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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.
A 15-minute angel investing podcast unpacking portfolio construction, conviction, deal evaluation, and the realities of early-stage investing.
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.
A practical framework for evaluating startup founders, avoiding common angel investing traps, and building conviction in your early-stage investments.
A practical framework for evaluating early-stage startup deals, building pattern recognition, and developing your angel investing thesis.
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.
How experienced angels evaluate founders, spot red flags early, and make better decisions with fewer, sharper questions.
Andrew Eil shares how he evaluates climate deep tech startups, de-risks commercialization, and builds conviction in early-stage sustainability investments.
A founder-first case for fixing angel investing infrastructure, reducing the fragmentation tax on early-stage companies, and coordinating the long tail of capital.
A reflection on angel investing, capital allocation, and why funding creation — not extraction — may be the highest-leverage civic act in private markets.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Are $30M+ seed valuations too high? Learn how angel investors should evaluate YC-backed startups, valuation caps, institutional signaling, and ownership math.
A practical guide to angel investing strategy: diversification, startup return distributions, budgeting, deal selection, and how experienced angels pick winners.
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.