Late last month, Jason Calacanis messaged me on Twitter to invite me to dim sum in New York. We had never exchanged messages on Twitter before, but I must have followed him at some point because he was an early investor in Uber. “Alison, dim sum in nyc this week for my book launch,” he wrote. “Angel broke the top 50 on Amazon, in it I talk about my five unicorn angel investments 🦄🦄🦄🦄🦄.” This was followed by a link to his book on Amazon and another unicorn emoji.
Uber is the preeminent startup in Silicon Valley, last valued at nearly $70 billion. It is also one of the OG “unicorns,” private technology companies valued at or above $1 billion. Calacanis knows a thing or two about unicorns. Over a six-year career as an angel investor, he has bet on at least four of them: Uber, Thumbtack, Robinhood, and Desktop Metal. Calacanis also counts DataStax, a data management company last valued at $967 million in September 2014, and Wealthfront, an asset management platform last valued at $700 million in October 2014, among his unicorn investments. “i put startups in my [Twitter] bio when they are unicorns,” he messaged me, when I pointed out that DataStax and Wealthfront hadn’t publicly confirmed valuations over $1 billion. “but you should present what you found,” he added. “i cant comment on information i might have that you dont 🦄😂”
Calacanis came into angel investing as Silicon Valley was picking itself up from the dot-com collapse. His first payout, for $16,000, came from advising ZeroDegrees, a pre-LinkedIn professional network that sold to IAC in 2004. A year later Calacanis made his real money when Weblogs, Inc., a blogging company he co-founded with longtime friend Brian Alvey, was acquired by AOL for $25 million. An unabashed self-promoter, Calacanis parlayed that win into Silicon Valley microcelebrity, aided by his blog, Twitter (@Jason), liberal use of expletives and emojis, and pair of Tesla Model S cars (serial numbers 00001 and 00073). To date, Calacanis says he has put in just under $10 million and returned more than $150 million on 40-plus angel investments. It was only natural that he take part in the time-honored tradition of authoring a self-help business book, and write Angel.
Angel has been out for less than a month, but it is already a roaring success on Amazon, where it has amassed almost exclusively five-star reviews. Calacanis noted this multiple times at his dim sum on July 26. “There are three one-star reviews,” he said, when he stopped by the table where I was seated. “Two of them are like, ‘Fuck Jason Calacanis,’ and that’s the whole review. And I’m like, ‘thanks mom.'” (I later checked online; there are indeed three one-star reviews of his book on Amazon, but none of them says this.)
The dim sum was held at 6:30pm in the second-floor dining room of Golden Unicorn, a gaudy restaurant in Manhattan’s Chinatown with golden drapes, gold-upholstered chairs, and a “B” grade from the New York City health department. The price of admission was buying a copy of Angel ($30). “Everybody, whether you have the book or not, you have to buy a book,” a woman from Books on Call NYC, an independent bookseller, told me when I arrived. There were a dozen hardcover copies of Angel stacked in front of her. The online r.s.v.p. form for the dinner had explained that buying a book was expected, but as a journalist covering the event I assumed it was optional, especially since I already had a review copy from the publisher. After a brief discussion—it was not, it turned out, optional—the woman called over Alvey, Calacanis’s close friend and Weblogs co-founder, who agreed to let me join his table anyway.
The room was filled with about 100 people, many with ties to the tech community, gathered around eight-seat circular tables. A second seating, on the restaurant’s third floor, was scheduled to begin at 8:30pm. The man sitting to my right, Sherman Hu, introduced himself as an aspiring angel investor and the first direct sales hire at LinkedIn. “If this book was written, I don’t know, five years ago, I probably would have had a clearer path for what I want to do next,” Hu, 38, told me. “You have guys like Jason who are out there, but not everyone can really pull off—it’s not really replicable what he did, but it’s inspiring.”
Inspiration is a central theme of Angel. “This book has a singular goal: to teach you how massive wealth is created in the twenty-first century,” reads the opening line. “I’m just gonna tell you how a C-minus student from Brooklyn (before Brooklyn was cool) clawed his way into the tech industry, got lucky seven times (and counting), and made tens of millions of dollars.” The book’s refrain is “do the work.” Calacanis’s enthusiasm is tempered only by the advisory printed just inside the front cover: “This book is designed to provide readers with a general overview of angel investing. It is not designed to be a definitive investment guide or to take the place of advice from a qualified financial planner or other professional. Given the risk involved in investing of almost any kind, there is no guarantee that the investment methods suggested in this book will be profitable.”
Dim sum at the Golden Unicorn included shrimp dumplings, piggy custard buns, oily spring rolls filled with some sort of meat, sweet and sour chicken, beef with broccoli, and chicken fried rice. Calacanis appeared at our table somewhere between the spring rolls and the chicken. He wore a dark blue suit jacket with a change pocket over a pale pink dress shirt, and his thin brown hair was combed over to one side. “Anybody want to me to sign a book? Anybody buy a book?” he said. “You have to, or they won’t let you in!” A man sitting across the table, Mike, handed his book to Calacanis. “Mike!” Calacanis barked. “What do you do, Mike?” He flipped open the book and, while Mike explained, scrawled in green sharpie, “Mike, do the work!”
When Calacanis got to me, I introduced myself as a journalist from Quartz and said we’d exchanged messages on Twitter. I handed him the review copy of Angel I’d been sent by a HarperCollins publicist. “They told me to buy a second copy,” I joked. “Yeah, that’s how it works.” Calacanis said. “You buy a copy, I buy you dinner. It’s a wash.” I told him I hoped the dinner was a little less than $30. “No, it’s exactly 30,” he said. “They were going to do it for, like, 20, and then I was like, ‘get the duck!’ I don’t want people to think I’m cheap.”
Much as every good startup has a creation myth, Calacanis has spun an origin story for Angel. It goes like this: People asked him for years to write a book but he demurred, telling his agent, “one more win.” That win finally arrived in Uber. Once Calacanis agreed to a book deal he was offered a ghostwriter, which he declined. He went on to write Angel in “19 long days.” The story appeals to Silicon Valley’s obsession with productivity hacks. Alvey sighs when it is told. “He says it all the time, it pisses me off,” Alvey said. “It was five or six months doing research. So it was 19 solid days spread across five or six months.”
Despite its rags-to-riches framing, Angel is not written for the masses. Generally speaking, only SEC accredited investors—individuals who earned more than $200,000 in each of the last two years, or whose net worth exceeds $1 million, excluding the value of their primary residence—are supposed to invest in startups. (The SEC recently adopted rules that let less wealthy people make limited investments in startups via crowdfunding.) This point is largely glossed over in the book, aside from a brief discussion of how “broke angels” can advise startups in exchange for equity. It was also notably absent from the speech Calacanis gave during dinner about angel investing as a new path to upward mobility and the American Dream.
“Capitalism and democracy are very important to society,” he said. “If people feel like they can move up in society, they won’t be desperate and they won’t be looking to close the borders, and beat people up, and kill people in bars.” Calacanis believes entrepreneurship, democracy, and capitalism come together to create our best flawed system. “I think it’s noble to build companies that make a lot of people rich and let them move up in the world and improve their lot in life,” he said. “And I do believe that trickles down.” He was speaking from a podium under a crystal chandelier, which clinked loudly due to a draft from a nearby air vent. The chandelier was surrounded by neon lights that created a purplish glow around his head.
“This has been amazing,” Calacanis said some 30 minutes later, as he prepared to head upstairs. His second seating of the night was getting started, and on our floor people had lost interest in the cold remains of their dim sum. “Please read the book. And please, write a review.”
The image above was taken by Jason Jacobs and shared under a Creative Commons 2.0 Generic license on Flickr.