20Sales: What I Learned Scaling Datadog from $60M to $1BN in ARR | How to do Outbound in 2024 | Why Discounting is Dangerous and Contract Sizes are Misleading with Dan Fougere

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 Apr 1h 24min

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 Apr 1h 6min

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 Apr 1h 15min

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 Apr 1h 9min

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 Apr 1h 27min

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 Mars 45min

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 Mars 50min

Mitchell Green is the Founder and Managing Partner of Lead Edge Capital. Mitchell has led or co-led investments in companies including Alibaba, Asana, Benchling, ByteDance, Duo Security, Grafana, Mindbody, and Xamarin, among several others. In Today’s Episode We Discuss: 04:31 How Bessemer Taught Me The One Golden Rule of Investing 06:48 Why AI Infrastrcture is the Worst Investment to Make 08:51 Why it is Comical to think there will be $BN one person companies? 09:26 WTF Happens To The Cohort of SaaS Companies With Slow Growth, Not Yet Profitable and $50M-$200M in Revenue 16:12 What is the Biggest Problem with the IPO Market 23:24 When is the Right Time to Sell in VC and How a Generation F******* it Up 27:37 Biggest Advice to Smaller Emerging Managers 40:13 The One Question That Tells You if a Business is Good 43:01 Why LPs are More Important than Founders 45:03 One Question Every LP Should Ask Their VCs 46:03 Why TikTok Does Not Matter to ByteDance and It Is a Screaming Buy 51:30 Why We Drastically Underestimate the Power of Chinese AI? 55:18 Why Social Media is the Most Dangerous Thing in Society 01:00:07 Quick Fire Questions

28 Mars 1h 19min