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Token Budgeting Panic Hits Corporate America | Cognition Raises $1BN at $26BN Valuation

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 01:24 Anthropic Files to Go Public 07:27 The "Billion-Dollar Position" Era: VCs Reset Their Expectations 18:15 The Trillion-Dollar Cash Grab: Google, SpaceX, and OpenAI Rush the Queue 21:37 Is the SaaS Apocalypse Over? 30:02 Cognition Raises $1 Billion at a $26 Billion Valuation 32:46 Token Budgeting Panic Hits Corporate America 01:00:36 Big Law Flex: Kirkland & Ellis Pledges $500 Million to Build In-House AI 01:12:41 Robinhood's AI Move: Automating Financial Planning vs Beating the Market 01:21:05 Apollo Warns PE Software Returns Are About to Be Disastrous 01:30:27 The 996 Work Ethic: Performative Theatre or Startup Reality? ---------------------------------------------------------------------------------------------- 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 #anthropicipo #ai #cognition #token #996

Rory O’DriscollguestHarry StebbingshostJason Lemkinguest
Jun 4, 20261h 38mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

AI mega-IPO rush, VC bar resets, and token-spend backlash intensifies

  1. Anthropic’s move toward an IPO (alongside OpenAI) is framed as both ecosystem-validation and a psychological reset that raises expectations for founders, employees, and investors seeking trillion-dollar outcomes.
  2. Panelists argue the venture bar is shifting toward requiring “billion-dollar positions,” which may reduce meeting-taking and increase founder pressure to present credible uncapped upside rather than merely solid outcomes.
  3. Public SaaS stocks appear to have bounced from an overdone panic, but the group believes underlying headwinds remain as budgets reallocate from seat-based software toward AI/agentic spend.
  4. Cognition’s $1B raise at a $26B valuation is treated as a bet on autonomous software engineering (not just copilots), in a market where leadership can change quickly and hyperscalers may attack incumbents.
  5. A corporate “token budgeting panic” is emerging as CFOs discover runaway usage, pushing firms toward caps, cost controls, and explicit trade-offs between headcount and token spend—potentially accelerating role compression in QA, CS, and other ‘marginal’ functions.

IDEAS WORTH REMEMBERING

5 ideas

AI is pulling the tech ecosystem back to public markets—fast.

They argue companies have shifted from CapEx-light cash machines to CapEx-heavy AI spenders, making public equity a more practical funding source; the ‘staying private is cool’ era is described as ending abruptly.

The new VC mindset is concentration: fewer bets, bigger potential ownership outcomes.

Jason Lemkin’s “not interested if it can’t be a billion-dollar position” captures a reset in time-to-scale expectations; Rory counters with base-rate realism but agrees founders must tell an uncapped-upside story.

SaaS multiples rebounded, but the budget war is still on.

They interpret the SaaS bounce as an overcorrection reversal (“not going to zero”), while noting Gartner-style AI software growth implies cuts elsewhere—especially in per-seat tools that don’t attach to agents.

Agentic winners are the ‘picks and shovels’ of AI workflows, not generic seat software.

Examples cited include Datadog and Twilio benefiting from agent usage; the implication is that software used by agents (observability, comms, identity, infrastructure) may re-accelerate while human-only seat expansion stalls.

Cognition’s valuation is a thesis on autonomous engineering replacing ‘B’ talent, not just speeding up ‘A’ talent.

They see Devin’s promise as delegating work end-to-end (commits, tasks) rather than assisting; Rory emphasizes competitive risk because trillion-dollar players will try to “eat your lunch.”

WORDS WORTH SAVING

5 quotes

Losing money is like sex. You can talk about it all you like, but until you feel it, you don't know what it's like.

Rory O’Driscoll

I’m not interested if it can’t be a billion-dollar position anymore.

Jason Lemkin

You can grow up and be a fucking adult and say, "I wish I'd done that deal. I'd give my left arm to have done that deal, but I didn't. Now I got to go on and do perfectly good deals that will have great outcomes."

Rory O’Driscoll

I would quit as a developer if you told me I could not use the model of my choice. I would quit.

Jason Lemkin

I really do think by the end of the year we're gonna choose tokens over humans for engineering and product.

Jason Lemkin

Anthropic/OpenAI IPO timing and ecosystem effectsVC expectations: ‘billion-dollar position’ standardAI-driven capital intensity and mega equity raises (Google/SpaceX)SaaS ‘apocalypse’ rebound vs structural seat contractionCognition/Devin and autonomous engineering agentsToken spend shock, budgeting, and multi-model optimizationLegal industry response: Kirkland build vs buy, IP anxietyRobinhood agents: financial planning vs alpha generationPE software returns risk (Apollo) and overpaying for mature SaaS996 work culture, incentives, and performative intensity

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