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.
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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.
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.
BlogJune 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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.