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Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1

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 01:19 Anthropic Eyes $900B Valuation & Andrej Karpathy's Shock Move 05:40 Unpacking Anthropic's $30 Billion War Chest 08:37 The True Cost of AI Tokens 23:12 Public Tech Rebound: Figma & Datadog Crush Expectations 27:26 The Death of Traditional Web Builders? The Decline of Wix & Squarespace 38:50 Compute Starvation: Is the Semiconductor & Hardware Boom Sustainable? 48:27 Cerebras IPO Smashes Day One 52:03 SpaceX Sets Date For the Largest IPO in History 01:02:30 YCombinator's Mic Drop Deal & The Drama Behind Elon Musk's OpenAI Lawsuit 01:13:03 The Looming Backlash: Mass Tech Layoffs and the Politics of AI ---------------------------------------------------------------------------------------------- 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 #anthropic #andrejkarpathy #elonmusklawsuit #openai #layoffs

Rory O’DriscollguestHarry StebbingshostJason Lemkinguest
May 21, 20261h 27mWatch on YouTube ↗

CHAPTERS

  1. AI hype meets political reality: why America is souring on the AI wave

    The episode opens with a blunt framing: outside of tech hubs, the AI boom is not broadly popular. The hosts set up a recurring theme—brilliant technologists often communicate poorly and invite backlash, while savvy political actors can weaponize public resentment.

  2. Anthropic targets a $900B valuation and hires Andrej Karpathy

    The panel reacts to two headline items: Anthropic’s prospective mega-raise and Karpathy joining. They discuss why elite talent moves matter for perception and why Anthropic can effectively set terms given demand.

  3. Do ARR multiples still work for frontier AI—or is it all DCF now?

    Rory and Jason argue about how investors are underwriting Anthropic at enormous scale. They claim late-stage Anthropic rounds look ‘post-IPO’ with reduced existential risk, making valuation risk the primary variable.

  4. Why raise $30B if the deal is so attractive to investors? Capex, burn, and balance-sheet war

    They argue the raise is rational because compute commitments are massive and the capital de-risks another year of burn. Anthropic can give up a small slice of equity to secure runway and negotiating leverage with hyperscalers spending on its behalf.

  5. Founder strategy contrast: Anthropic’s ‘low-drama cash’ rounds vs OpenAI’s structured mega-deals

    Jason posits Dario runs fast, clean financings (even at a perceived discount) to avoid drama, while OpenAI’s deals involve complex contingencies. The panel contrasts simplicity (cash in, done) with heavily structured commitments tied to future events.

  6. The real cost of tokens: Salesforce’s $300M spend and what it implies for AI TAM

    They break down Benioff’s claim that Salesforce spent $300M on Anthropic tokens, mostly for coding. The math shows it’s ‘normal’ per engineer, but the macro implications are huge: to justify frontier AI valuations, token spend may need to consume a meaningful share of payroll.

  7. Bear case on tokens: agents can be cheaper than expected (Klaviyo example)

    Jason shares how his team runs many agents with modest monthly spend, and recounts Klaviyo’s internal agent framework and surprisingly low agent operating costs. The implication: efficiency gains and better tooling could reduce required token volumes, challenging lofty revenue forecasts.

  8. Public SaaS rebounds: Datadog and Figma re-accelerate—but 2021 multiples won’t return

    They review strong quarters (Datadog, Figma) and argue the market has shifted permanently from ‘prospects’ valuation to more traditional revenue/growth/cash-flow metrics. SaaS can recover operationally, but attention and peak multiples have moved to AI.

  9. AI threatens web builders: why Wix/Squarespace look ‘terminal’ and Shopify squeezed the middle

    Wix’s decline sparks a broader discussion on traditional website builders being attacked from two sides: AI ‘vibe coding’ tools on one end and Shopify’s dominance in commerce on the other. They also critique buybacks when businesses face structural disruption.

  10. Compute starvation and the hardware boom: Nebius/CoreWeave, data centers, and the bubble question

    They debate whether skyrocketing growth in compute providers is justified by scarcity or reflects an unsustainable capex frenzy. A key argument: permitting and build constraints might prevent oversupply and ‘save’ the market from overbuilding.

  11. Cerebras IPO surges: what it signals (and doesn’t) for the IPO window

    Cerebras’ strong first day is treated as an ‘N of one’—a rare intersection of hot category (semis/inference), marquee demand, and a clear AI exposure proxy. They caution that buying after the pop has poor base-rate returns, and doubt it broadly opens the IPO door for smaller names.

  12. SpaceX S-1 and the $1.75T IPO rumor: excitement, incomplete financial story, and retail dynamics

    They anticipate SpaceX’s filing and argue the S-1 may not reflect major recent AI-related acquisitions/deals, forcing storytelling into the roadshow. They debate whether retail enthusiasm can drive a meme-like surge from an already massive valuation, and note price-target dynamics could create volatility.

  13. YC’s OpenAI token-for-equity offer: tokens as marketing, valuation anchoring, and surplus-capacity signal

    The panel analyzes OpenAI offering YC startups token credits in exchange for equity. They argue it can inflate valuations via anchoring, shrink round sizes, and encourage aggressive freemium/token-heavy go-to-market—while also implying OpenAI has surplus capacity (vs Anthropic).

  14. Elon vs OpenAI lawsuit aftermath and the coming political backlash from layoffs

    They revisit the dismissal of Musk’s OpenAI case (statute of limitations) and argue the broader effect is continuing legal/PR pressure on OpenAI. The episode ends on a warning: mass layoffs plus careless AI messaging will intensify public hostility and drive political responses, potentially forcing tech to ‘re-inflate’ hiring to maintain social stability.

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