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Angel: How to Invest in Technology Startups--Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 Hardcover – July 18, 2017
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"Warlight" by Michael Ondaatje
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“there is something refreshing and clarifying about Mr. Calacanis’s frankness regarding his tech-fueled riches.” (Farhad Manjoo, The New York Times)
“It’s easy to snigger at the swagger, but Calacanis has reason to preen. He hasn’t merely survived the bust; he’s thrived in it. The qualities that made him annoying to his New York colleagues during the boom—his abrasive demeanor, his hucksterism, his incessant networking—serve him well in the postbubble economy.” (Wired)
“And that’s the thing about Calacanis. Only a sucker would bet against him.” (Fast Company)
“The sort of person who is frequently described as a character out of a movie.” (The New Yorker)
“Sequoia Capital has funneled millions of dollars to scores of well-connected entrepreneurs, academics, and other people known as scouts. . . .Mr. Calacanis was one of the earliest scouts and ran an online news startup called Inside.com, in which Sequoia had invested.” (The Wall Street Journal)
“Jason would never stab you in the back. He might stab you in the face, though.” (Douglas Rushkoff)
“Arguably the world’s greatest angel investor.” (The Twenty Minute VC)
From the Back Cover
Please read this if you want to be rich.
You just picked up this book and you’re wondering if spending a few bucks on these 288 pages could change your life and make you rich beyond your wildest dreams. I’m the author, Jason, and I was born in Brooklyn to a bartender and a nurse, and I now live in a big house with a bunch of Teslas in the driveway and an ATM balance receipt that makes me smile from ear to ear every time I see it.
In this book, I explain how I did it, without having an MBA or a rich dad, but simply by hustling my way into early-stage tech startups in Silicon Valley. No one thought I would ever make it in this business, and many folks actively tried to stop me, but I’ve now gotten lucky eight times and taken home tens of millions of dollars, and I’m only forty-six years old. I’ve done so well that my plan is to quit the game in the next couple of years, so this playbook is my gift to you. Yep, you: the mom in the bookstore with screaming kids, the sales executive in the airport exhausted from layovers, or the kid graduating from college wondering, “What now?”
I hope you will have the audacity to buy this book, read it every year for the next five, make fifty outrageous bets in tech startups, and hit one that goes one hundred or five hundred or even five thousand times your initial investment.
Some of you will put this book down and go back to your predictable lives in the matrix. But I’m guessing more than a few of you will read this book jacket and say, “F— it, I’m going to take my shot!”
I’m ready. Are you? Let’s get to work.
Top customer reviews
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Give credit where credit is due: Calacanis made an all-time great investment in Uber that made both him and Sequoia Capital many tens of millions of dollars. But here’s the key issue with the book: Calacanis wrote Angel to advise individuals how to invest their own capital as angel investors. However nearly all of Calacanis’ investment history is deploying the capital of others -- first through the Sequoia Capital Scout program, then as a GP in the $10 million LAUNCH fund he raised. And when investing other people’s money, you follow an entirely different strategy as your risk tolerance is higher and you often can raise more before realizing any gains. Thus, Calacanis deployed Sequoia’s funds at a level and pace far different from what he advises individuals, risking little to none of his own money.
Unwittingly or not, Calacanis outlined a strategy in this mass-market book that only can and should be followed by the select few that already have a net worth above $10 million. His rule of thumb is to deploy up to 10% of your net worth in angel investment (despite stating on his Angellist syndicate page that “angel investing should never be more than 1% of your total portfolio/net worth"), and he writes that you need to invest in at least 50 startups to receive outsize returns. Given that many startups have minimum investment thresholds, you’ll likely need at least $20k per startup, which entails $1 million+ for 50 companies, requiring a $10 million net worth for this $1 million invested.
At one point he mentions he’ll provide advice on ways to get in the game with less capital, but in the chapter “Going Straight from College to Angel Investing” he provides no such alternatives, and simply rifts on how he wished he would have gotten in early on companies like Microsoft and Hewlett Packard. In “How to Be an Angel Investor with Little or No Money” the alternatives he mentions to being an angel are: being a VC, buying shares on the secondary market, becoming an advisor, or founding a company. None of these are ways to build and scale an angel portfolio. While he does suggest getting started by investing some capital in syndicates, he (rightfully) never suggests that this alone is a solid path to a strong portfolio; it's a smart tactic to help you build credibility and a network, but not something that on its own provides a path to a portfolio with a desirable risk/reward profile.
It would be one thing if the book clearly addressed why Calacanis followed path A but you should follow path B, but this doesn't happen. Unfortunately what I believe gets buried in this are the decades of hustle that it took for Calacanis to have access to the opportunities he did - namely Sequoia Capital funds to invest risk free, and an audience with early-stage Uber (which attended a startup pitch event he hosted, attended by several other VCs). These came about because of his dogged approach to building (and sometimes failing with) startups, networking, self-promoting, and running the single most well-known startup launch/pitch event, originally with TechCrunch.
Finally, it bothered me to see clear inaccuracies in the book that made it in through insufficient editing and review. In chapter 3, he outlines a hypothetical angel portfolio that he says returns $315k, when the numbers add up to only $270k. In the analysis of this, he conflates returns on the angel portfolio with returns on one’s entire net worth, ultimately unintentionally outlining a horrendous risk/return scenario in a section intended to do the opposite.
Angel covers Jason Calacanis' playbook for investing in startups. The book weaves advice and examples from Jason's many years of investing (and generally being a part of the Valley's ecosystem), with a few autobiographical details here and there.
The best parts of the book include Jason's approach to due diligence and interviewing founders. I particularly liked the four questions he asks when he first meets a founder: wonderful open ended questions meant to get to the meat of the problem. Jason advises us to listen intently to the answers.
But this isn't enough to outweigh the negatives of this book. Jason's advocating for listening and asking these questions is nothing new. If you're even a casual observer of how Sequoia communicates to the outside world, you'll immediately recognize the same building blocks - just check out Doug Leone's bio on their website or look up their famous pitch checklist. Additionally, as other reviewers have pointed out, the book seems most appropriate for someone who already has a net worth of eight figures and above - which is not yours truly.
I guess the thing that I disliked the most is Jason's arrogance. He argues that he's "gone from being viewed as an outsider to one of the most considered and knowledgeable strategists in the business." He gripes about being banned from a Y Combinator Demo Day - how dare they do that to the best angel investor there is?! He's ticked off that "dopey people" get board seats at high profile firms but he, clearly the more deserving one, hasn't been asked to join a high profile board yet.
I have a hard time imagining how someone with such a big ego can have the self restraint to truly listen to founders. I recently listened to him interview Laura Huang from Wharton - she repeatedly had to correct him when it was clear he missed her point. Not a good sign. I also have a hard time imagining that what I write here will trigger even a sliver of self reflection.
Separately, the book needs a better editor. I rolled my eyes at mistakes such as "esprit DES corps" being allowed in the published version. We all make mistakes, but I'm not charging for a book. Using fancy French words isn't a must - but if you do use them, don't mess it up. It just makes you look silly. The profanity may ruffle some feathers, but I didn't mind - tighten up the writing though!
Bottom line: I have a nagging feeling that this book was written because Jason wanted to add another line to his LinkedIn profile / a few more words to his Twitter bio. I'm not convinced it was written for the benefit of its readers.