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OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber

Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more. Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others. ----------------------------------------------- Timestamps: 00:00 Intro 01:13 Anthropic Surpasses OpenAI in Revenue 12:07 OpenAI Management Reboot 17:51 OpenAI Buys TBPN 30:01 SpaceX Files for IPO Targeting $2 Trillion Valuation 38:56 Doug Leone Returns to Sequoia Capital 43:19 YC Kicks Out Delve 48:07 The Rise of Open Router 01:02:11 Supabase Targeting $10B Valuation 01:14:10 The Mercor Hack and AI Cyber Threats Moving Forward 01:24:09 The $1.8B Two-Person Company ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: https://x.com/harrystebbings Follow Jason Lemkin on X: https://x.com/jasonlk Follow Rory O’Driscoll on X: https://x.com/rodriscoll Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- Legal Disclaimer: The content of this podcast is for informational and entertainment purposes only and does not constitute financial or investment advice. Any discussion of stocks, public markets, or investment strategies reflects the personal opinions of the speakers and should not be relied upon when making investment decisions. Figures, valuations, and financial data referenced may be estimates or subject to error. Always consult a qualified financial adviser before making any investment decision. The views expressed are those of the individual speakers and do not represent the views of 20VC or its affiliates. ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #openai #anthropic #supebase #mercor #ai #spacex #ycombinator

Rory O’DriscollguestHarry StebbingshostJason Lemkinguest
Apr 9, 20261h 32mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

AI market power shifts, OpenAI turmoil, and cyber threats surge

  1. Anthropic’s reported revenue surge (to a $30B run rate) and lower training costs versus OpenAI reframes the competitive landscape and intensifies scrutiny on OpenAI’s valuation and execution.
  2. OpenAI’s leadership churn is interpreted as an attempted “code red” reboot, but the TBPN media acquisition is criticized as inconsistent with a focus-first mandate and likely a legacy deal from earlier priorities.
  3. SpaceX’s rumored $2T IPO plan is discussed as a power-law moment where a few mega-companies could outweigh decades of IPO value, with IPO-day pricing driven more by demand dynamics and Elon “premium” than fundamentals.
  4. Sequoia bringing Doug Leone back is seen as a “gravitas” move—helpful for deal-winning and continuity amid competition—while YC’s expulsion of Delve is framed as enforcing community norms after alleged fraud and code theft.
  5. The Mercor breach is treated as a warning that AI will amplify attack velocity and scale, making cybersecurity a top-tier budget priority even as many startups remain underprepared.

IDEAS WORTH REMEMBERING

5 ideas

Compute constraints drive pricing and product access decisions.

They argue that when model providers can’t expand capacity quickly, they ration via pricing and plan restrictions (e.g., limiting heavy agentic usage on flat-rate plans) and de-emphasize compute-expensive products with weak monetization.

Anthropic’s cost advantage compounds if revenue parity is real.

A competitor growing faster while spending materially less on training is described as a “double code red,” because it enables reinvestment, margin flexibility, and faster iteration—especially if the rival is distracted by internal turmoil.

OpenAI’s management reboot is understandable, but risky and incomplete.

Replacing/reshuffling multiple executives can be a rational response to competitive pressure, yet the panel flags “perfect LinkedIn” external hires with huge mandates as low-odds bets when the organization is already in flux.

The TBPN acquisition is mainly criticized as a focus-signaling error.

Even if it’s a “small chip” deal requiring limited executive time, they argue it clashes with a public/internal message of ruthless prioritization; several note it likely originated months earlier and wouldn’t be approved under today’s conditions.

Liquidity windows should be treated as rare opportunities—even at elite companies.

For employees holding private-company equity, the advice is to take tenders seriously because market conditions and company trajectories can change quickly, and future liquidity may not arrive on schedule.

WORDS WORTH SAVING

5 quotes

I'm gonna call bullshit, start to finish, on this whole discussion

Rory O’Driscoll

Their training costs for models are a quarter of the OpenAI. ... you're out accelerating your competitor, and your training costs are a fraction of your competitor. Good God, it, that, that just compounds.

Jason Lemkin

It's not a sign of strength where the majority of the round is not cash up front. Like, that's not... I don't think that's a sign of strength. That's a sign of, like, classically at least barely getting the round done, barely getting the round done

Jason Lemkin

To me, no matter what you get, I mean, we can discuss whether it's stupid on its face and whether, you know, buying media assets is the way to go... But stepping back one level, you're running a $25 billion company, the most exciting company on the planet. If the number... A- and you just told your entire internal team that you need to focus, and then buying... There's nothing that's more of a vanity project than buying a media company, right?

Rory O’Driscoll

The only reason we've been ha- hacked is no one cares about us.

Jason Lemkin

Anthropic vs OpenAI: growth, compute constraints, pricingOpenAI management turnover and go-to-market leadership betTBPN acquisition: media ownership vs focus and distractionSpaceX IPO dynamics and valuation power lawsSequoia leadership signaling and competitive positioningYC/Delve controversy: fraud, IP theft, ecosystem enforcementOpenRouter and Supabase as AI-infrastructure “picks-and-shovels”Mercor hack and AI-driven escalation of cyberattacksAI-enabled hyper-personalized marketing and the “two-person” company narrative

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