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Harry Stebbings

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. 

If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.

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

Joelle Pineau is the Chief Scientist at Cohere, where she leads research on advancing large language models and practical AI systems. Before joining Cohere, she was VP of AI Research at Meta, where she founded and led Meta AI's Montreal lab. A professor at McGill University, Joelle is renowned for her pioneering work in reinforcement learning, robotics, and responsible AI development.
 
AGENDA: 
 
00:00 Introduction to AI Scaling Laws
 
03:00 How Meta Shaped How I Think About AI Research
 
04:36 Challenges in Reinforcement Learning
 
10:00 Is It Possible to be Capital Efficient in AI
 
15:52 AI in Enterprise: Efficiency and Adoption
 
22:15 Security Concerns with AI Agents
 
28:34 Can Zuck Win By Buying the Galacticos of AI
 
32:15 The Rising Cost of Data
 
35:28 Synthetic Data and Model Degradation
 
37:22 Why AI Coding is Akin to Image Generation in 2015
 
48:46 If Joelle Was a VC Where Would She Invest?
 
52:17 Quickfire: Lessons from Zuck, Biggest Mindset Shift

20VC: Cohere's Chief Scientist on Why Scaling Laws Will Continue | Whether You Can Buy Success in AI with Talent Acquisitions | The Future of Synthetic Data & What It Means for Models | Why AI Coding is Akin to Image Generation in 2015 with Joelle Pineau

🎧 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: 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

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: 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

Chris Olsen is the Founding Partner @ Drive Capital, the venture firm that believes the Midwest is the opportunity of our lifetime with more entrepreneurs building billion-dollar companies in the Midwest than in the last 50 years combined. Since inception in 2012, Drive have built an exceptional portfolio including the likes of Duolingo, FarmLogs, LeadPages and Udacity. As for Chris, prior to founding Drive he was a Partner @ Sequoia Capital on the West Coast where he learned the craft from some of the very best in the business. Before that he spent time at both TCV and UBS.
 
In Today's Episode You Will Learn:
 
1.) How Chris came to found the largest venture fund in the midwest, Drive, from being a Partner @ Sequoia Capital and learning the craft of venture there?
 
2.) Why does Chris believe that the biggest trend we will live through is the decentralisation away from Silicon Valley? What are the essential ingredients an ecosystem requires in order to foster this thriving tech hub? What does Chris believe it is fundamentally essential for companies to be in close proximity to?
 
3.) How does the lack of venture funds in the Midwest affect Chris' views on pricing? Would Chris agree with Peter Fenton, "never turn down a company based on valuation, it is a mental trap"? How does Chris look to differentiate between expensive and too expensive?
 
4.) How does Chris think about reserve allocation with Drive? What framework does Drive adopt to determine where to allocate reserve dollars? How does the shortage of follow-on investors in the midwest impact Chris' approach to follow on financing? What level does a company need to be in order to attract attention from larger growth funds?
 
Items Mentioned In Today's Show:
 
Chris' Fave Book: The Old Man and The Sea
 
Chris' Most Recent Investment: Duolingo
 
As always you can follow Harry, The Twenty Minute VC and Chris on Twitter here!
 
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
 
Cooley is a global law firm built around supporting start-ups and the venture capital firms that fund them. Now we have spoken before about their forming the first venture fund in Silicon Valley, and forming more VC funds than any other law firm in the world but Cooley also represents more than 6,000 high-growth startups across the globe – through the full company life cycle. They are the #1 law firm for VC-backed exits (M&A and IPO) ranked by PitchBook, and since 2014 has represented more companies in their IPOs than any other law firm. Simply head over to Cooley.com or you can check them out at Cooleygo.com.

20VC: The Biggest Trend Of Our Lifetime Is The Decentralisation of Entrepreneurship Away From The Valley, The Biggest Lessons From Learnings The Craft of VC at Sequoia & The Benchmarks Required to Attract Growth Investors with Chris Olsen, Founding Partne

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

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

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

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

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: 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

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: 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

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: 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

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: $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

Annie Kadavy is a General Partner @ Charles River Ventures. The prestigious VC fund that is now on it's 16th fund and has backed the likes of Twitter, Yammer and Mailbox just to name a few. At CRV, Annie focuses on all things consumer and has either led or sourced their investments in ClassPass, Cratejoy, Patreon, Laurel & Wolf and DoorDash. Prior to CRV, Annie spent time with SV Angel and Warby Parker.
 
In Today's Episode You Will Learn:
 
1.) How Annie made her way into the world of VC?
 
2.)Why have we seen the explosion of marketplaces in recent years? What are the inherent challenges of two sided marketplaces; typically consumers and micro-entrepreneurs? Does Annie agree with Jeff Jordan in stating that these marketplaces need to nurture and manage conditions of perfect competition?
 
3.) What are the core components to growing traditional producer consumer marketplaces? How do they broach the chicken and the egg problem of supply and demand?
 
4.) Why is Annie so excited for the potential of bots? Will the transition to bots and conversational interfaces represent a major point of disruption or more of an evolution in the interface paradigm?
 
Items Mentioned In Today's Show:
 
Annie's Fave Book: Mindset: How You Can Fulfill Your Potential by Carol Dweck
 
Annie's Fave Blog: The Skimm
 
Annie's Most Recent Investment: Roam

The Twenty Minute VC

20VC: Why Bots Are The New Black, Conversational Interface Is The Next of For Consumerisation and The Determinants Of A Successful Marketplace with Annie Kadavy, General Partner @ CRV

20VC: Why Bots Are The New Black, Conversational Interface Is The Next of For Consumerisation and The Determinants Of A Successful Marketplace with Annie Kadavy, General Partner @ CRV

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