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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

Carl Rivera is the Chief Design Officer at Shopify, where he previously led both Merchant Services and the Shop App as VP of Product. Before joining Shopify through its acquisition of Tictail, Carl was the co-founder and CEO of Tictail, the "Tumblr for e-commerce," where he built one of the most beloved design-forward commerce platforms of its era.
 
AGENDA:
 
05:05 Biggest Lessons from Selling My Company to Shopify
 
09:55 Where Does Shopify Suck at Product: Lessons from that?
 
17:37 What makes Truly Great product Design: The Five Pillars
 
31:02 The Future of Design in an AI-Driven World
 
36:00 Do We Skip the Design Phase in AI: Figma's Evolving Role in Design
 
40:09 Remote Work vs. In-Person Collaboration: Where Remote Loses?
 
42:43 What Happens to the Vibe Coding Market
 
47:06 Product Management and Team Dynamics
 
59:48 Does AI Favour Incumbents or Startups

20Product: How AI Changes Product Design | Does the Design Phase Become Irrelevant in a World of Vibe Coding | The Five Pillars of Truly Great Product Design with Carl Rivera, Chief Design Officer at Shopify

AGENDA:
 
04:22 Sequoia's Leadership Transition
 
09:46 Michael Burry's Big Short on Nvidia and Palantir
 
17:41 Gamma Raises $100M at a $2BN Valuation
 
32:34 Does Defensibility Exist Today When Copying is Easy
 
40:31 Should All Funds Be Way More Diversified
 
47:12 How to Run a Fundraising Process & What Not To Do
 
57:57 Datadog Surges 20% and Duolingo Crashes: What Happened

20VC: Sequoia's Leadership Transition | Michael Burry Shorts NVIDIA and Palantir | Gamma Raises $100M at $2BN | Has Defensibility Died in a World of AI | Datadog Surges as Duolingo Plummets: What is Happening

Ev Randle is a General Partner @ Benchmark, one of the best funds in venture capital. In their latest fund, they have Mercor ($10BN valuation), Sierra ($10BN valuation), Firework ($4BN valuation), Legora ($2Bn valuation) and Langchain ($1.4Bn valuation). To put this in multiples on invested capital, that is a 60x, two 30x and two 20x. Before Benchmark, Ev was a Partner @ Kleiner Perkins and before Kleiner, Ev was an investor at Founders Fund and Bond. 
 
AGENDA:
 
05:25 Biggest Investing Lessons from Peter Thiel, Mary Meeker and Mamoon Hamid
 
14:36 OpenAI Will Be a $TRN Company & OpenAI or Anthropic: Who Wins Coding?
 
22:27 Why We Should Not Focus on Margin But Gross Dollar Per Customer
 
30:25 Why AI Labs are the Biggest Threat to AI App Companies
 
44:26 Do Benchmark Fire Founders? If so… Truly the Best Partner?
 
54:38 People, Product, Market: Rank 1-3 and Why?
 
57:36 Why the Mega Funds Have Just Replaced Tiger
 
01:04:08 GC, Lightspeed and a16z Cannot Do 5x on Their Funds… 
 
01:14:09 Single Biggest Threat to Benchmark

20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid

Chad Peets is one of the greatest sales leaders and recruiters of the last 25 years. From 2018 to 2023, Chad was a Managing Director at Sutter Hill Ventures. Chad has worked with the world's best CEOs and CROs to build world-class go-to-market organizations. Chad is currently a member of the Board of Directors for Lacework and Luminary Cloud and on the boards of Clumio and Sigma Computing. He previously served as a board member for Astronomer, Transposit, and others. He was an early-stage investor at Snowflake, Sigma, Observe, Lacework, and Clumio.
 
In Today's Discussion with Chad Peet's We Discuss:
 
1. You Need a CRO Pre-Product:
 
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Why does Chad believe that SaaS companies need a CRO pre-product?
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Should the founder not be the right person to create the sales playbook?
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What should the founder look for in their first CRO hire?
 • 
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Does any great CRO really want to go back to an early startup and do it again?
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2. What Everyone Gets Wrong in Building Sales Teams:
 
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Why are most sales reps not performing?
 • 
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How long does it take for sales teams to ramp? How does this change with PLG and enterprise?
 • 
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What are the benchmarks of good vs great for average sales reps?
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How do founders and VCs most often hurt their sales teams and performance?
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3. How to Build a Hiring Machine:
 
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What are the single biggest mistakes people make when hiring sales reps and teams?
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Are sales people money motivated? How to create comp plans that incentivise and align?
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Why does Chad believe that any sales rep that does not want to be in the office, is not putting their career and development first?
 • 
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Why is it harder than ever to recruit great sales leaders today?
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4. Lessons from Scaling Sales at Snowflake:
 
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What are the single biggest lessons of what worked from scaling Snowflake's sales team?
 • 
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What did not work? What would he do differently with the team again?
 • 
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What did Snowflake teach Chad about success and culture and how they interplay together?
 •

20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets

AGENDA:
 
04:27 Navan's IPO: Winners, Losers and 20% Crater
 
12:55 Harvey Raises $150M at an $8BN Valuation
 
35:36 Was Sam Altman Wrong to Snap at Brad Gerstner
 
41:25 Why GOOG is a Buy and Amazon is a Short
 
47:43 Meta Down 10%, Buy or Sell? 
 
51:12 If You Have Not Accelerated with AI, You Are Dead
 
01:05:20 Why Now is the Best Time for Series A and Worst for Seed

20VC: Navan IPO: Winners, Losers and is a $4.5BN Exit Enough in VC Today | Harvey Raises $150M at $8BN Price | Why Google is a Buy and Amazon is a Sell | Meta Down 10%, Is Zuck Struggling?

Joelle Pineau is the Chief AI Officer 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 AI Officer 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

20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid

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