Apr 9, 2026 · 1h 32m · news
OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
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In this episode of 20VC, host Harry Stebbings, Jason Lemkin, and Rory O'Driscoll dissect the financial and executive shifts at OpenAI and Anthropic, the historic scale of SpaceX's projected IPO, and the broader technical implications of AI agents, database infrastructure, and cybersecurity threats in the venture landscape.
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 11.3% of the talking time here. How this is scored →
Harry as informed peer 3.2 Guest teaching 4.2 Guest disagreement 2.8 Harry pushing back 2.3
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 20:21 Rory calls bullshit on OpenAI acquiring media assets
Rory forcefully rejects Jason and Andreessen's strategic justification for OpenAI buying TBPN, calling media acquisitions a distraction and vanity project.
Hardest push from Harry ▶ 42:09 Harry refutes Jason's dismissive take on Doug LeoneHarry directly refuses Jason's framing that Doug Leone was brought back to satisfy LPs or that young founders don't know him, passionately arguing Leone closes competitive growth deals.
Biggest teaching moment ▶ 1:29:02 Jason explains the shift to agentic marketing arbitrageJason breaks down how AI marketing tactics mirror the golden era of SEO arbitrage, prompting Rory to admit Jason crystallized a major strategic insight.
Harry holds his own ▶ 42:09 Harry showcases founder and deal knowledge against JasonHarry steps out of host-listener mode to challenge Jason's premise, citing specific European founders and competitive deal dynamics with Founders Fund and Andreessen Horowitz.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Anthropic's Meteoric Rise vs. OpenAI's Cost Structure | 3 | 3 | 2 | 2 | Harry prompts the topic regarding Anthropic's $30B ARR and OpenAI's cost structure. The guests engage in a collaborative analysis of compute constraints, valuation multiples, and public short/long dynamics while Harry largely moderates. | |
| OpenAI's Management Team Turnover & "Reboot" | 2 | 3 | 2 | 1 | Harry lists the recent executive departures at OpenAI and asks the guests how to interpret the management turmoil. Jason and Rory analyze the operational risks of bringing in high-profile external leaders during organizational reboot. | |
| OpenAI's Acquisition of TBPN | 4 | 4 | 8 | 3 | Rory aggressively attacks the acquisition of TBPN as an insane vanity project, forcefully calling bullshit on Jason's bull case argument about turning balance sheet cash into marketing assets. Harry asks questions to explore both sides while the guests debate intensely. | |
| SpaceX's Projected $2 Trillion IPO & The Power Law in Tech | 3 | 4 | 2 | 2 | The panel discusses SpaceX's confidential IPO filing and the psychological impact of power law distributions in venture capital. Harry asks whether public markets will digest the $2 trillion valuation, prompting guests to detail the Elon premium. | |
| Doug Leone's Return to Sequoia Capital | 6 | 3 | 5 | 7 | Harry actively resists Jason's premise that Doug Leone returned to Sequoia solely to calm LPs. Citing specific competitive dynamics against Founders Fund and Andreessen, Harry forcefully argues that Leone was brought back as an elite deal closer. | |
| The Delve Fraud Scandal & YC Community Code | 2 | 4 | 2 | 1 | Harry raises the expulsion of Delve from Y Combinator following compliance misrepresentations. Jason and Rory explain why breaking the founder code by stealing code from a batchmate triggers swift removal. | |
| OpenRouter & The Multi-Product Playbook | 3 | 5 | 2 | 2 | The guests detail OpenRouter's business model, take rates, and revenue trajectory, comparing it to Twilio, RevenueCat, and Visa. Harry prompts on valuation sustainability while the guests explain multi-product expansion requirements. | |
| Supabase & The AI-Driven Database Explosion | 3 | 5 | 2 | 1 | Jason educates the panel on how autonomous agents are generating more databases than human software developers, establishing Supabase as a primary beneficiary. Rory adds historical comparisons to MongoDB and past cloud shifts. | |
| VCs as Enablers vs. Founder-Honest Boards | 4 | 4 | 4 | 4 | Jason argues that overly supportive VC cheerleaders enable company death spirals during AI disruption. Harry defends the need for supportive board relationships before Rory articulates the balance of being founder-honest. | |
| The McCaw Security Breach and Customer Fallout | 3 | 4 | 1 | 2 | Harry brings up the Mercor/McCaw security breach and customer fallout transparently. Jason outlines the zero-tolerance policy enterprise hyperscalers maintain regarding third-party vendor breaches. | |
| AI Cybersecurity and the Future of Automated Attacks | 2 | 5 | 1 | 1 | The guests break down how AI agent swarms will automate cyberattacks at scale, rendering traditional security infrastructure obsolete. Harry listens as Jason and Rory outline why security budgets must surge. | |
| Agentic Marketing and the $1.8B GLP-1 Arbitrage Case Study | 3 | 6 | 2 | 1 | Jason explains the case study of a two-person team generating massive GLP-1 sales via AI marketing arbitrage, drawing parallels to early SEO growth tactics. Rory acknowledges Jason's insight as a key take for the episode. |
Statements from this episode (38)
Rory O'Driscoll: Owning media assets yields less money and takes more time
“Owning a media asset invariably takes way more time than you think for way less money than you expect.”
Jason Lemkin: Anthropic's training costs are one-quarter of OpenAI's
“Their training costs are a quarter of OpenAI.”
Jason Lemkin: OpenAI investors received worse terms than Anthropic investors
“It really feels like the investors in OpenAI got a much worse deal in the last round than the Anthropic ones did.”
Jason Lemkin: SpaceX, OpenAI, Anthropic combined IPO values will top past 20 years
“The big three, SpaceX plus OpenAI plus Anthropic, their value at IPO will exceed every other IPO for the last 20 years combined.”
Lemkin: Anthropic reached $30B valuation in five years versus Salesforce's 25 years
“Getting to thirty billion up from nine billion at the start of the year. I mean I think it took, I mean, Salesforce is the largest software company, right? Or at least cloud one. And it took them 25 years to get there. Anthropic got there in five, but maybe th…”
O'Driscoll: Startup employees should always take advantage of liquidity windows
“When the liquidity window opens, take it seriously, because it might not open again for a while, right?”
Lemkin: OpenAI's executive reboot stems from Anthropic outpacing them
“If we step back a minute, it ties to Anthropic passing them. You don't just sit there and make no changes on the team when your competitor over the last six months has radically changed the competitive posture.”
Lemkin: Bringing in external executives during corporate turmoil fails 70% of the time
“In my experience, I don't know what you guys think. In my experience, that has about a 30% chance of success. Just roughly. That bringing in the big, the perfect LinkedIn, giving them a massive portfolio and either attaching them to, and attaching to this some…”
O'Driscoll: OpenAI's rapid executive departures smack of management carelessness
“To me, even all these people change, you know, I, I'm tempted to make that, you know, that the famous Oscar Wilde quote in the importance of being earnest, you know, to lose one parent might be an accident when he was talking to the, this woman was talking to …”
O'Driscoll: OpenAI's acquisition of TBPN is an absurd vanity project
“So I challenge that. I think it's a vanity project and absurd.”
Lemkin: Probability of corporate champions staying committed after 12 months is single digits
“Because the odds that VP that wants to do the deal is there in 12 months and that their priorities have not changed, you know, approaches single digits.”
O'Driscoll: OpenAI at $380B valuation is a better buy than Anthropic at $850B
“I would argue that you would buy OpenAI on one proviso. You could sit down with the board and say, what are you going to do about this? Because it doesn't take a lot to fix this thing, right? To just stop screwing around and focus, right? And, you know.”
O'Driscoll: AI compute constraint will be a major bottleneck in 2026 and 2027
“But now it looks like compute constraint is a real thing in 26 and early 27. You have that asset. Maybe you figure out how to deploy that aggressively with Codex. So there's buttons you can press, there's things you can do if you focus and do them.”
Lemkin: Investing in OpenAI at high valuations is too risky due to non-technical leadership
“I'm just not into the tumult at open AI. I'm not into the drama. I'm not into a non tech, non deeply technical founder leadership. It's just not my vibe. Like I wouldn't invest in anything like open AI at a high price. It doesn't matter what it is. Cause it's …”
Lemkin: Small acquisition safety nets are necessary for startup M&A
“No one loses their job in Adobe over the small chip deal. Otherwise it would never happen. No one would take any risk in buying an emerging company, right? They just wouldn't do it.”
O'Driscoll: Power law dynamics make venture capital psychologically brutal
“Psychologically, the thing about a power law they don't tell you is you can have the third best outcome in venture history and be only one-tenth as large as The largest outcome in venture history, and if you're going to let that into your head, it's going to b…”
Lemkin: Elon Musk will force underwriters to meet SpaceX target IPO valuation
“I think Elon, what Elon said Publicly on X, it ain't going to be two trillion. Maybe he'll change his mind. He said two trillion was too high. So whatever his number is, I think he's going to get it on IPO day. He's going to will it into existence. The underwr…”
O'Driscoll: xAI is at best fourth in LLMs while burning $12B yearly
“We just had a long conversation on Entropic versus OpenAI, And they're kind of number one and two in this space, and Gemini, Google is almost certainly number three, so x.ai is number four in the kind of model LLM space at best, burning twelve billion dollars …”
Lemkin: VC limited partners are uncomfortable with firm leadership changes
“LPs are uncomfortable with change. LPs say that they're looking at the new generation and the Vanguard. But they are comfortable when the old leadership is still actively involved in the fund. It does make LPs more comfortable whether they're writing, investin…”
O'Driscoll: Test VC partner hires on whether their deals beat existing partners
“One of the check questions we always ask when we're hiring someone and thinking about it, and in this case you are effectively hiring someone, is do you think the next check that they'll write will be better than a check that one of us will write?”
O'Driscoll: Sequoia's initial leadership transition to Botha was unsuccessful
“The transition, having made one transition to Roloff and having had to make another transition abruptly means the first transition wasn't that successful.”
Lemkin: Investors will discover more portfolio companies fabricating audits with AI
“We're going to find more, more portfolio companies did that.”
O'Driscoll: OpenRouter will not reach $10B valuation without multi-product expansion
“So, do I think OpenRoto will get to ten billion in value on just what they do today? No. And if they just keep doing what they're doing today, no more than the inference guys, no more than the labeling guys, when things slow down, all these businesses will get…”
Lemkin: Low-ACV AI startups must build 5 distinct products to hit $1B ARR
“The reality is you have to go truly multi-product earlier in this type of situation. Not, not just a little feature, right? Not just a little enhancement. But you literally probably have to build five distinct products to get to that billion and not you know, …”
O'Driscoll: Foundation model AI companies will survive any market crunch
“Because look, the truth, even when the crunch comes, the foundation model companies make it. Because they, they're on top of the heap. They have the high intellectual property asset, right? They're going to make it.”
Jason Lemkin: AI Agents Now Create More Databases Than Humans
“Database is a world where already the agents are creating more databases than humans. We've already crossed that line”
Rory O'Driscoll: Supabase Will Become a Legacy Database Within 10 Years
“Over the next five years, that will mean adding complexity, adding functionality. And in 10 years time, someone, and it won't be me at that point, will be saying, oh, my God, those legacy Superbase products, they're almost as bad as MongoDB, and there'll be a …”
Lemkin: VCs are acting as pre-AI enablers instead of declaring code red
“I just see too many VCs running a pre AI enabler playbook. Where, where, where when folks do fall behind a tick or two, the, you see kumbaya activity instead of code red activity.”
Lemkin: Portfolio company with $100M+ revenue faces severe AI competition
“For example, I'm a, I'm an investor in a company that's crossed nine figures in revenue, but it is hitting massive AI competition and issues.”
O'Driscoll: Board members are useless without product knowledge and competitive honesty
“You're not a useful board member unless A, you understand what the company does and how it compares to the direct competitors, ideally with hands-on experience of the products. And then B, you find a way without being a jerk, To keep the company honest about w…”
Lemkin: Recent security breach could be fatal for AI startup Mercor
“I just don't see how you would come back from this. If you've crossed, there's just no, unless you have to, I think it's potentially death.”
Lemkin: Enterprise buyers historically gave software vendors one pass on security breaches
“In the old days, like through 20, 23 in our lifetimes, you always got to pass once as a vendor. Even for the worst breaches, the worst issues, unless your app was down for weeks, you'd get called into the CISO's office. You'd get yelled at. It was brutal, but …”
O'Driscoll: Mercor will survive its security breach and rebuild customer trust
“And my guess is the likely outcome is You lose a fair amount of revenue. You lose a fair amount of time. You're going to have to spend a ton of money to bolster your defenses, but if you do the right thing, you'll be able to earn your way back slowly and over …”
Lemkin: Most B2B Startups Will Suffer Worse Cybersecurity Breaches Than Mercor
“I genuinely think that most B to B companies are going to get hit worse than Merkur.”
O'Driscoll: Drop in Security Stocks Following Anthropic Announcement Was Absurd
“The response of security stocks going down to the Anthropic announcement was absurd. I think anyone who's cutting back on the security budget in twenty-twenty-six is missing the point, right?”
Lemkin: Current Marketing Tactics Will Be Obsolete in Two Years
“The way we're doing advertising and marketing will seem incredibly dated in two years. Like only, only the creakiest companies will be doing marketing and advertising the way they do it today in two years.”
Shorts cut from this episode
▶ Anthropic has caught OpenAI in half the time · 20VC with Har (@0:32)
▶ Every business owner needs to hear this in 2026 · 20VC with (@1:01:25)
▶ This week's #technews with Jason & Rory · 20VC with Harry St (@0:01)
▶ The bull case for Open router · 20VC with Harry Stebbings (@48:36)
▶ "the acquisition of TBPN was just insane" · 20VC with Harry (@15:46)