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Unlocking Liquidity

How Direct Secondaries Are Reshaping The VC Model

Available on Amazon as: Coming Soon.

In venture capital, trillions of dollars in value remains trapped in private companies and aging funds—a crisis of liquidity that threatens the entire ecosystem. Unlocking Liquidity reveals how direct secondaries are transforming venture capital, offering a revolutionary approach to realizing returns without waiting for traditional exits.

Drawing from my experience at Carta and deep analysis of thousands of venture-backed companies, I demonstrate how direct secondaries are reshaping the industry's fundamentals. This isn't just theory—it's a practical blueprint for how LPs can achieve superior risk-adjusted returns, how GPs can better manage their portfolios, and how founders can provide life-changing liquidity to their employees.

Through real-world case studies and data-driven insights, Unlocking Liquidity explores how the secondary market is evolving from occasional transactions into a systematic solution for the venture ecosystem. You'll discover why secondary funds consistently outperform traditional VC, how to evaluate opportunities, and what the future holds for private market liquidity.

Whether you're an LP seeking more predictable returns, a VC adapting to longer private company lifecycles, or a founder navigating liquidity options, this book provides the frameworks and insights needed to thrive in venture capital's next chapter.

Ready to transform how you think about realizing value in venture capital?


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Table of Contents:

Preface

Introduction

Part I: Liquidity Revolution –The Untold Story

Chapter 1: The Liquidity Paradox in Venture Capital

1.1 Why Venture Capital Faces a Liquidity Problem

1.2 The Evolution of Market Gaps: LP, GP, and Direct Secondaries

1.3 Why LP- and GP-Led Transactions Aren't Enough

1.4 How Direct Secondaries Solve the Liquidity Puzzle

1.5 Performance Analysis Beyond The J-Curve

Chapter 2: Historical Innovation in Secondary Markets

2.1 Historical Evolution

2.2 Platform Innovation Attempts

2.3 Dedicated Secondary Funds

2.4 Key Lessons from Market Evolution

Part II: Mastering the Art of Direct Secondaries

Chapter 3: Deal Sourcing in a Fragmented Market

3.1 Leveraging Information Asymmetry

3.2 Building an Intelligence backbone

3.3 Avoiding Common Sourcing Pitfalls

Chapter 4: The Science of Valuation and Pricing

4.1 Untangling Complex Cap Tables

4.2 Valuation Methodologies for Secondaries

4.3 Practical Considerations for Valuation

4.4 Why Liquidation Preferences Matter

4.5 When to Trust (or Ignore) the Last Round Price

4.6 Red Flags in Price Assessment

Chapter 5: Structuring for Success

5.1 Essential Terms for Securing Deals

5.2 Navigating Legal and Regulatory Hurdles

5.3 Aligning Interests

Part III: Building a Future-Ready Platform

Chapter 6: Reinventing Portfolio Strategy

6.1 Why Standard VC Portfolio Theory Doesn't Work

6.2 Optimal Position Sizing

6.3 Portfolio Management Best Practices

Chapter 7: The LP Advantage

7.1 Positioning Your Fund to LPs

7.2 Advanced Performance Metrics

7.3 Customized Solutions for Different LP Types

Chapter 8: Competitive Moats

8.1 Building Authority

8.2 Technology and Data Science

8.3 Long-Term Differentiation

Part IV: Charting the Future of Liquidity

Chapter 9: Navigating Risks and Pitfalls

9.1 Common Misconceptions in the Venture Secondary Market

9.2 Learning from Failures in the Venture Secondary Market

9.3: Future-Proofing the Venture Secondary Market

Chapter 10: The Future of Direct Secondaries

10.1 The Technology Revolution in Venture Secondaries

10.2 The Role of Data in Shaping the Secondary Market

10.3 The Role of Platforms in Scaling the Secondary Market

Conclusion


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