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Instinct Worth 30BN? | Microsoft Cuts 27,000 Jobs While Meta Taps Equity Markets for $95B CapEx

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 00:49 Anthropic Files S1 02:18 Why Anthropic May Still Be Underestimated 04:49 The Scariest Metric in Anthropic’s S1 07:14 Is AI Debt Financing Starting to Break? 08:04 Why Equity Markets Could Keep the AI Spending Boom Alive 09:54 Will Anthropic Have a Monster IPO? 11:17 What OpenAI Should Learn From Anthropic’s S1 13:03 Microsoft Offers Buyouts to 27% of Employees 16:33 Why AI CapEx Could Drive Even More Layoffs in 2027 17:43 Cloudflare’s 20% Layoff: The New Playbook for CEOs? 19:27 Meta Taps Equity Markets for a $95BN CapEx Spending Spree 21:59 Are Chinese Open-Weight Models Finished in the US? 24:48 What Happens to Modal, Fireworks and OpenRouter if Chinese Models Decline? 33:14 Could OpenRouter’s Boom Be Just a Moment in Time? 35:03 “Black October”: Why AI Could Expose Every Software Vulnerability 37:32 Instinct at $30BN 40:07 Could Instinct Become the Super App of the West? 45:10 Why Investors Are Throwing Money at Proven AI Executives 46:55 Put 20% of the Fund Into OpenAI at $1.25TRN? 51:21 WarHounds at $1.5BN 55:10 Why Mega-Funds Are Raising Bigger and Coming Back Faster 57:20 Zuckerberg vs California: How Much Does a Billionaire Tax Really Matter? ---------------------------------------------------------------------------------------------- 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 #anthropic #instinct #microsoft #ai #ipo

Jason LemkinguestHarry StebbingshostRory O’Driscollguest
Oct 29, 20261h 0mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Anthropic’s S1, AI capex funding shifts, and second-order layoffs

  1. Rory O’Driscoll says Anthropic’s S1 looks strong across key dimensions—margins, operating income, customer concentration, compute efficiency, and cash—making it hard to find near-term negatives beyond a few missing or nuanced disclosures.
  2. The discussion flags a structural dynamic in frontier AI: most revenue comes from very new models while training dominates compute costs, creating a high-stakes cycle where companies must continuously spend billions to stay ahead.
  3. Jason Lemkin worries AI infrastructure debt is getting harder to place, while Rory O’Driscoll argues the broader system can keep funding capex by shifting from debt to equity dilution among companies with low cost of capital.
  4. Microsoft’s voluntary buyouts are framed as a particularly demoralizing layoff mechanism, and Rory O’Driscoll links future workforce cuts to the delayed impact of capex depreciation on hyperscaler profitability, with 2027 highlighted as a pressure point.
  5. The episode debates whether security incidents and policy restrictions could effectively end US momentum for Chinese open-weight models, reshaping the economics for inference providers and model “routers,” while benefiting closed frontier providers like Anthropic.

IDEAS WORTH REMEMBERING

5 ideas

They view Anthropic’s S1 as broadly “haters-and-worriers” silencing.

Rory O’Driscoll argues the filing answered most near-term doubts: margins, operating income (including after stock-based comp), customer concentration, compute efficiency, and the cash position all looked better than many expected, leaving only a small set of open questions.

Anthropic’s biggest risk signal is the short shelf-life of its revenue-driving models.

Rory O’Driscoll highlights that 80% of revenue coming from models less than six months old, combined with most compute costs being training (not inference), implies a treadmill: expensive model creation followed by a short monetization window.

Debt capacity for AI infrastructure may be tightening, even for leaders.

Jason Lemkin frames the most concerning signal as difficulty placing/financing compute-related debt (citing a Broadcom guarantee and higher-than-expected interest), suggesting limits to how much AI debt markets can absorb even for top players.

Equity markets (not debt) may keep the AI spending boom alive.

Rory O’Driscoll counters that the system is shifting from debt to equity issuance, pointing to major equity raises and arguing that companies with cheap cost of capital and willingness to dilute can keep the capex cycle going.

They expect AI capex to translate into headcount pressure as depreciation “comes due,” especially by 2027.

Jason Lemkin and Rory O’Driscoll view Microsoft’s broad buyout offer as a harsh signal to employees; Rory also connects coming layoffs to the lagged arrival of depreciation hitting hyperscalers’ income statements, especially looking toward 2027.

WORDS WORTH SAVING

5 quotes

80% of their revenue comes from models that are less than six months old, right?

— Rory O’Driscoll

This is a game where you have to spend, like, billions and billions and billions of dollars just to play.

— Rory O’Driscoll

It says one thing, no matter what the people are gonna say on LinkedIn, these 27%, we don't want them.

— Jason Lemkin

This is when the bill for AI comes due, and this is how it'll be paid.

— Rory O’Driscoll

Everyone basically, including Sam, just said it's gonna get worse and worse and worse and worse, right?

— Jason Lemkin

Anthropic S1 strengths and open questionsModel shelf-life and training vs inference economicsAI debt financing constraints vs equity dilutionMicrosoft voluntary buyouts and layoff dynamicsCapex depreciation timing and 2027 margin pressureMeta raising equity for large capex plansChinese open-weight model security and US bans impact

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