Angel: How to Invest in Technology Startups

Written by one of the most prominent Silicon Valley angel investors, Angel is a comprehensive overview and how-to guide for anyone who wants to dip their toes into the investment world. As the title suggests, Jason Calacanis boasts a 9-digit net worth after a string of early bets on startups that went on to become unicorns, most notably with Uber.


At 288 pages separated into 32 chapters, the book is broken down into one to five-page sub-sections, where readers can efficiently identify topics that interest them. While Calacanis touches on his personal experiences from time to time, the majority of the book is a straightforward explanation of what the angel investment profession encompasses, from big picture concepts like evaluating a deal to more nuanced subjects like bringing a paper and pen to your pitch meeting instead of being “that guy” writing on a tablet.


Industry insiders can probably do without reading the first few introductory chapters–such as ‘What’s Special About Silicon Valley’ or ‘Startup Funding Rounds Explained’–although they do lay the groundwork for understanding Calacanis’s approach and the environment he’s investing in. Chapters like ‘The Perfect Way to Decline a Deal’ and ‘The Disastrous Second Year as an Angel Investor’ really play to the depth of his 25 years of experience in the industry, and are sure to even be insightful to seasoned investors.


The later chapters are generally more technical–covering topics like minimal viable product or valuation–and jam-packed with advice newbie investors may not even know they needed, such as writing the perfect deal memo and managing their relationship with other angels. Investors can use sections like ‘Question Zero’ as a play-by-play for what they should ask at a founder meeting.


Calacanis explains that he wrote the book for anyone interested in angel investing, from “the mom in the bookstore with screaming kids” to “the kid graduating from college,” so he also includes sections about investing with little or no money.


Like his podcast ‘This Week in Startups,’ Calacanis has an effortless way of drawing listeners and readers in with his genuine demeanor and take-it-or-leave-it attitude. In one memorable section titled ‘Jason Calacanis does not eat shit,’ he details an incident where he tells another investor: “If you try and trample my rights on this deal, I will simply not pass the ball to you in the future–but I will pass the ball to your competitors, and not only that, I will take this current deal and walk it into Alpha, Beta, and Delta ventures personally.”


While this anecdote is amusing, it also relays the more important message of protecting oneself and encouraging collaboration rather than infighting within the startup community–a middle ground that exemplifies why the book is an enjoyable read throughout. –MC




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