20VC: The Two Biggest Mistakes Every Founder Makes, Why Founders Are Not Ambitious Enough Today, Why Having a Narrow Target Customer is Dangerous & The Three Possible Outcomes in Company Building with Matthew Prince, Co-Founder @ Cloudflare

20VC: The Two Biggest Mistakes Every Founder Makes, Why Founders Are Not Ambitious Enough Today, Why Having a Narrow Target Customer is Dangerous & The Three Possible Outcomes in Company Building with Matthew Prince, Co-Founder @ Cloudflare

Matthew Prince is the co-founder and CEO of Cloudflare, on a mission is to help build a better Internet. Matthew has scaled Cloudflare to over $1BN in revenue, $20BN in market cap, and over 3,200 employees. Today the company runs one of the world's largest networks, which spans more than 200 cities in over 100 countries. Matthew is a World Economic Forum Technology Pioneer, a member of the Council on Foreign Relations, winner of the 2011 Tech Fellow Award, and serves on the Board of Advisors for the Center for Information Technology and Privacy Law.

In Today's Episode with Matthew Prince We Discuss:

1. From Selling Fireworks to Public Company CEO:

  • How did Matthew first make money selling fireworks as a kid?
  • Does Mathew believe in the trope "you have to love what you do"?
  • What does Matthew know now that he wishes he had known when he started Cloudflare?

2. Money, Identity and Happiness:

  • Why does Matthew feel many of the most successful founders lose their way when they leave their companies? How does he assess Gates, Bezos and others?
  • Does Matthew tie his own identity to Cloudflare and the success of the company?
  • How does Matthew evaluate his own relationship to money today? How has it changed over time?
  • How does Matthew keep score today on how he is doing? What is success to Matthew?

3. The Three Outcomes for Companies Today:

  • What are the three outcomes available to companies today?
  • What is the worst and why?
  • What are the two biggest mistakes Matthew sees founders make today?
  • Why does Matthew know that diverse teams are more successful? What is the proof?
  • What is Matthew's single biggest advice to founders when it comes to selecting a co-founder?

4. Focus is BS: You Have to Have Mega Ambition:

  • Why does Matthew believe it is BS to have a very specific target customer from the offset?
  • What does Matthew believe are the benefits of not having an ICP in the early days?
  • What are the biggest pieces of VC advice to founders that Matthew knows to be wrong?

Episoder(1410)

20VC: From Only OpenAI to Die-Hard Anthropic: The Downfall of OpenAI in Enterprise | Harvey vs Legora: Legal AI is a Winner Take All | $7M ARR in a Single Day and Raising $200M Across 3 Rounds with No Deck with Max Junestrand, CEO @ Legora

20VC: From Only OpenAI to Die-Hard Anthropic: The Downfall of OpenAI in Enterprise | Harvey vs Legora: Legal AI is a Winner Take All | $7M ARR in a Single Day and Raising $200M Across 3 Rounds with No Deck with Max Junestrand, CEO @ Legora

Max Junestrand is the Co-Founder and CEO @ Legora, the legal AI company that has scaled to 750 of the world's leading law firms as customers and over 300 employees in just 2 years. They have raised over $200M from some of the best in the business including Benchmark, General Catalyst, Redpoint and ICONIQ.  AGENDA: 04:16 Why Does Everyone Think Harvey When They Hear Legal AI? 07:35 Why OpenAI is Toast? Switching to Anthropic! 11:47 24 Months: Which Foundation Models Will Win?  23:53 Lessons Scaling from Europe into the US 28:53 Do Americans Work As Hard As They Say? 32:20 Why Seat Models Are Not Dead in SaaS? 36:17 How to Use Competition To Drive a Fire in Your Team? 40:59 Is Legal AI a Winner-Take-All Market? How Does It End? 47:18 The Future of Law Firms: Do Juniors Get Fired? 53:19 How We Raised $200M and 3 Rounds with No Deck 57:21 Quickfire Round: Best Advice, Closest Mentor, Biggest Mindset Shift

26 Jan 1h 3min

20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)

20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)

AGENDA: 00:03:00 – Harry's Wild Start: Making £1.75M at 19 in 36 Hours 00:06:00 – How Harry Got Marc Benioff on 20VC with Cold Emailing Alone 00:07:30 – Raising $70M on WhatsApp – Relationship Building Secrets 00:12:00 – Decision Framework: What Would Pat Grady (Sequoia) Do? 00:15:00 – Chase Your First Million – It Unlocks Everything 00:16:30 – Advice for 19-Year-Olds Today: Niche Down, Interview Leaders, Publish 00:18:00 – University Is a Waste for Most | Leverage Youth & Risk 00:22:30 – How Getting Kicked Out of School Changed Everything 00:30:00 – Why Should Everyone Be Creating Content Today and How to Start 00:35:30 – 7 Lessons from Billionaires 00:36:00 – #1: Never Accept No (The $12M Turnaround Story) 00:37:30 – #2: Beat Down the Door (53 Emails to Marc Benioff) 00:39:00 – #3: Just Start – 99% Never Do 00:40:30 – #4: Use a Role Model Framework for Hard Decisions 00:42:00 – #5: Chasing Money Won't Make You Happy – Enjoy the Art 00:44:00 – #6: Break Big Visions into Achievable Milestones 00:45:30 – #7: Win Over the Partner (Power of Pillow Talk)

24 Jan 42min

20VC: Sam Altman vs Elon Musk: The $100BN Battle | The Implosion of Thinking Machines | Can VC Survive Public Market Pricing Today? | ClickHouse and Replit's New Rounds: Analysed

20VC: Sam Altman vs Elon Musk: The $100BN Battle | The Implosion of Thinking Machines | Can VC Survive Public Market Pricing Today? | ClickHouse and Replit's New Rounds: Analysed

AGENDA: 03:30 Can VC Survive With Public Market Prices Today 15:20 The Implosion of Thinking Machines 21:13 Elon Musk vs. OpenAI: The Legal Battle 40:50 Can OpenAI Win Ads? 55:50 ClickHouse's $15BN Deal: Analysed 58:55 Replit's $9BN Deal: Analysed 01:08:35 There Are Only Two Types of Deals VCs Want To Do Today

22 Jan 1h 18min

20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

Winston Weinberg is the CEO and Co-Founder of Harvey, the leading professional services platform engineered with AI for law, tax, and finance. Winston has raised over $980M for Harvey from Sequoia, a16z, GV, Elad Gil and more with a last round price of $9.2BN post-money. Before founding Harvey in August 2022, Winston was an attorney at O'Melveny & Myers LLP, specializing in antitrust and securities litigation.  AGENDA: 04:10 #1 Thing Every Founder Needs to Do Everyday 05:33 Must Do Daily Routines and Productivity Tips for CEOs 12:45 How to Get Sequoia and a16z Term Sheets 15:06 Why VCs Suck at Helping Companies Hire? 27:01 What No One Understands About Enterprise AI Adoption 38:06 AI's Impact on Professional Services 39:26 Future of Law Firms: Do They Die? 43:38 What Everyone Should Know That No One Tells You About Hiring in Europe 47:08 I Have Massive Trust Issues… 54:17 Biggest Lessons on Effective Deal-Making  59:20 Cold Emailing OpenAI and It Leading to a Term Sheet 01:02:33 Quick Fire Round Try NEXOS.AI for yourself with a 14-day free trial: https://nexos.ai/20vc

19 Jan 1h 13min

20Product: Is the Design Phase Dead in a World of AI | Has Claude Code Crushed Anthropic Already | What Roles of a PM Are Less and More Important with AI | How the Best Product Leaders Tell Stories with Noam Lovinsky, CPO @ Superhuman

20Product: Is the Design Phase Dead in a World of AI | Has Claude Code Crushed Anthropic Already | What Roles of a PM Are Less and More Important with AI | How the Best Product Leaders Tell Stories with Noam Lovinsky, CPO @ Superhuman

Noam Lovinsky is the CPO @ Superhuman (formerly Grammarly). Prior to Superhuman he was a Senior Director of Product Management at Facebook. In his earlier years, he was CPO @ Thumbtack and spent 5 years as a Director of Product Management at Google where he was responsible for all of Youtube's applications.  AGENDA: 03:43 What is Great Product Leadership in a World of AI 07:45 Does the Design Phase Die in a World of Vibe Coding 12:21 How AI Changes Product Development Most 22:23 Accelerating Product Development 29:32 AI's Impact on Product Building 34:19 Predictions for 2026 34:45 Quick Fire Round 38:41 Reflections and Future Plans

16 Jan 45min

20VC: Anthropic's $10BN Fundraise: Have They Beaten Cursor Already | a16z's $15BN Fundraise: Is the Middle Dead in VC Today? | How OpenAI Could Go to Zero and ElevenLabs at $11BN: Buy or Not?

20VC: Anthropic's $10BN Fundraise: Have They Beaten Cursor Already | a16z's $15BN Fundraise: Is the Middle Dead in VC Today? | How OpenAI Could Go to Zero and ElevenLabs at $11BN: Buy or Not?

AGENDA: 05:02 Anthropic's $10 Billion Fundraise 07:54 Has Claude Code Beaten Cursor Already 15:54 OpenAI Could Still Go to Zero 26:33 Andreessen Horowitz's $15 Billion Fundraise 45:16 The Middle is Dead: Boutique vs. Large Platforms in Venture 50:01 The Future of Venture Capital 01:08:06 The Impact of Wealth Taxes on the Industry

15 Jan 1h 28min

20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital

20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital

Alex Rampell is a General Partner at Andressen Horowitz, where he leads their $1.7BN apps fund. Just last week, a16z announced they had raised $15BN for their latest funds, over 20% of all capital raised by venture firms. At a16z, Alex has led deals into Plaid, Mercury and OpenDoor to name a few.  AGENDA: 04:55 How to Do 5x on a $15BN Fund Pool?  09:21 What Two Groups of Funds Will Win the Next Decade in VC? 14:39 What Three Things Are the Best Founders Able to Do?  19:22 The Best Companies Have Hostages, Not Customers 31:37 The Two Types of Deals You Want To Do In VC 38:52 The Importance of Founder/Capital Fit 40:34 Multiple Successive Rounds Are Dangerous… Here is Why? 42:13 Challenges of High Valuations 45:27 The Importance of Ownership in Deals 52:47 Is Triple, Triple, Double, Double Dead 58:33 Advice on Selling Companies 01:11:55 What is the Future of Venture Capital

12 Jan 1h 17min

20Growth: The $6.6B Growth Engine Behind ElevenLabs | Why ElevenLabs Do Not Have PMs | The 7 Part Launch Playbook to Crush All Launches with Luke Harries, Head of Growth @ ElevenLabs

20Growth: The $6.6B Growth Engine Behind ElevenLabs | Why ElevenLabs Do Not Have PMs | The 7 Part Launch Playbook to Crush All Launches with Luke Harries, Head of Growth @ ElevenLabs

Luke Harries is Head of Growth at ElevenLabs, where he leads marketing, product, engineering, and developer experience. ElevenLabs has raised $281M with the latest round pricing the company at a $6.6B valuation. Previously, Luke held roles at PostHog and Microsoft, and is also an angel investor supporting startups like Lovable and Runna. AGENDA:  The $6.6B Growth Engine Behind ElevenLabs Why Luke Said "No" to Investing in ElevenLabs (and Why He Was Wrong) How ElevenLabs Makes a Horizontal Product Strategy Work How to Build Sharded Growth Teams That Actually Scale The 7-Part Launch Playbook That Gets 700K+ Views Per Product The Truth About CAC, Payback, and Performance Marketing in AI SEO Isn't Dead: The Mini-Tool Strategy You Should Steal Kill Your Inbound SDRs—The Case for Voice AI in Sales Why You Don't Need PMs and the Rise of Growth-Led Product Teams

11 Jan 1h 13min

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