Notes on first checks

Weekly notes on angel investing, deal flow and building wealth.

The archive

Everything else we’ve published, newest first.

2026

25 posts

  1. NewsletterEmotional Armor When the Zeros HitNewsletter3 min
  2. NewsletterHow Hidden Capital Unlocks Angel InvestingNewsletter1 min
  3. NewsletterWhy Angels Aren’t Small VCs (And Why That Matters)Newsletter1 min
  4. NewsletterThe Angel Advantage in Venture Capital’s “Black Hole”Newsletter1 min
  5. NewsletterWhen Founder Brilliance Becomes a Trap for Angel InvestorsNewsletter2 min
  6. NewsletterThe Diligence Trap Every Angel Falls IntoNewsletter3 min
  7. NewsletterThe New Founder Playbook in the Age of AINewsletter1 min
  8. Newsletter$9 Trillion New CapitalNewsletter2 min
  9. NewsletterThe Echo Chamber Problem in Venture CapitalNewsletter1 min
  10. NewsletterAngel Investing in an AI World: Why Your Own Conviction Matters More Than EverNewsletter2 min
  11. NewsletterBuilding Your Own AI Investment FrameworkNewsletter1 min
  12. NewsletterThe Emotional Cost of Optimism in Angel InvestingNewsletter1 min
  13. NewsletterSAFE Notes: Simple, Fast… and FuzzyNewsletter1 min
  14. NewsletterWhat Angels Get Wrong About SAFEsNewsletter2 min
  15. NewsletterSmall Checks, Big Impact — The Real Math of Angel InvestingNewsletter2 min
  16. NewsletterThe Math Behind Your Angel Check SizeNewsletter3 min
  17. NewsletterThe Truth About Cap Tables and Angel InvestingNewsletter2 min
  18. NewsletterWhy SPVs Are the “Professional Grade” Way to Angel InvestNewsletter2 min
  19. NewsletterAngel Investing Taxes Explained: K-1s, Phantom Income, and What Actually Triggers a Tax EventNewsletter3 min
  20. NewsletterThe Math of More: Why 30 is the Magic Number for Angel PortfoliosNewsletter2 min
  21. NewsletterAngels Decoded: A Podcast for Angel Investors Who Want to Get SmarterNewsletter2 min
  22. NewsletterHow to Evaluate Startup Founders: An Angel Investor’s FrameworkNewsletter3 min
  23. NewsletterYour First 5 Angel Investments: A Framework for Evaluating Startup DealsNewsletter3 min
  24. NewsletterSeries SAFE vs SAFE: What Changed (And Why Angels Should Care)Newsletter4 min
  25. NewsletterThe One Question That Tells You If a Founder Is InvestableNewsletter5 min

2025

16 posts

  1. NewsletterHow to Evaluate Climate Deep Tech Startups: Andrew Eil’s PlaybookNewsletter3 min
  2. NewsletterWhy Angel Investing Infrastructure Is Broken (And What We’re Building Instead)Newsletter2 min
  3. NewsletterAngel Investing as a Civic Act (Creation vs Extraction)Newsletter3 min
  4. NewsletterWhy Angel Investing Misses Big Returns Without Portfolio DiversityNewsletter3 min
  5. NewsletterHow AI Is Changing Angel Investing (And Why It Matters)Newsletter2 min
  6. NewsletterEarly vs. Later-Stage Angel Investing: Risk, Returns, and Portfolio StrategyNewsletter3 min
  7. NewsletterHow Angel Investors Actually Get Paid: IRR, Earn-Outs, and Preference Stacks ExplainedNewsletter3 min
  8. NewsletterWhat Happens When a Startup Shuts Down? Angel Investing Losses ExplainedNewsletter2 min
  9. NewsletterHow Angel Investing Exits Work: IPOs, Acquisitions, and SPV Distributions ExplainedNewsletter2 min
  10. NewsletterDo Small Angel Checks Matter? Valuations, SPV Fees, and QSBS ExplainedNewsletter3 min
  11. NewsletterShould Founder Identity Matter in Angel Investing? Mission, Money, and ReturnsNewsletter2 min
  12. NewsletterIs Venture Capital Broken? Why Angel Investors Are Building Another WayNewsletter2 min
  13. NewsletterQSBS Explained: How Angel Investors Can Pay 0% Capital Gains TaxNewsletter2 min
  14. NewsletterAngel Investing During Market Volatility: 3 Investor Mindsets That WinNewsletter2 min
  15. NewsletterWhat Happens to Your Angel Investment When a Startup Raises a Series A?Newsletter2 min
  16. NewsletterHow to Evaluate CPG Startups as an Angel InvestorNewsletter2 min