20VC: Segment Founder Peter Reinhardt on His Learning Process, How Great Leaders Listen and Encourage Debate within Their Organisation & How To Use Data Intelligently To Improve Decision-Making

20VC: Segment Founder Peter Reinhardt on His Learning Process, How Great Leaders Listen and Encourage Debate within Their Organisation & How To Use Data Intelligently To Improve Decision-Making

Peter Reinhardt is the Founder and CEO @ Segment, the leading customer data platform with over 20,000 companies using Segment to collect, clean, and control their customer data. Prior to their $3.2BN acquisition by Twilio in 2020, Peter raised over $283M for Segment from Accel, Thrive, Meritech, GV, General Catalyst and Kleiner Perkins to name a few. Peter is also an active angel investor having made investments in the likes of Retool, Newfront, Pilot and more.

In Today's Episode with Peter Reinhardt You Will Learn:

1.) How Peter made his way into the world of startups and how he came to found a company, Segment, by actively trying to prove to his co-founder that it would not work? Why does Peter believe the Airbnb story is the most destructive myth for founders to follow?

2.) Learning: How does Peter think about learning frameworks for new topics? How does he construct his? How does Peter use data within this learning process to increase his rate of learning? Where do the majority of people go wrong in constructing their framework for learning?

3.) Listening and Debate: What does Peter believe is required to be "a good listener"? What questions do the best listeners ask? What tone do they use to ask these questions? How does Peter create an environment of safety internally where people feel they can debate? How does one balance between debate and thinking vs putting those thoughts into action?

4.) Problem-solving: How does Peter breakdown problems into their component parts? Through what mechanism does he determine what to prioritise first? How would Peter describe his decision-making process? How does he determine between head vs heart in decisions? In what way does Peter use data to further inform the decisions he makes?

5.) How would Peter describe his management style today? Has it changed over time? In what way has working with a coach changed the way Peter thinks about leadership? What elements do they focus on? How often does he see his coach? What have been some of his biggest takeaways?

Item's Mentioned In Today's Episode with Peter Reinhardt

Peter's Favourite Book: The Chalice and the Blade, Crucial Conversations

As always you can follow Harry and The Twenty Minute VC on Twitter here!

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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

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

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 1h 15min

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

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

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 1h 25min

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

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

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 1h 9min

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?

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?

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 1h 16min

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: 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

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 57min

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

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

🎧 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 1h 31min

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

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

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 1h 24min

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: 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

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 1h 14min

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