Review of Jason Calcanis’ Angel: Looking Down at You from a Useful Vantage

Calacanis’s Angel contains useful insight if you’re interested in dipping your toes in funding startups, if you’re thinking of starting one and want to know what the other side sees, and for those of us who are around or just interested in the world.

That insight costs putting up with Jason himself, and that’s enough to make this hard to recommend to anyone without this advice:

Do not under any circumstances read Chapter 1
Skip anything about how great Jason is or his history

The rest of the book is relatively tolerable, but I wrote “fuck you” in the margins repeatedly in this chapter. It kicks off some themes that keep coming up in the book that are problematic.

I’m going to entirely ignore Calacanis’s opinion of himself and his abilities, and how important he seems to find it that you too believe in him. I’m personally extremely skeptical of the kind of rabid, persistent self-promotion he engages in throughout. The book’s here, we can roll our eyes to the sky, and move forward. There are much larger issues here. You can check out this profile of him in the NYT titled “Should the Middle Class Invest in Risky Tech Start-Ups?”

Skip past this section if you’re already familiar with the problems with Calacanis (and much of Silicon Valley)’s attitude.

Jason thinks you’re pitiable moron if you for some inexplicable reason aren’t also a VC

First, privilege

Our parents and grandparents took factory and white-collar jobs and rode them for all they were worth in the last century. Now the robots — who never sleep and self-improve on an exponential curve — are taking these jobs. Meanwhile, we humans, with our nagging psychological and emotional needs, struggle to keep up.

Most of you are screwed.

But you’re here, so you’re clearly willing to learn and I can radically improve your odds if you do the work.

First, note his use of “you.” It’s “our” for the parents, but when it comes to who’s screwed, he’s clearly comfortable on his lifeboat seat.

This is important. In order to participate in this new economy, he suggests starting in a “syndicate” where someone like Jason finds investments, you and his crew of small investors jump in with him, and Jason takes a fee for making the match. To do this, you must be an accredited investor. Here’s the standard for that, which changed in 2011.

You must be:

  • worth more than $1 million dollars
  • your primary residence doesn’t count towards that

Angel was published this year. A million dollars is about 90th percentile in the net worth of US families (and I believe that counts home equity, but figure it doesn’t so we can forge ahead with even 10% qualifying). There’s an assumption throughout that you, the chump, can just start doing this. He refers to it as “taking the red pill” at one point (and let’s for a moment ignore that term’s association with some deeply toxic people).

For 90% of people, there’s no option on the investing path. Calacanis can’t “radically improve your odds” if you can’t participate. He has another option for those people, I’ll get there.

Second, that’s paired with contempt.

Calacanis goes back and forth in the book from being insufferable to being able to look at his own history and even at times in his own luck to heaping shit on people who aren’t in the tech industry.

Cafe X and other startups will also eliminate millions of jobs in which humans get paid to stand behind a counter and repeat back your seven precious little instructions on how to prepare your morning libation, before pressing one button and masturbating a milk-frothing pitcher for two minutes.

I’m not going to argue even that he’s wrong that baristas could be endangered. His tone is fucking unacceptable though. Think about someone you know that has a “service” job and does it amazingly well. Doesn’t even have to be a barista, though it would warm my heart if it was entirely counter to Calacanis’s example. It’s almost certain that what they do beyond the core and potentially mechanizable task is what makes them great.

What does a great city bus driver, for instance, do beyond drive the bus? They’re getting people in wheelchairs on or off and secured, they’re doing customer service like helping people navigate a public transit system, and infrequently but critically they’re defusing dangerous situations or dealing with crimes as they happen. Why shit on them for not having a million dollars and investing in startups that will put their fellow co-workers on the street?

Now, to his credit, Chapter 8 is “How to be an Angel Investor with Little or No Money” and then 9 is “The Pros and Cons of Advising” — but this chapter’s about signing on as an advisor, a probably unpaid position in which you work for equity. Which, and again, Calacanis doesn’t seem to realize this — requires you both have skills useful to a startup, like his internet marketing expertise, which very very few of the 90% of people without a million dollars will, and also the connections to the startup, which that 90% won’t have, and time to make that happen, which the 90% are probably not going to have — particularly since the jobs being created by Calacanis & Co. are frequently high-effort, no benefit gigs that I’m sure Calacanis would express contempt for if he thought to (“…eliminate millions of jobs where humans get paid to pick up your overly-precious sushi order and ride their overly-burdened bikes in their ridiculous helmets, weaving to dodge potholes and confusing my autonomous car’s prediction sensors causing it to slow and making me several moments late for my next pitch meeting…”)

This is — and despite being written in first-person, it’s possible he did not write this — a stark contrast to what the book promises, that if you’re a “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?”” that you can be like Calacanis and “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.”

They can’t. That college student’s almost certainly graduating with crippling debt and joining an economy with little to offer them. The mom with the screaming kids? Is she going to take them to the pitch meetings? Tech bros don’t need daycare to meet with founders. And — yeah.

What’s good here?

Once we’re well into it, there’s some legitimately worthwhile stuff regardless of Calacanis himself.

Chapter 11 starts into how you can start by making tiny deals in angel syndicates, and use that to gain experience in how to evaluate founders and make connections with other investors and people in the community, and how you can help your founders.

The sections on evaluating startup pitches and what you should do to prepare for and how to be in those meetings are great.

Chapter 22, “Why Angels Should Write Deal Memos” is great advice for almost any kind of decision like investing in a startup (investing generally, for instance) — that you need to create a clear case for why you’re acting not only as a clarifying thought exercise but so that you can look back at it in the future and compare it to where you are, offering a valuable reality check.

Then the walk through of what it’s like to be an investor of a startup in those early years, and how it will be challenging, are all excellent advice.

This is also where Calacainis’ experiences can make the story — when you hear about him getting screwed over in a deal, or acting poorly, it’s easy to sympathize and learn from him. When he’s rude in response to something, you get it, and there are lessons there both in how to conduct yourself as an investor but in what to watch for to avoid being in that situation.

For founders, you’ll be able to see it all through the investor’s eyes, and walking through the pitfalls of investing (in particular, that the money is not going to get you where you think it will and everyone outside the startup knows this). Knowing the expectations of a good investor in both communication and what they want to hear so they can try to help is excellent to set yourself up well.

On balance

I was well into this book still angry about its opening attitude and considering a pointed email to Calacanis. Once I took a walk and could set it aside, I returned to get into the nuts-and-bolts, and it was entirely worthwhile.

If you take my advice and skip that first chapter and then gloss over any of his “I’m amazing” self-reassurance, you’ll have a much more pleasant experience in getting all the good stuff.

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