The book that started it all for me—it was the first time I ever conceived that people invested in startups for a living. Great book with a lot of actionables (such as the Calacanis Characteristics I use to evaluate startups.) My only frustration with the book is that Calacanis buries the lede until some chapter in the teens to unveil that this book was written for those with $2.5m in net worth. Equity crowdfunding and constraints caused me to publicly embark on my quest to invest in 50 startups on a string of a budget, relatively speaking.


  • If you invest 10% of your net worth, you're likelihood are between losing 1-3% of your net worth to increasing it by 20%. So, assuming $100k net worth and you invest $10k, your expected returns are range from returning $7k-$9k to returning $30k. This means for what you invest, losing 10%-30% is possible, or tripling your money.
  • Calacanis believes the only way to get a unicorn is to invest in 50 startups in Silicon Valley within 3-5 years as a full-time investor.
  • Unicorn = a company that is worth $1 billion. If you invest in a company that is worth $10 million, and it grows to $1 billion, you get 100x your return. (One billion is one thousand million, so take one zero away.)
  • Generally angels cut $25,000 checks per deal.
  • Good angels combine some combo of: money, time, network, and expertise
  • Get pro rata rights so when your winners raise future rounds, you can pump more money at the new price to keep your % stake.


  • Calacanis's three most famous investments are Uber, Thumbtack, and Dyn. Though he's also an investor in and many other fanciful startups. Most notably, he was a scout for Sequoia (yet another gold standard firm in VC, will do an explainer on them at some point,) and scouted Uber for them.
  • Calacanis is from Brooklyn, his father was a bartender and his mother was a nurse.
  • Calacanis sold Weblogs to AOL for a sum of money.
  • Calacanis' biggest miss was Twitter, because he had a philosophical beef against Ev's hypothesis on cutting out the meat of a blog post. He still gets along with Ev.
  • YouTube's Deal Memo.
  • There are 12-24 unicorns created every year, about 1 decacorn a year, and 1 centicorn a decade.


  • Write deal memos!
  • Use equity crowdfunding platforms and syndicates to practice in angel "dagobah"
  • Expect investor updates from your founders

Bonus Resources

Notes on Angel by Jason Calacanis
One of my favorite books from last year was Angel: How to Invest in Technology Startups--Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 by Jason Calacanis. It was...
Calacanis' strategy for hacking angel syndicates to build insane network of investors. Great notes in general.
Book Summary — Angel
Angel gives a holistic overview of angel investing. Jason has a short, sharp and entertaining way of getting his point across. The book is great for anyone starting out in the investment world, but…
Explanation of fundraising rounds for startups.

The Four Founder Questions

  1. Why has this founder chosen this business?
  2. How committed is this founder?
  3. What are this founder’s chances of succeeding in this business — and in life?
  4. What does winning look like in terms of revenue and return?
I have a game where I try to say things with as few words as possible because it reminds me that this meeting is not about me, it’s about them.

How do you know the person who referred you? — warm up question

What are you working on? — because it’s about the founder

Why are you doing this? — it’s all about the founder

Why now? — timing is everything

What’s your unfair advantage?

My 12 Favorite Quotes from Jason’s Book Angel
Looking for a book summary? Check Max Mednik’s Notes on Angel by Jason Calacanis or read my Angel Investor Checklist I made from Jason’s book. For more wisdom from Jason, check out his twice-weekly…
Fun quotes from Angel.
Behind the Scenes: My Angel Investor Checklist
Want to know how I approach Angel Investing? Maybe so you can learn how to pitch angels? Or maybe you are a new angel looking for ideas? In this post, I’m going to share with you how I’ve been angel…
Fun checklist from David Silva Smith.
Best angel investing book: Jason Calacanis’s 288 page “Angel” in 2 Infographics
The Sport’s Almanac in hand, knowing exactly how to succeed. But instead of the results from sports competitions, I had 288 pages on investing in the future of startups. Jason Calacanis is one of the…
More infographics showing Calacanis actionables.