20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan

20VC: Why Investors Have The Biggest Problem with Bias, Why Our Job Is To Maximise Risk & Why It Is Essential To Get Good at Losing with True Ventures Founder, Jon Callaghan

Jon Callaghan is a founder of True Ventures, one of the West Coast's leading early stage funds with a portfolio including the likes of Fitbit, recent unicorn Peloton, Automattic (makers of Wordpress) and more amazing companies. Jon also led the deals and sits on the board of Fitbit, Brightroll, Peloton and Glu Mobile, just to name a few. Prior to True, Jon founded 3 of his own companies, the first being in 1986 with Mountain Bike Outfitters Inc. Following several years founding companies, Jon made his move into VC with Summit Partners and then enjoyed roles with AOL's venture incubator, CMGi's Venture group and Globespan Capital.

In Today's Episode You Will Learn:

1.) How Jon made his first forays into the world of VC and came to co-found True with Phil Black?

2.) How does Jon look to straddle the divide of "founder/VC"? Why does Jon believe it is crucial to have an entrepreneurial mindset as an investor?

3.) Why does Jon believe VCs biggest bias is loss aversion? Why does Jon always believe that the role of the VC is to maximise risk? What 1 thing must all prospective investors get good at very quickly?

4.) How does Jon view reserve allocation? True invest -1% per deal in each company, how do they look to efficiently deploy reserves? What must the communication be between founder and VC with regards to attaining follow on funding?

5.) Why does Jon believe that current board meetings do not serve startup founders? What are the characteristics of the best board members and how they conduct themselves? What is the single biggest problem boards bring to founders?

Items Mentioned In Today's Show:

Jon's Fave Book: Moby Dick

Jon's Fave Blog: Dave Pell: NextDraft

Jon's Most Recent Investment: Brava

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

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

Pendo delivers the only complete platform that helps companies create great products. The Pendo Product Experience Platform enables product teams to understand product usage, collect user feedback, measure NPS, assist users, and promote new features in-app – all without requiring any engineering resources. This unique combination of capabilities helps companies improve customer satisfaction, reduce churn, and increase revenue. Pendo is the proven choice of Salesforce, Cisco, Optimizely Citrix, BMC and many more leading companies. Start a free trial at http://go.pendo.io/harry

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Jaksot(1410)

20VC: From Only OpenAI to Die-Hard Anthropic: The Downfall of OpenAI in Enterprise | Harvey vs Legora: Legal AI is a Winner Take All | $7M ARR in a Single Day and Raising $200M Across 3 Rounds with No Deck with Max Junestrand, CEO @ Legora

20VC: From Only OpenAI to Die-Hard Anthropic: The Downfall of OpenAI in Enterprise | Harvey vs Legora: Legal AI is a Winner Take All | $7M ARR in a Single Day and Raising $200M Across 3 Rounds with No Deck with Max Junestrand, CEO @ Legora

Max Junestrand is the Co-Founder and CEO @ Legora, the legal AI company that has scaled to 750 of the world's leading law firms as customers and over 300 employees in just 2 years. They have raised over $200M from some of the best in the business including Benchmark, General Catalyst, Redpoint and ICONIQ.  AGENDA: 04:16 Why Does Everyone Think Harvey When They Hear Legal AI? 07:35 Why OpenAI is Toast? Switching to Anthropic! 11:47 24 Months: Which Foundation Models Will Win?  23:53 Lessons Scaling from Europe into the US 28:53 Do Americans Work As Hard As They Say? 32:20 Why Seat Models Are Not Dead in SaaS? 36:17 How to Use Competition To Drive a Fire in Your Team? 40:59 Is Legal AI a Winner-Take-All Market? How Does It End? 47:18 The Future of Law Firms: Do Juniors Get Fired? 53:19 How We Raised $200M and 3 Rounds with No Deck 57:21 Quickfire Round: Best Advice, Closest Mentor, Biggest Mindset Shift

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24 Tammi 42min

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22 Tammi 1h 18min

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19 Tammi 1h 13min

20Product: Is the Design Phase Dead in a World of AI | Has Claude Code Crushed Anthropic Already | What Roles of a PM Are Less and More Important with AI | How the Best Product Leaders Tell Stories with Noam Lovinsky, CPO @ Superhuman

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Noam Lovinsky is the CPO @ Superhuman (formerly Grammarly). Prior to Superhuman he was a Senior Director of Product Management at Facebook. In his earlier years, he was CPO @ Thumbtack and spent 5 years as a Director of Product Management at Google where he was responsible for all of Youtube's applications.  AGENDA: 03:43 What is Great Product Leadership in a World of AI 07:45 Does the Design Phase Die in a World of Vibe Coding 12:21 How AI Changes Product Development Most 22:23 Accelerating Product Development 29:32 AI's Impact on Product Building 34:19 Predictions for 2026 34:45 Quick Fire Round 38:41 Reflections and Future Plans

16 Tammi 45min

20VC: Anthropic's $10BN Fundraise: Have They Beaten Cursor Already | a16z's $15BN Fundraise: Is the Middle Dead in VC Today? | How OpenAI Could Go to Zero and ElevenLabs at $11BN: Buy or Not?

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15 Tammi 1h 28min

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Alex Rampell is a General Partner at Andressen Horowitz, where he leads their $1.7BN apps fund. Just last week, a16z announced they had raised $15BN for their latest funds, over 20% of all capital raised by venture firms. At a16z, Alex has led deals into Plaid, Mercury and OpenDoor to name a few.  AGENDA: 04:55 How to Do 5x on a $15BN Fund Pool?  09:21 What Two Groups of Funds Will Win the Next Decade in VC? 14:39 What Three Things Are the Best Founders Able to Do?  19:22 The Best Companies Have Hostages, Not Customers 31:37 The Two Types of Deals You Want To Do In VC 38:52 The Importance of Founder/Capital Fit 40:34 Multiple Successive Rounds Are Dangerous… Here is Why? 42:13 Challenges of High Valuations 45:27 The Importance of Ownership in Deals 52:47 Is Triple, Triple, Double, Double Dead 58:33 Advice on Selling Companies 01:11:55 What is the Future of Venture Capital

12 Tammi 1h 17min

20Growth: The $6.6B Growth Engine Behind ElevenLabs | Why ElevenLabs Do Not Have PMs | The 7 Part Launch Playbook to Crush All Launches with Luke Harries, Head of Growth @ ElevenLabs

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Luke Harries is Head of Growth at ElevenLabs, where he leads marketing, product, engineering, and developer experience. ElevenLabs has raised $281M with the latest round pricing the company at a $6.6B valuation. Previously, Luke held roles at PostHog and Microsoft, and is also an angel investor supporting startups like Lovable and Runna. AGENDA:  The $6.6B Growth Engine Behind ElevenLabs Why Luke Said "No" to Investing in ElevenLabs (and Why He Was Wrong) How ElevenLabs Makes a Horizontal Product Strategy Work How to Build Sharded Growth Teams That Actually Scale The 7-Part Launch Playbook That Gets 700K+ Views Per Product The Truth About CAC, Payback, and Performance Marketing in AI SEO Isn't Dead: The Mini-Tool Strategy You Should Steal Kill Your Inbound SDRs—The Case for Voice AI in Sales Why You Don't Need PMs and the Rise of Growth-Led Product Teams

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