20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram

Gokul Rajaram is one of the greatest operators turned investors of the last 2 decades. He is trusted as the go to advisor for the greatest founders in the world. Today he serves as a Board Director at three public companies: Coinbase, Pinterest and The Trade Desk. Prior to Marathon (his firm), Gokul served on the executive team at DoorDash and Block. Before Block, he served as Product Director of Ads at Facebook. Earlier in his career, Gokul served as a Product Management Director for Google AdSense. Gokul is also a prolific angel investor, having invested in 700+ companies, including Airtable, Figma, Groq, Runway, Supabase, and Vercel.  AGENDA: 03:53 — Investing Lessons from Google, Doordash and Facebook 05:32 — Why Mark Zuckerberg is the Greatest Distribution Genius Alive 07:23 — Why Every Company Today Needs to be Multi-Product 09:16 — Negative Gross Margins: Are the Best Companies Actually Built on "Shit" Economics? 10:50 — The SaaS Apocalypse: Is the Entire Sector Going to Zero? 12:15 — The 8 Moats of Enduring Software Companies: How to Analyse Companies 14:50 — Why Brand is No Longer a Strong Moat (And What Replaced It) 16:13 — Salesforce vs. Atlassian: Which Systems of Record are Dying? 18:13 — Outcome-Based Pricing: Is This the Total Death of Seat Pricing? 20:16 — The Bolt-On AI Trap: Why Rebuilding Your Entire UX is Non-Negotiable 23:44 — Are the Outcome Sizes of Vertical SaaS Large Enough for VC Today? 28:16 — The Zombie Cohort: What Happens to Private Companies with High Valuations? 32:44 — Is "King Making" Complete Bullshit? 34:21 — Durability Over Margins: What Really Matters in a 100x Growth World 35:36 — The Non-Consumption Miracle: Why Granola and Gamma are Crushing It 38:50 — The PayPal Rule: Can You Raise Prices 5 Times in 3 Years? 42:47 — My Biggest Miss: How I Misread the Shopify Billion-Dollar Mark 45:18 — The Courage to Bet: Why Instacart is the Best VC Deal Ever 46:33 — Seed vs. Growth Pricing: When Does Price Actually Destroy Returns? 50:53 — Does "Proprietary Founder Access" Even Exist? 54:33 — Double Down or Diversify? The Truth About Fund Reserves 59:44 — The Vanta Anti-Portfolio: A Mistake I'll Never Forget 01:01:21 — When to Sell: The "Sell a Third, Hold a Third, Trade a Third" Rule 01:04:12 — Why Remote Early-Stage Companies are Dying 01:07:33 — Why Mid-Level Partners are Fleeing Mega Funds 01:09:47 — The Best CEO Superpowers: Larry, Mark, Jack, and Tony 01:12:33 — The Next 10 Years: Why Dropouts are "AI Maxing" the World    

Elena Verna is the Head of Growth at Lovable, one of the fastest growing companies in the world having hit $400M in ARR in just 18 months. Prior to Lovable, Elena was Head of Growth at both Dropbox and Miro.  AGENDA: 00:00 – Why "Growth Is Now a Trust Problem" (Not a Marketing Problem) 06:10 – Is SEO Dying Because of AI Search? 07:00 – Did Lovable's Growth Come From the Founder's Personal Brand? 08:30 – Why Every Founder Should Push Employees to Be Marketers? 13:10 – Why Every Employee at Lovable Ships Code (Even Marketing) 21:20 – Why Paid Marketing in Year One Is a "Death Trap" 31:50 – Why Annual Subscriptions Are the Wrong Monetization Model for AI 37:00 – If Elena Had an Unlimited Marketing Budget, What Would She Do? 48:00 – How Lovable Does Product Launches  

AGENDA: 00:00 - ANTHROPIC VS. THE PENTAGON: The Billion Dollar Supply Chain War 07:11 - B2B PANIC: Why Leading Companies Are Losing Deals to OpenAI 12:19 - THE ANTHROPIC ENDGAME: Will Claude Eclipse ChatGPT? 17:39 - THE DATA CENTER ARMS RACE: Is the AI Hype Cycle Finally Dead? 24:43 - 24/7 PERSISTENT AI: Why You'll Soon Need Data Centers in Space 30:37 - THE DEATH OF THE JUNIOR: Why Entry-Level Jobs are Vanishing 41:55 - AGENT-LED GROWTH: The Secret Reason Startups are Exploding in 2026 46:58 - THE ERA OF GENTLE DECELERATION IS DEAD: Public Markets Turn Brutal 55:54 - FIGMA MAKE IS TERRIBLE? The Failure of Quarterly Software Releases 01:00:54 - THE ULTIMATE STOCK PICKS: What to Buy and Sell Right Now    

Miles Clements is a Partner @ Accel where he helps to lead their growth fund. At Accel, Miles has led or invested in Atlassian, Cursor, Linear, and more.  AGENDA:  03:38 Where is True Alpha and Value in a World of AI  05:10 Why it is Total BS that Cursor is Dead 07:55 Why Cursor Were Not Wrong to Build Their Own Models 09:38 What is the Upside When Investing in Cursor at $27BN? 15:12 Do Sub $10BN Outcomes Even Matter to a Fund the Size of Accel? 17:07 Losing ServiceTitan: Investing Lesson Learned… 19:55 Missing Rippling: What We Learned 27:20 What is Accel's Win Rate 30:22 How VCs Approach Ownership Has Changed 35:09 Does Miles Feel Happier or Sadder to be an Anthropic Investor Post Pentagon Debacle 36:45 What Happens to Companies Like Miro and Snyk with High Prices to Live Upto? 38:05 Why it is a Great Time to Be Thoma Bravo and Vista  38:36 Why Founder-Led Companies Are Always Better 41:12 Why Would Any Founder Go Public Today 43:48 When is the Right Time to Take Chips Off The Table? 45:24 Should VC Firms Have Evergreen Funds and Be Responsible for Public Positions 50:28 You Can Pick Any VC to Join Accel, Who Does Miles Choose…     

Mitchell Green is a legendary growth equity investor and the Founder and Managing Partner of Lead Edge Capital, a firm with over $5 billion in assets under management. Known as a relentless "money maker", Mitchell has led investments in the likes of Bytedance, Toast, Procore, Duo Security and more. AGENDA: 0:00 The SaaS Apocalypse: Why Incumbents Aren't Going to Zero 05:50 "Dead Money": Why Public Software Estimates Were Too High 08:15 Leverage is the Enemy: Lessons from the 1999 Retail Crash 11:50 The Truth About Growth Equity: Zeroes vs. 10X Returns 15:40 Mainframes to AI: Why Oracle and SAP Will Thrive 20:35 The "Stock-Based Comp" Scandal: Silicon Valley's Hidden Crime 24:35 ByteDance vs. The World: Why China Could Win the AI War 31:50 Selling is the Job: Why Buying is the Most Glamorous Part of VC 35:45 Too Many Tourists: Why 50% of VCs Shouldn't Be in the Business 44:10 The Gross Dollar Retention Rule: The Only Number That Matters in SaaS

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