Play Money Blog

Notes on first checks.

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

Play Money's Tuesday breakdown of why 90% of startup exits happen under $100M and how a diversified angel portfolio of base-hit exits beats public markets. July 2026.

NewsletterJuly 14, 2026

VC needs grand slams. You don't.

90% of startup exits happen under $100M, with a median of $44M. A diversified angel portfolio built on these base hits beats public markets 88% of the time.

Play Money's Tuesday breakdown of why great startups now come from regional ecosystems — better valuations, local exits, and public matching capital. June 2026.

NewsletterJuly 1, 2026

The Deal You're Waiting For Is in Your Backyard

56% of angels aren't in CA or NY. Regional startup ecosystems offer better entry valuations, faster local exits, and public matching capital VCs overlook.

Play Money's Tuesday breakdown of startup revenue terms — GMV vs. revenue, the two ARRs, unit economics, and how AI deals dress up the numbers. May 2025.

NewsletterJune 24, 2026

3 Revenue Terms Angels Get Wrong

Startup revenue numbers mislead. GMV, ARR, unit economics — learn the three terms angels most often misread, plus the AI-era tricks to spot.

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.

NewsletterMay 29, 2026

Why Angel Money is the Best Capital a Founder Ever Takes

Most founders think angel funding is a stepping stone to VC. Ep#16 challenges that, arguing angel capital may be the most valuable money a founder ever takes.

NewsletterMay 21, 2026

Why Your Angel Thesis Shouldn't Exist Yet

Your angel thesis isn't something you invent upfront — it's something you earn through experience. Cheryl and Andy on why new investors should stop waiting for the perfect framework.

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.

NewsletterMay 14, 2026

How Hidden Capital Unlocks Angel Investing

Most people think angel investing requires new money. Ep#14 makes the case that the capital already exists — it’s just hiding in plain sight.

Angels Decoded Episode 13: Why Angels Aren't Small VCs. Hosts Andy Walsh and Cheryl Kellond.

NewsletterMay 8, 2026

Why Angels Aren’t Small VCs (And Why That Matters)

Angel investing isn’t complicated — we’ve just made it feel that way. Ep#13 reframes what angels actually are, and how to get started.

NewsletterApril 30, 2026

The Angel Advantage in Venture Capital's “Black Hole”

When venture capital crowds into AI deals, opportunity doesn't disappear — it moves. Ep#12 explores the angel advantage in overlooked sectors.

NewsletterApril 28, 2026

When Founder Brilliance Becomes a Trap for Angel Investors

A founder who can explain 4 levels of unit economics in 30 seconds should be a sure bet. So why did the room lean in — and then hesitate? The trap every angel falls into, and the one question that cuts through it.

NewsletterApril 28, 2026

The Diligence Trap Every Angel Falls Into

When a founder can explain four levels of unit economics across six cities, angels stop imagining and start auditing. Here's the one question that cuts through.

NewsletterApril 22, 2026

The New Founder Playbook in the Age of AI

The traditional founder traits angels look for may no longer be enough in the AI era. Ep#11 explores what great founders look like now.

NewsletterApril 21, 2026

$9 Trillion New Capital

A VC told Play Money founder Cheryl Kellond that the new angel investor doesn't exist. Here's why $9 trillion says otherwise — and which sectors.

NewsletterApril 16, 2026

The Echo Chamber Problem in Venture Capital

Traditional VCs believe there are no new angel investors entering the market. Ep#10 explores why that assumption may be completely wrong.

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.

NewsletterApril 9, 2026

Building Your Own AI Investment Framework

When AI evolves this fast, borrowed conviction isn't enough. Ep#9 explores how angels can build their own framework for evaluating startups.

NewsletterApril 3, 2026

The Emotional Cost of Optimism in Angel Investing

When the world feels unstable, even experienced angels pull back. Andy Walsh and Cheryl Kellond explore the emotional cost of optimism in angel investing.

NewsletterMarch 20, 2026

SAFE Notes: Simple, Fast… and Fuzzy

SAFE notes are fast and flexible — but if you don't understand them, you won't know what you own until it's too late. Andy and Cheryl decode the fuzzy math behind SAFEs.

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 13, 2026

Small Checks, Big Impact — The Real Math of Angel Investing

Small checks, smart portfolio. Andy & Cheryl unpack why bigger isn't better in angel investing and how the 30-investment rule changes the math.

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.

NewsletterMarch 6, 2026

The Truth About Cap Tables and Angel Investing

Small checks can create large headaches when angels don't understand cap table mechanics. Ep#4 of Angels Decoded breaks down dilution, ROFR, and why SPVs exist.

NewsletterFebruary 27, 2026

Why SPVs Are the "Professional Grade" Way to Angel Invest

Direct cap table investing creates hidden burdens for founders. Ep#3 of Angels Decoded explains why SPVs are the professional-grade structure for angels who want to add real value.

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.

Angels Decoded podcast — hosts Andy Walsh and Cheryl Kellond.

NewsletterFebruary 20, 2026

The Math of More: Why 30 is the Magic Number for Angel Portfolios

Why does 30 matter so much in angel investing? Cheryl and Andy unpack the data science behind portfolio construction and why volume — not expertise — drives startup returns.

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.

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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.

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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.