Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000

by Jason Calacanis

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.

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.

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.

It’s okay to start small, but it’s not okay to be a small thinker.

It’s not who gets there first. It’s who gets there first when the market’s ready.

I love that fact that people are drawn to the light, even if it may singe them and eventually burn out. At least they tried.

“The empty can makes the most noise,”

All relationships that start with lies will end in tears.

Avoid the liars. Embrace the delusional.

Life is short. Loyalty is all about intent. So if you’re not loyal to your angels, you’re an unworthy idiot or brilliant narcissist. Either way, go fuck yourself.