May 28, 2026 · 1h 27m · news
OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds · 20VC with Harry Stebbings
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Host Harry Stebbings, Rory O'Driscoll, and Jason Lemkin deliver a high-energy, financial analysis of the AI ecosystem, examining OpenAI and SpaceX's S-1 filings, massive infrastructure funding rounds, and the broader shift toward hyper-efficient corporate structures.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 8% of the talking time here. How this is scored →
Harry as informed peer 3.4 Guest teaching 3.4 Guest disagreement 4.3 Harry pushing back 3.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 24:09 Jason aggressively rejects Harry's COVID overhiring premise
When Harry attributes recent tech layoffs to COVID overhiring rather than AI efficiency, Jason calls it the dumbest take on Twitter and directly attacks the logic.
Hardest push from Harry ▶ 16:44 Harry calls out Rory on Anthropic's margin expansionHarry explicitly interrupts the guest narrative to state that Rory missed the core number, citing exact gross margin expansion from 38% to 70% and a $559M projected operating profit.
Biggest teaching moment ▶ 24:25 Jason educates Harry on natural attrition compounding mathJason breaks down annual attrition rates of 15-25% over five years, proving mathematically why blaming current tech layoffs on 2020 overhiring is logically unfeasible.
Harry holds his own ▶ 16:44 Harry demonstrates specific financial expertise on AnthropicHarry showcases detailed preparation by pulling specific margin trajectory numbers and quarterly operating profit projections to correct Rory's earlier revenue focus.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| NVIDIA's Massive Earnings & AI CapEx ROI | 3 | 3 | 2 | 3 | Harry facilitates the discussion on NVIDIA's earnings and asks whether Jensen Wang's $3-4 trillion CapEx projection is realistic. He offers a brief hypothesis about core business differences at 14:04, which Rory gently corrects by refocusing on software developer leverage. | |
| Anthropic's Margin Expansion & Layoffs Debate | 6 | 7 | 8 | 6 | Harry opens strongly by highlighting Anthropic's gross margin expansion to 70% and projected operating profit, catching Rory slightly off guard. However, when Harry suggests recent tech layoffs stem from COVID overhiring rather than AI efficiency, Jason aggressively calls it the dumbest take on Twitter and schools Harry on compounding attrition math over five years. | |
| OpenAI's Confidential S-1 Filing & Public Market Race | 3 | 3 | 2 | 2 | Harry guides the conversation around OpenAI's confidential S-1 filing and asks if they are rushing to beat Anthropic to market. Rory and Jason dominate with detailed revenue run-rate comparisons and public market positioning logic while Harry prompts smoothly. | |
| SpaceX's Massive S-1 Drop & the Elon Premium | 2 | 3 | 4 | 2 | Harry asks Rory to break down the key figures in SpaceX's S-1 filing. Jason strongly criticizes the valuation at 100x trailing sales as madness and financial engineering, while Rory analyzes the sum-of-the-parts and data center possibilities. | |
| Pulsia ("AI Slop") & the Ethics of Cold Outreach | 4 | 2 | 5 | 4 | Harry introduces Pulsia ('AI Slop') and its $250M valuation, noting he met the founder during the raise and highlighting it is a one-person team. Jason tests the app live on air, praising the onboarding flow but sharply criticizing its paywall before value delivery. | |
| Exa and OpenRouter's Mega Rounds & Agentic Infrastructure | 3 | 3 | 4 | 2 | Harry prompts analysis on Exa and OpenRouter's mega-rounds, asking for the upside case for agentic infrastructure at a $2.2B valuation. Jason argues that seed investing is for suckers when AI companies break out instantly, prompting Rory to defend early-stage venture risk-reward dynamics. | |
| Rage Bait: Vibe Coding & the Human-Token Balance | 3 | 3 | 5 | 2 | Harry presents three viral rage bait statements from an interview regarding vibe coding away Salesforce and token pricing tolerance. Jason and Rory pick apart the premises, with Jason calling vibe-coding away enterprise CRMs unhelpful clickbait and Rory demonstrating why willingness to pay double for tokens implies under-investing in AI projects. |
Statements from this episode (34)
O'Driscoll: Anthropic Matched Its Full Prior Year Revenue in Q1
“So, Anthropic has done as much in Q-one as all of last year, and OpenAI has done 30% of what they've done last year in Q-one.”
O'Driscoll: Anthropic Will Pass OpenAI in Scale and Profitability Shortly
“Within a couple of quarters, Anthropic will be visibly and obviously ahead. Profitable, growing more quickly, and bigger.”
O'Driscoll: Current Tech S-1 Filings Are 'Madness' and Unbuyable
“I think it's all madness. I wouldn't buy a share.”
Lemkin: High-Flyer AI Valuations Are 'SolarCity on Steroids'
“It's solar city on steroids, and we're all here for it because we love AI, but it makes no sense.”
O'Driscoll: Nvidia's $50B Quarterly Profit Makes It World's Most Profitable
“It's the 50 something billion in profits, which makes it the most profitable company on the planet, because typically Google clocks in around a hundred to a hundred and twenty billion now a year. Right? These guys, in a quarter, made fifty billion plus, fifty-…”
Lemkin: 7% of All Americans' Life Savings Are Concentrated in Nvidia
“Seven percent of all Americans life savings are essentially in Nvidia this morning with concentration.”
Lemkin: Corporate AI Spend Will Bifurcate Based on Revenue Per Employee
“We're going to enter a world where things are more and more bifurcated and we will see folks who get more and more gains from AI spend. They will token max forever, right? Often folks well north of a million in revenue per employee, two million in revenue per …”
O'Driscoll: Aggregate AI Serving Costs Increase Despite Cheaper Per-Token Prices
“Price per token, price for all those metrics going down amazingly every year, but token consumption going up every year, because as these models do more agentic reasoning, the total compute cost of that goes up. So, so the net cost of serving the customer goes…”
O'Driscoll: Meta Is Spending Billions on AI Without Demanding ROI
“There's no one at Facebook yet, or that might change, saying, are we getting value from our billions of dollars in AI? We just assume we are and keep going, right?”
O'Driscoll: Anthropic GAAP Revenue Doubled From $5B to $10B
“The proof that the sluice gates are open is you just look at Entropic going from five billion in gap revenue to ten billion in gap revenue.”
Stebbings: Anthropic Gross Margins Reached 70% With $559M Projected Q2 Profit
“Gross margin, gross margins expanded from 38% to 70%, and they're going to have a five hundred and fifty nine million operating profit in QT, QT projected.”
Lemkin: Anthropic Doubled Enterprise Pricing and Costs Twice as Much as OpenAI
“It has become a premium product since the end of last year. It is twice the cost of its competitor, right? Especially at the, after four, six, it started to charge enterprises clearly per token per use case. They charge them directly. Prices doubled. It is a p…”
Lemkin: Blaming Tech Layoffs on COVID Overhiring Is Mathematically False
“I'm saying there is already more natural attrition since Twenty-twenty than these numbers. So blaming it directly on overhiring is clickbait. It's clickbait because it's not mathematically true.”
Lemkin: My Team Does With 2.5 People What Used to Require 20
“I mean, we've gone not to be a broken record we're doing with two and a half people. We're doing what we did with 20 and everyone's get paid more on my little team, right?”
Lemkin: $2M Revenue Per Employee Is New Normal For Scaling Startups
“I think two million per employee is going to become the new normal as you scale. And that will mean that your high performers can make two to three times what they used to make, just like an anthropic because you just don't need as many people and you're going…”
O'Driscoll: Market Runner-Ups Must Not Wait for the Leader to IPO
“When you're number two, what you do not do is wait till the number one prices goes public, and then you come out as a pale version of that.”
O'Driscoll: Anthropic Requires $4 to $5 CapEx Per Dollar of Revenue
“In the case of Entropic, even though you are not bearing those capital needs today because you are lucky enough to have hyperscalers foolish enough to build on your behalf, for every dollar of revenue that you add, someone has to invest four or 5,000,000,004 o…”
Lemkin: SpaceX Is Allocating 30% of Its IPO to Retail Investors
“Elon's putting 30% of the, you know, this massive IPO, the largest in history so far, into retail.”
Lemkin: X Revenue Has Shrunk 50% Since Musk's Acquisition
“Twitter's, Twitter's just, growth has fallen off, it's shrunk 50% since he bought it.”
O'Driscoll: xAI Rented Colossus Cluster to Anthropic for $1.25B Monthly
“They've rented that to Entropic for 1.25 billion a month, right, with a, I think, a ninety-day cancellation clause on either side.”
O'Driscoll: Starlink Will Drive Most of SpaceX's Value by 2030
“I think Starlink will be the vast portion of the value. The value, I don't think data centers in space will be a meaningful percentage of revenue.”
Lemkin: CoreWeave and Nebius Have No Special Technology
“I mean, Corweave has nothing. What do Nebius and Corweave have? Nothing, no special technology, right?”
O'Driscoll: Low Cost of Capital Is Key to Data Center Success
“Cause remember the one thing you need to be successful in a CapEx intent of data center business is a low cost of capital.”
Stebbings: Pulsia Raised $30M–$40M at a $250M Valuation
“They raised 30 to forty million bucks, I can't remember the exact amount, at a two hundred and fifty million dollar valuation.”
Lemkin: AI Tools Charging Before Delivering Value Usually Disappoint
“My general experience in agentic tools like this is that when they ask for money before they deliver any value, it's not that good. Like the marketing exceeds the value of the tool.”
Stebbings: $250M Startup Pulsia Is Operated by a Solo Founder
“I met them as part of the fundraise to be very candid. It is one founder. There's no team. There's no them.”
Lemkin: In AI Venture, Seed Investing Is for Suckers
“And I just think this going back to seed is for suckers. Like you want to invest the hour it blows up. The minute it blows up, you want to get the DM and just wire the money in AI. That's the play.”
O'Driscoll: Startup Risk Drops Non-Linearly When Moving to Initial Revenue
“There's a quantum reduction in risk when you go from no revenue to revenue, and then there's a linear reduction in risk thereafter.”
Lemkin: Over 90% of Neon Databases Are Built by AI Agents
“At Databricks neon, which is their super base competitor, over 90% of the databases are built by agents, not by humans.”
O'Driscoll: Standalone AI Infra Tools Will Emerge Outside OpenAI and Anthropic
“There probably is going to be five or six things like a database, like a search engine, like some kind of observability where, you know, over the next two or three years, revealed preference will say, you know, the vast majority of developers realize they need…”
Lemkin: SaaStr Moved to Headless Salesforce and No Longer Logs In
“We moved to headless Salesforce. Okay. We don't log into Salesforce anymore.”
Lemkin: SaaStr's AI VP of Marketing Costs $257 Per Month
“Our AI VP of marketing customer success costs, 257 dollars a month.”
Lemkin: The AI Bottleneck Is Human Processing Capacity, Not Cost
“There's a different issue coming, which is coming for more of us in tech, which is that our humans just can't process all the output.”
O'Driscoll: AI Output Overload Will Increase Demand for High-Value Humans
“In that case, you need to hire another human. Because if the AI is giving more good ideas than the humans can process, and this is kind of a whole nation of compliments and substitutes. If the AI is now giving more ideas than one human can process, and they're…”