20VC: Hubspot Co-Founder Dharmesh Shah on The 3 Risks All Startups Face, Angel Investing Rules; No Founder Meetings and No Due Diligence, SMB vs Enterprise; Lessons on Pricing, Distribution and Why You Should Resist Going Enterprise

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

13 Marras 20251h 15min

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

10 Marras 20251h 25min

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: Why does Chad believe that SaaS companies need a CRO pre-product? Should the founder not be the right person to create the sales playbook? What should the founder look for in their first CRO hire? Does any great CRO really want to go back to an early startup and do it again? 2. What Everyone Gets Wrong in Building Sales Teams: Why are most sales reps not performing? How long does it take for sales teams to ramp? How does this change with PLG and enterprise? What are the benchmarks of good vs great for average sales reps? How do founders and VCs most often hurt their sales teams and performance? 3. How to Build a Hiring Machine: What are the single biggest mistakes people make when hiring sales reps and teams? Are sales people money motivated? How to create comp plans that incentivise and align? 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? Why is it harder than ever to recruit great sales leaders today? 4. Lessons from Scaling Sales at Snowflake: What are the single biggest lessons of what worked from scaling Snowflake's sales team? What did not work? What would he do differently with the team again? What did Snowflake teach Chad about success and culture and how they interplay together?

7 Marras 20251h 9min

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

6 Marras 20251h 16min

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

3 Marras 202557min

🎧 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."

31 Loka 20251h 31min

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

30 Loka 20251h 24min

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

27 Loka 20251h 14min