Angel: How to Invest in Technology Startups--Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 Hardcover – 27 July 2017

PROLOGUE/PREFACEI have always been skeptical towards "Investing literature" (except for a few rare exceptions), but since I have been following Jason and "This Week in Startups" since high school, I gave it the benefit of the doubt. And it paid off. Needless to say I finished the book the same day it arrived.On page 1 Jason will mention 3 different words by which people have labeled him:- Lucky,- Fraud,- BrilliantKeep these words in mind, because after P1 you'll doubt whether this is written by the lucky, the fraud or the brilliant. Maybe in the end is by all of them.If you could pick 10 words to describe startup founders these would appear. Being angel investing a close second, the same list would apply, because independently of the path you'll choose, at every step, these words will jump to your mind.- you'll feel lucky that you've survived another day,- you'll feel like a fraud because of constant hustling and chutzpah (leading to impostor syndrome and thinking others are more competent) and- you'll feel brilliant, because you have been able to execute your idea and/or maybe you've been crushing it since week 1.First of all, this is a fundamentals book of angel investing. It explains the different ways capital enters into the startup ecosystem, but focuses on the early stage part. This is where the angels enter.The book is divided in 32 chapters, which could be roughly categorized in 3 parts: Before, During and After the hunt.PART ONE: BEFORE THE HUNTThis first chapters introduce the reader to Jason's background, his angel investing career, Silicon Valley, why you have to be there, etc. laying all the cards on the table beforehand.This part also explains why you have to be in Silicon Valley, the different rounds of start-up funding and in which ones you'll ideally be participating in. It is also useful to assess your options, which type of angel investor you could be and which percentage of your capital to allocate. Are you an individual with more than 1M in the bank or you're broke student that wants to try his/her luck. While the learning process, the mindset and the first steps of both would be the same, your paths will diverge pretty fast.PART TWO: DURING THE HUNTIn this part, which would start at Chapter 12 you are provided with a field guild on how to start going to pitch meetings, how many of these you should take and in how many of these start ups you should invest, if any. If you are willing to pursue angel investing as a full time endeavor you can consider this part as your progress meter. It is filled with examples on how to approach this specific part of the journey and there is some useful advice on how to network in general.It also cover various topics on what to do before, during and after taking these meetings, bearing in mind that you are playing the big number game. The information you will gather will be invaluable in your investment decisions, so in order to be able to quantify and qualify, and analyse your meetings more easily you should try ordering this information. The notebook example is one of them.Pay extreme attention to the chapter on founder question. This is not as obvious as it seems, but the advice given here will reduce the amount of misses and errors during your career. Adding to this idea one should also look at the Founder or Fraud chapter. Put it in simple terms it addresses with examples the classic "if it looks like a duck...", this will help you differentiate between a founder that is a fraud and a founder that hustles. The line is thin but it exists.Finally. Due diligence.PART THREE: AFTER THE HUNTIn this final chapters, Jason goes through what you should expect after you have invested in a startup. It explains what would be considered as your reasonable rights, like "pro rata", monthly updates, and what you could expect after big players, like venture capital firms, enter the game.To maintain your feet on earth there is also a chapter dedicated on the "second year". Explaining if you're in the game that means you're relatively risk tolerant, so in order to keep your expectations in check, you should know that after 12 months, a bloodbath will happen. Some of the companies will go away, some will stay the same and one will grow.Finally Jason provides a a great summary of the exit strategies that you could count on.EPILOGUE/AFTERMATHBefore finishing I would like highlight some "caveat emptor". For those that are not familiar with Jason and his speaking and thinking manner, be prepared for a direct and blunt style.Also bear in mind that angel investing is not for everyone, you can work the hardest in your life, but result may be meager or may not come entirely. This is a long term game and you have to be always on the move, be it networking, going to meetings, conferences or constructing your portfolio.Having said that, by describing not only the technical parts of angel investing, but also the emotional ones, it pursues to give you the necessary tools, so you will have the correct mindset and the discipline of work that will be essential in your future.Maybe angel investing is not for everyone, but the book certainly is.- If you you're an Optimist and you believe that tech and Silicon Valley are only just getting started, read the book. In the worst case, you'll learn something new, in the best you'll start a new adventure.- If you're a Realist and you believe that tech and Silicon Valley are here to stay, think about the books as your first long term investment. In 100 years the first edition could be considered as one the foundational texts of angel investing. By the way, keep the dust jacket.- If you're a Pessimist and you think that the modern day tech 2.0 bubble will crash soon and the Silicon Valley hubris will disappear, buy the book so you can have one of the documents to prove where the decadence started. Also keep the dust jacket, just in case.

I've slowly been a fan of Jason Calacanis who produces the brilliant - This Week in Startups.He has changed my life with the legendary interview with Chris Sacca who inspired and spurred me to pay off all my household debt (no mortgage) and my student loan debt (no debt here either). This led to me having more money to enjoy my time / freedom and pursue my own interests and have a better quality of life. My parents are pretty happy they are also owners of their home and the bank can never call them again.This book is the second way he may have changed my life, Angel is a hands on / practical book for doers not dreamers. It lays out clearly in Jason's style how to become an angel whether you have a net worth in the millions or one closer to the gutter. This is all practical and do-able advice but the challenge for any reader is whether they will roll up their sleeves and do the work.In the past week since I've read the book: i've met 10 startups (promising ideas with revenue and profit), no venture money but some small angel money and a requirement for me to help them with their marketing. Some are paying me in cold cash, some are giving me equity 0.10% for advising and in exchange I do some work for them. Actual work.Maybe I'll make £0.00 or maybe I'll make £10k or £100k or maybe even £1ml. The point is I'm going to do the hard work and see where it lands because the book lays everything out clearly but for folks willing to do some actual work.10/10 work, recommended!

Although not a masterpiece, this book is an earnest account of angel investing by one of the most successful angel investors today.The primary value of this book is author's experience, some of which finds its way to the reader in the form of his lessons learned. Further value is an insight in Calacanis' methodology of investing, which is quite relevant and valuable, given his track record.Calacanis attempts to define a how-to for aspiring angels, which I find a bit of a mixed success. This is the central theme of the book, and its nominal mission, but author's ego got in a way of this being a timeless masterpiece. This way it's kinda stuck between a biography, and a technical book on angel investing. And not in a good way.The overall impression is a bit of an amateurish attempt at writing the ultimate book of angel investing, which this book could have been, given the author's experience.The four-star rating is a bit generous for this book, but it's more fair than a three.If you want to get in on the tech investment game, or you're a startup founder, well worth a read.