20VC: Lessons From 2x $Bn Exits in Trulia and lastminute.com, 3 Leading Indicators That Suggest Potential Marketplace Success & Why We Are Going To See A Fundamental Change To The World of VC with Pete Flint, Managing Partner @ NFX

20VC: Lessons From 2x $Bn Exits in Trulia and lastminute.com, 3 Leading Indicators That Suggest Potential Marketplace Success & Why We Are Going To See A Fundamental Change To The World of VC with Pete Flint, Managing Partner @ NFX

Pete Flint is a Managing Partner @ NFX, one of Silicon Valley's newest and most exciting funds with the recent announcement of their new $150m fund late last year. Prior to VC, Pete was a serial entrepreneur building one of today's most successful marketplaces, as the co-founder of Trulia. Pete led the company from inception to more than 50 million monthly unique users, $250m in VC funding from the likes of Sequoia and Accel culminating in their merger with Zillow in 2015 that valued Trulia at $3.5 billion. Before Trulia, Pete was part of the founding team of lastminute.com, a leading European online travel site that was acquired in 2005 for over $1 billion.

In Today's Episode You Will Learn:

1.) How Pete made his way into the world of startups joining the founding team of lastminute.com and how that led to the founding of Trulia and entry into VC?

2.) Why does Pete believe that startup timing is so crucial? How does Pete analyze market timing risk when investing? What is the right way for investors to think about the innovation cycle we are in today? On review, what does Pete believe lastminute.com did most right? What would he most want to change?

3.) What are the leading indicators that suggest potential in a network effect business? Would Pete agree with Josh @ Jackson Square that not all GMV is created equal? How does Pete anlyse the lack of free and open distribution today and how that affects marketplace scaling? Why does Pete still believe marketplaces are some of the most capital efficient businesses to grow?

4.) What has been Pete's greatest time of failure in his career? What is the framework Pete uses to analyse and assess his own ego? What are the commonalities in how Pete has seen truly great founders overcome failure? How does Pete balance between realism when something is not working and the mission and vision of the founder?

5.) How does Pete think about optimising decision-making, both in investing and operating? How does Pete approach the balance of head vs heart? When is the right time to decide with your head? When is the right time to decide with your heart? Why does Pete argue early stage investing must be decided with your heart?

Items Mentioned In Today's Show:

Pete's Fave Book: Leonardo Da Vinci

Pete's Most Recent Investment: Ribbon

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

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

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20Product: How Scale AI and Harvey Build Product | Why PMs Are Wrong: They are not the CEOs of the Product | How to do Pre and Post Mortems Effectively and How to Nail PRDs | The Future of Product Management in a World of AI with Aatish Nayak

20Product: How Scale AI and Harvey Build Product | Why PMs Are Wrong: They are not the CEOs of the Product | How to do Pre and Post Mortems Effectively and How to Nail PRDs | The Future of Product Management in a World of AI with Aatish Nayak

Aatish Nayak is the Head of Product at Harvey where he oversees product vision, strategy, design, analytics, marketing, and support. This is his third hypergrowth AI unicorn having previously held product leadership roles at Scale AI from 40 to 800 people, and Shield AI from 20 to 100 people. In Today's Episode We Discuss: 04:21 Biggest Product Lessons from Scale AI 7:18 Why Product Managers Are Wrong: They are not the CEO of the Product 12:28 Why Market Selection is More Important than Anything Else 16:40 If Distribution is King then Product is President 22:06 Effective Product Strategy and Execution 26:24 How to Write the Best PRDs 31:01 Balancing New Features and Technical Debt 33:17 Analysing Retrospectives and Postmortems 33:55 Introduction to Pre-mortems 38:25 Biggest Product Mistakes and Lessons Learned 41:40 Evaluating AI Models and Lessons Learned 45:03 The Future of AI in Product Management 55:21 What Should Product People Learn to Win in a World of AI 59:37 The AI Talent War in San Francisco 01:01:26 Quickfire Round

11 Huhti 1h 5min

20VC: How to Fix the UK Tech Ecosystem | Why We Need to Flood the UK with Venture Capital | What the UK Can Learn From Sequoia, Stripe and Norway | Why Now is the Time to be Bullish on China & Lessons from Jensen Huang with Tom Hulme & Stan Boland

20VC: How to Fix the UK Tech Ecosystem | Why We Need to Flood the UK with Venture Capital | What the UK Can Learn From Sequoia, Stripe and Norway | Why Now is the Time to be Bullish on China & Lessons from Jensen Huang with Tom Hulme & Stan Boland

Tom Hulme is a General Partner @ GV and leads GV's European investing. He has led rounds in Monzo, Nothing, GoCardless, Lemonade, Snyk and is widely considered one of the best investors in Europe. Stan Boland is one of the most successful and respected entrepreneurs in the UK. In 1999, he co-founded Element 14 which was acquired by Broadcom in 2000 for $640 million. Following this, Boland co-founded Icera Inc. in 2002, a fabless semiconductor company which he sold to Nvidia for $367 million. In Today's Discussion We Cover: 04:26 Is The UK's Biggest Problem a Talent Problem 09:50 Why We Need to Flood the UK With Venture Capital 10:38 What Europe Can Learn from Stripe and the Collisons 15:21 How the UK Can Use Visas to Retain the Best Talent 16:46 Why the Government Needs to Put 10x More Cash Into Fund of Funds 24:32 Is the London Stock Exchange F****** and Does it Matter? 34:38 What The UK Can Learn From Sequoia and the Norwegian Sovereign Wealth Fund 40:42 What is a "National Goal for Wealth Creation" & How Do We Implement It? 48:10 What are the Most Broken Elements of the UK Tax Regime 52:11 Is It Stupid to Remove the Non-Dom Tax Status 53:15 Why is Now the Time to Be Bullish on China 01:00:19 Biggest Lessons from Working with Jensen Huang 01:08:04 Quick Fire Round: Insights and Predictions

10 Huhti 1h 24min

20VC: Carvana CEO on Buiding a $50B Company, Losing 99% and Coming Back | Ernest Garcia: Inside the Mind of the Most Misunderstood CEO in America

20VC: Carvana CEO on Buiding a $50B Company, Losing 99% and Coming Back | Ernest Garcia: Inside the Mind of the Most Misunderstood CEO in America

Ernest Garcia is the Co-Founder and CEO @ Carvana. Under Ernie's leadership, Carvana went from a back-of-the-napkin idea to a $50+ billion public company, became the fastest-growing online used car retailer in U.S. history, and landed on the Fortune 500 in under 10 years. However, it was not all up and to the right, in 2022, the stock plummeted 99% to a market cap of just $400M. Today they are back with a market cap of $35BN, that is a 100x in the public markets and selling 400,000 cars sold annually, with a logistics network that rivals Amazon. In Today's Episode with Ernie Garcia We Discuss: 04:12 Are all great founders just "stubborn egomaniacs"? 06:55 How Carvana Almost Died on Several Occasions 08:46 Is Carvana's Inability to get VC Funding a Sign the VC Model is Broken? 11:58 Operators vs. Strategists: What Hires Can Make or Break a Company? 21:46 Billionaire's Biggest Lessons on Parenting 26:52 Is Life About Happiness or Achieving 32:21 The Reality of Being a Public Company CEO 39:07 Why Companies Should Go Public 43:55 Why You Should Price Your IPO to Perfection with No Pop 50:50 "What I Wish I Had Known About Debt in Building Carvana" 52:32 Quick Fire Round: Favourite CEO, Marriage Advice, Carvana in 10 Years

7 Huhti 1h 6min

20VC: Why To Win in AI, Investors Need to Change Their Approach | Why VC is Run by Principals and Associates and is a Broken System | The Bull Case for Anthropic & Whether Deepseek Changes Their Strategy with Nabeel Hyatt @ Spark Capital

20VC: Why To Win in AI, Investors Need to Change Their Approach | Why VC is Run by Principals and Associates and is a Broken System | The Bull Case for Anthropic & Whether Deepseek Changes Their Strategy with Nabeel Hyatt @ Spark Capital

Nabeel Hyatt is a General Partner @ Spark Capital, one of the leading firms of the last decade with portfolio companies including Twitter, Anthropic, Coinbase, Affirm, Discord, Deel and more. In Todays Show with Nabeel Hyatt We Discuss: 1. The Rules of Investing: What have been Nabeel's biggest lessons on price sensitivity? When did he not pay up and with the benefit of hindsight, wish he had of paid up? How important is ownership to Nabeel and Spark? How does Nabeel think about reserve investing and doubling down? Why does Nabeel not engage in secondary markets? How does Nabeel think about when is the right time to sell? Why does Nabeel think the majority of market sizing is total BS? 2. The Venture Landscape: Run by Principles and Broken: Why does Nabeel believe this generation of AI investing will require a different mindset to the one that made VCs successful over the last decade? Why does Nabeel believe that venture is currently run by principals and associates? Why is that such a problem? Why does Nabeel believe that the majority of venture firms today are dead but do not know it yet? What does Nabeel believe happens to the mega multi-stage firms who have raised billions and billions? 3. How to Win the VC Game in a World of AI: Infrastructure, models, apps: where does Nabeel believe the most value will accrue in the next decade of AI investing? What does Nabeel mean when he says there are three categories of AI apps today? Where does Nabeel believe the most valuable will be built? Does Nabeel believe Deepseek hurt or helped the future for Anthropic? How could Anthropic be a $100BN company from this point? What does no one see about the next 10 years of AI that everyone should see?

4 Huhti 1h 15min

20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox

20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox

Ishan Mukherjee is the Co-Founder/CEO of Rox, a Sequoia-backed AI-powered sales productivity platform. Before Rox, he was the Chief Growth Officer at New Relic where he scaled the self-serve business from $0-$100M in ARR. Prior to New Relic, Ishan founded Pixie Labs (acq by New Relic). Before that he led product at Siri Knowledge Graph at Apple, Lattice Data (acquired by Apple), Premise Data, and Amazon Robotics. Ishan was also an early engineer in Kiva (acquired by Amazon) where he joined after graduating from MIT. In Today's Episode We Discuss: 04:50 Biggest Lessons Scaling New Relic's PLG to $100M in ARR 05:59 How to Do PLG and Enterprise at the Same Time 07:00 How to do Content in a PLG World 08:50 Performance Marketing or Organic Content: What Works for PLG 10:27 Why You Should Stop Marketing at Events 11:47 Why SEM is a Cartel 14:15 Why Unpaid Design Partners are BS 17:17 How AI Changes the World of Enterprise Sales: Commit-Based vs. Usage-Based 20:49 How to do Sales Compensation Plans 24:44 How to Ramp New Sales Reps 25:03 The Impact of AI on Sales Research 29:18 How to do Deep Customer Research in an AI World 35:56 Changing Spending Patterns in SaaS 41:41 Retention and Churn in Enterprise AI 43:31 The Future of Sales Teams with AI 44:45 Hiring and Scaling Sales Teams 54:28 Quickfire

4 Huhti 1h 9min

20VC: The Daily Deal: Coreweave IPO | Scale Hits $25BN on $2BN EOY Revenue | Sequoia's 25x Return on Wiz | Tech Stocks Tank with Tariffs | Cursor: Defensible or Dangerous Example of Lost Moats in Tech

20VC: The Daily Deal: Coreweave IPO | Scale Hits $25BN on $2BN EOY Revenue | Sequoia's 25x Return on Wiz | Tech Stocks Tank with Tariffs | Cursor: Defensible or Dangerous Example of Lost Moats in Tech

Welcome to The Daily Deal — the new show with Harry Stebbings and Jason Lemkin, where we break down the biggest stories in tech, venture, and B2B. From market meltdowns to billion-dollar raises, wild valuations, and the drama behind the deals. We're covering it all! Plus, we'll be joined by some incredible guests to go deeper on the moves shaping the future of our industry. Today we discuss: Tech stocks were hammered in late trading today in response to the Trump administration's plans to levy tariffs of between 10% and 49% on imported goods, with Apple shares falling more than 6%. Rippling Deal: Illegal or Hustle? Emergence Raises $1B for B2B Investments Cursor, Replit, Windsurf: Who Wins? Lots of gen AI startups are crossing into the $100M ARR club. The latest entrant is talent marketplace Mercor, last valued at $2B. Is triple triple double double dead? ScaleAI at $25B: Pricey or Potential? Discussion with Bhavin Shah @ Moveworks: ServiceNow Acquires Moveworks for $2.5B: AI Craze Continues Sequoia Makes 25x on Wiz: Is M&A Open Again? USD Stablecoin issuer Circle has filed to go public. The company, which has raised $1.2 billion in VC money, reported $1.7 billion in 2024 revenue, with $155.7 million in net income. Oracle Cloud Revenue Up 23%: Old Guard Wins in AI? Salesforce Customers Love AgentForce, But Will They Pay? Dustin Moskovitz Retires from Asana: Is SaaS Too Tough? Discussion with Andrew Feldman @ Cerebras: Coreweave's Redemption Provision: A Time Bomb for Coatue? Can OpenAI's $12B Deal Save Coreweave from $5B Loss? OpenAI Won't Profit Until $127B in Annual Revenue A lot of young founders raising big in chips; bullish or bullshit?

3 Huhti 1h 27min

20VC: Microsoft CTO on Where Value Accrues in an AI World | Why Scaling Laws are BS | An Evaluation of Deepseek and How We Underestimate the Chinese | The Future of Software Development and The Future of Agents with Kevin Scott

20VC: Microsoft CTO on Where Value Accrues in an AI World | Why Scaling Laws are BS | An Evaluation of Deepseek and How We Underestimate the Chinese | The Future of Software Development and The Future of Agents with Kevin Scott

Kevin Scott is the CTO of Microsoft, where he leads the company's AI and technology strategy at global scale and played a pivotal role in Microsoft's partnership with OpenAI. Prior to Microsoft, Kevin spent six years at Linkedin as SVP of Engineering. Kevin has also enjoyed advisory positions with Pinterest, Box, Code.org and more. In Today's Episode We Discuss: 04:10 Where is Enduring Value in a World of AI 10:53 Why Scaling Laws are BS 12:26 What is the Bottleneck Today: Data, Compute or Algorithms 15:38: In 10 Years Time: What % of Data Usage will be Synthetic 20:04 How Will AI Agents Evolve Over the Next Five Years 23:34: Deepseek Evalution: Do We Underestimate China 28:34 The Future of Software Development 31:53 The Thing That Most Excites Me in AI is Tech Debt 35:01 Leadership Lessons from Satya Nadella 41:13 Quickfire Round

31 Maalis 45min

20VC: Will Revolut and Monzo List in the UK | How Does London Compete Against the US To Win The Best UK IPOs | Are UK Public Companies Punished on Price for Listing in London | The Myths and the Reality of The London Stock Exchange with CEO, Julia Hoggett

20VC: Will Revolut and Monzo List in the UK | How Does London Compete Against the US To Win The Best UK IPOs | Are UK Public Companies Punished on Price for Listing in London | The Myths and the Reality of The London Stock Exchange with CEO, Julia Hoggett

Dame Julia Hoggett is the CEO of the London Stock Exchange. Julia previously worked at the UK's Financial Conduct Authority as Director of Market Oversight and Head of Wholesale Banking Supervision. In Today's Episode We Discuss: 04:25 How to Become CEO of a National Stock Exchange 05:36 Why The Domestic Economy is F***** Despite the Boom in Financial Services 06:45 How Pension Fund Reform Dmaaged the UK Economy 09:31 Should the UK Copy the Canadian Pension Fund Structure 16:30 Will the Best Companies Like Revolut and Monzo List in London 24:17 Why Are Revolut Wrong to Want to List in the US 27:32 Are Companies Priced Lower in the UK vs US 32:05 Why is Stamp Duty a Perversity We Have to Change 35:46 Why is the Way the UK Thinks About Financial Services So Wrong 40:31 Quick Fire Round: Insights and Reflections

28 Maalis 50min

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