20VC: eShares' Henry Ward on Why Portfolio Theory Is Wrong? Why Investors Will Never Take Market Risk & Why You have To Have A Line of Sight To A $Bn Outcome

20VC: eShares' Henry Ward on Why Portfolio Theory Is Wrong? Why Investors Will Never Take Market Risk & Why You have To Have A Line of Sight To A $Bn Outcome

Henry Ward is the Founder & CEO @ eShares, the No 1 cap table management platform providing equity management, 409A valuations and liquidity all in one place. They are backed by leading investors and past guests including USV, SV Angel, Spark Capital, Semil Shah, Manu Kumar, Tim Draper and Kamal Ravikant, just to name a few. Prior to eShares, Henry was Founder @ SecondSight, the first registered investment advisor to go direct to your brokerage and improve your portfolio.

In Today's Episode You Will Learn:

1.) How Henry made his way into the world of startups and came to found eShares?

2.) How does Henry challenge the notion that investors should have such high fail rates? How does Henry believe investors can build a strong and sustainable portfolio without home runs?

3.) Why does Henry believe that investors will never accept market risk? How much of a role does Henry believe herd mentality plays in the VC ecosystem?

4.) How does Henry view the increasing exit horizons for startups? Is this a problem? How can we create liquidity options pre large exits?

5.) How does Henry view the role of regulation in private markets? How does this differ to public markets? What would Henry like to see change in the VC ecosystem?

Items Mentioned In Today's Show:

Henry's Fave Blog: Hacker News

Henry's Fave Book: The Essays Of Warren Buffett

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

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

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Episoder(1416)

20VC: Sam Altman vs Elon Musk: The $100BN Battle | The Implosion of Thinking Machines | Can VC Survive Public Market Pricing Today? | ClickHouse and Replit's New Rounds: Analysed

20VC: Sam Altman vs Elon Musk: The $100BN Battle | The Implosion of Thinking Machines | Can VC Survive Public Market Pricing Today? | ClickHouse and Replit's New Rounds: Analysed

AGENDA: 03:30 Can VC Survive With Public Market Prices Today 15:20 The Implosion of Thinking Machines 21:13 Elon Musk vs. OpenAI: The Legal Battle 40:50 Can OpenAI Win Ads? 55:50 ClickHouse's $15BN De...

22 Jan 1h 18min

20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

20VC: How Model Performance is Plateauing | Two Key Rules for Effective Deal-Making | Company Building Lessons from Keith Rabois, Brian Halligan and Pat Grady | Why Enterprise AI Adoption is Years Off with Harvey CEO Winston Weinberg

Winston Weinberg is the CEO and Co-Founder of Harvey, the leading professional services platform engineered with AI for law, tax, and finance. Winston has raised over $980M for Harvey from Sequoia, a1...

19 Jan 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

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

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 yea...

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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?

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?

AGENDA: 05:02 Anthropic's $10 Billion Fundraise 07:54 Has Claude Code Beaten Cursor Already 15:54 OpenAI Could Still Go to Zero 26:33 Andreessen Horowitz's $15 Billion Fundraise 45:16 The Middle is De...

15 Jan 1h 28min

20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital

20VC: a16z's $15BN Fundraise with Alex Rampell | The Best Companies Have Hostages Not Customers | The Best Founders Materialise Capital, Customers and Labour | Mid-Sized Funds with Die and The Future of Venture Capital

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 rai...

12 Jan 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

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

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...

11 Jan 1h 13min

20Sales: Why the Best Sales People are F***** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets

20Sales: Why the Best Sales People are F***** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets

Chad Peets is one of the great sales leaders of our time. Previously, he was the sales saviour at Snowflake and was an advisor to the CEO there. He was also an MD at Sutter Hill where he sat on the bo...

9 Jan 1h 9min

20VC: Groq's $20BN NVIDIA Acquisition | Manus Acquired by Meta for $2BN | Why Sam Altman Does Not Care About Dilution | Navan Trading at 4x ARR & Why Going Public Does Not Make Sense Anymore | The Rise of Invisible Unemployment and Labour Markets in 2026

20VC: Groq's $20BN NVIDIA Acquisition | Manus Acquired by Meta for $2BN | Why Sam Altman Does Not Care About Dilution | Navan Trading at 4x ARR & Why Going Public Does Not Make Sense Anymore | The Rise of Invisible Unemployment and Labour Markets in 2026

AGENDA: 04:30 Groq Acquired by NVIDIA for $20BN: The Breakdown 17:13 Meta's $2BN Acquisition of Manus: Did They Sell Too Early 36:04 OpenAI's Stock-Based Compensation Strategy 47:42 Will AI Replace Ve...

8 Jan 1h 23min

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