Play Money Blog

Notes on first checks.

Essays and updates from the Play Money team.

Play Money's breakdown of pre-money vs post-money SAFEs, valuation caps, discounts, and uncapped notes for angel investors. July 2026.
BlogJuly 29, 2026

Pre-Money vs Post-Money SAFEs, Explained

Pre-money caps, post-money caps, discounts, and uncapped notes each change how a SAFE converts to equity, and the right structure depends on deal stage.

Play Money guide illustration on deciding whether angel investing is right for you before writing your first check.
BlogJuly 23, 2026

Is Angel Investing Right for You? What to Know Before Your First Check

Most angel deals lose money, and you do not need a finance degree. The three tests that decide whether angel investing is right for you before your first check.

Explainer on carried interest in angel investing, showing how a 20% carry applies only to the profit on an SPV deal, not to the investor's original capital.
BlogJuly 22, 2026

What Is Carried Interest? Carry, Explained With Real Angel-Deal Math

Carried interest (carry) is the profit share paid to a deal's organizer, and only after investors get their money back. Here is the real angel-check math.

Diagram of an angel investor's pro-rata rights decision, weighing a follow-on check against portfolio concentration and new-deal opportunity cost.
BlogJuly 22, 2026

Pro-Rata Rights, Explained: The Angel's Exercise-or-Pass Framework

Pro-rata rights protect your ownership percentage, but exercising them isn't automatically right. Here's the math and a three-check decision framework.

Explainer on pre-money versus post-money startup valuation and how an angel's ownership percentage is calculated from the post-money figure.
BlogJuly 22, 2026

Pre-Money vs Post-Money Valuation: What Angels Own

Pre-money is value before the round. Post-money adds the new money. The same "$8M valuation" can mean 20% or 25% ownership. Here is the math angels use.

A guide to the term sheet clauses that matter most to angel investors: liquidation preference, pro-rata rights, no-shop, and information rights.
BlogJuly 22, 2026

What Is a Term Sheet? The Clauses Angels Actually Need to Read

Most term sheet guides are written for the lead VC. Here are the four clauses an angel writing a $500 to $3,600 check should actually read closely.

Diagram of a special purpose vehicle pooling multiple angel investors into one startup on the cap table.
BlogJuly 22, 2026

What Is an SPV? Special Purpose Vehicles in Angel Investing

An SPV pools a group of angels into one startup through a single-deal entity. Here's the capital call, K-1s, fees, and carry, in the order you live them.

An angel investing glossary grouping 16 core startup-finance terms by the investor decision each one drives.
BlogJuly 22, 2026

Angel Investing Glossary: 16 Terms Every Angel Needs, Grouped by Decision

Angel investing has its own language. Here are the 16 core terms in plain English, grouped by the decision in front of you instead of the alphabet.

Illustration for a guide explaining what an accredited investor is under SEC Rule 501(a) and the three ways to qualify.
BlogJuly 22, 2026

How to Become an Accredited Investor (and How to Tell If You Already Are)

An accredited investor meets an SEC income, net worth, or license bar to buy private deals. The three ways to qualify, how it's verified, and why the bar was never the real constraint.

Explainer on equity dilution for angel investors, showing how ownership percentage shrinks while a stake's dollar value can still grow.
BlogJuly 22, 2026

What Is Dilution? Why Your Percentage Shrinks as Your Stake Grows

Dilution isn't automatically a loss. See the math on how a $3,600 angel check shrinks from 0.045% to 0.031% ownership and still grows past $40,000.

How a SAFE note converts into startup equity, from valuation cap and discount to the pre-money versus post-money math that sets an angel's return.
BlogJuly 22, 2026

What Is a SAFE Note? How It Converts to Equity, Explained

A SAFE gives you equity later for cash now. See how it converts, why a post-money cap locks your ownership at signing, and what pre-money math can cost you.

A new angel investor weighing pre-IPO AI secondary shares against a diversified early-stage portfolio.
BlogJuly 21, 2026

Should New Angels Buy Pre-IPO AI Shares? The Beginner Portfolio-Math Answer

Late-stage AI secondaries like Anthropic trade near $625 at about 70x revenue. Here's the beginner portfolio math on whether new angels should buy them.

Explainer on how fees stack across layered pre-IPO SPVs and how a small-check angel can count the layers before investing.
BlogJuly 21, 2026

Pre-IPO SPV Fee Layering: Count the Layers Before You Invest

Buying pre-IPO shares through an SPV rarely means owning the shares. Fees stack across each layer. Here's how to count them and price each one before you wire.

Three-gate angel investor evaluation framework covering founder quality, market and model, and deal terms.
BlogJuly 21, 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.

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

Best Angel Investing Groups and Communities: How to Find and Join One

Ten named angel groups and communities compared on what you pay before you invest, the per-deal minimum, how you get in, and where each one falls short.

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

Angels Decoded Episode 18: Dilution Isn't the Problem. Not Understanding It Is. Hosts Andy Walsh and Cheryl Kellond.
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.

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

How to check if you are accredited, why your first check can be $500, and what changes once you stop reading about angel investing and start doing it.

Comparison of angel investing platforms by regulation type, minimum check, and fees
BlogJune 12, 2026

Best Angel Investing Platforms: 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.

Angels Decoded Episode 5: Small Checks, Big Impact — The Real Math of Angel Investing. Hosts Andy Walsh and Cheryl Kellond.
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's Tuesday newsletter breakdown on whether angel investors need a thesis — featuring four real investor stories from the Angel 101 community session, May 2026.
BlogJune 3, 2026

Write Checks First. Build the Thesis Later.

VCs need a thesis to raise OPM. Angels don't. Four Play Money investors share how writing checks — not planning them — shaped their real investment philosophy.

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.

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.

Startup team collaboration
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.

Stock market investing concept
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.

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