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)

Author: Harry Stebbings January 24, 2026 Duration: 42:54
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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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)

 


Hosted by Harry Stebbings, The Twenty Minute VC (20VC) pulls back the curtain on the high-stakes worlds of venture capital and startup building. Each episode is a compact, twenty-minute dive into the minds shaping the future of technology. You’ll hear candid conversations with legendary investors, the very individuals who fund and guide the next generation of companies, featuring voices like Sequoia's Doug Leone and Benchmark's Bill Gurley. Beyond the capital, this podcast dedicates time to the founders themselves. Weekly, Stebbings sits down with transformative entrepreneurs such as Spotify's Daniel Ek, LinkedIn's Reid Hoffman, and Snowflake's Frank Slootman, unpacking the real journeys behind their iconic companies. The format is direct and focused, cutting straight to the core insights on funding strategies, pitch dynamics, and the personal philosophies that drive success. Tuning into this podcast means gaining an unfiltered perspective from both sides of the table, all delivered in a concise and accessible style that fits into your day.
Author: Language: English Episodes: 100

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The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
Podcast Episodes
20VC: Is SaaS Dead in a World of AI | Do Margins Matter Anymore | Is Triple, Triple, Double, Double Dead Today? | Who Wins the Dev Market: Cursor or Claude Code | Why We Are Not in an AI Bubble with Anish Acharya @ a16z [not-audio_url] [/not-audio_url]

Duration: 1:24:15
Anish Acharya is a General Partner at Andreessen Horowitz (a16z), where he leads consumer and fintech investing at Series A. He serves on the boards of standout portfolio companies including Deel, Mosaic, Clutch, Titan,…
20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company CEOs Actually Happy? | Why Navan Built It's Own Customer Service AI and What it Could Mean For Customer Service AI with Ariel Cohen [not-audio_url] [/not-audio_url]

Duration: 54:18
Ariel Cohen is the Co-Founder and CEO of Navan (formerly TripActions), an AI-powered travel and expense platform. Last month, Ariel took the company public, since being a public company, they have faced a torrid time see…
20VC: SpaceX Completes Acquisition of xAI | The 2026 SaaS Massacre: Public Market Collapse | Microsoft's $360 Billion Market Cap Loss | NVIDIA's $100BN Investment Dispute with OpenAI | Waymo Raises $16 Billion at a $110 Billion Valuation [not-audio_url] [/not-audio_url]

Duration: 1:34:19
AGENDA: 00:00 - SpaceX Completes Acquisition of xAI in $1.25 Trillion Merger 08:44 - The Rehabilitation of the IPO and the End of "State Private Forever" 15:53 - The 2026 SaaS Massacre: Public Market Collapse 31:20 - Nex…
20VC: Brex Acquired for $5.15BN | a16z Companies are 2/3 AI Revenues | Anthropic Inference Costs Skyrocket | OpenEvidence Raises at $12BN Valuation | The IPO Market: EquipmentShare, Wealthfront and Ethos Insurance [not-audio_url] [/not-audio_url]

Duration: 1:15:55
AGENDA: 03:36 Brex Acquisition by Capital One for $5.15BN 10:54 Does Brex's Acquisition Help or Hurt Ramp? 16:28 TikTok Deal Completed: Who Won & Who Lost: Analysis 19:30 Anthropic Inference Costs Higher Than Expected 37…
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 [not-audio_url] [/not-audio_url]

Duration: 1:03:20
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 o…
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 [not-audio_url] [/not-audio_url]

Duration: 1:13:53
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…

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