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Anthropic Raises $13BN & OpenAI Buys Statsig for $1.1BN All Stock

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](http://bill.com/) (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others. Cliff Obrecht is the co-founder and COO of Canva, the visual-communication platform he built with Melanie Perkins and Cameron Adams, where he leads operations, monetization, and growth. He helped scale Canva from Fusion Books into a global, product-led business driving acquisitions like Pexels, Pixabay, and Flourish and champions its philanthropy through the Canva Foundation. ----------------------------------------------- In Today’s Episode We Discuss: 00:00 Intro 01:03 Anthropic Raises $13BN: The Analysis? 16:58 Is Zuck’s $14BN Scale bet the biggest blunder in AI? 25:37 Lovable Raising at $4BN and Vercel at $9BN: Justified or Madness? 35:53 Quarterly Results for Snowflake, Mongo, Okta, Zoom Skyrocket: Is B2B SaaS back from the dead? 48:38 Is Jensen Huang right there will be $4TRN in AI gains? 50:01 Will AI wipe out SaaS margins with 10% GPU taxes? Or is Notion the exception? 01:06:35 The VC Regret Pathway ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: / harrystebbings Follow Jason Lemkin on X: / jasonlk Follow Rory O’Driscoll on X: / rodriscoll Follow Cliff Obrecht on X: / cliffobrecht Follow 20VC on Instagram: / 20vchq Follow 20VC on TikTok: / 20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #cliffobrecht #canva #zuckerberg #anthropic #saas #ai #salesforce #jensenhuang

Rory O’DriscollguestCliff ObrechtguestHarry Stebbingshost
Sep 4, 20251h 14mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

AI mega-rounds, SaaS rebound, and the new economics of compute

  1. Anthropic’s reported growth makes its $13B raise at ~$183B post look less irrational if forward revenue expansion persists, turning a seemingly huge price into a plausible forward multiple bet.
  2. OpenAI’s all-stock $1.1B Statsig acquisition is framed as a “cheap” outcome for an experimentation platform with ~$75M ARR, and as a strategic way for investors and operators to roll into OpenAI exposure.
  3. Meta’s ~$14B Scale wager is criticized as structurally messy—talent retention issues, evolving data-labeling needs, and the likelihood of future write-down pressure if the remaining asset can’t justify the balance-sheet mark.
  4. Late-stage private AI valuations (Lovable/Vercel) are attributed to a mix of genuine acceleration, mispricing, and social proof/validation effects, with debate over whether rapid step-ups reflect new information or capital excess.
  5. Public B2B SaaS shows signs of recovery as some incumbents gain AI tailwinds, while the panel argues distribution plus AI integration should enable re-acceleration—yet margin pressure from inference introduces a new “GPU tax.”

IDEAS WORTH REMEMBERING

5 ideas

In hypergrowth AI, forward multiples can flip ‘expensive’ into ‘reasonable.’

If Anthropic’s ARR trajectory truly goes from roughly 1 to 9 and then to ~30, the implied forward revenue multiple compresses dramatically; the real question becomes durability of growth rather than headline valuation.

All-stock M&A can be a “forced upgrade” for investors and founders.

Statsig selling at the prior round price looks flat on paper, but rolling into OpenAI stock may be attractive for late investors and operators when access to primary OpenAI allocation is constrained.

The Scale/Meta structure creates predictable human and accounting fallout.

Mixing large payouts and new reporting lines invites attrition, while moving cash out and talent away can leave an asset that’s difficult to justify at the original $14B mark—setting up potential auditor-driven write-downs.

Rapid private-market step-ups often reflect psychology as much as performance.

The panel outlines three drivers—new information, initial mispricing, and validation/social proof from a brand-name lead—arguing multiple forces can coexist in back-to-back rounds.

AI is reviving some incumbents, but not uniformly—and expectations matter.

Mongo’s surge is framed as a combination of real demand (AI app proliferation) and low prior expectations; modest beats can produce outsized stock moves when sentiment has been overly negative.

WORDS WORTH SAVING

5 quotes

Wall Street is the madman in the backseat. In the end, the thing that bails out our incompetence is your growth rate.

Rory O’Driscoll

There is an early adopter syndrome that pulls forward a lot of revenue.

Cliff Obrecht

In 2021, were worth $40 billion, uh, at, which was a, I think it was a 50X multiple on our revenue at the time. Uh, 2022, everything came crashing down.

Cliff Obrecht

It took discipline to take the 50X. 'Cause we... I won't name names, but we had people coming in at higher multiples, and even we were like, "This is, this is batshit crazy."

Cliff Obrecht

That is the tax you pay for being stupid. Pay the tax and just get off the stupid train.

Rory O’Driscoll

Anthropic valuation vs forward revenue mathOpenAI–Statsig acquisition dynamicsMeta–Scale deal structure and write-down riskAI startup step-up rounds and validation effectsB2B SaaS earnings rebound (Mongo/Snowflake/Okta/Zoom)AI inference costs, margin compression, and pricing modelsIPO vs secondary liquidity and direct listing trade-offsLLM-driven discovery replacing classic SEO ("LLM SEO")VC regret pathway and follow-on concentration

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