Jun 11, 2026 · 1h 15m · news
SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, Harry Stebbings, Rory O'Driscoll, and Jason Lemkin dissect late-stage market trends, including the landmark IPO strategies of SpaceX and OpenAI, the operational economics of AI-driven startups, and the strategic plays of tech giants like Uber, Microsoft, and Bending Spoons.
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 12.6% of the talking time here. How this is scored →
Harry as informed peer 3.2 Guest teaching 4.0 Guest disagreement 3.1 Harry pushing back 2.6
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 8:54 Rory mocks Harry's focus on short-term predictions
Rory aggressively ribbs Harry for asking about day one and day ninety price targets, calling him a little media slut who only cares about horse-race commentary.
Hardest push from Harry ▶ 39:03 Harry rejects Rory's take on LP rejectionsHarry directly refuses Rory's premise that LP turndowns stay with you forever, asserting that true revenge is completely forgetting those LPs ever existed.
Biggest teaching moment ▶ 14:05 Rory corrects Harry's LP geography errorRory explicitly calls out Harry's confusion between the Ontario Teachers Pension Plan and Ohio teachers, mocking his lack of distinction between Canadian and US geography.
Harry holds his own ▶ 58:56 Harry counters Rory with precise semiconductor dataHarry interrupts Rory's generalized macro market explanation by citing precise figures on Broadcom's sixteen billion dollar guidance missing expectations.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Analyzing SpaceX's Fixed-Price IPO Roadshow | 2 | 6 | 5 | 3 | Rory dominates the financial analysis of SpaceX's fixed-price IPO structure, explaining mechanics of price discovery and base rates. He playfully attacks Harry for asking about day one price predictions, calling him a media slut. Harry accepts the framing and lets the guests lead the technical analysis. | |
| OpenAI's Public Filing Strategy | 2 | 5 | 4 | 2 | Rory explicitly corrects Harry when Harry confuses the Ontario Teachers Pension Plan with Ohio teachers and jokes about Harry conflating Canada and the US. Jason and Rory analyze OpenAI filing expectations while Harry asks standard transition questions. | |
| The Evolution of Always-On AI and Siri's Future | 2 | 4 | 2 | 1 | Jason and Rory explain AI memory architectures, token economics, and Ben Thompson's analysis of consumer versus enterprise AI. Harry functions primarily as a topic prompt generator and observer of Rory's facial expressions. | |
| Uber's HR Cuts and Autonomous Driving Rollout | 3 | 3 | 3 | 3 | Harry boasts about his stance on HR departments before asking about Uber's headcount cuts. Rory questions whether 23 percent cuts are actually AI-driven or just standard rationalization, steering the conversation to autonomous driving. | |
| Revolut and international Fintech Disruption | 5 | 4 | 4 | 6 | Harry directly pushes back against Rory's assertion that LP turndowns cut deep and stay with you forever. Harry shares his personal experience as a founder/fundraiser, arguing that forgetting LP rejections exist is the best revenge. | |
| startups Reaching Scale with Extreme Headcount Efficiency | 2 | 3 | 5 | 1 | Jason and Rory engage in a heated peer debate over headcount efficiency and sales team sizes in AI startups. Rory pushes back on Jason's model by pointing out high token compute costs versus employee spend. | |
| Elon Musk's Masterclass in GPU Capacity | 3 | 5 | 2 | 1 | Harry asks if Elon Musk's acquisition and GPU capacity strategy was the play of the year. Rory provides a detailed breakdown of Musk's compute infrastructure moves and arbitrage strategy. | |
| Fintech and AI Valuations: Ramp and Suno | 2 | 4 | 2 | 1 | Rory explains financial services valuation multiples versus growth adjustments for Ramp and Revolut. Jason shares personal usage metrics and skepticism regarding Suno's valuation path. | |
| Macro Market Dynamics and the Bravery of Capital | 5 | 3 | 3 | 5 | When Rory attributes recent market dips to general sentiment and interest rate fears, Harry interrupts with specific earnings data regarding Broadcom's guidance miss. Harry uses hard stats to challenge Rory's generalized macro narrative. | |
| Bending Spoons' High-Margin Consumer Roll-up Playbook | 3 | 5 | 3 | 2 | Rory details the Bending Spoons roll-up playbook of aggressive cost-cutting and price hikes on sticky consumer cohorts. Harry adds playful banter about Rory paying for Evernote. | |
| Organic vs. Inorganic Growth in the Markets | 3 | 4 | 2 | 2 | Harry asks whether private market mega-rounds undermine the public market bar, citing Databricks. Rory explains the fundamental difference between software cash flow needs and foundation model capital requirements. | |
| Microsoft's Model Stagger and Model Consolidation Risks | 6 | 2 | 2 | 4 | Harry demonstrates strong domain context by citing specific arguments from his recent interviews with the CEOs of Nabius and Perplexity. Rory acknowledges the significance of Microsoft attempting to reduce reliance on OpenAI. |
Statements from this episode (39)
Lemkin: SpaceX IPO will be a dud and will not trade up
“I think the IPO nominally will be a dud. I don't think it will trade up dramatically.”
O'Driscoll: Market contractions stem from investor fear, not lack of capital
“There's always money when people aren't afraid. When things get scary, it's not that money runs out, it's that money gets scared.”
O'Driscoll: The 2020s will produce two trillion-dollar startup outcomes
“I think you're going to have one trillion dollar outcome from the last decade and two, it looks like from this decade, if it all happens according to plan.”
O'Driscoll: Larger VC fund sizes require proportionately larger exit valuations
“Fund size dictates the level that, the amount of market cap it takes. It's a Josh Koppelman thing from ages ago, you know, the Venture Arrogance Index, whatever, right? The bigger the fund, the bigger the deal it has to be to make it work.”
O'Driscoll: Ontario Teachers' Pension Plan will make over $10B on SpaceX
“Who will make, I think, over ten billion dollars from their SpaceX. To clarify, I know you think the entire Midwest is the same, Harry, but I think it's Ontario teachers.”
O'Driscoll: SpaceX is the highest-returning VC deal ever in absolute dollars
“This is the best Venture capital deal ever in terms of absolute return.”
Lemkin: Non-persistent AI will look archaic within two years
“I do think we're gonna look back in two years And think of this non-persistent AI as almost archaic, right? It's almost sort of desktop-like.”
O'Driscoll: Apple pays Google $1B for Gemini while receiving $20B for search
“I think, to some extent, they're giving in the sense that they're paying Google a billion dollars to use their model as the default model, but reminder, Google pays them, I think, 12 or 20, I used to know the number, twenty billion dollars to be the default se…”
O'Driscoll: Consumer AI will be tougher for OpenAI than enterprise
“I think actually, you know, the consumer space is going to be a tougher space for open. The enterprise space has really been validated. Cause an enterprise is all about automation efficiency and a consumer space. It's about experiences. Apple's well-placed to …”
Lemkin: AI will manage parts of HR better than biased humans
“But I do think HR is one of these areas that in many parts of it will be better managed by AI. I think an AI can be a better VP of HR for certain parts of the job than a biased human.”
O'Driscoll: Autonomous vehicle deployment is moving much slower than expected
“This stuff is still moving way slower than I think people anticipated. It hasn't been, you know, way more in San Francisco resulting in, you know, way more everywhere within six months. It's been a long, steady progress. For Waymo.”
O'Driscoll: Revolut's valuation stems from fat, inefficient European banks
“Because the European banks, unlike the American banks in general, are so crappy. There's a reason that Revolut's worth a hundred and fifteen billion, because the incumbent European banks were fat, dumb, and happy, and making margin off their customers.”
O'Driscoll: Non-lending fintech giants like Revolut threaten banking economics
“At some point we're going to have to deal with the fact that the largest bank by market cap Doesn't do much lending, and that's actually going to be a real problem in the aggregate because the whole point is of banking is to recycle savings into lending.”
Lemkin: Founders Hold Grudges Far More Than Venture Capitalists Do
“Founders hold grudges in a way that VCs actually, I think don't because VCs, you miss the deal. You got to find another bus, right?”
Lemkin: Uber Leaders Are Justified in Hating Benchmark Capital
“I think the folks that hate benchmark from Uber, I think they deserve to hate benchmark.”
O'Driscoll: Vinod Khosla Achieved Forbes Midas List Success 30 Years Apart
“He was on the Juniper list for the first, he was on the Midas list the first time for Juniper and he's on the Midas list this year for OpenAI. And there's 30 years between those two events.”
Stebbings: Lovable Reached $500M ARR With 146 Employees
“Lovable, so literally just before we came on, Lovable hit five hundred million of error. The number, number was wrong. So five hundred million of error with 146 employees.”
Stebbings: Cursor Hit $4B Valuation, Targets $6B By Year-End
“Cursor has hit four billion, and it's targeting six billion at the end of the year.”
O'Driscoll: Anthropic Sales Force Will Resemble Oracle's Within 5 Years
“The entropic sale force in five years will look like the Oracle sales force, the Microsoft sale force, and the IBM sale force, 50 years ago”
Lemkin: Replit Is Hiring 250 Sales Reps This Year
“I know Replit's hiring 250 sales reps this year, so that's going to look very much like a traditional organization.”
Lemkin: Future Startups Will Be Half the Size Per Revenue
“My sense is that roughly over the coming years, startups will be half the size that they used to be for revenue, including enterprise.”
O'Driscoll: Musk earns $2B monthly selling compute to Anthropic and Google
“He found two of his biggest competitors who want to buy from him. You know, he's getting two billion a month, 1.25 from an topic and nine 50 from, no, the other way around, nine 50 from a topic, 1.25 from Google, the other way around, two billion a month. Two …”
Stebbings: Ramp Raised $750M at $44B Valuation, Surpassing $1B ARR
“Ramp raises seven 50 at 44. We've discussed Ramp a lot. Tripled in a year. Cross a billion in ARR. Positive free cash flow.”
Stebbings: Suno Raised $400M at $5.4B Valuation Led by Bond
“Suno the AI music creator company raised four hundred million and a 5.4 billion. Teasing first license model. Bond led that one. It was double the previous valuation just six months ago.”
O'Driscoll: Fintechs Trade on Financial Multiples Adjusted for Growth
“They'll trade like financial companies, financial services companies, but they will be adjusted for growth.”
O'Driscoll: Revolut Generates $4.5B Revenue and $1.5B Operating Income
“And it's the same bet with Revolut. They raising at a hundred and something, they're doing what? Four and a half billion in revenue, you know, 1.5 billion in operating income, which is fricking amazing.”
Lemkin: Skeptical of Suno's path to a $20 billion outcome
“You know, the rate at which that valuation doubled and you know, the twenty billion dollar outcome for it, I'm not smart enough to see it yet. So it feels a little bit to me like risk on, right?”
Stebbings: Bending Spoons filing US IPO at $20B valuation
“Evernote, Vimeo, WeTransfer, AOL, Eventbrite, a very massively executed roll-up strategy, a 1,000,000,003 in revenue, and they're filing to go public at twenty billion dollars on in the US from Italy.”
Lemkin: Bending Spoons reaccelerated Evernote growth with 20% of staff
“Evernote reaccelerate, Evernote was dead and they reaccelerated the growth of Evernote, right? With a fifth of the employees.”
O'Driscoll: Bending Spoons' $20B IPO valuation lacks organic growth justification
“Should it go public at 20 times revenues or 15 times revenues? Maybe not, because you are relying on the acquisition for, I mean, you're not getting organic growth. You're getting a profitable business and, you know, you probably have to look at the sustainabl…”
O'Driscoll: Legacy consumer tech shares vertical SaaS pricing power
“What these guys realize is there's similar opportunity in the consumer side, which, you know, just as, you know, the whole idea was in these verticals, no one's going to change their car dealer accounting system because they put prices up 20%. In the same way,…”
Lemkin: Public markets do not care if growth is organic or inorganic
“I'm not even convinced the markets care as much as we think, whether it's organic or inorganic.”
Lemkin: Bending Spoons raised Evernote's average subscription price from $75 to $250
“If they can do what they did with Evernote, which is raise the pricing from 75 to 250 dollars a year on average, right?”
Stebbings: Databricks raised privately at $165B, up from $134B
“Databricks come out today. No, no. We're going to do another round. We're going to do another round. One hundred and sixty five billion price up from one hundred and thirty four billion earlier this year.”
O'Driscoll: Databricks fetches a higher private multiple than public Snowflake
“Databricks can get capital at a higher revenue multiple because they're higher growth rate than Snowflake can and on hassle-free terms.”
O'Driscoll: Foundation models require 100x to 1,000x more capital than software
“The amount of money that you need to build a foundation model is two or three orders of magnitude more than anything else.”