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Angel: How to Invest in Technology Startups--Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 Hardcover – July 18, 2017

by Jason Calacanis (Author)
4.6 4.6 out of 5 stars 1,434 ratings
See all formats and editions
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One of Silicon Valley’s most successful angel investors shares his rules for investing in startups.

There are two ways to make money in startups: create something valuable—or invest in the people that are creating valuable things.

Over the past twenty-five years, Jason Calacanis has made a fortune investing in creators, spotting and helping build and fund a number of successful technology startups—investments that have earned him tens of millions of dollars. Now, in this enlightening guide that is sure to become the bible for twenty-first century investors, Calacanis takes potential angels step-by-step through his proven method of creating massive wealth: startups.

As Calacanis makes clear, you can get rich—even if you came from humble beginnings (his dad was a bartender, his mom a nurse), didn’t go to the right schools, and weren’t a top student. The trick is learning how angel investors think. Calacanis takes you inside the minds of these successful moneymen, helping you understand how they prioritize and make the decisions that have resulted in phenomenal profits. He guides you step by step through the process, revealing how leading investors evaluate new ventures, calculating the risks and rewards, and explains how the best startups leverage relationships with angel investors for the best results.

Whether you’re an aspiring investor or a budding entrepreneur, Angel will inspire and educate you on all the ins of outs. Buckle up for a wild ride into the world of angel investing!

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  1. Print length
    288 pages
  2. Language
    English
  3. Publisher
    Harper Business
  4. Publication date
    July 18, 2017
  5. Dimensions
    6 x 0.97 x 9 inches
  6. ISBN-10
    0062560700
  7. ISBN-13
    978-0062560704
  8. See all details
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Editorial Reviews

Review

“there is something refreshing and clarifying about Mr. Calacanis’s frankness regarding his tech-fueled riches.” — Farhad Manjoo, The New York Times

“It’s easy to snigger at the swagger, but Calacanis has reason to preen. He hasn’t merely survived the bust; he’s thrived in it. The qualities that made him annoying to his New York colleagues during the boom—his abrasive demeanor, his hucksterism, his incessant networking—serve him well in the postbubble economy.” — Wired

“And that’s the thing about Calacanis. Only a sucker would bet against him.” — Fast Company

“The sort of person who is frequently described as a character out of a movie.” — The New Yorker

“Sequoia Capital has funneled millions of dollars to scores of well-connected entrepreneurs, academics, and other people known as scouts. . . .Mr. Calacanis was one of the earliest scouts and ran an online news startup called Inside.com, in which Sequoia had invested.” — The Wall Street Journal

“Jason would never stab you in the back. He might stab you in the face, though.” — Douglas Rushkoff

“Arguably the world’s greatest angel investor.” — The Twenty Minute VC

From the Back Cover

Please read this if you want to be rich. 

You just picked up this book and you’re wondering if spending a few bucks on these 288 pages could change your life and make you rich beyond your wildest dreams. I’m the author, Jason, and I was born in Brooklyn to a bartender and a nurse, and I now 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.

In this book, I explain how I did it, without having an MBA or a rich dad, but simply by hustling my way into early-stage tech startups in Silicon Valley. No one thought I would ever make it in this business, and many folks actively tried to stop me, but I’ve now gotten lucky eight times and taken home tens of millions of dollars, and I’m only forty-six years old. I’ve done so well that my plan is to quit the game in the next couple of years, so this playbook is my gift to you. Yep, you:  the 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?” 

I hope you will have the audacity to buy this book, read it every year for the next five, make fifty outrageous bets in tech startups, and hit one that goes one hundred or five hundred or even five thousand times your initial investment.

Some of you will put this book down and go back to your predictable lives in the matrix. But I’m guessing more than a few of you will read this book jacket and say, “F— it, I’m going to take my shot!” 

I’m ready. Are you? Let’s get to work. 

Product details

  • Publisher ‏ : ‎ Harper Business; Standard Edition (July 18, 2017)
  • Language ‏ : ‎ English
  • Hardcover ‏ : ‎ 288 pages
  • ISBN-10 ‏ : ‎ 0062560700
  • ISBN-13 ‏ : ‎ 978-0062560704
  • Item Weight ‏ : ‎ 2.31 pounds
  • Dimensions ‏ : ‎ 6 x 0.97 x 9 inches
  • Customer Reviews:
    4.6 4.6 out of 5 stars 1,434 ratings

About the author

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Jason Calacanis

Jason Calacanis

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JASON CALACANIS is a technology entrepreneur, angel investor, and the host of the popular weekly podcast This Week in Startups. He's the founder of a series of conferences that bring entrepreneurs together with potential investors.

As a “scout” for top-tier Silicon Valley venture capital firm Sequoia Capital and later as an angel investor, Jason has invested in 150 early-stage startups including 4 that have achieved billion-dollar valuations (so far).

Jason's book "Angel: How to Invest in Technology Startups: Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000" was released by Harper Collins on July 18th, 2017. He lives in San Francisco, California.

Customer reviews

4.6 out of 5 stars
1,434 global ratings

Customers say

Customers find the book has great lessons and anecdotes for investors and entrepreneurs alike. They also describe the overall quality as great, effective, and digestible. Customers say the book is concise, full of wit, and wisdom. They find the reading pace fast and skim-friendly. Customers also mention the book provides actionable strategies and watch-outs for angel investing.

AI-generated from the text of customer reviews

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ContentOverall qualityReadabilityEnjoymentReading pacePracticalityStructureContent depth
156 customers mention "Content"156 positive0 negative

Customers find the book has great lessons and anecdotes for investors and entrepreneurs alike. They also appreciate the clear strategy and solid information on angel investing. Readers mention that the author is self-aware, self-reflective, and brutally honest.

"Angel is perfect for investors willing to risk some hard earned money and do a lot of work trying to make life-changing money and perfect for..." Read more

"This book is brutally honest and a must read for wanna-be angel investors and founders...." Read more

"It is a reasonable look at the reality of angel investing. It is 100% delivered with the swagger and hype that only Calacanis can deliver...." Read more

"...There are tons of great lessons and anecdotes for investors and entrepreneurs alike, from setting aside 3 hours per meeting to taking notes with a..." Read more

88 customers mention "Overall quality"88 positive0 negative

Customers find the book great, entertaining, and pure gold. They also say the author has proven himself as an expert in the start-up world.

"...Angel is a fantastic book...." Read more

"...the world of high-stakes angel investing, this is, without a doubt, worth a read...." Read more

"...It was pretty awesome and got me totally psyched to read the book...." Read more

"...Overall, the book was a fun read with many great quotes!..." Read more

79 customers mention "Readability"76 positive3 negative

Customers find the book concise, honest, humorous, and educational. They say it provides a good framework for thinking about the numbers game and provides specific steps and processes to get started in angel investing via syndicates. Readers also appreciate the bit-size information, wit, and wisdom.

"...times readers need to "do the work", but his writing is so step-by-step and exciting it's easy to forget - investing takes work, risk, and..." Read more

"...It provides a good framework for thinking about the numbers game that is angel investing...." Read more

"...It was good to hear his voice.CONS:1...." Read more

"...Really, what more do you want? Well, the book also gives you easy ways to start saying no, which is probably the most important word for anyone who..." Read more

21 customers mention "Enjoyment"21 positive0 negative

Customers find the book funny, entertaining, and relatable. They also say the straight talk and occasional LOL make Jason feel relatable and make the book a quick read.

"...It is easy to read and it's entertaining. I found out about this book from James Altucher's podcast interview with Jason Calacanis...." Read more

"...There is also a ton of good comedy in here and overall the content is delivered with gusto...." Read more

"...The book is funny (Jason calls his haters "Jaters," I look forward to calling my haters "Laters"), very straightforward about the..." Read more

"Calcanis has a great sense of humor, which does not detract from the brutal clarity with which he presents his experience and the theses that have..." Read more

16 customers mention "Reading pace"16 positive0 negative

Customers find the book fast, to the point, and actionable. They also say the podcast moves fast and covers a lot of questions and answers.

"...The pace is solid and engaging throughout; I plowed through this book in 4 hours on a recent plane flight...." Read more

"...book is akin to Brad Feld's "Venture Deals" - in that it's a fast, cheap way to get up to speed on the particular subject at hand...." Read more

"...It was a quick read that kept me highly engaged from start to finish. There is a lot of tools in this book that can be added to your tool belt." Read more

"...straight talk and occasional LOL made Jason feel relatable and made this a quick read...." Read more

7 customers mention "Practicality"7 positive0 negative

Customers find the book practical and actionable. They also say it provides watch-outs and strategies for angel investing.

"...Topic - how to make lots of money in less than a decadeActionable - step by step advice...." Read more

"...And I got it! Solid info, strategies, tactics, how-to interrogate a founder and more...." Read more

"...The investing strategies are enjoyable to read and actionable if the reader has some experience in deal making and founder psychology...." Read more

"...A straight-forward approach to angel investing with actionable strategies and watch-outs, I feel like I've been professionalized through the reading..." Read more

7 customers mention "Structure"7 positive0 negative

Customers find the book well structured and easy to read. They also say it has great material.

"...The structure of the book is amazing...." Read more

"...he as an investor likes to see as an investor are so methodical, well thought out and based on experience that I believe every startup should at..." Read more

"...What it is is a well organized book to get folks with disposable cash quickly up to speed with a good plan to dip their toes into the angel..." Read more

"...Well-articulated, easy to read and absorb, no nonsense, and direct to the point, it feels like Jason is telling the book's content directly you..." Read more

6 customers mention "Content depth"3 positive3 negative

Customers have mixed opinions about the content depth of the book. Some find it easy to read and absorb, with no nonsense and direct to the point. They also mention that it has step-by-step moves, mistakes to avoid, and longer-term strategies. However, others feel the book lacks depth and is overly simplistic.

"...candid and to the point, this book tells it like it is; no academic jargon or fluff, just raw value..." Read more

"...Mostly, "Angel" is insanely self-serving, especially as the entire book seems designed to eventually funnel folks into Calacanis's own syndicate...." Read more

"...Well-articulated, easy to read and absorb, no nonsense, and direct to the point, it feels like Jason is telling the book's content directly you..." Read more

"...His thesis of 'invest in job killers' is cynical, oversimplistic, and completely invalidated by the advent of UBI which is now a serious political..." Read more

Must Read for Founders and Angel Investors alike
5 out of 5 stars
Must Read for Founders and Angel Investors alike
Angel investing guide from someone who has actually succeeded in the game.Investors should read this book for the knowledge of how to create a successful investing thesis and learn as they go. Founders should read this to learn what information Angel Investors need and how to build a pitch that will get you noticed.Angel investing is risky. Just like the poker player that he is, Jason outlines the strategies that can get you the best possible odds against the house.I've followed Jason for years on This week in Startups and now the Angel podcast series and there is plenty of great content there as well.The only downside about the Audible version of this book is that since Jason has to read slowly and deliberately in order for the Whispersync technology to work correctly so he's had to tone down some of his bombastic speaking style in order for this to work. But the content itself is pure gold.I've used this information so much that I bought the book as well so I can go back for easy reference. This book will continue to be valuable resource. You may want to buy the Kindle version with the Whispersync option.
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Top reviews from the United States

David Smith
5.0 out of 5 stars Absolute buy for those about to start Angel investing and early stage founders.
Reviewed in the United States on August 3, 2017
Verified Purchase
Angel is perfect for investors willing to risk some hard earned money and do a lot of work trying to make life-changing money and perfect for founders planning to raise money from angel investors.

I like Angel for four reasons:
Topic - how to make lots of money in less than a decade
Actionable - step by step advice.
Experience - written by someone who excelled at Angel investing. Jason candidly shares his hard-won experience to advise readers helping them avoid costly mistakes and achieve success faster.
Terse - Jason’s writing is short and to the point. He spends a sentence or paragraph on ideas where other authors might spend a page or a few pages.

Jason delivers actionable steps starting from the beginning. He starts by covering investing terminology follows by how to get in the startup game without any money, how to learn angel investing with minimal capital which keeps risk low, and finally details how to improve your investment skill. Jason speaks from experience having invested in 6 companies when they were valued in the millions that are now valued at more than a billion as well as multiple opportunities for similar returns that he passed on. Jason uses these experiences to substantiate the advice he writes about.

Angel is a fantastic book. If I had to find one criticism I’d say the book made me feel angel investing seem fun and easy - even though I know it is not. His step-by-step instructions made me feel it was a guaranteed easy recipe for creating massive wealth. I have to keep reminding myself it is not guaranteed and it is not easy. Instead a lot of work, risk, and sacrifice along with a sprinkling of good luck. More capital is needed than the title suggests, other suggestions (such as moving) may be a hard for some readers to execute.

Jason does mention multiple times readers need to "do the work", but his writing is so step-by-step and exciting it's easy to forget - investing takes work, risk, and luck.
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Ivaylo
5.0 out of 5 stars 10 Insights from the Book ‘Angel’
Reviewed in the United States on July 20, 2017
Verified Purchase
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 them."

"The best angels in the world have four qualities, giving them the ability to (1) write a check (money), (2) jam out with the founders over important issues (time), (3) provide meaningful customer and investor introductions (network), and (4) give actionable advice that saves the founders time and money— or keeps them from making mistakes (expertise)."

"Your job as an angel investor is to block out the haters, doubters, and small thinkers, because if you think small you’ll be small. I’d rather see my founders fail at a big goal than succeed at a small one."

"Remember there are a hundred reasons why these things fail, so you’re not going to have a hard time saying no, and there are typically only one or two reasons to say yes."

"Founders always share investor meeting details with each other and your reputation is everything in our industry. If you are helpful, present, and considerate, then you’re going to get a great reputation. If you are unprofessional, cavalier, or conceited, or use your position of power in any way that isn’t in service of the founder, then you’re toast."

4. The best deals are not available to just anyone.

"The best deals are typically not on platforms like AngelList or at incubators like Y Combinator or 500 Startups. The best deals never see the light of day. They’re quickly filled by insiders who are sharing deal flow, and by elite founders with killer startups tapping their existing network."

5. On the best investment, you can make.

"I passed on investing in Twitter because I was, at the time, a founder of companies. I stupidly thought that the best investment I could make was in my own company."

"It was at that point I realized that I didn’t need to know if the idea would be successful. I only needed to know if the person would be. It was clear as day to me that whatever Ev worked on would be successful, but my own ego and my need to be right and understand everything got in the way of me hitting my first big home run."

6. There’s no difference between the founder and their company

"As you go through your angel investing life, take some time to evaluate the person and their motivations. Ask yourself a simple question: “Would I buy stock in this person if I could?” If you wouldn’t buy stock in a founder, you shouldn’t buy stock in their company— because there is no difference between the founder and their company; they are one and the same."

7. Why are you doing this?

"If folks are building a startup for money, they will eventually quit when they realize there are many better ways to make money faster and with more certainty. If you want to make a lot of money, you’re better off being a world-class programmer on a very esoteric and in-demand vertical and getting Google or Facebook to give you $ 1 million-plus a year in stock and cash for ten years in a row. You have no downside, you can work a couple of hours a day, and you get unlimited free food."

8. Why startups fail

"The number one reason a startup shuts down is not actually running out of money, which is what most people believe. The number one reason a startup fails is that the founder gives up."

9. On communication between founders and angels

“If a startup isn’t sending you monthly investor updates, it’s going out of business.”

"The more concise and professional the updates, the greater the chances that angels will be able to help you, including investing more money and introducing you to their friends as a responsible founder who’s a delight to work with. Angels want to feel needed, and founders who don’t make their angels feel needed have lost their most likely source of follow-on funding— their current investors."

10. The market is constantly changing

"What worked when I started investing, when there were one-tenth as many startups being formed every year, doesn’t work today. It was wise to invest in great teams, pre-product back then, where today you almost universally want to wait for the founders to finish their product and get to market before investing."
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T. Kilroy
4.0 out of 5 stars Angel - Is It Possible to Be an Angel Investor? Calacanis Opines & Shows A Real Portrait of the Brutality of Angel Investing
Reviewed in the United States on September 18, 2017
Verified Purchase
It is a reasonable look at the reality of angel investing. It is 100% delivered with the swagger and hype that only Calacanis can deliver. It provides a good framework for thinking about the numbers game that is angel investing. And Calacanis is sure that if you follow his rubrik & plan, it is nearly inevitable that you will create massive wealth.

However, Calacanis does, I think, focus too much on the inevitability of wealth (if you plan the work and work the plan, then the inevitable is bound to happen), and also on the primacy of Silicon Valley. While SV is the absolute hotbed of activity, I think that the world is a bigger place - and that amazing companies are popping up all of the world. The next angel investing bazillionaire will undoubtably have a global view, not just a SV view.

If you want to learn about the world of high-stakes angel investing, this is, without a doubt, worth a read. But the game is not as easy as Calacanis makes it seem, but it is also not as rarified and out of reach as he makes it seem, as well. Investing is a hugely difficult game, and it is not for the faint of heart. Angel is a real description of what it is like, but the Calacanis way is not the only way.

Worth a ready, however.
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Top reviews from other countries

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Arjun Verma
5.0 out of 5 stars Indispensable!
Reviewed in India on May 10, 2024
Verified Purchase
The book offers compelling insights into the VC/angel ecosystem!
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Cesar
5.0 out of 5 stars insightful book about angel investing
Reviewed in Spain on October 28, 2023
Verified Purchase
It is a very useful book for anyone that is looking into becoming an angel partner for startups with plenty of good examples and priceless advice to not to give up and get better chances to do it properly
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Rai
5.0 out of 5 stars Utilissimo
Reviewed in Italy on July 21, 2022
Verified Purchase
Veramente un ottimo libro
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Snejana
5.0 out of 5 stars new book, fast shipping.
Reviewed in Germany on October 25, 2021
Verified Purchase
new book, fast shipping.
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Global Traveller
5.0 out of 5 stars An invaluable part of my startup library !!!
Reviewed in Canada on May 26, 2019
Verified Purchase
I have been following Jason through his blog and his podcasts for a very long time and I also had the opportunity to hear him speak at the Collision conference a couple of years back. A really good friend of mine has also secured an early stage investment from him, so I have been curious about this book for some time. Recently I started playing with the idea of joining a local angel syndicate and I finally decided to buy the book to better understand Jason's perspective on angel investments. While I may not agree with everything that Jason postulates, it is a deep knowledge base that brings together his significant experience and background in the field. I am still processing the specifics of the different strategies and positions he shares in the book, but I can already state that this book was an incredible source of wisdom, knowledge and food for thought for me personally.
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