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.

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20VC: Monday.com CEO on Is SaaS Dead: Will Everything Be Vibe Coded | Will Systems of Record Become Valueless Databases in an Agentic World | Will LLMs Own the Value in the Application Layer with Eran Zinman

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23 Feb 1h 6min

20VC: Codex vs Claude Code vs Cursor: Who Wins, Who Loses | Will All Coding Be Automated - Do We Need PMs | The Real Bottleneck to AGI | The Three Phases of Agents and What You Need to Know with Alex Embiricos, Head of Codex at OpenAI

20VC: Codex vs Claude Code vs Cursor: Who Wins, Who Loses | Will All Coding Be Automated - Do We Need PMs | The Real Bottleneck to AGI | The Three Phases of Agents and What You Need to Know with Alex Embiricos, Head of Codex at OpenAI

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20VC: Anthropic Raises $30BN at $380BN Valuation | Thrive Raises New $10BN Fund | OpenAI Buys OpenClaw | Stripe Raises at $140BN: Is Adyen Wildly Undervalued? | Monday, Figma, Shopify: Which are Buys vs Sells?

20VC: Anthropic Raises $30BN at $380BN Valuation | Thrive Raises New $10BN Fund | OpenAI Buys OpenClaw | Stripe Raises at $140BN: Is Adyen Wildly Undervalued? | Monday, Figma, Shopify: Which are Buys vs Sells?

AGENDA: 04:14 Anthropic's $30B Raise at $380B 06:18 Why SaaS Stocks Keep Getting Crushed 18:15 Wall Street's New Religion: AI Replaces Headcount  22:42 The Bear Case for Shopify: What Could Go Wrong? ...

19 Feb 1h 34min

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20VC: SaaS is Dead: Why Systems of Record Will Die in an Agentic World | What Revenue Multiple Will Software Companies Trade At? | From 7,000 to 3,000: We Need Less People Than Ever with Sebastian Siemiatkowski

Sebastian Siemiatkowski is the co-founder and CEO of Klarna, the global digital bank with over 114 million global active users and 3.4 million transactions per day. Seb is one of the leading public co...

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20Sales: Inside ElevenLabs $330M ARR Sales Machine | The 20x Sales Comp Plan Reps Must Hit | How to Land and Expand in a World of AI | Why Product-Market-Fit is BS, Reps Should Not Be in the Office and Outbound is King with Carles Reina

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14 Feb 1h 14min

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