“Angel” by Jason Calacanis

My review with takeaways

Jason Calacanis is a smart dude. I’ve been listening to him for years, and there’s a real sophistication to his process, theories, and way of looking at things. (Sometimes, it directly contrasts his “candid” personality.)

I went into “Angel: How to Invest in Technology Startups — Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000” knowing two things. First it was an obvious must read for an aspiring angel investor (accredited or not). Second, I kept hearing what a big deal Jason makes about having to live in SF to do well angel investing…

Both of those are true (there’s a one-word chapter called “Do You Need to Be in Silicon Valley to Be a Great Angel Investor?”). As an Austinite, that’s not great news, but it can be hedged by following the techniques outlined in the rest of the book.

“…if they were willing to throw Jay Z under the bus, they would have no problem throwing Jay C under the bus…”

Aside from that line, which was my favorite in the book, here are a few actionable takeaways.

Learn at the low stakes tables

This is exactly why I started the Bootstrapped Investor blog and why I started investing with as little as $300 or buying one share of a public stock. It’s all about learning. Jason defines low stakes as 10 investments of $2,500 in syndicate deals, and I started even lower.

I’m taking my hits at the low stakes table out of necessity, but I’m grateful to learn lessons in the hundreds rather than hundreds of thousands.

Another notable benefit of lower stakes is that less money per deal can mean a higher volume of small deals, so you don’t only learn how to invest, you also grow your network (and future deal flow).

Live in the Bay Area

This one is sad for those of us who don’t live there, but really, it’s more of a current assessment than a future prediction. It’s also not as gloomy as it seems… just a practical and unemotional observation of the current state of things.

The real lesson is that investing is largely a numbers and odds game, and if there’s a geographic location with disproportionate odds, you’re a fool not to go there.

I’m not accredited today, so I can’t even get the deals where it matters that I live there. My hope is that by the time I am, the investment game will look a lot different (I predict it will), and geography will be less important. The signs are already here (tokens *cough*).

Deal memos and other systems

Another key takeaway- one that lines up with my motives for this blog also- is to write about the thought processes behind investments and ideas. It’s great for planning, reflection, and general organization, and it’s something I need to get more diligent with. I believe it’s one of the few things that separates the lucky from the unlucky.

Deal memos separate the lucky from the unlucky.

Bottom line

Read the book and follow the plan. It’s shaped my approach for sure, and it also reinforced it. Having a plan and carefully executing on it is the only way to have win at something where the odds are ridiculously stacked against you. And also the book is great.

Here’s a link to buy the book. 👈