Play Money Blog

Notes on first checks.

One feed for every Play Money post — essays, updates, and weekly newsletters.

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.

Comparison of the five 2026 SPV platforms: AngelList, Sydecar, Carta, Allocations, and Play Money, showing fees, minimums, and carry.

BlogJuly 9, 2026

Best SPV Platforms Compared: AngelList, Sydecar, Carta, Allocations, Play Money

A syndicate lead's honest comparison of the five SPV platforms US angels use in 2026, ranked on fee transparency, minimums, and post-Assure track record.

Comparison of 14 angel investor networks and communities for women in 2026, grouped into established old-guard networks and next-generation networks, showing named woman leader, minimum check, accreditation, and fees.

BlogJuly 9, 2026

The 14 Best Angel Investor Networks and Communities for Women

Seven established networks and seven next-generation communities for women angels, ranked by minimum check, accreditation, fees, and named leader.

Angels Decoded Episode 20: The Three Deadly Sins of Angel Investing. Hosts Andy Walsh and Cheryl Kellond.

BlogJuly 8, 2026

Angels Decoded Ep#20: The Three Deadly Sins of Local Angel Groups

Hoarding diligence, big minimum checks, and cap table ego are quietly costing founders funding. Cheryl Kellond unpacks the three sins and the SPV fix.

Guide to finding and joining an angel investing group, comparing formal groups, syndicates, and learning networks.

BlogJuly 6, 2026

How to Find and Join an Angel Investing Group: A First-Timer's Guide

Three types of angel communities, what each costs, and the portfolio math check to run before you apply to any group.

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.

Feasibility matrix scoring angel investing platforms, programs, and groups on fees, check minimums, deal-flow diversity, and time for a $10,000 starter budget.

BlogJune 30, 2026

How to Start Angel Investing With $10,000: A Realistic First-Portfolio Framework

Yes, $10,000 builds a real first angel portfolio. Here is the platform-by-platform feasibility matrix, scored on fees, check minimums, and time.

Map of the DMV angel investing market across DC, Maryland, and Northern Virginia

BlogJune 25, 2026

DMV Angel Investing: A Guide to DC, Maryland, and Virginia Startups

The DMV is one of the few U.S. markets where federal proximity is a structural edge. Here's how it works, who's deploying capital, and how to get in.

Map of the Atlanta startup ecosystem showing fintech, SaaS, and logistics anchors across Tech Square, Buckhead, and Midtown

BlogJune 25, 2026

Atlanta Startup Investing: A New Angel's Guide to the Southeast Market

Atlanta produced Mailchimp, Calendly, and Flock Safety while staying uncrowded. A practitioner's guide to angel investing in the Southeast's power-law market.

Map of Alabama's startup investing market across Birmingham and Huntsville for new angels

BlogJune 25, 2026

Alabama Startup Investing for New Angels: Exits, Deal Flow, and Public Capital

Alabama has produced three power-law exits in a decade. Here's the deal flow, the dual-hub map, and the public capital that wants angels in the room.

Comparison of GMV and ARR for angel investors, showing what each startup revenue number measures and the diligence questions to ask.

BlogJune 24, 2026

GMV vs ARR: How Angel Investors Read Startup Revenue

The revenue terms founders use to tell their story, and the three AI-era tricks every angel should spot before believing the number, from Play Money.

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.

BlogJune 19, 2026

Dilution Isn't the Problem. Not Understanding It Is.

Why dilution is a reason to celebrate, not panic—plus how to spot a cram-down round dressed up as a late-stage opportunity. Angels Decoded Ep#18.

Donor-advised fund deployment: the hidden questions DAF holders ask

BlogJune 13, 2026

The DAF Holder's Hidden Questions: A Field Guide to Deployment

The questions DAF holders Google at 2am but never ask their sponsor: deferral guilt, succession, direct investing, and building a personal impact fund.

Play Money guide to managing a financial windfall with a 90-day decision framework

BlogJune 13, 2026

The Lurker's Guide to a Windfall: A 90-Day Decision Framework

A calm, stewardship-first framework for managing a sudden windfall: pause 90 days, build the boring base, and decide what comes next.

A guide to angel investor taxes including QSBS, Section 1244, K-1s, and charitable strategy after the One Big Beautiful Bill Act

BlogJune 13, 2026

The Angel Investor's Tax Toolkit: QSBS, K-1s, and Charitable Strategy After the OBBBA

Five federal tax provisions determine how much an angel investor keeps after an exit. Updated for the One Big Beautiful Bill Act, effective July 5, 2025.

Guide to self-directed IRA angel investing covering Roth vs Traditional accounts, UBIT on SPVs, IRC 4975 prohibited transactions, QSBS, and 2026 custodians.

BlogJune 13, 2026

Self-Directed IRA Angel Investing: Roth vs. Traditional, UBIT, and Prohibited Transactions

Roth vs Traditional, the UBIT gotcha on SPVs, §4975 prohibited transactions, why QSBS doesn't apply, and the 2026 SDIRA custodian landscape.

Three-gate angel investor evaluation framework covering founder quality, market and model, and deal terms.

BlogJune 13, 2026

How to Evaluate Startup Founders and Deals: An Angel Investor's Framework

A practitioner's 3-gate framework for vetting founders, market, and deal terms, anchored in the ACA research on what actually predicts returns.

A horizontal bar chart showing the power-law distribution of angel investing returns: about 40% of investments go to zero, 50% return 1x to 3x, 8% return 10x to 50x, and 2% become generational outliers driving most portfolio returns.

BlogJune 13, 2026

How Angel Investors Make Money: Returns, Exits, and the Real Distribution

Angel investors get paid through exits. Here's the real return distribution, the mechanics of each path to liquidity, and the waterfall math.

Comparison of angel investing deal structures: SAFE, Series SAFE, convertible note, and priced round

BlogJune 13, 2026

Angel Investing Deal Mechanics: SAFEs, SPVs, and Priced Rounds

SAFEs, the Series SAFE, priced rounds, and SPVs explained from the angel investor's side, with the post-money ownership formula and real carry math.

Angel investing portfolio strategy: power law returns, the 30-check threshold, and position sizing

BlogJune 13, 2026

Angel Investing Portfolio Strategy: The Power Law, the 30-Check Threshold, and How to Size Your Checks

Angel returns follow a power law. How many checks you need, how to size each one from your net worth, and how to spread them across vintage years.

A beginner's guide to angel investing covering accredited investor requirements, historical returns data, and portfolio diversification math.

BlogJune 13, 2026

How to Start Angel Investing: A Beginner's Guide Built on the Data

What accreditation requires, what returns the data actually shows, and how many investments you need before diversification starts working.

Comparison of angel investing platforms by regulation type, minimum check, and fees

BlogJune 12, 2026

Best Angel Investing Platforms in 2026: Reg CF, Reg D, and How to Choose

Six angel investing platforms compared on regulation, minimums, fees, and curation, with an honest read on where each one is the wrong choice.

Diagram of the climate deep tech funding gap between government grants and institutional venture capital, where angel investors write checks.

BlogJune 10, 2026

How to Angel Invest in Climate and Deep Tech: Andrew Eil's Six-Part Framework

Most VCs won't fund the gap between lab and first customers. Andrew Eil's six-part framework shows angels how to evaluate climate hardware deals.

BlogJune 3, 2026

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

Most angels assume size equals impact. Ep#5 breaks down the 30-investment rule and why small checks, deployed through SPVs, can move founders more.

Play Money explainer: SPV vs RUV, how pooled angel investing structures compare from closing mechanics to fees and exits.

BlogJune 2, 2026

SPV vs RUV: Two Angel Investing Structures Explained

SPVs and RUVs both pool angel investors into one entity, but they work differently. Here's how each structure works, what you pay, and when each makes sense.

Angels Decoded Episode 15: Why Your Angel Thesis Shouldn't Exist Yet. Hosts Andy Walsh and Cheryl Kellond.

BlogJune 1, 2026

Angels Decoded Ep#15: Why Your Angel Thesis Shouldn't Exist Yet

Most new angels wait for a thesis before investing. Cheryl and Andy unpack why that keeps people stuck — and how conviction actually forms through small bets.

Angels Decoded Episode 16: Why Angel Money is the Best Capital a Founder Ever Takes. Hosts Andy Walsh and Cheryl Kellond.

BlogMay 31, 2026

Angels Decoded Ep#16: Why Angel Money is the Best Capital a Founder Ever Takes

Most founders think angel money is just a VC stepping stone. In Ep#16, Cheryl and Andy argue it may be the most important capital a founder ever takes.

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.

How DAF capital flows from sponsor accounts through Inspire Access to startup investments on Play Money

BlogFebruary 13, 2026

Can You Invest Your Donor-Advised Fund (DAF) in Startups? Here’s How It Works

Learn how to invest your donor-advised fund in startups through Play Money's partnership with Inspire Access. Turn idle DAF capital into a diversified impact portfolio.

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.

BlogJanuary 10, 2026

5 Things Every Angel Investor Should Know About Startups

Angel investing in startups can be incredibly rewarding, but it comes with unique challenges. Here are five crucial things every angel investor should understand before writing their first check.

BlogJanuary 3, 2026

Investing 101: A Beginner's Guide to Building Wealth

Starting your investment journey can feel overwhelming. This comprehensive guide breaks down the fundamentals of investing and helps you take your first steps toward building long-term wealth.

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.

Angel Investing During Market Volatility Newslette Thumbnail

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.