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Wall St's $725BN AI Question | The Rise of Open Source & How it Threatens OpenAI & Anthropic

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 01:09 Google Loses Two Generational Scientists in 48 Hours to Anthropic 13:28 Why Being #3 in AI Is the Most Dangerous Position 18:00 DeepSeek's $7.4B Series A at a $50B Valuation: Is China Winning? 29:00 Wall St’s $725B AI Question: Who's Actually Going to Pay for AI? 49:09 Gross Margin Is Now the New Growth 53:00 Menlo Ventures Raises $3B: Why Not More After the Anthropic Win? 1:04:30 Accenture Plummets 19%: Why AI Is Destroying the Consulting Business 1:12:22 Work From Home Is White Collar Fraud 1:18:10 OpenAI Launches the Jalapeño Chip 1:19:07 Open Source Is Hollowing Out the Middle of the AI Market ---------------------------------------------------------------------------------------------- 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 #deepseek #wallstreet #google #openaichip #jalapeno #saas

Jason LemkinguestHarry StebbingshostRory O’Driscollguest
Jun 25, 20261h 28mWatch on YouTube ↗

CHAPTERS

  1. DeepMind talent exodus to Anthropic: why top researchers are leaving Google

    The episode opens with two high-profile departures from Google DeepMind to Anthropic—Naom Shazeer and Nobel laureate John Jumper—and what that signals about the AI talent market. The hosts debate whether it’s about freedom to research, the ability to ship product, or “momentum” at the frontier labs.

  2. The ‘#3 is most dangerous’ thesis: routing, token economics, and open-source pressure

    Jason argues that being the third-best closed model is uniquely perilous as enterprises increasingly route workloads across multiple models. The discussion frames how open-source, cost pressure, and developer mindshare can swamp a #3 provider even if it has capital.

  3. Sovereign models and China’s open-source engine: DeepSeek, access blocks, and state subsidies

    The conversation shifts to sovereignty and how China is building parallel AI infrastructure and distribution. Jason’s on-the-ground observations (limited OpenAI/Anthropic access, DeepSeek behavior differences) reinforce the strategic nature of Chinese open models and state involvement.

  4. DeepSeek’s $7.4B ‘Series A’ at ~$50B: governance, founder check, and what it implies

    They unpack the unusual mechanics of DeepSeek’s mega-round: founder financing, few investors, and the state retaining voting control. The group compares valuations to US frontier labs and argues the numbers are rational relative to trillion-dollar peers.

  5. Benchmark ‘breakthrough’ rumors vs. reality: science timelines and why people move

    A rumor surfaces that Anthropic has a secret breakthrough that attracted Jumper, but Rory challenges the premise using commercialization timelines in medicine and deep science. The segment highlights how incentives differ between LLM product cycles and scientific discovery cycles.

  6. AI infrastructure spillovers: DRAM/memory cost shocks and economy-wide price effects

    AI capex is creating real resource shortages, with memory and related components surging in price. Rory connects it to broader economic “price mechanism” impacts—iPhones, electricity, and even local cost-of-living pressures.

  7. Wall Street’s $725B question: who actually pays for AI capex?

    They tackle the widening gap between hyperscaler capex and current AI revenue, revisiting the Sequoia-style “AI spend vs. revenue” mismatch. The group debates how long bull-market conviction can persist and what must be true for the investment to earn returns.

  8. Token-maxing ends; ROI era begins: enterprise spend discipline and allocation politics

    The discussion moves from early ‘just spend to learn’ behavior to the coming demand for measurable ROI. They outline how CIOs will shift from broad experimentation to budget gating based on productivity, layoffs, and business unit performance.

  9. Agents in practice: building an ‘AI VP of Finance’ and the new skill of managing agents

    Jason describes building an end-to-end finance/billing agent that drafts contracts, invoices, updates CRM, and reconciles books. The segment explores why ‘prompt engineering’ fades while ‘agent mastery’—debugging behavior, setting constraints, handling failures—becomes crucial.

  10. Gross margin becomes the new growth: why investors are re-pricing AI businesses

    A founder tweet claims Series A/B fundraising failures are increasingly driven by weak margins, not lack of growth. Rory pushes back historically, but the group converges on a new reality: negative margins only work with truly explosive growth—or the company dies when the market tightens.

  11. Menlo raises $3B after the Anthropic win: fund sizing, SPVs, and cycle survival

    They analyze why Menlo didn’t raise a much larger fund despite exceptional AI performance. The conclusion: smaller main funds can preserve strategy and returns, while SPVs provide flexible capacity for rare mega-winners.

  12. Kalshi’s surge and regulatory arbitrage: prediction markets vs. sports betting

    Kalshi’s scale and IPO prep are explained as a function of enormous US demand for betting plus clever regulatory positioning under the CFTC. They discuss whether Meta could copy the model and how regulatory shifts could change the outlook.

  13. Accenture’s 19% drop: AI disrupts consulting’s ‘bodies-based’ business model

    They argue Accenture’s AI-adoption advisory may be growing, but its core systems-integration and outsourcing business is directly threatened by LLMs. The segment highlights why services priced by headcount are structurally vulnerable as AI compresses delivery cost and timelines.

  14. Work-from-home debate under AI-era competition: small elite teams, intensity, and sprints

    A viral quote—‘WFH is white-collar fraud’—triggers a broader argument about how startups must operate to win in AI markets. Jason claims the winning model is smaller, higher-paid, office-centric teams running at sustained high intensity due to relentless competitive releases.

  15. OpenAI’s ‘Jalapeño’ chip and the ‘hollowing middle’: cost defense vs. focus risk

    They close by debating OpenAI’s custom inference chip strategy and whether it’s a distraction or a necessary cost weapon. Jason ties it to the threat of open source hollowing out mid-tier workloads, while Rory argues OpenAI should rely on supplier competition rather than deep vertical integration.

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