20VC: CEO Whisperer Jerry Colonna on How Investors Mimic Aggressive Behaviour To Cover Insecurity and Why Vulnerability is Key To Success In VC

20VC: CEO Whisperer Jerry Colonna on How Investors Mimic Aggressive Behaviour To Cover Insecurity and Why Vulnerability is Key To Success In VC

Jerry Colonna is a Founder @ Reboot, the coaching company that helps some of the world's greatest entrepreneurs and investors with the internal ups and downs in their life and support the growth they need to improve their performance. Prior to Reboot, Jerry was a Partner @ JP Morgan. Before that Jerry was a VC, having launched Flatiron partners in 1996 with his partner, Fred Wilson. Flatiron became on the of the most successful early stage investment firms in New York with investments in the likes of Geocities, Gamesville and The New York Times Digital. In Today's Episode You Will Learn:

1.) How did Jerry enter the world of VC and then make the transition to be the ultimate CEO/VC coach, aka, 'The CEO Whisperer'?

2.) What is Jerry's first step for anyone looking to self-evaluate in what Jerry calls, 'radical self-inquiry'?

3.) Once self-evaluated, how can one look to be their true self in a world that is not necessarily accepting of such vulnerability, compassion and emotion, for example, VC and startups?

4.) How does Jerry evaluate the current crop of VCs in terms of them being their inner self to the external world? Why is Jerry so optimistic?

5.) Questions from Brad Feld: 1.) What should VCs be spending more time on? 2.) If Jerry could give one piece of advice to VCs what would it be?

Items Mentioned In Today's Episode:

Jerry's Fave Blog: Fred Wilson: AVC, Brad Feld: Feld Thoughts, The School of Life

Jerry's Fave Book: When Things Fall Apart

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

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

The Twenty Minute VC is proudly sponsored by Luma, Luma is the world's first ever Surround WiFi system that brings speed, security and control to the home network. And Unlike traditional routers, Luma comes in a pack of two or three sleek devices to place in different rooms in your home. Luma then creates a mesh network that work together to create an outrageously-fast, ultra-secure Surround WiFi network. Lastly, Luma's app lets you easily see and control which devices, users and content are on your network. To buy your Luma, simply dead to getluma.com or amazon.com.

Jaksot(1404)

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 20251h 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 20251h 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 20251h 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 202557min

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 20251h 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 20251h 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 20251h 14min

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

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

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

24 Loka 20251h 16min

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