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

To the women who raised, supported, and inspired me: my mother, Cathie, and her mother, Anne; my wife, Jade; and our three daughters, London, Johanna, and Caterina.

and

In loving memory of my friend Dave Goldberg, who was a true angel among men. We miss you, Goldie.

STOP! DONT READ THIS BOOK IF YOU CANT HANDLE LOSING YOUR MONEY INVESTING IN THE RISKIEST ASSET CLASS ON THE PLANET: STARTUPS.

This book has a singular goal: to teach you how massive wealth is created in the twenty-first century.

Its not a system or a secret, so Im not going to build this up into something fancy like those bullshit self-help books youve already bought.

Im just gonna tell you how a C-minus student from Brooklyn (before Brooklyn was cool) clawed his way into the tech industry, got lucky seven times (and counting), and made tens of millions of dollars.

Most folks think Im lucky, some say Im a complete fraud, and a handful think Im a brilliant hype man, and I dont agree with any of themI agree with all of them.

Thats why this will be the greatest business book ever written. I shouldnt be the one writing it, yet here we are. Im the outsider who made it in, letting you know how he pulled it off.

I am as shocked as anyone I made it here, and its a hell of a story: the son of a nurse and bartender watches his family lose everything when the fedswearing raid jackets just like in the moviesburst in with shotguns to take back his dads bar. He crosses the bridge to Manhattan with something to prove and, ultimately, he heads to the West Coast to make his fortune.

The American Dream still exists, its just not as widely distributed.

Our parents and grandparents took factory and white-collar jobs and rode them for all they were worth in the last century. Now the robotswho never sleep and self-improve on an exponential curveare taking these jobs. Meanwhile, we humans, with our nagging physiological and emotional needs, struggle to keep up.

Most of you are screwed.

But youre here, so youre clearly willing to learn and I can radically improve your odds if you do the work.

The world is becoming controlled by the few, powerful, and clever people who know how to create those robots, or how to design the software and the tablet on which youre reading this. But please dont stop reading, because Im going to show you how anyone can get a seat at the table with the digerati, illuminati, and moneyrati and, perhaps, tap into this hundred-year boom.

Yeah, Ive got my own formula like those other business books youve bought, but there is a major difference between my formula and theirsmine is forward-looking.

All of the other books out there, and some are great, try to explain to you how people made money in real estate, by mastering the art of the deal or by getting the right people on the bus (and the wrong ones off), but they are largely historical documents now.

The world has changed more in the last ten years than it did in the last ten decades.

Thats not just some clever one-liner to say in a conference keynote or at a dinner party. Its an undebatable fact.

The changes weve seen with the internet, with mobile phones, with robotics, with sensors, and in biology are mind-blowing not just to civilians, but also to the people working in these fieldsand the pace is increasing.

I could give you a list of mind-blowing breakthroughs to prove my point about how fast things are moving, but Id like this book to stand the test of time, and the truth is that giving you examples like a computer beating a human at chess, or an encyclopedia made with no paid writers, or computers flying airplanes and cars without steering wheels, or wars being won with robots, are so commonplace that science fiction is having a hard time remaining, well, fiction.

I know because the top-tier investors who invested in the last fifty big things call me to find the next big thing. I live on the edge of the future of business and technology.

As an angel investor, its my job to write the check when no one else believes in youand thats the most thrilling bet in the world.

Every week I meet a dozen dreamers with insane ideas who want me to give them my money, advice, and access to my Rolodexbut mostly the money.

Oftentimes Im the first money in, the first investor willing to take a chance with a company like Uber or Thumbtack when they are only worth four or five million bucks and almost everyone else has said no.

This year I invested $750,000 in a company that makes a robotic cafe called Cafe X. It eliminates the two most expensive aspects of Starbuckss business: real estate and humans.

When the founders emailed me a video of the prototype in action at a college in Hong Kong, I wrote back to them, Is this a joke?

They said, No, it is not a joke, so I invited them to come to my incubator where we spent three months refining the product and helping them craft their pitch. Then I introduced them to my rich, powerful, and, in many cases, compulsive-gambling, narcissistic friendswho funded the company for millions of dollars.

If we succeed with Cafe X, we will reduce the price of a latte to $2 (again), make it perfectly every time (a computer never forgets how much foam you asked for), and reduce your wait from more than five minutes to under thirty seconds (the machines know where your smartphone is and they make your coffee when youre ninety seconds away).

Instead of a Starbucks on every other corner in a city, there will be a Cafe X machine in the lobby of every building on the block.

Instead of being open fourteen hours a day, these robots will serve us twenty-four hours a day.

Cafe X and other startups will also eliminate millions of jobs in which humans get paid to stand behind a counter and repeat back your seven precious little instructions on how to prepare your morning libation, before pressing one button and masturbating a milk-frothing pitcher for two minutes.

If right now you think Im a horrible, marauding, free-market monster, youre only half-rightIm also a humanist who thinks there are better things for our children to do with their time.

The quicker we eliminate the low-paying, repetitive, and menial jobs, the quicker our species can get to work on bigger issues like sustainability, being multiplanetary, and perhaps retiring the last couple dozen dictators and despots who are murdering, raping, and otherwise oppressing the weakest among us.

Of course, I could be wrong.

When we eliminate all these jobs, the world might spin into a global version of the long-forgotten dry run Occupy Wall Street where a group of savvy but poorly organized hippies and millennials slammed their feet down and said, No more! Were not leaving until things change!

Until, of course, the economy rebounded and they got cool jobs with free food and their own private drivers from uberPOOL, then realized that, net-net, things are actually pretty fucking awesome and they dont need to storm Michael Bloombergs town house or stink up the Goldman Sachs lobby anymore.

In my mind, candidly, weve got a 70 percent chance of figuring out this massive sea change without starting a full-on revolution in the streets, like we saw in Greece or Egypt, or any other place where unemployment among young adults breaks 20 percent.

But I dont invest in this future because I want to sit in an ivory tower laughing at people whose jobs are replaced. I invest in this future because its inevitable and I think I can help accelerate the efforts of the founders and innovators who are missionaries, not mercenaries. Of course, I plan to make a great deal of money in these revolutions, but I also plan to look back proudly and know that I helped propel changes that made our planet better.