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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

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

Jerry Murdock is the Co-Founder of Insight Partners, which manages over $90 billion in assets. Jerry personally backed companies including Twitter, Nest and Docker, while Insight's portfolio includes giants such as Shopify, Wiz and monday.com. Across three decades, Insight has helped produce 55+ IPOs and become one of the most powerful technology investment firms in the world. 
 
AGENDA:
 
00:00 — Is the AI Bubble About to Burst?
 
11:00 — Will Half of All Neoclouds Disappear Within 36 Months?
 
13:00 — Can Open Source Models Actually Beat OpenAI and Anthropic?
 
22:00 — Are We Entering the Golden Age of Cybersecurity Attacks?
 
32:00 — Have AI Valuations Completely Lost Touch With Reality?
 
42:00 — Is AI About to Wipe Out an Entire Generation of SaaS & Private Equity?
 
47:00 — Should We Ban U.S. Chips From Being Exported to China?
 
48:00 — Should We Be Fearful of Open-Source Chinese Models?
 
49:00 — Will Continuous Learning Kill Every AI Model We Use Today?
 
53:00 — Why Microsoft Remains a Mega Buy
 
56:00 — Which Mag 7 Giant Would You Short — and Is Apple's AI Strategy a Disaster?

20VC: The AI Bubble Will Burst: Half the Neoclouds Will Die | China: Should We Ban Chip Exports & Be Fearful of Chinese Open-Source | Mag7: Who Dies and Who Thrives: Why Meta is Meh and Microsoft is Mega

James Borow is Chief Product Officer at Brand Networks which delivers social marketing and advertising to 650 enterprise customers, following their acquisition of Shift where James was CEO and Co-Founder and led the business to being the No 1 marketing software company for social advertisers with clients such as Linkedin, Twitter and Facebook. James was named a semi-finalist for Ernst & Young’s Entrepreneur Of The Year Award in 2014, and is a thought leader in digital advertising, with articles in Forbes, The New York Times, Bloomberg and Business Insider. James is also an active angel investor, having invested in Kixer, a mobile advertising platform, Gradient X, a mobile DSP (acquired by SingTel) and Conversion Logic, an online advertising attribution platform.

 

In Today's Episode You Will Learn:

1.) What were James' entrepreneurial origins and what was his aha moment?

2.) How did James get his first clients and what were the hardest aspects of growing the business?

3.) What was it like working with these tech titans like Twitter, Facebook and Linkedin?

4.) Shift obtained $14m in VC funding. How did James meet his investors? How was the fundraising experience for James? What were the surprises and challenging aspects?

5.) Shift was acquired by Brand Networks for $50m but what were James' reasons for selling? Was there any clash between James and his investors when it came to the sale?

6.) What advice would James give to founders contemplating selling their business to larger acquirers?

 

Items Mentioned In Today's Show:

James' Fave Book: John Adams by Dave McCullough

James' Fave Apps: Snapchat, Business Insider and ProductHunt

As always you can follow Harry, The Twenty Minute VC and James on Twitter here!

If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

FF 013: 'Make Bets And Believe In What You Are Doing' with James Borow @ Shift & Brand Networks

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