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Disconnect between author's experience and advice given
on July 20, 2017
Within its first page, this book proclaims that it “will be the best business book ever written.” However, despite Calacanis’ 19 days of work writing this book (a fact he shared on his blog), I see this one falling short of the pantheon of all-time greats.
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.