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

Jason offers great insight into his personal journey to achieve success in Silicon Valley and helps unveil the process to the outside world. As someone who has invested and participated in Silicon Valley myself, I still found several chapters worth reading with valuable insights that I've noted for later reference.

This book is perhaps, unintentionally so, most helpful for founders seeking funding as this gives a very transparent look into the process that is difficult to find elsewhere. Anyone who has done their homework reading VC blogs and the like could likely patch together a similar blueprint but most of those blogs are targeted for founder benefit versus investor benefit. Ironically, I think understanding early stage investor mindsets are more important for founders (especially first time founders) so that you can assess your business from their perspective and prepare a better pitch.

I'm the same age (46) as Jason Calacanis and have been an entrepreneur starting and running various businesses for the last 16 years. I've seen first hand that you win some and you lose some when you are in business, no matter what. Jason's book hooked me because in it he teaches how to take a chance on lots of businesses. You do so by angel investing. Chances are some investments will win. In fact, in technology, some win will extremely big.

But how could anyone learn the ropes of this complex and risky opportunity, especially without the huge piles of money and living in Silicon Valley? That's what I hoped Jason's book would teach and I was not disappointed. I knew it was coming out today, so last night I listened to his interview on "The Forbes Interview with Steven Bertoni" podcast dated July 4, 2017. It was pretty awesome and got me totally psyched to read the book. I woke up this morning like a kid at Christmas and bought the Kindle AND Audible versions and have been listening off and on today... while getting ready, while driving, and even while eating lunch. Now, after reaching about the half way point less than 18 hours after it was released, I'm glad I did. Here's my further observations:

PROS:
1. Jason tells it like it is. He does not sugar-coat of fluff around. He speaks truth and what is in his heart.
2. Jason's experience in angel investing is probably about the best there is.
3. Jason is not holding back any secrets. He tells exactly what he's done and we know this because he has incentive to do so.
4. Jason reads the Audible version. I have listened to his TWIST podcast off and on since it started years ago. It was good to hear his voice.

CONS:
1. If you can't handle the truth (or swearing) or don't like the Brooklyn style of communication, you won't keep reading. (Personally, I love it.)
2. If you do like that style and are used to Jason, go with the Kindle version, not the Audible version. Jason was clearly coached to read slowly and carefully, not his fast-talking, bold, and brash style that those of us (AKA his super-fans) love most.
3. To be a good angel investor, Jason explains very reasonably that you need to be in Silicon Valley and have a pretty significant disposable income, which disqualifies myself and most others. However, to be fair, he does explain in detail how to get started with far less money using syndicates, which I find fascinating.

BOTTON LINE:
I'm only about half-way through the book, but I wanted to be an early reviewer in case anyone is on the fence for buying this book. If you are even thinking about doing any tech investing, you owe it to yourself to read the book and get a glimpse inside the mind of Jason Calacanis. It is definitely making me think and I'm going to keep reading and keep learning more. Of course, if you just find the topic of angel investing and tech investments entertaining, there's no better entertainment than reading or listening to this self-proclaimed Brooklyn hustler who has made it big.

PS: Jason, I know you're going to read this review and you have no idea who I am. But I have been listening to you for quite a while. I was a very early listener to your podcast, but only listen occasionally lately because I'm busy with my own business(es). But you're really got me thinking about dabbling in angel investing with this book. Thanks for writing it, sir. Best wishes.

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.

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.

I am a recovering business attorney, and have been following the success of the author, Jason Calacanis, with great interest for many years. I was thrilled when he announced the publication of this book on Twitter, and was one of the first 100 to purchase the Kindle version of this book.

This book is the unsanitized truth related to angel investing – specifically in technology in Silicon Valley. If you are to look to a trailblazer for an experienced recitation of the good, bad and ugly of angel investing, this is the book for you.

At the end of the day, I love Jason’s outlook on life and business. His writing (and his business philosophy) epitomizes everything that is good about capitalism and American business.