Jason Calacanis, one of Silicon Valley's most prominent angel investors with early stakes in companies including Uber, Tumblr, and Robinhood, provides a candid and practical guide to angel investing that is unusual for its transparency about both the extraordinary upside and the brutal realities of the asset class. Calacanis begins with an honest accounting of why angel investing is a genuinely difficult and illiquid activity where most participants lose money despite the headline returns of the rare winners, and makes clear that the approach he describes only makes sense for sophisticated investors with sufficient diversification and patience to see a long-term portfolio play out. The book covers how to source deals — a critical and systematically underestimated challenge — through building genuine relationships in startup communities, how to evaluate early-stage companies when there is almost no financial data to analyze, what to look for in founders, how to structure investments using SAFEs and convertible notes, how to add value as an investor beyond just writing a check, and how to manage a portfolio that will include many complete losses alongside occasional transformative winners. Calacanis is also unusually frank about the ethical dimensions of angel investing, including the temptation to overvalue weak companies, the obligations that come with pro-rata rights, and the challenge of maintaining relationships with founders through difficult decisions. One of the most realistic and practically useful guides to the angel investing process available.