Skip to content
The Twenty Minute VCThe Twenty Minute VC

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 ↗

At a glance

WHAT IT’S REALLY ABOUT

AI mega-rounds, token economics, IPO frenzy, and looming backlash risks

  1. Anthropic’s rumored $30B raise at a ~$900B valuation is framed as an unusually attractive late-stage “post-IPO-like” risk profile where the main risk is valuation rather than survival or liquidity.
  2. Token spend is treated as the core driver of AI model TAM, with Salesforce’s reported $300M Anthropic spend used to estimate how much of engineering and knowledge-worker payroll must shift to tokens to justify trillion-dollar revenue projections.
  3. Public SaaS is depicted as leaving the 2021 “prospects-driven” valuation era and settling into tighter outcome bands, with Datadog and Figma praised for re-acceleration while Wix/Squarespace are described as facing structural decline.
  4. Compute scarcity is the key variable behind the boom in “AI picks-and-shovels” (data centers, semis, GPU clouds like CoreWeave/Nebius), with permitting and build-speed constraints potentially preventing catastrophic oversupply.
  5. Cerebras’ strong IPO is viewed as an N-of-1 “hot intersection” (semis + inference + OpenAI adjacency), while SpaceX’s potential mega-IPO is expected to be sentiment-driven and volatile, and the episode closes warning that layoffs and AI messaging are creating political backlash.

IDEAS WORTH REMEMBERING

5 ideas

Anthropic’s round is positioned as “low existential risk, high valuation risk.”

The speakers argue Anthropic is large enough and close enough to an IPO that the usual venture risks (company failure, no liquidity) are reduced, leaving investors primarily exposed to paying too high a price.

If ARR multiples remain the market heuristic, mega-AI may look ‘cheaper’ than early-stage SaaS.

They claim Anthropic trading around ~18x near-term revenue can compare favorably to 20–50x ARR paid for much smaller, earlier companies that are years from IPO—though the metric may be misleading for model businesses.

Token spend must become a meaningful slice of payroll to justify AI model valuations.

Using Salesforce’s $300M as a benchmark, Rory suggests the industry may need something like ~20% of engineering wage spend and ~5–7% of knowledge-worker wages flowing to tokens to reach trillion-dollar token revenue outcomes.

There’s a real bear case: better models and efficiency could cap token spend.

Jason cites examples (SaaStr usage; Klaviyo’s agent framework) implying agents can be cheaper than assumed, meaning token TAM projections could be overstated if efficiency gains outpace usage growth.

For SaaS, 2021 multiples are gone; the game is ‘become a great normal company.’

They argue the ‘prospects veneer’ moved from SaaS to AI, compressing SaaS outcomes toward revenue/growth/cash-flow multiples; re-acceleration (Datadog, Figma) matters more than reclaiming peak multiples.

WORDS WORTH SAVING

5 quotes

As it's becoming painfully clear now, no one in America, other than us here in California, likes the AI trend. We have people who are brilliant scientists who politically are utter morons, and the people who are utter morons at AI but brilliant at politics are gonna have us for lunch.

Rory O’Driscoll

Because it de- because you're giving away 30 over 900, which is like, um, let me see, 3% of your business, to de-risk it for another year of monstrous burn... I mean, this is a big ass balance sheet war, so to me, it's a no-brainer to do it. They're gonna raise, and they're gonna raise again, and then they're gonna raise again.

Rory O’Driscoll

At 1% of R&D spend, it's lost in the noise. At 5%, it's real. That's a layoff, right? At 20%, which, let me repeat, is what it takes to get to for these overall models to work, right, for these overall TAM analysis to work, that's huge. It's one-fifth of your payroll costs in engineering.

Rory O’Driscoll

Every tech in- cycle has a set of industries that for the f- once in their life get valued on prospects and futures. It's like being 21. It literally is like being 21. And people will believe everything about you.

Rory O’Driscoll

We're gonna have to reflate and hire thousands and thousands of people per tech leader, um, to avoid social unrest. We're gonna have to do it.

Jason Lemkin

Anthropic $30B raise and $900B valuation debateARR multiples vs DCF in late-stage AI roundsToken cost benchmarks (Salesforce) and AI TAM mathPublic SaaS rebound: Datadog, Figma; valuation compression post-2021Wix/Squarespace decline; Shopify and vibe-coding substitutionCompute starvation and data-center build constraintsCerebras IPO pop and what it signals for IPO windowSpaceX S-1/mega-IPO mechanics, float, and retail sentimentYC–OpenAI token-for-equity offer and downstream valuation effectsElon–OpenAI lawsuit outcome and secondary investigationsAI layoffs, political backlash, and potential social-response hiring

High quality AI-generated summary created from speaker-labeled transcript.

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.