20VC: Anthropic vs The Pentagon: Who Wins | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR | Block's 40% Headcount Reduction: AI or Overhiring

AGENDA:  04:13 Anthropic vs The Pentagon: Who Wins 13:54 Was Sam Altman Wrong to Take the Deal  24:28 OpenAI's $110BN Mega Round: The Breakdown 28:22 Who Has a Bigger Valuation Premium: Sam Altman or Elon Musk 34:38 Why We Got the SaaS Apocalypse Wrong? 43:24 Why Salesforce Could be the Best Buy in Public Markets 47:46 Block Lays Off 40% of Team: AI or Overhiring 01:00:16 Cursor Hits $2BN in ARR… so not Dead? 01:18:15 How to Pick Winners in AI?      

Monday has been hit harder than almost any other public SaaS company. With $1.3BN in ARR, the company is valued at just $3.8BN; a more than 60% fall since IPO. Today, Eran Zinman, Monday's CEO joins Harry Stebbings in the hotseat to walkthrough six of the biggest threats to Monday's business; what is real, what is not and what are the unknowns.  AGENDA: 05:47 Six Threats Monday Faces Today  07:04 Threat #1: Vibe Coding: Will Companies Vibe Code Everything 11:24 Threat #2: Will OpenAI and Anthropic Own the Application Layer  13:52 Threat #3: Will Agents Turn Monday and Salesforce into a Database 18:43 Why is Monday Adding 15% Headcount When Everyone is Cutting? 21:40 How Monday is Using AI to be More Efficient 27:49 What Happens to Seat Pricing? What Comes Next? 34:17 What No One Sees About Enterprise AI Adoption 37:13 How Google AI Overview Smashed 10% of our Customer Acquisition 38:49 If Bullish on Monday, Why Has Eran Not Bought More Stock… 40:38 How to Manage Internal Morale When Stock is Down 60% 44:08 Do Private Companies Have Advantages Public Companies Do Not Have 47:28 With $1.5BN in Cash, Why is Eran Not Buying More Companies… 53:30 What is the Most Offensive Bet Eran Would Like to Take? 57:13 Quickfire: Marriage, Biggest Short, Mentors  

Jerry Murdock is the Co-Founder of Insight Partners, one of the most formidable growth investors of the last three decades, with over $90 billion in AUM and a portfolio that has shaped the modern software economy. Jerry never does podcasts, and so this is his first-ever long-form interview.  AGENDA: 03:50 There is an AI Tsunami Beginning 05:43 Cursor is F***** and Everyone Knows It 07:28 How Open Source Will Crush in an Agent First World 10:20 Is NVIDIA F**** 17:32 Are Systems of Record Dead in an Agent-First World 21:04 Humans Will Not Buy Software, Agents Will… 24:57 Universal Basic Income Will Have to Happen, Mass Unemployment is Coming 30:54 What Happens to Tech Private Equity: Is Thoma Bravo F****** 37:50 What Single Decision Does Jerry Regret Most… Why? 41:45 Single Biggest Mistake With Insight… What Did Jerry Learn? 45:26 Why is Now the Best Time to Start a Fund 47:03 The Twitter Bet that Made $90BN Insight 49:34 Biggest Marriage and Parenting Advice 56:04 Will Agents Help Us Live Forever    

AGENDA: 03:55 Anthropic Security Product Wipes Billions Off Public Markets 11:17 Do Agents Turn SaaS Incumbents into Valueless Databases 22:07 Anthropic Secondary Sale Makes Hundreds Decamillionaires 23:20 Citrini Research Piece: Everything You Need To Know 26:04 Will DoorDash Be Replaced by Agents 34:22 Will "Ghost GDP" Soften Consumer Spending Power 42:46 Why No Public Company Has Created a Good Agent Product 47:19 Is Tech Private Equity and Thoma Bravo F***** in this Market 51:05 OpenAI Massively Increases Spending Plans: Analysis 56:24 Figma Fights Back: Earnings Through the Roof 01:02:12 Momentum Versus Value: Four Public Stocks to Buy 01:09:30 Jack Altman Joins Benchmark Capital    

Lucas Swisher co-leads the growth fund at Coatue where he has partnered with iconic companies like OpenAI, Harvey, Deel, Canva, Openevidence, Anthropic, and others. Prior to Coatue, he was on the investment team at Kleiner Perkins, where he focused on growth stage software businesses.  AGENDA: 04:23 Why Public SaaS Is Getting Crushed in the AI Wave 06:01 How to Find Value in the Deluge of Public SaaS 10:34 Durability of Revenue in AI 17:42 Market Size vs. Founder Quality: What Wins? 19:04 Why Price is the Last Thing to Matter 24:58 Mega-Funds Math: Can $5B+ Funds Still Generate Venture Returns? 28:04 What Returns Are 'Enough'? Why 3x Isn't Exciting at Growth 30:34 When Double-Downs Go Wrong: Overestimating TAM and Multi-Product Expansion 33:03 Margin Matters… But at Scale: AI Gross Margins, Cost Curves & Efficiency 36:42 Why it has never been harder to be a seed investor 39:25 Is 'Kingmaking' a Myth: When Capital Helps (and When It Hurts) 44:12 Is Canva Really a Platform Company? Multi S-Curves and Leaning into AI Early 46:05 Lessons from Mary Meeker: Modeling, Storytelling with Data, and Not Missing the Forest 48:27 Lessons from Mamoon Hamid: Spotting Inflection Points with Minimal Data (Figma Story) 49:54 LP 'Pick One' Games: Mamoon Hamid, Mary Meeker, Insight Partners 51:41 OpenAI vs Anthropic: Who Wins? 56:52 Most Memorable Founder Meeting: Harvey and Founder-Market Fit 59:00 Career Decisions & Misses: Leaving Insight, Missing Anduril, and Looking Ahead  

Alexander Embiricos is the Head of Codex at OpenAI, leading the development of the company's flagship AI coding systems that power automated software generation, debugging and developer workflows. Under his leadership, Codex has become one of the most widely adopted AI developer platforms.  AGENDA: 05:13 Will Coding Be Automated? Why AI Could Create More Engineers, Not Fewer 07:17 Do We Need PMs? The "Undefined" Product Role and When It Matters 08:06 The Real AGI Bottleneck: Human Prompting, Validation, and "Too Much Effort" 13:04 Three Phases of Agents: Coding → Computer Use → Productized Workflows 13:52 Enterprise Reality Check: Security, Permissions, and Safe Agentic Browsing 17:57 Is Inference the New Sales and Marketing?  18:49 What % of Codex Was Written by AI? 21:33 Do OpenAI Use AI for Code Review? 23:31 Is there any stickiness to AI coding tools? 28:22 What Does "Winning" Mean at OpenAI? Mission, Competition, and Moats 32:04 The Future UI: Chat or Voice 34:10 Agent-to-Agent Workflows: Designing for Approvals, Compliance, and Automation 35:39 Do Coding Models Have a Data Moat? 36:50 How does Codex View Data: Will They Build Their Own Mercor and Turing? 37:27 How Does Codex View Consumer: Will They Compete with Lovable? 41:56 Benchmarks vs "Vibes": How People Actually Judge Models 42:43 Cursor's Edge and the Case for Building Your Own Models 47:37 Is SaaS Dead? What Still Defends Value (Humans + Systems of Record) 51:28 Talent Wars and Career Advice for New Engineers in the AI Era 01:01:03 Guardrails, the Fully AI-Managed Stack, and a 10-Year Vision for Everyone      

AGENDA: 04:14 Anthropic's $30B Raise at $380B 06:18 Why SaaS Stocks Keep Getting Crushed 18:15 Wall Street's New Religion: AI Replaces Headcount  22:42 The Bear Case for Shopify: What Could Go Wrong? 31:51 Replit and Lovable are Proof Figma Missed Out: Figma; Buy or Sell?  48:42 Stripe Raises at $140BN: Is Stripe Wildly Overvalued or Adyen Undervalued?  54:36 OpenAI Buys OpenClaw 01:06:28 Thrive's $10B Growth Fund 01:09:10 Arif Janmohamed Leaves Lightspeed for New Firm 01:17:12 Workday's Founder Returns as CEO: Will it Work?  01:20:34 Which Founder Returns Next: HubSpot, Twilio, Gitlab? 01:24:03 Is Monday.com a Screaming Buy? 01:28:25 Jason and Harry Bet $200,000  

Sebastian Siemiatkowski is the co-founder and CEO of Klarna, the global digital bank with over 114 million global active users and 3.4 million transactions per day. Seb is one of the leading public company CEOs pushing the boundaries of AI.  AGENDA: 04:50 — The Real Threat to SaaS is The Switching Cost Coming Down 05:57 — What revenue multiple will software companies trade at in the future? 14:12 — Why you need to build your own customer service AI to win 23:51 — Klarna has two times the customer base of Revolut. They will beat Revolut 25:39 — How I lost a billion dollars not investing in Nubank 30:57 — Why Nubank are more likely to win the US than Revolut? 34:28 — We used to be 6,000 people. Now we are just 3,000 39:58 — When is a high valuation too high and can be dangerous? 42:45 — How we got Sequoia to invest and Michael Moritz to join the board 53:14 — If you are an investor today that is not building then you're at a fundamental disadvantage 01:11:43 — I have changed my mind on the adoption cycle... I think it will take longer than people think 20VC: Is SaaS Dead: Klarna Replaces 1,500 Internal SaaS Products | Why Systems of Record Will Die in an Agentic World | What Revenue Multiple Will Software Companies Trade At? | From 7,000 to 3,000: We Need Less People Than Ever with Sebastian Siemiatkowski

Carles Reina is VP of Sales at ElevenLabs, where he was the first investor and fourth employee. Carles has scaled the revenue org from Day 1 to over $330M in just 3 years. Carles is also an active investor with investments in ElevenLabs, Revolut, Happy Robot and more.   AGENDA: 0:00 How I Turned $20K into $16M with Revolut Angel Investment 10:45 Why I Don't Believe in Product-Market Fit 15:40 How to do Land and Expand: Turning $12K Deals into Millions 19:40 The 20X Rule: A "Ruthless" Comp Plan for Elite Reps 24:35 Public Shaming? Why Honest Pipeline Reviews Save Companies 28:50 Why Your Sales Reps Should Never Be in the Office 35:45 The Outbound King: How to Pivot from 90% Inbound 45:45 "Vibe Coding" & The Death of Technical Ceilings 55:35 Why I'd Fire Myself: The Secret Psychology of High-Performers    

AGENDA: 03:43 Anthropic Predicts $149B in ARR in 2029 09:27 Will FDEs Become More or Less Powerful 26:17 Harvey Raises $200M at an $11BN Valuation 42:45 Is Customer Support a Terrible or Terrific Investment Category 56:14 Anthropic's Superbowl Ad: Who Won and Who Lost 01:11:30 Do CEOs Have to Work Harder Today Than Ever