The Twenty Minute VC (20VC): Venture Capital | Startup Funding

Latest Episodes:

20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable Oct 31, 2025

Show notes

🎧 20VC x Tim Ferriss — Full Episode Timeline

00:00 – "How Do You Stay True to Yourself When You Have to Perform for the World?"

06:00 – "Why Tim Ferriss Refused to Go All-In on YouTube"

09:00 – "You Don't Need 10 Million Fans—You Need 1,000 True Believers."

12:00 – "The Internet Is Not a Relevance Machine—It's a Sensationalism Machine."

15:00 – "Money Fixes Money Problems—And Nothing Else."

22:30 – "When Did Tim Ferriss Feel Completely Lost?"

27:00 – "The Million-Dollar Mistake That Still Haunts Tim Ferriss."

36:00 – "Why Tim Ferriss Never Raised a Fund—Even Though He Could Have."

45:00 – "The Truth About Uber, Duolingo, and the Power of Relationship Investing."

54:00 – "Why Tim Ferriss Stopped Angel Investing at His Peak."

1:04:00 – "The Podcast That Changed Everything."

1:15:00 – "The Real Cost of Love: Is Efficiency Killing Connection?"

1:31:00 – "What Tim Ferriss Has Changed His Mind About Most."

1:36:00 – "Erections Matter."

20VC: a16z Raises $10BN in New Funds | Mercor Raises $350M at a $10BN Valuation | OpenAI Restructuring: Who Wins and Who Loses | Why IRR is a BS Metric and Three Ways to Win in VC Today Oct 30, 2025

Show notes

AGENDA:

05:17 OpenAI's Restructuring: Winners and Losers

17:17 Andreessen Horowitz's Raise $10BN in New Funds

26:38 Mercor Raises $350M at a $10BN Valuation

43:08 Spray and Pray: Does it Work: Data Breakdown

47:04 The Role of Option Checks Venture Capital

48:36 The Three Ways to Win in VC Today

54:26 Why IRR is a BS Metric and What Matters More

01:08:47 Amazon's Struggles: How Do They Return to Greatness in AI

20VC: Sequoia's David Cahn on The Winners and Losers in AI | The $0-$100M Revenue Club: Is Triple, Triple, Double, Double Dead? | The Future of Defence: Who Wins and Who Loses | How to Analyse Margins and Growth Rates in a World of AI Oct 27, 2025

Show notes

David Cahn is a Partner at Sequoia Capital and one of the world's leading AI investors. At Sequoia David has led investments in Clay, Juicebox, Sesame, Kela, Stark, etc.. Before Sequoia, David was a General Partner @ Coatue where he led investments in Notion and Hugging Face.

AGENDA:

00:00 We Are in an AI Bubble

05:04 Why Building Physical Data Centres is a Moat

13:58 Winners and Losers in a World of AI

19:13 The Role of Big Tech and Monopolies

23:37 Breaking Down Circular Deals in AI: The Truth No One Sees?

38:19 Why Kingmaking is BS and VCs Do Not Make or Break Companies

41:30 The Importance of Margins in AI Investments

43:41 The Required Growth Rates in AI to Get Funded by Sequoia

45:30 The $0-$100M Revenue Club: Is Triple, Triple, Double, Double Dead?

51:53 Why the Most Important Hire for Startups Today is 23 Year Olds

01:01:19 The Future of Defence: Who Wins and Who Loses

01:10:15 Quickfire: Biggest Miss, Parenting Advice, Doug Leone Advice

20Growth: How to Build a Paid Marketing Machine: ROAS (Return on Ad Spend) 101 | The Rise of User Generated Content and How to Use It | TikTok Ads: Expectations vs. Reality | Hiring for Growth: When and Who with Sandy Diao Oct 24, 2025

Show notes

Sandy Diao is one of the most exceptional growth leaders of the last decade. Sandy has scaled products to over 200M+ users and led growth teams at Descript, Meta and Pinterest. She is also a prolific writer all on things growth here.

AGENDA:

03:59 Biggest Growth Lessons from Pinterest

08:01 What is a Good vs a Bad Growth Hypothesis

11:11 Common Mistakes in Growth Strategies

14:57 Channel Fit: When You Have It & What To Do

25:43 Return on Ad Spend (ROAS) 101: How to Build a Paid Marketing Machine

30:08 How to Do SEO and Long-Term Growth Investments

33:22 Doubling Down on Successful Channels

36:31 The Unchanging Foundations of SEO

37:52 Generative AI Engines vs. Traditional Search Engines

41:12 Paid Marketing Channels: What's Overrated?

43:42 The Rise of User-Generated Content (UGC)

46:34 TikTok Ads: Expectations vs. Reality

49:55 Brand Marketing: What is Real vs What is BS?

53:33 The Importance of Feature Launches

01:01:50 Hiring for Growth: When and Who?

01:08:55 Quick Fire Round: Onboarding, Notifications, and Growth Channels

20VC: Why VC Today is Worse Than 2021 | Why Vertical SaaS is a Bad Investment Today | Why We Are Deluding Ourselves on Growth Expectations | Revolut Raises $3BN at a $75BN Valuation | Benchmark Adds Their Newest General Partner Oct 23, 2025

Show notes

AGENDA:

04:50 Benchmark's New Partner: Everett Randall

10:19 Revolut Raises $3BN at a $75BN Valuation: Another Loss for Public Markets?

28:39 Why Today is as Bad as the Hype of COVID in 2021

32:10 Why Vertical SaaS is a Bad VC Investment Today

36:14 Why Everyone Investing in Legal SaaS Will Lose Money

44:16 Why King Making is More Real Than Ever

55:23 Why Your Smallest Customers Need to Pay $10K Minimum

01:01:37 Why VC is a S*** Asset Class

01:09:29 Why Today is Harder Than It Has Ever Been in VC

01:25:18 Closing Thoughts and Reflections

20VC: Deel CEO Alex Bouaziz on Raising $300M+ at a $17BN Valuation | Deel vs Rippling: WTF is Going On | Management Lessons from Ben Horowitz and Nik Storonsky | Deel's M&A Playbook: Lessons from 13 Acquisitions: What Works & What Doesn't Oct 22, 2025

Show notes

Alex Bouaziz is the Co-Founder and CEO @ Deel, the $17BN global payroll juggernaut that just last week announced their latest $300M fundraise led by Ribbit, a16z and Coatue. Deel has been on the most insane journey, they do $1BN+ in ARR, they just had their first $100M revenue month and they have been profitable for over 3 years.

AGENDA:

03:38 Announcing $300M Fundraise at a $17BN Valuation

06:24 Rippling vs Deel: WTF is Going On? Where is the Lawsuit?

14:01 Why 1-1s Are BS and Leaders Should Stop Doing Them

17:31 Do Rich Leaders Make Better Leaders

28:33 Biggest Lesson from Ben Horowitz? Why Most CMOs Are Bad?

34:48 Lessons from Nik @ Revolut and Why Companies Need to Make Their Own Software

42:23 Deel's Acquisition Playbook: Lessons from 13 Acquisitions

45:17 How to Price Acquisitions? How to Align Incentives with Founders?

55:45 Deel is Profitable and Growing Fast: When is the IPO?

01:01:35 Best Acquisition Ever + Worst Ever: What Did We Learn?

20VC: The Startup Adding $1M ARR Every Week | Competing Against OpenAI's Codex and Claude Code: Who Wins | Why Gemini is Failing and GPT-5 Is Winning | Do Margins Matter in a World of AI | The Ugly Truth About AI Coding with Zach Lloyd, Warp Oct 17, 2025

Show notes

Zach Lloyd is the Founder and CEO of Warp, the next-generation developer terminal reinventing how engineers build and collaborate. Warp has raised over $70M from top-tier investors including Sequoia Capital, GV, Dylan Field, and Elad Gil. Before founding Warp, Zach was Principal Engineer at Google, where he led development of Google Docs, and later served as CTO at Time. He's one of the most respected engineering minds redefining the future of developer tools.

AGENDA:

04:14 Biggest Product Lessons from Rewriting Google Sheets

07:10 Why I Would Short Google: Leadership and AI Strategy

09:55 Comparing AI Models: GPT, Claude, and Gemini: Who Wins and Loses

17:04 Do Margins Matter in AI?

24:57 Adding $1M in ARR Every Week: Is Triple, Triple, Double, Double Dead?

33:58 How to Build Defensibility in a World of AI?

43:05 OpenAI vs Anthropic: Who Wins and Why?

44:25 Biggest Fundraising Lessons Raising from Sequoia, Elad Gil and GV

50:56 Why Sequoia are the Best VC

53:51 What Every Founder Gets Wrong in Fundraising

01:01:30 Quick Fire Questions and Final Thoughts

20VC: $3.5BN - The Price Zuck Paid for Thinking Machines Co-Founder | Goldman Sachs Acquires Industry Ventures for $665M | Softbank Borrows $5BN Against ARM Holding to Invest More Into OpenAI Oct 16, 2025

Show notes

AGENDA:

03:44 Rory Is So Old He Worked with Arthur Rock!!!

07:28 Goldman Sachs Acquires Industry Ventures for $665M

16:37 Thinking Machines Co-Founder Raises $2BN and Then Leaves for Meta

29:36 SoftBank Goes for $5BN Leverage Against ARM Stock To Buy More OpenAI

39:35 More Data Centres Than Offices: Are We In a Bubble

43:28 Where is the Alpha in Venture in 2025

51:48 What 90% of Managers Get Wrong About Portfolio Management

20VC: Atlassian CEO on Why Everything is Overvalued & Are We in an AI Bubble | Do Margins Matter & Does Defensibility Exist in an AI World | Is Per Seat Pricing Dead & The Future of Vibe Coding with Mike Cannon-Brookes Oct 13, 2025

Show notes

Mike Cannon-Brookes is the Co-Founder and Co-CEO of Atlassian, the $50BN software giant behind products like Jira, Confluence, and Trello. Since founding the company in 2002, he has scaled it to over 300,000 customers globally, generating more than $5BN in annual revenue. Atlassian now employs over 10,000 people across 13 countries and is one of the most successful bootstrapped-to-IPO stories in tech history. Mike is also a leading climate investor and co-owner of several major sports teams.

AGENDA:

00:00 Why Unreasonable Men Win in Startups

07:22 How to Make Co-CEOs Work

13:22 Are We in an AI Bubble? Is Everything Overvalued?

26:46 The Future of Software Development: More or Less Devs

32:53 Do Margins Matter in a World of AI

34:02 The Future of Vibe Coding…

36:35 Does Defensibility Exist in a World of AI

42:09 Is Per Seat Pricing Dead in a World of AI

49:01 The Founder Journey and Leadership

54:28 Quick Fire Round: Parenting Advice, Relationship to Money

20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan Oct 10, 2025

Show notes

Chris Degnan is the former Chief Revenue Officer at Snowflake, where he was instrumental in scaling the company from less than $1M in ARR to over $3B in annual revenue. He joined as the first sales hires and built Snowflake's go-to-market engine from scratch, growing the team from to more than 6,000 globally. Under his leadership, Snowflake became one of the fastest-growing enterprise software companies in history, achieving a record-breaking IPO in 2020.

AGENDA:

04:34 How to Build a Sales Team from Scratch 07:49 How to Hire and Evaluate Sales Leaders 15:23 Four Big Lessons Scaling Snowflake to $3BN ARR 31:30 Comparing Snowflake and Databricks: What Databricks Did Better? 35:26 How to Manage Sales Team Morale in Competitive Markets 43:53 Why Customer Success is BS and What To Do With It 48:31 How Every Sales Leader Needs to Change in An AI World 49:37 Biggest Reflections on Sales Leadership 54:38 Quick Fire Questions and Final Thoughts 20Sales: Scaling Snowflake from $0-$3BN in ARR | Snowflake vs Databricks: My Biggest Lessons | Why Customer Success is BS and What Replaces It with Chris Chris Degnan

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