NewsletterJune 19, 2026
Why Smart Angels Invest Where VCs Won't
VCs are chasing AI at $50M+ valuations. Meanwhile CPG, climate tech, women's health, and family tech offer angel investors lower entry points and faster exits.
Newsletter
Explore our latest newsletters on investing, startups, and building wealth.
NewsletterMay 19, 2026
Emotional Armor When the Zeros Hit
Four real angel investors share how they found their investing thesis by writing checks first — and why your thesis is emotional armor when the zeros hit.
NewsletterApril 14, 2026
Angel Investing in an AI World: Why Your Own Conviction Matters More Than Ever
AI is changing the math on every startup investment. A simple two-question framework to build your own angel investing thesis instead of following smart money.
NewsletterMarch 17, 2026
What Angels Get Wrong About SAFEs
Post-money SAFEs protect angels from dilution until conversion — but stacking too many creates cap table chaos. Here's how the math works.
NewsletterMarch 10, 2026
The Math Behind Your Angel Check Size
Most angels write one check that's too big or never start. The portfolio math — 5-7% of alternatives, divided by 30 bets — sizes your check in minutes.
NewsletterFebruary 24, 2026
Angel Investing Taxes Explained: K-1s, Phantom Income, and What Actually Triggers a Tax Event
Confused about K-1s, phantom income, and taxes in angel investing? Learn when SPVs generate K-1s, what counts as a tax event, and how SAFEs and convertible notes are treated.
NewsletterFebruary 17, 2026
Angels Decoded: A Podcast for Angel Investors Who Want to Get Smarter
A 15-minute angel investing podcast unpacking portfolio construction, conviction, deal evaluation, and the realities of early-stage investing.
NewsletterFebruary 10, 2026
How to Evaluate Startup Founders: An Angel Investor’s Framework
A practical framework for evaluating startup founders, avoiding common angel investing traps, and building conviction in your early-stage investments.
NewsletterJanuary 28, 2026
Your First 5 Angel Investments: A Framework for Evaluating Startup Deals
A practical framework for evaluating early-stage startup deals, building pattern recognition, and developing your angel investing thesis.
NewsletterJanuary 20, 2026
Series SAFE vs SAFE: What Changed (And Why Angels Should Care)
Most SAFEs don’t start the QSBS clock. Series SAFE turns future equity into equity today. Here’s how it works and what it means for angel investors and SPVs.
NewsletterJanuary 13, 2026
The One Question That Tells You If a Founder Is Investable
How experienced angels evaluate founders, spot red flags early, and make better decisions with fewer, sharper questions.
NewsletterDecember 2, 2025
How to Evaluate Climate Deep Tech Startups: Andrew Eil’s Playbook
Andrew Eil shares how he evaluates climate deep tech startups, de-risks commercialization, and builds conviction in early-stage sustainability investments.
NewsletterNovember 26, 2025
Why Angel Investing Infrastructure Is Broken (And What We’re Building Instead)
A founder-first case for fixing angel investing infrastructure, reducing the fragmentation tax on early-stage companies, and coordinating the long tail of capital.
NewsletterNovember 18, 2025
Angel Investing as a Civic Act (Creation vs Extraction)
A reflection on angel investing, capital allocation, and why funding creation — not extraction — may be the highest-leverage civic act in private markets.
NewsletterNovember 11, 2025
Why Angel Investing Misses Big Returns Without Portfolio Diversity
A reflection on angel investing, SPVs, and why a lack of portfolio diversity can cause both founders and angels to miss out on outsized returns.
NewsletterSeptember 9, 2025
How AI Is Changing Angel Investing (And Why It Matters)
Artificial intelligence is reshaping how angel investors evaluate deals, understand investment terms, and make decisions in private markets. Here’s how AI tools can reduce friction without reducing rigor.
NewsletterAugust 19, 2025
Early vs. Later-Stage Angel Investing: Risk, Returns, and Portfolio Strategy
What’s the difference between early-stage and later-stage angel investing? Here’s how to think about risk, valuation, information asymmetry, secondaries, and portfolio construction when evaluating private market deals.
NewsletterJuly 29, 2025
How Angel Investors Actually Get Paid: IRR, Earn-Outs, and Preference Stacks Explained
Most angel portfolios don’t return 10x. The messy middle — asset purchase agreements, earn-outs, private equity roll-ups, and liquidation waterfalls — is where returns are made or lost. Here’s how it really works.
NewsletterJuly 22, 2025
What Happens When a Startup Shuts Down? Angel Investing Losses Explained
In angel investing, 40% of startups may go to zero. Here’s what actually happens when a company shuts down — from tax deductions and SPV logistics to the emotional side of backing founders.
NewsletterJuly 14, 2025
How Angel Investing Exits Work: IPOs, Acquisitions, and SPV Distributions Explained
How do angel investors actually get paid? From IPO lockups and private secondary sales to SPV distributions and carry, here’s how startup exits work in angel investing.
NewsletterJuly 7, 2025
Do Small Angel Checks Matter? Valuations, SPV Fees, and QSBS Explained
How should angel investors think about $20M valuations, small check sizes, SPV fees, and QSBS tax benefits? Here’s how to evaluate ROI beyond the headline numbers.
NewsletterJune 24, 2025
Should Founder Identity Matter in Angel Investing? Mission, Money, and Returns
Should angel investors factor founder identity into their investing thesis? Here’s the tension between mission-driven capital, performance data, and how platforms should surface diversity in deal flow.
NewsletterJune 17, 2025
Is Venture Capital Broken? Why Angel Investors Are Building Another Way
Venture capital has scaled capital but not innovation inside its own model. After reading 'World Eaters', here’s why angel investors may be the real path to rebuilding early-stage funding.
NewsletterMay 28, 2025
QSBS Explained: How Angel Investors Can Pay 0% Capital Gains Tax
Qualified Small Business Stock (QSBS) can eliminate federal capital gains tax on startup investments. Here’s how it works, what qualifies, and how SPVs affect eligibility.
NewsletterApril 8, 2025
Angel Investing During Market Volatility: 3 Investor Mindsets That Win
Market volatility doesn’t stop angel investing. It clarifies it. Here are the three angel investor archetypes that thrive during uncertain markets — and how to decide which one you are.
NewsletterMarch 18, 2025
What Happens to Your Angel Investment When a Startup Raises a Series A?
When a startup you invested in raises a Series A, what actually happens to your shares? Learn how SPVs handle signing, how convertible notes convert to equity, and why paper gains get harder to calculate.
NewsletterMarch 11, 2025
How to Evaluate CPG Startups as an Angel Investor
Angel investing in CPG is very different from SaaS or biotech. Learn how to evaluate consumer packaged goods startups, including gross margins, retail strategy, founder resilience, and exit timelines.
NewsletterAugust 13, 2024
Seed Extension and Bridge Rounds: Red Flag or Buying Opportunity for Angel Investors?
What is a seed extension or bridge round? Learn how angel investors should evaluate flat rounds, red flags, fresh leads, and valuation resets before investing.
NewsletterJune 25, 2024
Are High Seed Valuations a Red Flag? How Angel Investors Should Think About YC Deals
Are $30M+ seed valuations too high? Learn how angel investors should evaluate YC-backed startups, valuation caps, institutional signaling, and ownership math.
NewsletterJune 11, 2024
Angel Investing Strategy: Portfolio Diversification, Returns, and How Angels Pick Winners
A practical guide to angel investing strategy: diversification, startup return distributions, budgeting, deal selection, and how experienced angels pick winners.
NewsletterJune 4, 2024
Angel Investing 101: A 5-Day Beginner Guide to Startup Investing
New to angel investing? This 5-day beginner guide explains startup investing basics including SAFEs, SPVs, diversification, and how to make your first angel investment.