A-List Angels: How a Band of Actors, Artists, and Athletes Hacked Silicon Valley

by Zack O'Malley Greenburg

Combining high-octane storytelling with landmark financial reporting in the tradition of Michael Lewis, Zack O'Malley Greenburg delivers a transformative account of how Hollywood cashed in on the latest tech boom while bringing a blast of creativity and diversity to Silicon Valley.
How much is celebrity really worth? In a growing trend, Hollywood's biggest stars from Ashton Kutcher to Beyoncé have set out to turn their fame into bankable capital by tossing out traditional endorsement deals in favor of strategic partnerships that grant them a stake in today's top companies. Ushered in by 50 Cent's deal with Vitamin Water -- in which the rapper took equity instead of cash, eventually walking away with a nine-figure haul -- celebrities of all different colors, genders, and talents have learned to capitalize on the invaluable benefits of their platform and visibility.
The ever-evolving, mutually beneficial relationship between Hollywood and Silicon Valley has led to everything from laughable flops and billion-dollar profits to rock star CEOs and paparazzi-worthy boards of directors. Through extensive reporting and exclusive interviews with stars like Shaq, Nas, Sophia Bush, and Steve Aoki, Forbes senior editor Zack O'Malley Greenburg takes an up-close-and-personal look at the rise of celebrity investors and their impact on companies including AirBnB, Spotify, and Uber.

A-List Angels is a book about business that reads like a thriller: entertaining, edifying, and not to be missed.

Genres: Business, Nonfiction

Audiobook

First published March 10, 2020

About the author

After a decade as a Forbes senior editor, Zack O’Malley Greenburg now writes exclusively at Substack, where he’s serializing his fifth book, We Are All Musicians Now (sign up here). His other books include A-List Angels: How a Band of Actors, Artists, and Athletes Hacked Silicon Valley and the Jay-Z biography Empire State of Mind. He has also written for the New York Times, Washington Post, Vibe, McSweeney's and Sports Illustrated, tackling topics from public pension fund scandals to Kanye West's quest to overtake Air Jordan. Zack has lectured at Yale, Harvard and Princeton, and appeared as an expert source for 60 Minutes, BBC, MTV and others. Full bio here.

Reviews

[Jasmine from How Useful It Is · Rating 5 out of 5]

This book is an excellent read! I invest small sums of money on different companies and mutual funds so I enjoy reading about investments and how others invest their money. This book caught my attention because I didn't realize that celebrities invested their money on startups and creating their own business instead of relying on their main job such as acting, singing or sports. It makes sense because they have the money and really this is where they can grow their money besides continue working. I like learning about celebrities in this area of life. I didn't realize Rocawear brand was founded by Jay-Z. Definitely fascinating learning about entrepreneur Bill Gross. It's amazing how people have so many ideas and able to create into something worth a lot of money. I'm amazed by the rapper, 50 Cent with his money making adventures.


This book started with an introduction about how celebrities pour their money into startup companies to earn a big sum of money. Startups like Google, Uber, Lyft, Vitaminwater, etc. Only celebrities and venture capitalists can afford to invest in startups because they have extra money to spend and able to sacrifice a few years of not getting paid from their investments until the startups grow big enough to sell or going public in order for the investors to get paid. First chapter introduce Shaquille O'Neal, basketball player. He invested in himself by getting an education after his basketball career and then invested his basketball earnings in startups like Google and Uber to grow his wealth. As the story move forward, readers will learn of musicians making money by creating a business of their own as well as buying a piece of an existing company.


A-List Angels is very well written and an interesting fast paced read! I am a small individual investor who only join the stock market 4 years ago. I do wish that I joined earlier to take advantage of Amazon and Google but then again, from this book, I learned the dot com has its ups and downs. So I guess I don't feel so bad to join late. Definitely fascinating learning about well known brands and how much it was purchased for when it exchanged from one owner to another like Vitaminwater and Skype. The money 50 Cents, Shaq, Kutcher, Dre, Diddy, Jay-Z earned from their investments are mind blowing. No wonder the rich are getting richer! I'm reading this book word for word because I don't want to miss out on cool information. I admire entrepreneurs who created amazing companies and then earning big returns for their time and efforts. I like reading about companies and celebrities I recognize like Jessica Alba's The Honest Company. Also, one million YouTube views earn only $1,000? I thought it's a lot more! This book is a fantastic read and too many good parts to list them all so I recommend everyone to read this book!

xoxo, Jasmine at www.howusefulitis.wordpress.com for more details

Many thanks to Little Brown Books for the opportunity to read and review. Please be assured that my opinions are honest.

[CatReader · Rating 3 out of 5]

In A-List Angels, child actor-turned-entertainment journalist Zack O'Malley Greenburg writes about wealthy celebrities who've leveraged their disposable income into venture capital, either via actively seeking out promising startups themselves and sometimes even learning to speak, act, and think like an investor (O'Malley Greenburg cites Ashton Kutcher here), or delegating members of their team to source those opportunities for them.

Though the author portrays this story as remarkable, it's hardly that. There are successful people in every industry who, instead of or in addition to founding businesses themselves, actively look for opportunities to invest in up-and-coming organizations (I know I get probably half a dozen such random solicitations every month on LinkedIn from people in my industry). Most of these investments don't become Instagram or Pinterest or Uber -- and in many cases, angel investors lose their investment as most startups fail. The key is to 1) know enough about the industry you're investing in to take calculated risks, and 2) identify the key skills beyond just a bolus of cash you can bring to the venture (though sometimes just a bolus of cash works -- most of the actors namedropped in this book seem to only be contributing that, which isn't really impressive).

Overall, a short read (Goodreads lists this book as 288 pages, but actually it's <200 of actual book text, and nearly 100 pages of glossaries and references) that won't set the world on fire, but may be of interest to those contemplating the venture capital space.

My statistics:
Book 59 for 2025
Book 1985 cumulatively

[Joe · Rating 5 out of 5]

Very enjoyable deep dive into the relationship between Hollywood/artists and Silicon Valley/tech investors. A lot more Nas than I was expecting when I opened it.

[Kuang Ting · Rating 4 out of 5]

When you hear about investment, what comes to your mind? Most people normally think about investment bankers in sharp suits with impeccable hairstyle. They belong to the top echelon of the capitalistic world. They are the guardians of capital. They maximize investors’ returns by allocating the capital efficiently. The market could be very volatile. That is why experts exist. They are able to use their expertise to make investments click. In tradition, large financial institutions play the major role in the investment world. You know the key players: Goldman Sachs, JP Morgan, etc. They are the pillars of the finance world. Though sometimes scandals hit, these financial behemoths are both important and essential to the society. They are infrastructure, like conduits connecting markets worldwide. Multinational companies rely heavily on them to manage capital flows.

However, there is also a new force gaining momentum in the past few decades. Some financial professionals who start their career in The Wall Street want to make a difference. The large investment banks are subject to tight government regulations. Sometimes it slows down financial innovation. Just like a giant vessel, it could be hard to navigate the treacherous waters. The technology is disrupting every industry, including finance. Some experts think it would be better if they could respond more effectively to the current status. Since they are not permitted to do so in the traditional powerhouses, they start their own investment firms instead. Therefore, a new breed of investment firms start emerging, and they are called venture capital (VC) firms.

Compared to its predecessor that raises money mostly from open market, venture capitalists could raise money from private sources such as angel investors or wealthy individuals. VC has more flexibility. It is also less scrutinized by regulations. Thus, it offers a good alternative for start-ups to raise money. VC as an industry grows larger and stronger. Nowadays, almost every start-up relies more or less on VC to grow the business. VC has become a new pillar of our society. It drives innovation from Silicon Valley to Taiwan. It’s a new trend worth learning about.

There are several books about VC and I wish to read them in the future. One book catches my eyes because the subject matter is very interesting. This book titled ‘A-List Angels: How a Band of Actors, Artists, and Athletes Hacked Silicon Valley’ is a nice book to learn about VC. It introduces a lesser known world to readers. We all have our favorite Hollywood stars and NBA players. We listen to music by famous singers. They are part of our collective entertainment memories. We admire their creativity and originality. They are icons in pop culture. But interestingly, many of them are also smart investors who put large amount of wealth into investments. While some become angel investors, some are so successful that they even set up their own VC firms. This book introduces these behind-the-scene stories to us. I find it very enlightening.

At the beginning, Hollywood and the investment world (The Wall Street and Silicon Valley) are parallel universes that don’t have any connection. The former is the center of global pop culture. The latter is where money clusters. Historically, creative artists despise the greedy mindset of investors, and investors don’t think highly of Hollywood because of their Bohemian lifestyle. Things start to change though.

Since the turn of 21st century, internet becomes part of our daily lives. Technology enables us to keep in touch on the fingertip. The way we communicate changes forever. Cinema, TV, radios are no longer the mainstream medium for entertainment. The invention of smartphone makes everything mobile. The disruption leads to loss of huge profits in the entertainment industry. Therefore transformation ensues. Movie stars, singers, athletes all start to adopt new technology to reach out directly to the fans. Social platforms (such as FB and IG) become foundation of a successful career in entertainment industry.

The emergence of technology has pros and cons. On the good side, it provides better chances for stars (and creative professionals in general) to enjoy longer career influence. In history, these stars are also ‘worker’ for agency, film company, music record company, and athletic teams. Sometimes they are traded like commodity. Sometimes they are mistreated by misleading contract. In many cases, stars are like us, who could be vulnerable in the labor market. The rise of social media breaks the chain. Stars could now get in touch with fans without agents. It gives them more independence. But admittedly, there are also negative effects as well. The social networks monopolize the channel, and may take a disproportionate profit from the stars.

That is why some influential figures like Lady Gaga, Taylor Swift, Shaq O'Neal, Jaz-Z, A-Rod to name just a few, start to take parts in the investment world. They want to turn the table. They wish to build a fairer environment for their peers. They are influencers who can use their fame to attract clients and customers for their investment companies. To their surprise, many investments pay off and the rewards could be multiple times higher than their salary as a singer, actor, or athlete. This trend catches fire. More and more celebrities join the game. Among them, actor Ashton Kutcher is the leading pioneer. He co-founded a VC firm called A-Grade Investments. This VC firm is the major protagonist in this book. Nowadays, celebrities from entertainment industry have a big say in the VC game. This book is about their ascendance from nobody to somebody.

The author, Zack O'Malley Greenburg, is a senior editor from Forbes. This is his fifth book. Greenburg is a veteran reporter on the entertainment industry with over 10 years of experience. Interestingly, he even starred in a famous movie in his childhood. He has access to a wide array of luminaries in this field and it makes his reporting insightful. If you are interested in learning about the intersection of finance, technology, and entertainment, this book is an ideal choice to add to your reading list.

[Tej Dhawan · Rating 3 out of 5]

An interesting chronology that at times reads like name-dropping for emphasis and at others a hodge-podge set of stories pulled together for cumulative effect. However, the book is an interesting dive into the world of celebrity angel investing.

The core lesson I took away from the book is that high net worth actors, directors and athletes with a penchant for investing, eye on their future, and an interest in others' ideas surround themselves with talent scouts, advisors, and seekers who spot burgeoning trends. They enable their scouts with information and don't shy from seeking advice, firing when necessary, writing big checks, and lending their name to deal-flow.

It is a different world of angel investing than I see in our Midwestern market so the book is, additionally, voyeuristic and titillating.

[Shivakumar Srinivasan · Rating 3 out of 5]

When one talks of investments, people generally talk of the famous legendary investors or hedge fund or PE firms who operate on the main street. This book , with surprisingly well researched works, tells the fascinating story of the emergence of Sports and Movie and Rap Stars who rose above and beyond their core identity as starts carved a brilliant-career as startup investors. A bit long,which makes the stories a bit boring and repetitive, it’s still a good read if you are curious about a bunch of investors who became billionaires by their astute business sense which were many a times nothing more than common sense , loosely speaking.

[Faloni ©]

What a sad world we live in . 😌

[Ishan S · Rating 5 out of 5]

Incredibly helpful for anyone who wants a peek inside the glamourous trend of startups marrying U.S. celebrities.
The case study of Spotify is my favourite.