPO, smashes expectations and breaks the $300 mark. And then finally, SpaceX, they set June 12th for the largest IPO in history, $1.75 trillion market cap, raising $75 billion.
But before we dive into the show today, let me tell you about Omni. It's an AI analytics platform and it solves a problem every scaling company hits. Your team needs insights, not just data lookups, the stuff that really matters, and it's critical to get it right. Like CAC payback periods and net dollar retention. For AI agents to act on your company data, they need your business context, your definitions, your logic, your permissions. And that's what Omni's governed context graph provides. Your data team defines it once, then anyone, your Ops lead, your CFO, your PM, can ask a question in English and get an answer in seconds. Perplexity, Mercury and DBT run on Omni, and 20 VC listeners get a free three week trial, three week, very specific, not a month, but three weeks. Go to omni.co/20vc, that's omni.co/20vc.
After Omni helps you find the right customers, Checkout helps you close them. Over the past 15 years, Guillem Puzas has led checkout.com through what he calls the velocity years, a period of hyper growth with relentless product building. The lesson, high growth is a gift, but it demands ruthless focus. As his mother put it, play the game you're good at. For checkout.com, that game is digital payments, obsessing over data, chasing basis points and compounding learnings over time. And that discipline is paying off. 2025, checkout.com processed over 300 billion in total volume, up 64% year over year and returned to full year EBITDA profitability. They now support over a thousand enterprise merchants globally, including 63 that process more than a billion annually, with brands like eBay, Vinted, Amex, Asos and Tmoo. Guillem's message though, it's pretty clear. They've earned the right to win anywhere. Now, they're investing in innovation across marketplaces, issuing, financial experiences and agentic commerce. If you want payments built for what's next, talk to the team at checkout.com. That's checkout.com. While Checkout powers the moment money changes hands, Invisible powers the people behind the work. Why don't we hear more real AI success stories from big companies? The models are insanely good, but implementation is the problem. It's really, really hard. There's data all over the place. There's legacy tech and manual workarounds. It's a Ferrari engine in a shopping cart. Meet Invisible. Invisible trains 80% of the top models and then adapts them to the messy reality of your business. Take the Charlotte Hornets NBA team. Invisible took years of game tape and analog scouting notes to go from uncertainty to a draft pick and Summer League Championship win in weeks, not seasons. Get the data in order first, and suddenly AI can do almost anything for you in the enterprise. If you want AI that hits the P&L, go to invisibletech.ai/20vc.
**Rory O'Driscoll** (3:58)
You have now arrived at your destination.
**Harry Stebbings** (4:01)
Boys, it is so good to be back. So we're going to kick off with our This Week in Anthropic. We have two. We have Anthropic in talks for $30 billion at above a $900 billion price, nearly tripling from $380 billion in February. Greeno, Sequoia, Altimeter, Dragoneer. And then yesterday, we had Andre Karpathy announcing that he was joining Anthropic. Over to you. How did we read this news?
**Rory O'Driscoll** (4:26)
Well, I did divide up the two. I mean, the financing, yes, they can pick their price. They can pick their investors. They can tell the amount and they can tell Evan to jump and Evan will say, how high, sir? It's all happening. They're going to raise $30 billion. We discussed. Obviously, the question is, you know, how those folks pencil out the return.
85 more minutes of transcript below
Try it now — copy, paste, done:
curl -H "x-api-key: pt_demo" \
https://spoken.md/transcripts/1000651996090
Works with Claude, ChatGPT, Cursor, and any agent that makes HTTP calls.
From $0.10 per transcript. No subscription. Credits never expire.
Using your own key:
curl -H "x-api-key: YOUR_KEY" \
https://spoken.md/transcripts/1000768877225