A-List Angels

It could be argued that Zack O’Malley Greenberg tries to do one too many things with his book A-List Angels: How a Band of Actors, Artists, and Athletes Hacked Silicon Valley.

The book, meant to be an examination of how Hollywood celebrities have begun to intersect with the venture capitalists and angel investors of Silicon Valley, is an often uneven affair. Greenberg can’t seem to help namedropping, be it a Hollywood personality, famous musician, prominent venture capitalist, or hot startup, resulting in a breezy narrative where all too often it’s difficult to keep track of who’s who. A-List Angels also lacks a consistent throughline, with Greenberg imposing on readers’ attention by many times shifting focus even within chapters.

But if one can get past these stylistic choices, there’s a lot of fun to be had with A-List Angels.

Certainly, A-List Angel’s strongest chapters are those that maintain a tight(er) focus. The book only really begins to gel once Greenberg centers on actor-turned-investor Ashton Kutcher, and chapters that similarly stay on point rather than “bounce around” are much more insightful. While anecdotes abound, which is par for the course given the book’s topic, there are a number of interesting takeaways that readers might take for granted from the outside looking in.

For instance, it’s fascinating to consider that professionals from the music industry were better poised to explore startup opportunities compared to their silver-screen counterparts, which in hindsight is understandable considering how Napster completely upended their unit economics. It’s also interesting to note that in the early days of the dalliance between the celebrity and investor camps, the former would frown upon equity participation and insist upon being paid upfront for services rendered—that is, until the likes of rapper 50 Cent hit it big with securing a stake in VitaminWater in exchange for being its celebrity endorser.

Of course, today it’s no longer surprising to hear of stories like Kutcher’s or that of The Honest Company’s Jessica Alba, nor how athletes like Joe Montana, Shaquille O’Neal, and Lebron James have extensive startup investment portfolios of their own. It seems almost inevitable that early stage startups would eventually gravitate to Hollywood for venture funding; you just have to follow the money, after all.

Yet, even in the best of times investing is a risky affair. In that regard, perhaps the most surprising thing about A-List Angels is how much more sophisticated the Hollywood types have become at playing the game, and how becoming angels in their own right has created yet another path for the rich to generate real outsize wealth.