20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport

20VC: Why Remote Work is White Collar Fraud | Why Revenge and Patriotism are the Best Founder Traits | Two Questions Every Founder Needs to Ask | The Wild Story of Raising $1BN from Masa Son in an Hour Long Meeting with Ryan Peterson, Founder @ Flexport

Ryan Peterson is the Founder & CEO @ Flexport, the logistics darling of the venture capital world that has raised $900M+ with the last round valuing the company at $8BN. Today, the company does $450M in revenue growing 30% YoY.

AGENDA:

00:00 — Why Does Ryan Petersen Call Remote Work "White Collar Fraud"?

08:30 — Does Having More Money Actually Make You a Better Founder?

11:40 — When Will Flexport IPO? What Price Would It Go Out At?

19:00 — Can AI Actually Automate Entire Companies or Is the Productivity Boom Overhyped?

22:00 — Which Jobs Will Exist in 5 Years That Don't Exist Today?

26:00 — OpenAI vs Anthropic: If Ryan Could Only Own One, Which Would He Buy?

27:45 — Are Chinese Open-Source Models a National Security Threat—or Is Silicon Valley Overreacting?

30:15 — The $500M Fundraising Mistake Ryan Wishes He Never Made

35:00 — Why Flexport Abandoned San Francisco & Remote Work Damaged Flexport's Culture

41:00 — Why Marketing Is the Hardest Executive Hire in Startups

43:00 — Do Great CEOs Hate HR?

46:00 — Why Most Startup Founders Hire Executives Too Early

48:00 — What Ryan Learned Investing Alongside the Greatest YC Founders

55:00 — The Single Biggest Mistake Founders Make When Fundraising

1:09:00 — Does Founder Brand Actually Drive Enterprise Value?

1:11:00 — What Makes a Great Board Member—and Why Most Boards Add Negative Value

1:13:00 — The Sports Team Ryan Dreams of Buying Just to Troll His Biggest Competitor

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Episoder(1522)

20VC: The Pro-Rata Battle: Valar Atomics Sues Day One Ventures | Meta Returns to the AI Frontier With Muse Wonder | NVIDIA Eyes $30B Reflection Deal & Jev Raises $870M at a $7.5B Valuation

20VC: The Pro-Rata Battle: Valar Atomics Sues Day One Ventures | Meta Returns to the AI Frontier With Muse Wonder | NVIDIA Eyes $30B Reflection Deal & Jev Raises $870M at a $7.5B Valuation

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Mike Cannon-Brookes is the Co-Founder and CEO of Atlassian, the company behind Jira, Confluence, Trello and Loom. Atlassian generated $6.5BN in ARR in 2026, and serves more than 350,000 customers, inc...

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20Sales: Inside Ramp's Sales Playbook: How to Build a Sales Machine with Max Freeman, SVP Sales @ Ramp

Max Freeman is SVP of Sales at Ramp. He joined the company as its first sales hire. By 2025, he was leading more than 300 salespeople, helping build Ramp's sales organisation from the ground up. Ramp'...

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20VC: Cognition vs Factory: Vinod Khosla Creates a Storm | OpenAI Nears $70B Run Rate: Anthropic Under Threat | ElevenLabs Doubles Its Valuation to $22B & Salesforce Buys Listen Labs for $2B

20VC: Cognition vs Factory: Vinod Khosla Creates a Storm | OpenAI Nears $70B Run Rate: Anthropic Under Threat | ElevenLabs Doubles Its Valuation to $22B & Salesforce Buys Listen Labs for $2B

Joinin the trio today we have Dev Ittycheria, CEO @ MongoDB.  AGENDA:  04:00 OpenAI Nears $70B Run Rate—Anthropic's Lead Under Threat 12:00 Factory vs Cognition: Silicon Valley's Talent War Turns Ugly...

8 Okt 1h 13min

20VC: Is Seed Investing Dead Without a $1BN Fund? | Does Ownership and Price Matter When Companies Can Be $1TRN Exits | Are AI Revenue Numbers Real and What to Watch Out For with Venky Ganesan, Menlo Ventures

20VC: Is Seed Investing Dead Without a $1BN Fund? | Does Ownership and Price Matter When Companies Can Be $1TRN Exits | Are AI Revenue Numbers Real and What to Watch Out For with Venky Ganesan, Menlo Ventures

Venky Ganesan is a Partner at Menlo Ventures, whose portfolio includes Anthropic, Lovable, Legora and Higgsfield, alongside earlier hits Uber and Roku. Venky's own investment track record includes Pal...

5 Okt 1h 6min

20VC: The Future of Datacentres: What You Need to Know | Why Everyone Gets GPU Depreciation and AI's Energy Costs Wrong | Who Really Makes Money From AI & Why Most Moats Don't Exist with Chase Lochmiller

20VC: The Future of Datacentres: What You Need to Know | Why Everyone Gets GPU Depreciation and AI's Energy Costs Wrong | Who Really Makes Money From AI & Why Most Moats Don't Exist with Chase Lochmiller

Chase Lochmiller is the Co-founder and CEO of Crusoe. Crusoe builds and powers the data centres that companies use to train and run AI. It has raised approximately $6.4 billion in equity, including it...

3 Okt 1h 1min

20VC: Instinct Raises $1B at $10B Valuation | AMD Buys Fei-Fei Li's World Labs for $8.2B | Meta Poaches MongoDB's CEO | Bessemer Raises $5.75B | Oura Pulls IPO & Nubank Eyes $8–12B Monzo Takeover

20VC: Instinct Raises $1B at $10B Valuation | AMD Buys Fei-Fei Li's World Labs for $8.2B | Meta Poaches MongoDB's CEO | Bessemer Raises $5.75B | Oura Pulls IPO & Nubank Eyes $8–12B Monzo Takeover

AGENDA:  00:00 Highlights: Jack Altman Joins The Trio 05:00 Anthropic's S-1 Leaks: $8B Operating Loss and $518B in Compute Commitments 10:00 Instinct Raises $1B at a $10B Valuation to Take On Meta 25:...

1 Okt 1h 18min

20VC: $1BN ARR in 18 Months; The Untold Story of Higgsfield | Spending $4M Per Month on Models | Why Moats in AI are BS | Scaling a Content Team to 150 People with Alex Mashrabov

20VC: $1BN ARR in 18 Months; The Untold Story of Higgsfield | Spending $4M Per Month on Models | Why Moats in AI are BS | Scaling a Content Team to 150 People with Alex Mashrabov

Alex Mashrabov is the Founder and CEO of Higgsfield, the third fastest scaling company to $1BN in ARR behind OpenAI and Anthropic. Reports suggest their latest funding round could place an $8BN valuat...

28 Sep 1h 9min

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