20VC: Raising Over $700m From The World's Best Investors, How To Innovate In Highly Regulated Markets & The 3 Superpowers of Insurance Companies with Mario Schlosser, Founder & CEO @ Oscar

20VC: Raising Over $700m From The World's Best Investors, How To Innovate In Highly Regulated Markets & The 3 Superpowers of Insurance Companies with Mario Schlosser, Founder & CEO @ Oscar

Mario Schlosser is the Founder & CEO @ Oscar, the startup that makes health insurance easy. They have raised over $700m in funding from some of the world's best investors including the likes of Founders Fund, Google Capital, Thrive Capital, Lakestar, Khosla Ventures and Jim Breyer just to name a few. Previously, Mario co-founded the largest social gaming company in Latin America and held roles with the likes of Bridgewater Associates and McKinsey. Fun fact, as a visiting scholar at Stanford University, Mario wrote 10 computer science publications, including one of the most-cited computer science papers published in the past decade.

In Today's Episode You Will Learn:

1.) How Mario made his way into the world of healthcare and Oscar from founding Latin America's largest social gaming company?

2.) Why is insurance one of the most complex spaces in tech? Why is there a chance for companies, not governments, to cut costs and innovate on the current system? Does Mario agree with Brian Singerman, "once we go to a single player, innovation ends", thesis?

3.) Oscar has raised over $700m, to what extent does Mario believe that too high a valuation can be a liability? How did Mario look to select his investors? What are the challenges of raising funds for a category-defining opportunity?

4.) Oscar now has over 600 in the team, where have been the inflection points in the scaling of the company? Where have things broken? How does Mario look to rectify and observe these inflection points ahead of time?

5.) How does Mario look to optimise team composition? How does he look to balance athletes with heavy domain experts? Does Mario believe that too much domain expertise can prevent innovation due to a lack of naivety?

Items Mentioned In Today's Show:

Mario's Fave Book: Herr Lehmann

Mario's Fave Blog: Spiegel

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

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

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Episoder(1377)

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 Apr 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 Apr 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 Apr 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 Mar 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 Mar 50min

20VC: Why Traditional VC is Broken: How VCs Learned Nothing from 2021 | Why LPs are More Important than Founders & Advice to Emerging Managers | Bull Case for Bytedance & Why TikTok's Ban Doesn't Matter with Mitchell Green, Lead Edge Capital

20VC: Why Traditional VC is Broken: How VCs Learned Nothing from 2021 | Why LPs are More Important than Founders & Advice to Emerging Managers | Bull Case for Bytedance & Why TikTok's Ban Doesn't Matter with Mitchell Green, Lead Edge Capital

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 Mar 1h 19min

20VC: The Insane Story of DeliveryHero: Losing $200M on a Gorillas Investment | Winning the Emerging Markets Delivery War with 35 Acquisitions | Competing with Uber and Doordash in a Capital Arms Race with Niklas Östberg

20VC: The Insane Story of DeliveryHero: Losing $200M on a Gorillas Investment | Winning the Emerging Markets Delivery War with 35 Acquisitions | Competing with Uber and Doordash in a Capital Arms Race with Niklas Östberg

Niklas Östberg is the Founder and CEO of Delivery Hero, a global juggernaut now present in over 70 countries across four continents. In Q4 2024, the company announced GMV of $49BN with $12.8BN in revenue and $750M in EBITDA. They have made an astonishing 35+ acquisitions including $2BN for Glovo. Before launching Delivery Hero, Niklas co-founded Pizza.nu, leading its expansion across Sweden, Poland, Finland, and Austria. In Today's Episode We Discuss: 04:09 How Skiing Prepared Me For Life As An Entrepreneur 10:12 Losing $200M on Gorillas Investment 17:58 Quick Commerce: Does the Business Model Work? 25:09 How to Master M&A: Lessons from 35 Acquisitions 31:45 Evaluating Acquisitions: The Glovo Example 32:39 Cohort Analysis: Lessons from $49BN in GMV 34:35 Growth Strategies: What Worked? What Did Not Work? 38:27 Competing Against Uber and Doordash 41:40 Is Cash a Weapon in the War for Food Delivery 44:29 Why Are Emerging Markets a Good Investment? 48:21 Why Are European Markets Broken? Are Regulators Killing Europe? 51:57 Quickfire Round: Insights and Reflections

27 Mar 1h 1min

20VC: AI Chip Wars: How Cerebras Plans to Topple NVIDIA's Dominance | Why We Have Not Reached Scaling Laws in AI | What Happens to the Cost of Inference | How We Underestimate China and Shouldn't Sell To Them with Andrew Feldman

20VC: AI Chip Wars: How Cerebras Plans to Topple NVIDIA's Dominance | Why We Have Not Reached Scaling Laws in AI | What Happens to the Cost of Inference | How We Underestimate China and Shouldn't Sell To Them with Andrew Feldman

Andrew Feldman is the Co-Founder and CEO @ Cerebras, the fastest AI inference + training platform in the world. In Sept 2024 the company filed to go public off the back of a rumoured $1BN deal with G42 in the UAE. Andrew is the leading expert for all things inference. In Today's Episode We Discuss: 04:23 Where Was AI Landscape in 2015 When Cerebras Founded 05:57 NVIDIA's Biggest Strength Has Become Their Biggest Weakness 07:09 What Happens to the Cost of Inference? 08:55 Why Are AI Algorithms So Inefficient? 20:30 Why is it Total BS That We Have Hit Scaling Laws? 23:07 What Will Be the Ratio of Synthetic to Human Data Used in 5 Years? 31:37 What Specifically Was So Impressive About Deepseek? 31:51 Why is Distillation Not Wrong and OpenAI Need to Look in the Mirror? 32:34 Where Will Value Accrue in a World of AI? 34:08 How Will NVIDIA's Market Position Change Over the Next Five Years? 39:59 Why is the CUDA Lockin for NVIDIA BS? What is Their Weakness? 40:46 Why is Trump Better for Business than Biden? 49:41 Do We Underestimate China in a World of AI? 52:33 What is the Most Underappreciated Segment of AI? 54:00 Quickfire Round

24 Mar 1h 3min

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