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Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued?

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 00:42 Anthropic's $30B Raise at $380B 05:53 Why SaaS Stocks Keep Getting Crushed 20:53 Wall Street's New Religion: AI Replaces Headcount 22:21 The Bear Case for Shopify: What Could Go Wrong? 33:13 Replit & Lovable are Proof Figma Missed Out: Figma; Buy or Sell? 50:27 Stripe Raises at $140BN: Is Stripe Wildly Overvalued or Adyen Undervalued? 56:51 OpenAI Buys OpenClaw 01:09:56 Thrive's $10B Growth Fund 01:12:46 Arif Janmohamed Leaves Lightspeed for New Firm 01:17:26 Workday's Founder Returns as CEO: Will it Work? 01:25:15 Which Founder Returns Next: HubSpot, Twilio, Gitlab? 01:28:58 Is Monday.com a Screaming Buy? 01:33:43 Jason and Harry Bet $200,000 ---------------------------------------------------------------------------------------------- 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... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #ai #anthropic #stripe #thrive #openai #saas #openclaw

Rory O’DriscollguestHarry StebbingshostJason Lemkinguest
Feb 19, 20261h 37mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

AI frenzy reshapes venture and public SaaS valuations dramatically today

  1. Anthropic’s $30B raise at a $380B post-money is framed as a momentum-driven “escape velocity” bet fueled by unprecedented multi-year 10x revenue growth but coupled with capital-intensity and compute fragility risk.
  2. They argue public SaaS is being repriced not just on fundamentals but on a narrative shift—Wall Street “fell in love with AI” and therefore “fell out of love with SaaS,” pushing many stocks into a presumption-of-failure regime.
  3. A central claim is that enterprises will “will AI into existence,” allocating major budgets and pursuing headcount reduction even if ROI proof lags, which could extend the AI spending boom for 1–2 years before a potential retrenchment.
  4. The panel debates specific company implications: Shopify’s UI/platform bypass risk via agentic commerce, Figma’s missed AI-adjacent prototyping opportunity to Replit/Lovable, and the Stripe vs Adyen valuation gap as a growth-vs-profitability (and narrative/communications) tradeoff.
  5. OpenAI’s acquisition of OpenClaw is treated as a tipping point for semi-autonomous agents: developer enthusiasm outran safety guardrails, raising urgent questions about responsibility, security, and inference/cost scaling.

IDEAS WORTH REMEMBERING

5 ideas

Mega-rounds are now a core venture strategy, not an outlier.

The group portrays $30B AI rounds and $10B+ growth funds as inevitable when $100B–$1T outcomes stay private; fund size expands simply to maintain meaningful ownership and pro-rata in a small set of winners.

Anthropic is priced on momentum plus unprecedented growth, but compute makes it fragile.

They cite “three years of 10x GAAP revenue growth” as singular, yet warn these model companies resemble capital-intensive semiconductor businesses; over/under-investing in compute can create existential risk.

Public SaaS is being punished by a narrative rotation as much as by fundamentals.

Their “voting vs weighing machine” framing argues that AI’s presumption-of-success has flipped many SaaS names into presumption-of-failure, pushing multiples down even when cash flow and growth remain decent.

Enterprise AI spend may persist because leaders want workforce reduction, not just productivity tools.

They suggest many executives will actively choose to shrink headcount and align AI programs to that goal, extending spend even if near-term ROI evidence is mixed—until a later “prove it” phase forces retrenchment.

Disruption speed is uneven; AI-adjacent categories are moving fastest.

Coding, prototyping, creative tools, and support show rapid adoption and revenue capture (e.g., Replit/Lovable), while some systems-of-record may change slower—yet “slower” doesn’t mean “safe.”

WORDS WORTH SAVING

5 quotes

The truth is, you've never seen a company grow 10X in GAAP revenue on runway year on year for three years, right? At this scale. It just hasn't happened. So you're leaning into the singularity here.

Rory O’Driscoll

I literally think you can make a decision, and I think by the end of this year, that, that train's gonna be so far out of the station that, that these nu- these growth numbers will be jaw-dropping because we will decide. Enterprises will- the Fortune 500 or Global 2000 will decide we are replacing humans with AI, even if it's not the right decision.

Jason Lemkin

In the short term, we're narrative and momentum creatures, and all that's happened now is the narrative and momentum has shifted to AI's gonna do everything.

Rory O’Driscoll

Give me a fucking break. I don't wanna, I don't wanna, like, have to pick which, which accounting software in four years might break out for AI. No one wants to do that. Just show me the carry.

Jason Lemkin

If the idea is every time you have to deal with a problem, you have to go private to fix it, that strikes me as a little absurd.

Rory O’Driscoll

Anthropic mega-round mechanics and valuation logicCapital concentration and “escape velocity” investingPublic SaaS selloff and narrative-driven multiplesEnterprise AI budgets, ROI, and headcount reductionAgentic/autonomous tools, guardrails, and security riskFigma vs Replit/Lovable and AI-adjacent disruptionStripe vs Adyen valuation gap and private vs public flexibilityThrive’s $10B growth fund and late-stage venture scalingFounder returns (Workday) as a response to disruptionPublic stock “durability” and the Monday.com debate

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