Angel Investing 101: A Guide to Investing in Technology Startups

Ice Linux: An interesting, easy to read book from an angel investor with an all-star track record a huge amount of street cred. Here’s a few comments:

- The investing strategy targets apps and software startups exclusively. This is also the theme of the TWIST podcast. I understand that this is probably the fastest path to outside returns, but it’s a shame that hardware is largely ignored. The world’s largest market cap company (Apple) builds and sells hardware.

- You gotta move to Silicon Valley. This is non-negotiable. However, some account must be given to the housing market being among the most expensive in the world, onerous regulations and taxes, congestion, and a lifestyle that many don’t find appealing. There are plenty of successful angels, angel consortiums, and tech hubs that are not located in and around Palo Alto.

- This book has a lot of profanity. I suppose this makes it edgy and more personal, but it also takes credibility down a few notches. The subject matter involves a ton of money to be put in play by individual, accredited investors and this demands professional discourse, not street talk. I can’t imagine another Hall of Fame angel investor...

United States on Apr 23, 2023

Paul Fan: An excellent book. I bought and read it, and also re-read it. Candid and to the point about how to start angel investing, what to look for, insights on the industry, founders, product, product market fit, and starting companies. Would recommend and have recommended the book to others

Canada on Sep 15, 2022

Rai: Veramente un ottimo libro

Italy on Jul 21, 2022

John B: If you are serious about being an Angel investor, VC or Entrepreneur you really need to read this book. If you are serious about being a founder you need to read this book. If you are serious about doing anything in the startup game you really need to read this book! Probably one of the most honest and candid books about startups and how to invest in them.

It’s aimed at new investors looking to break into what appears from the outside to be an exclusive club. This breaks down that perception and demonstrates that anyone with the right tenacity has the ability to become an Angel investor. It details a clear strategy on how to become a successful Angel investor but it also holds little nuggets of information which could be indispensable to founders. I’d also argue that it is a decent guidebook to becoming a venture capitalist too.

I’ve been following Jason’s podcast for sometime and eventually took the plunge, bought his book and became an angel investor. I know cliché right it’s what all the cool kids are doing these days that and investing in crypto.

It has been a great stepping stone towards me becoming an Angel investor. Obviously the proof will...

United Kingdom on Sep 10, 2018

Suren Harutyunyan: PROLOGUE/PREFACE
I 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,

- Brilliant

Keep 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...

United Kingdom on Aug 26, 2017

Thomas L. McLaughlin: A year and a half ago I was begrudgingly heading to my job at a large investment bank when I came across the "This Week in Startups" podcast by accident. Although I had no experience in the entrepreneurial community, Jason's no nonsense style flew in the face of the uptight corporate PC culture that I had become accustomed to. After some serious soul searching and having Jason drill it in my head week after week, I knew that the only true way for me to change my lot in life was to start getting on cap tables...not slaving 80-90 hours a week in a secluded cubicle punching out excel spreadsheets and powerpoint slides for the next 15 years of my life, which ironically is exactly what had been told to me in college. Rather than spending 25 hours a week watching Netflix, I committed to learning as much as I could about financial technology, growth hacking and going to two networking events per week within the NYC startup ecosystem.

Within three months of listening to TWIS, I truly began immersing myself in the startup ecosystem, offering to help startups with corporate finance and capital raising strategy in exchange for equity options in those start-ups. Slowly but surely I...

United States on Aug 09, 2017

AJ Tracey: 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...

United Kingdom on Aug 01, 2017

Ivaylo: This book is brutally honest and a must read for wanna-be angel investors and founders. Jason might sound a little condescending at times, but he is sharing valuable insights earned the hard way.

Here are ten of my favourite insights from the book:

1. What angel investing and the lottery have in common.

"I buy lottery tickets for a living, but unlike the normal schmucks on the street, I get to buy tickets that are in the top 1 percent of the winning pool.'

2. The people that dare to take more risks intelligently are typically luckier in life.

"If you learn anything from this book, it’s that you must take risks as an angel investor and in life if you want at least the chance of an outsized outcome."

"You can make your own luck in this life by putting yourself next to the people who are already winning."

3. The business of angels

"If these businesses didn’t look completely crazy, then everyone would want to invest in them and there would be no need for angels. In fact, the term “angel” is used because we are the investors who come to a founder’s rescue in their hour of need— when nobody else believes in...

United States on Jul 20, 2017