Angel Investing: Start to Finish

I co-authored Angel Investing: Start to Finish with Pete Baltaxe and published it through Holloway in 2020. It's a comprehensive guide for angel investors — written to be the book I wished existed when I started advising startups and their investors.

What It Covers

The book walks through the full arc of angel investing, from building a thesis and sourcing deals to structuring investments, negotiating terms, and planning your exit. Key topics include:

  • How to evaluate early-stage companies and founders
  • SAFE and convertible note mechanics — what the terms actually mean and when they matter
  • Priced round due diligence and deal structure
  • Portfolio construction and follow-on strategy
  • The tax implications of angel investing, including QSBS (Section 1202) and Section 1045 rollovers
  • What happens at exit — and how to maximize your after-tax return

Who It's For

The book is written for first-time and early-stage angel investors who want to invest intelligently rather than just write checks. It's also used by founders who want to understand how investors think, and by attorneys and advisors who counsel angel investors and early-stage companies.

Where to Get It

Buy Angel Investing: Start to Finish on Holloway →

Holloway publishes the book in digital format with ongoing updates. It's also available on Amazon in paperback.


If you have questions about angel investing, QSBS qualification, or deal structure, feel free to book a free introductory call.

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This site provides general information for educational purposes only and does not constitute legal advice. Reading or interacting with this site does not create an attorney–client relationship.