Book Review: Angel by Jason Calacanis

Read This Book If: You want to hear from a pretty interesting voice about how to get into Startup Investing.


The book Angel by Jason Calacanis is a wonderful tome that chronicles Jason’s experiences as an Angel investor in San Francisco and acts as a how-to guide for any would-be investors. He lays the books out pretty well, answering more obvious questions at the beginning and he scatters the book with reasons why you should be listening to him in the first place. And there are several reasons you should be listening to him – with investments in Thumbtack, Uber, and Wealthfront, Jason’s bona fides are hard to scoff at. This book is providing a pretty invaluable service as there are very little resources out there for wealthy individuals who want to learn how to invest in the manner he is proposing. His insights are also welcome for people who are just trying to learn how to better their business evaluation skills. That’s the reason I picked up this book – to add to my arsenal of knowledge as I develop as an investor.


Calacanis has an extremely unique voice. I have spent countless hours listening to his podcast This Week In Startups (which I highly recommend) and it’s very apparent that Jason has no issue speaking his mind. He frequently reminds his listeners that he can be abrasive but that’s just because he wants to be as honest as possible. It is very refreshing at times and helps put a lot of things in the startup world into perspective. His book is no different. Calacanis pulls no punches and has strong opinions, and as long as you know that (like any good investor) he probably isn’t infallible, that’s a good thing.


However, there are some issues I found with the writing. For one, I was hoping to learn a little more from his experiences – in an industry as volatile and unpredictable as venture investing, it can be very helpful to help frame the future by looking at the past. Calacanis has some invaluable lessons that he departs on the reader, but he could definitely share a little more. I am certain that he probably has a few things holding him back from disclosing all of his dirty laundry, but that doesn’t leave me with a feeling on wanting more. Hearing more about his history with his bigger investments could provide some critical insights.


I also take some issue with Chapter Five of the book. Calacanis clearly believes that the only place on the planet that should be invested in from a tech / venture perspective is Silicon Valley. His fifth and sixth chapters make it apparent and, although he never says it so much, he almost seems to have a level of disdain for any non-coastal place for tech. As someone from the Midwest, I do take issue with his sentiment – there are numerous advantages of starting a company somewhere outside of the Bay Area. Although, my own sense of regional pride does make me have some sympathy for Calacanis’ sentiments. He has built a life and career out there and I can only imagine how fond he is of his adopted hometown. There are too many reasons why I am partial to many places outside of Silicon Valley for me to enumerate here.


In conclusion, if you are trying to learn about angel / venture investing, Angel is a great place to start. I highly recommend picking up this book and finding out what it takes to successfully help provide early stage capital to entrepreneurs (hopefully all over the world). Calacanis has a great voice and an even better investing background. Hopefully, once you are done reading his book – you will have a great start to an even more promising investing career.



Peter G Schmidt