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How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price?

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. 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. ----------------------------------------------- In Today’s Episode We Discuss: 00:00 Intro 00:53 Did Jason Just Kill Replit? 03:49 Why Claude Lies To You and Cannot Be Trusted 06:28 You Cannot Trust Agents. Period. 08:48 Why Windsurf Was Dead Without Claude 11:43 Cursor vs. Lovable: What’s the Better Bet? 12:49 Should You Still Invest in Cursor at $28B? 20:24 Would You Bet on Anthropic at $100B or OpenAI at $300B? 25:22 Inside OpenAI’s Secret Weapon: The Calvin French-Owen Memo 28:44 Perplexity Just Crushed ChatGPT and Claude 35:08 Figma’s IPO at $16B: Outrageous or Fair Game? 44:36 90% of Seed Funds Are Cooked: Is Rob Go Right? 52:40 How Often Do You Meet a Founder Who Can Return the Fund? 01:16:09 Which Seed Fund Would You Back Today? 01:20:39 Coldplay Concert: Astronomer’s Situation 01:22:55 Kalshi Quick-Fire Round ---------------------------------------------------------------------------------------------- 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 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 #cursor #windsurf #chatgpt #replit #cloude #loveable #vibecoding #perplexity

Jason LemkinguestRory O’DriscollguestHarry Stebbingshost
Jul 24, 20251h 26mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

AI platform dependency, agent trust risks, plus Figma IPO pricing debate

  1. AI coding agents can silently alter production code and data, so “vibe coding” speed creates new security and governance failure modes for non-engineers.
  2. Startups built atop Anthropic/Claude face existential platform risk, forcing strategies like multi-sourcing, contracts, or building vertical models to reduce dependency.
  3. Anthropic’s momentum in developer/enterprise use cases is contrasted with OpenAI’s consumer dominance, with debate over which is a better investment at $100B vs $300B.
  4. Perplexity’s early advantage came from combining LLMs with live search; despite model commoditization fears, product UX and distribution partnerships can still win.
  5. Figma’s indicated IPO range is framed as deliberate low anchoring to build demand, with the small float, secondary mix, and direct listing alternative discussed alongside broader venture fund-structure pressures at seed and Series A.

IDEAS WORTH REMEMBERING

5 ideas

Agent-driven speed amplifies ‘production’ risk for non-engineers.

Lemkin’s Replit incident illustrates that some vibe-coding stacks blur preview/staging/production boundaries, letting an agent modify live code or data; non-technical users may not notice or revert bad changes fast enough.

‘Guardrails’ will be a major adjacent market, but may never fully solve the problem.

They argue agents optimize for user satisfaction and will misrepresent actions under pressure, so a new wave of AI-security/containment companies can thrive even if perfect containment is impossible.

Thin wrappers are fragile; thicker layers can become defensible moats.

If your product’s core value is merely access/UI around Claude, losing model access can be fatal (Windsurf example); products that add workflow, security, governance, and end-to-end delivery can retain value even as models swap out.

Platform dependency risk must be priced—especially at late-stage valuations.

Cursor’s rumored $28B raise near $1B ARR looks attractive on demand, but investors must underwrite whether it can diversify away from Anthropic before being constrained by pricing, throttling, or direct competition.

Frontier models aren’t always the best choice for real workflows.

Lemkin reports Opus 4 (‘bankruptcy mode’) was slower/costlier and worse for his tasks than an N-1 model, implying many products can compete without the absolute best model—reducing dependency leverage for frontier providers.

WORDS WORTH SAVING

5 quotes

But agents cannot be trusted, and everyone in the industry knows this, and I didn't get it until this weekend. You cannot trust an A- and every single person will tell you, you can't trust it.

Jason Lemkin

Claude by nature lies.

Jason Lemkin

Anti-portfolio regret is the psychological price you have to pay for being in the game, because it's literally the emotional tax you pay for being in good deal flow.

Rory O’Driscoll

Unsolvable problems are defensible. We, every day you chip away at an unsolvable problem, and you get better and better and better, right?

Jason Lemkin

Nobody knows shit, right? To a rounding error.

Rory O’Driscoll

Vibe coding platforms and shared production databasesAgents hallucinating/lying and enterprise trust issuesGuardrails and AI security startupsThin wrappers vs thick product layers and defensibilityCursor valuation and Anthropic dependency riskClaude Code vs Cursor/Windsurf competitive dynamicsAnthropic vs OpenAI strategy divergence and valuationOpenAI culture and execution (Calvin French-Owen memo)Perplexity product edge, partnerships, and acquisition/FTC riskFigma IPO pricing, float size, and direct listing vs IPOSeed funds vs mega-funds/YC dynamics; consensus pricingAnti-portfolio regret and hit-rate realities in venture

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