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Harry Stebbings

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. 

If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

David Morehead is one of the most respected CIOs in the endowment fund world as Chief Investment Officer at Baylor University, overseeing its $2.6BN endowment. Before joining Baylor in 2011, he was a senior portfolio manager at several Chicago hedge funds, investing across corporate securities, distressed debt and public and private energy.
 
AGENDA:
 
04:00 The Portfolio Construction of a $2.6 Billion University Endowment?
 
09:00 Why We Spend More Time on Porfolio Construction Than Manager Selection?
 
14:00 Should LPs Back VC's Biggest Names or Find the Next Breakout Manager?
 
21:00 How Baylor Made Millions in the SaaSpocalypse?
 
26:00 Are Public Markets a Casino or Are Private Valuations the Real Fiction?
 
34:00 How Do You Buy a Market Crash Without Catching a Falling Knife?
 
49:00 Would You Fire a Fund Manager Who's Making You Money?
 
57:00 Could the Backlash Against Data Centres Derail the AI Boom?
 
01:02:00 Which Asset Class Is Overhyped—and Where Is the Next Big Opportunity?

20VC: How LPs Allocate to Venture in 2026: What They Want, What They Do Not Want | Why Fund Multiple Does Not Matter Without a Timeline | Why Velocity of Cashback is the Most Important Thing with David Morehead, CIO @ Baylor

AGENDA: 
 
04:30 How Do You Hire Exceptional People in the AI Era?
 08:00 What Actually Works in Growth—and Why Can't You Trust Meta's Numbers?
 17:00 How to Run Hundreds of Millions in Marketing with Zero Employees 
 19:30 "Our Engineers Stopped Coding": What Stack Does Eight Sleep Use?
 24:00 Is China Leaving the Rest of the World Behind?
 35:00 How Do You Turn Superstar Athletes into Investors and Brand Ambassadors?
 43:00 What Happens When Your Co-Founder Is Also Your Wife?
 51:30 Should You Match Anthropic's Salaries—or Let Your Best People Leave?
 59:30 Will Children Born Today Ever Need to Work?
 01:05:00 What Drives You to Succeed—and Why Can't You Ever Switch Off?

20VC: 7 Predictions for How AI Changes the World: Labour, Engineering, Social Media, GrokBots Buying Cybercabs and more with Matteo Franceschetti, Co-Founder @ Eight Sleep

AGENDA: 
 
00:00 Jensen Huang Declares AGI Has Arrived
 04:05 Instinct and GrokBot Ignite the AI Assistant War
 13:32 OpenAI's GPT Astra Redefines What AGI Means
 26:00 GPT Astra and Fable 5.1 Accelerate the Model Race
 30:38 OpenAI's Chief Scientist Calls for Enforced AI Safety Limits
 40:50 Tesla Launches Cybercabs as Travis Kalanick Returns to Robotaxis
 45:55 Index Pulls Out of Town Deal Following Instinct Conflict
 49:45 Anthropic Abandons $6BN Descartes Acquisition After Due Diligence
 56:18 Robinhood Earns First Underwriting Role in Oura IPO
 01:00:28 Wonderful Doubles to $5BN and Approves $170M in Secondaries
 01:09:02 Thinking Machines Targets $40BN Valuation in $6BN Funding Round

20VC: Jensen Huang Declares AGI Has Arrived | GPT Astra and Fable 5.1 Accelerate the Model Race | Tesla Launches Cybercabs | Index Pulls Out of Town & Anthropic Pulls From Descartes Acquisition

Jean-Denis "JD" Grèze is the Co-Founder and CEO of Town, the AI work assistant reportedly in talks to raise funding at a $1BN valuation. Before founding Town, JD spent seven years as CTO of Plaid. Before Plaid, he was Director of Engineering at Dropbox. He is also a prolific angel investor backing companies including Modal, BaseTen, Merge and NexHealth.
 
AGENDA:
 
00:00 Why AI Assistants Are Silicon Valley's Hottest Market
 07:00 How Does Town Compete With Grokbot, Instinct and Big Tech?
 11:00 Will We Have One AI Agent or Different Agents for Every Part of Our Lives?
 17:00 How Many Mistakes Can AI Agents Make Before We Stop Trusting Them?
 20:00 How Does Town Choose the Best Models Without Destroying Its Margins?
 29:00 Is the AI Assistant Market Already Too Crowded?
 37:00 Can Apple Win the Agent Race—and Are We Entering a Cybersecurity Nightmare?
 41:00 What Does a Successful Town User Look Like—and Which Pricing Tier Makes Money?
 47:00 What Will AI Agents Be Able to Do in Three Years That They Cannot Do Today?
 54:00 Is the Skepticism Around Billion-Dollar AI Assistant Companies Justified?
 58:00 What Needs to Happen for Town to Become a $100BN Company?
 1:02:00 How Has AI Changed Hiring—and Why Does Town Spend $75K Per Engineer on AI Tools?
 1:06:00 What Is JD Most Excited About Over the Next Decade?

20VC: The $100 Billion AI Assistant Race: Town vs Instinct vs GrokBot | We Spend $75K Per Engineer on AI Tools | Why the AI Assistant Market Is Not a Bubble & AI Assistants Will Replace Every App on Your Phone with JD, Founder of Town

Cliff Weitzman is the co-founder and CEO of Speechify, the world's leading AI voice and text-to-speech platform, used by more than 60 million people globally. Diagnosed with dyslexia as a child, Cliff first built Speechify at Brown University to help him consume written material through audio. 
 
AGENDA: 
 
00:00 Cliff Weitzman Reveals His Biggest-Ever Strategic Mistake
 03:08 Why Speechify Is Paying Millions to Build Their Own Data Centres
 09:59 What No One Knows About Buying Chips That Everyone Should Know?
 20:19 The AI Data Gold Rush Has a Brutal Business-Model Problem
 23:42 How ElevenLabs Leapfrogged Speechify—and Why It Was Cliff's Fault
 31:00 The $15M AI Talent War: Can Startups Still Compete for the Best Talent?
 36:57 The New 10X Engineer: Ten Killer Decisions Every Day
 46:12 The Voice-AI Bloodbath: Who Survives Commoditisation?
 53:21 The Screen Is Dying—and Voice Will Replace It
 57:58 How Cliff Plans to Use AI to Cure His Brother's Disease

20VC: How to Build Your Own Data Center & Why Every Startup Should Do It | How ElevenLabs Leapfrogged Us: What I Learned | The AI Talent War: How Your Hiring Process Needs to Change with Cliff Weitzman, Speechify

AGENDA: 
 
00:00 Nvidia crushes $96.2B quarter and nears $12.9B Hugging Face deal
 13:52 OpenAI cuts off Cursor as the Altman–Musk feud escalates
 17:40 OpenAI's 1,000-agent cyberattack triggers an industry wake-up call
 22:58 Instinct hits $2.5B valuation as AI assistants gain spending power
 36:39 Cognition targets $1.6B ARR as the coding-agent market explodes
 40:31 AI forces every startup to become a compound company—or get left behind
 52:42 Salesforce embraces Claude and outcome-based pricing in major AI reset
 1:00:52 Stripe–PayPal deal collapses as both sides clash over price
 1:02:31 Clay hits $7B and Linear reaches $100M ARR as agents choose their tools
 1:11:52 Texas pauses Flock cameras as police-surveillance backlash grows

20VC: NVIDIA Crushes Quarter and Buys Hugging Face | OpenAI Cuts Off Cursor | Instinct Hits $2.5BN Valuation and The Race for AI Assistants | Cognition Raises at $46BN, Linear $2.5BN and Clay $7BN

Aaron Katz is the Co-Founder and CEO of ClickHouse, the real-time analytics database powering companies including OpenAI, Anthropic, Tesla and Microsoft. ClickHouse just surpassed $350M in ARR and raised over $1B from investors including Dragoneer, Khosla Ventures, Coatue, 20VC and Benchmark. Previously, Aaron was CRO at Elastic, where he helped scale revenue from approximately $5M to $500M and led the company through its IPO. Before Elastic, he spent 12 years at Salesforce, working alongside Marc Benioff and helping transform it from a 200-person startup into a global software giant.
 
AGENDA:
 
4:05 Are we in an AI bubble?
 13:40 How does software change when agents—not humans—make buying decisions?
 22:28 Will 90% of tokens flow through open models; can enterprises trust them?
 31:09 Why did ClickHouse sponsor Fulham; and could sports teams become $20B assets?
 35:49 When will ClickHouse hit $1B ARR? 
 38:31 Can startups still win elite talent from OpenAI? Biggest remote work mistake?
 44:54 Is zero-to-$100M ARR now table stakes; or is durable growth what matters?
 48:51 Is college still worth it; which jobs will survive AI?
 57:58 When will ClickHouse go public; and why not next year?

20VC: The AI Bubble Is Wrong | AI Margins Need to Improve | Revenue Concentration Should be a Concern | Why People Over-Estimate Open Models But Enterprises Still Fear Frontier Models with Aaron Katz, ClickHouse

Eno Reyes is the co-founder and CTO of Factory, the agent-native software development platform building autonomous "Droids" for enterprise engineering teams. Factory has raised $220 million, most recently a $150 million Series C at a $1.5 billion valuation, from investors including Khosla Ventures, Sequoia Capital, 20VC, NEA, Blackstone, Insight Partners and Nvidia. Before founding Factory, Eno worked as a machine-learning engineer at Hugging Face, training, optimizing and deploying large language models for enterprise customers.
 
AGENDA:
 
00:00 Are We Underestimating AI by an Order of Magnitude? 
 
06:35 Why Can the Smartest AI Model Be the Cheapest? 
 
18:51 Is Anthropic's Coding Business Really Worth $2 Trillion? 
 
33:41 Will Continuous-Learning Models Help or Hurt Factory? 
 
40:43 Will 80–90% of Neo-Labs Die in the Next 18 Months? 
 
44:33 Should American Enterprises Work With Open-Source Chinese Models? 
 
55:42 Must AI Founders Radically Rethink What a Great Outcome Looks Like? 
 
1:04:30 Do Pedigree and Credentials Still Matter in AI Hiring? 
 
1:19:17 Which Is the Biggest Threat: Claude Code, Codex, Cognition or Cursor? 
 
1:24:20 What Seems Crazy Today but Will Be Obvious in Five Years?

20VC: Is Anthropic's Coding Business Worth $2 Trillion? | Should American Enterprises Work With Open-Source Chinese Models? | Why 80–90% of Neo-Labs Die in the Next 18 Months? with Eno Reyes, Co-Founder @ Factory

AGENDA: 
 
00:00 NVIDIA Launches a Three-Deal Blitz Across the AI Stack
 04:31 NVIDIA's $12BN Poolside Deal Exposes Frontier AI's Capital Wall
 15:39 NVIDIA Moves to Back Mercor at $20BN and Perplexity at $30BN
 26:55 OpenAI Confirms 2027 IPO as Anthropic Seizes the Lead
 40:42 Hugging Face Draws $13BN Takeover Interest as Open Models Boom
 44:56 Citadel Cashes Out 80% of Its Leopold Aschenbrenner AI Trade
 51:51 AI Boom Is "Less Than One-Third Over"—But Token Addiction Has a Price
 01:04:07 Stripe Reaccelerates to 41% as AI Reshapes Software's Leaderboard
 01:07:45 Instinct Security Scare Exposes Why AI Agents Still Cannot Be Trusted
 01:23:55 VCs Name AI's Biggest Bubbles: Support, Defense, Humanoids and Roll-Ups

20VC: NVIDIA Bonanza: Buys Poolside & Invests in Mercor and Perplexity | Anthropic's $30TRN Revenue Assumption & OpenAI Confirms IPO | Why Customer Service, Defence and Robotics are Overinflated

Julien Bek is a Partner at Sequoia Capital, one of the most renowned venture firms in the world. At Sequoia, he has partnered with companies including Rillet, Tacto, and Auctor. Before joining Sequoia, Julien spent five years at Accel, where he worked with companies including Miro, Melio, and BeReal. He is also an angel investor in Revolut and Attio.
 
AGENDA:
 
06:35 – What did Julien only discover about Sequoia after joining the firm?
 08:05 – What does everyone get wrong about Sequoia?
 13:00 – Is Series A the hardest stage at which to invest today?
 14:00 – Is Sequoia less focused on ownership as outcomes become larger?
 19:20 – Does Sequoia simply pay more than everyone else to win deals?
 22:00 – Is the "triple, triple, double, double" growth model dead?
 25:00 – What is Sequoia's investment process really like behind the scenes?
 27:15 – Can a partner still invest when the rest of Sequoia votes against them?
 30:00 – Why can a flawless founder pitch actually be a warning sign?
 31:00 – How do you judge whether a founder is exceptional in just 30 minutes?
 33:00 – How can investors tell whether a founder's story is genuine?
 35:10 – Is arrogance a bad trait in a founder?
 36:00 – Which great founder did Julien completely misread?
 37:15 – How should investors adjust their founder assessment across different cultures?
 39:00 – What does a founder's childhood reveal about their future trajectory?
 40:30 – What has Julien learned from Doug Leone, Pat Grady, Alfred Lin and Shaun Maguire?
 47:00 – What does it mean when "agents become the new customer"?
 49:00 – Does UI become irrelevant in an agent-first economy?
 50:15 – Will answer-engine optimisation become larger than SEO?
 52:00 – Will AI agents destroy software margins and brand loyalty?
 53:00 – How quickly will enterprises allow agents to make purchasing decisions?
 54:00 – Is AI infrastructure a safer investment than applications?
 56:00 – Do software margins matter less when the potential outcomes are larger?
 58:00 – Could the next trillion-dollar company masquerade as a services business?
 01:00:00 – Which service industries can AI truly automate end-to-end?
 01:02:00 – Are enterprises simply crying out for more help implementing AI?
 01:03:10 – Will AI lead to dramatically smaller teams?
 01:06:15 – Is traditional private equity screwed?
 01:07:00 – The most overfunded and underfunded categories in venture
 01:08:15 – What is the best AI agent company outside Sequoia's portfolio?
 01:09:00 – Which missed investment still haunts Julien?
 01:09:45 – Which founder trait will Julien never compromise on?
 01:10:00 – Which competing fund makes Sequoia bring its A-game?
 01:10:45 – How Julien missed Revolut—and helped his mother retire by investing anyway
 01:14:00 – What does Julien believe that other Sequoia partners might disagree with?
 01:15:00 – What is Julien most excited about over the next five years of AI?

20VC: Inside Sequoia's Investment Committee: Lessons from Don Valentine, Doug Leone and Alfred Lin | How the SpaceX and Citadel Deals Went Down | What Sequoia Specifically Looks for in Founders with Julien Bek

Yamini Rangan is the CEO at HubSpot. The $32BN juggernaut that has revenues of $2.6BN, over 247,000 customers and 8,200 employees. Prior to Hubspot, Yamini served as Chief Customer Officer at Dropbox, and before Dropbox, she was VP of Sales Strategy and Operations at Workday. 
 
In Today's Episode We Discuss:
 
04:16 Taking Over the CEO Role from the Founders
 
07:58 Wartime vs Peacetime CEOship
 
11:18 How to Scale Into Enterprise: What Everyone Gets Wrong
 
22:20 Why is B2B Not Winner Take All
 
29:33 How Does HubSpot Compete Against Salesforce
 
33:26 Where Does Value Accrue in a World of AI
 
37:40 How Does Yamini Use AI Everyday
 
41:17 What Does HubSpot Do When It's Core SEO Channel Dies
 
44:10 Quickfire Round: Satya Nadella, Parenting Advice, Biggest Concern
 
51:35 Closing Thoughts and Reflections

The Twenty Minute VC

20VC: HubSpot CEO on Where Value Accrues in SaaS AI | How HubSpot Competes Against Salesforce | Why B2B Is Not a Winner Take All Market | How to Go From SMB to Enterprise an Win | How SEO Dying Changes HubSpot's Business with Yamini Rangan

20VC: HubSpot CEO on Where Value Accrues in SaaS AI | How HubSpot Competes Against Salesforce | Why B2B Is Not a Winner Take All Market | How to Go From SMB to Enterprise an Win | How SEO Dying Changes HubSpot's Business with Yamini Rangan

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