20Product: Calendly CPO Annie Pearl on Why All PLG Companies Eventually Need to Embrace Enterprise, Why it is Easier to Scale into Enterprise than Visa Versa and the Calendly PLG Playbook; What Works and What Does Not?

Jesse Zhang is the Co-Founder and CEO @ Decagon, the conversational AI platform for customer experience. As one of the fastest growing companies in the valley, they have raised over $230M at a last round price of $1.5BN. Prior to Decagon, Jesse founded Lowkey (acquired by Niantic), studied CS at Harvard, and worked at places like Google, HRT, Citadel, and Intel. AGENDA: 00:00 Introduction and Sponsor Messages 03:43 Olympiad Mathematician to Startup Founder 05:34 Selling to Niantic and What I Did Differently the Second Time 07:16 Why 90% of Founders Build Companies the Wrong Way 12:19 Scaling to $50M ARR in 15 Months 31:31 Is the AI Talent War Out of Hand: How To Compete with Meta Pay Packets 32:38 Why Remote Work is Total BS 34:06 Competitors in AI Customer Experience: Sierra, Intercom and more 37:34 AI Market Predictions 44:56 Embracing Stress and Winning Culture 50:13 Quick Fire Questions: Most Underrated AI Founder, Biggest Changed Opinion

19 Syys 202559min

AGENDA: 00:00 Opendoor's Potential and Market Valuation 03:32 Why Did Kaz Leave $300M on the Table to Join Opendoor 04:44 Why Does Kaz Believe OPEN Can Be a Good Business When the Market Doesn't 06:34 How does Kaz Feel About OPEN Becoming a Meme Stock? 17:25 Kaz's $0 Salary but $1BN Stock Based Compensation 23:41 Oracle and OpenAI Partnership: WTF is Going On? 42:21 Microsoft's Investment in OpenAI: A Financial Perspective & Who Has the Power 44:46 Why Sam Altman is the Greatest Politician of our Time 48:33 How Anthropic's Revenue Could Go to Zero Overnight? 50:12 Replit Raises $250M at $3BN Valuation and Higgsfield Raises $50M at $50M ARR 01:06:33 IPO Insights: Figure, Gemini, and Via All Go Public 01:11:26 Why Adobe Have Failed in an Age of AI and What Incumbents Have To Do? 01:13:20 Quick Fire Round: Adobe Up or Down by EOY? What Price Will OPEN Be EOY? Try NEXOS.AI for yourself with a 14-day free trial: https://nexos.ai/20vc

18 Syys 20251h 24min

Brendan Foody is the Co-Founder and CEO @ Mercor, the fastest growing company in history. The company solves talent allocation in the AI economy and they have scaled from $1M to $500M in revenue in just 17 months. With a rumoured new funding round pricing the company at a whopping $10BN, the company has the likes of Benchmark, Felicis, Emergence, and of course, 20VC, all on their cap table. AGENDA: 04:34 Why My Mother Thought I Was Selling Drugs as a Kid 07:48 In The Time My Peers Graduated, I Created a $10BN Business; Is College Worth it? 10:27 Scale, Surge, Mercor, Turing: How Do Data Providers Differentiate 20:57 Scaling from $1M to $500M: We Quadrupled Since Scale was Acquired 33:43 Is There Too Much Cash in Private Markets? 34:55 Why Evaluation Benchmarks in AI are Total BS 35:44 Revenue Sustainability in AI Companies 36:48 Should Investors Give a S*** About Margins When Analysing AI Companies 40:46 The Future of AI Model Providers: Who Wins 45:58 You Cannot Create a $10BN Company without 9-9-6 Work Culture 48:56 We Literally Have Too Much Money, We Cannot Spend It… 52:36 Quick Fire Round: OpenAI vs Anthropic, Lessons from Peter Fenton and Jack Dorsey

15 Syys 20251h 1min

Amit Bendov is Co-Founder & CEO of Gong, the leading AI-sales platform. The company has raised over $600 million from some of the best in the world including Sequoia, Thrive, Salesforce and more. Gong has surpassed $300M in ARR, serves thousands of customers (including multiple Fortune 10s), and is valued at over $7BN. AGENDA: 00:00 – Why CRM Was Always a Lie and Gong's Secret Insight 04:30 – Will AI Kill Salesforce? Mark Benioff's Nightmare 08:15 – Why 99% of VCs Said No to Gong's Seed Round 12:00 – The Shocking Trial Close That Changed Everything 18:00 – Can AI Make Every Seller Perform Like LeBron? 20:30 – Will Sales Software Shift from Software Budget to Human Labor Budget? 25:00 – Why AI SDRs Are "Stupid" and Bound to Fail 35:00 – Gong's Darkest Hour: Shrinking, Churn, and Losing Muscle 41:30 – The Re-Acceleration Playbook: How Gong Got Back to Hypergrowth 54:00 – Would Amit Ever Sell Gong—or Take It Public?

12 Syys 20251h 6min

AGENDA: [00:05] Musk's $1 Trillion Pay Package: The Breakdown? [00:15] Scale, Windsurf: Are Founders Just Mercenaries Chasing Cash Today? [00:21] Ramp at $1B ARR, Brex at $700M — Is AI Causing All Boats To Rise? [00:26] Sierra at $100M ARR Worth $10B — Bubble or Brilliant Bet? [00:30] Kleiner Perkins Invests $100M into Anthropic at $183BN… WTF? [00:36] $10B in OpenAI Secondaries — What Happens When 1,000 New Millionaires Hit SF? [00:40] Anthropic Pays $1.5B to Authors — Fair Deal or Pure Piracy? [00:44] Why Did ASML Just Invest into Mistral at $14BN? [00:52] Atlassian Buys the Browser Company for $610M — Genius Move or Panic Buy? [01:18] IRL CEO Arrested for Fraud: Is More To Come?

11 Syys 20251h 27min

Mati Staniszewski is the Co-Founder and CEO of ElevenLabs, the world's leading AI voice platform. Since launching in 2022, ElevenLabs has raised over $350M, most recently at a $3.3BN valuation, making it one of Europe's fastest AI unicorns. The company counts Andreessen Horowitz, Nat Friedman, Daniel Gross, and Sequoia Capital among its backers. Today, Mati announces that the company has hit a staggering $200M ARR. ElevenLabs took 20 months to hit $100M ARR. 10 months to hit $200M ARR. Can they do $300M in 5 months… AGENDA: [00:00] $100M in 20 Months?! ElevenLabs Untold Growth Story [12:20] Are AI Models Already Plateauing—or Just Getting Started? [14:00] Why OpenAI Can't Beat ElevenLabs [17:30] The Talent Wars: How Do You Retain World-Class AI Researchers? [23:10] PR vs Product: Why Most Startups Botch Their Launch [36:00] Are U.S. VCs Playing a Different Game Than Europe? [44:00] The Real Cost of AI: Why ElevenLabs Built Its Own Data Centers [59:00] Voice Agents = Multi-Billion Dollar Business of the Future? [01:05:00] Buy OpenAI or Anthropic? Which Foundation Model Wins? [01:09:30] Europe: Strengths, Weaknesses and What Needs to be Done

8 Syys 20251h 14min

Alex Schultz is the Chief Marketing Officer and VP of Analytics at Meta, where he has spent nearly two decades shaping the company's growth and marketing strategy. He has been instrumental in scaling Facebook, Instagram, and WhatsApp to billions of users worldwide. Alex is is also the author of Click Here: The New Rules of Marketing, the definitive guide to modern growth — available now on Amazon. AGENDA: 00:00 – Is All Marketing Actually Performance Marketing? 04:00 – When Did Facebook Have the Wrong North Star? What Did They Learn? 16:00 – Will AI Create Companies Run by Just ONE Person? 27:00 – Is AI About to Hit the Biggest Plateau Since Self-Driving Cars? 30:00 – Is China Secretly Winning the Global AI Arms Race? 38:00 – Does AI Kill Content or Supercharge It? 44:00 – Why Brand Marketing Is Harder (and More Important) Than You Think 47:00 – Will Glasses Replace Phones Forever? 51:00 – What Would Alex Do If He Were Sundar at Google Today? 59:00 – What is the Greatest Strength and the Greatest Weakness of Zuck?

5 Syys 20251h 10min

Agenda: 04:00 – Anthropic Raises $13BN: The Analysis? 19:00 – Is Zuck's $14BN Scale bet the biggest blunder in AI? 27:00 – Lovable Raising at $4BN and Vercel at $9BN: Justified or Madness? 36:00 – Quarterly Results for Snowflake, Mongo, Okta, Zoom Skyrocket: Is B2B SaaS back from the dead? 48:00 – Is Jensen Huang right there will be $4TRN in AI gains? 57:00 – Will AI wipe out SaaS margins with 10% GPU taxes? Or is Notion the exception? Items Mentioned in Today's Episode: Try NEXOS.AI for yourself with a 14-day free trial: https://nexos.ai/20vc

4 Syys 20251h 14min