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

Let that sink in for a moment, because in almost every investment decision you’ll face, some of your bias will be unknowingly triggered. Remember, we have more blind spots than we do clear vision, so you must unlearn what you have learned to be a successful angel.

Angel investing, as we’ve learned, is a unique vocation, because if you’re qualified to be an angel, you are overqualified to be a venture capitalist, and venture capitalists have a much easier and more financially rewarding life. Angels deal with a mortality rate in the 80 and 90 percent range, which can make your life feel more like that of a hos

If you were a Facebook or Twitter holder with 90-plus percent in those two companies, there was an obviously sound investment thesis you should have followed: diversification. If you are bullish on technology, which if you’re reading this book or were born in the years from 1960 to today you should be, you should have taken your $100 million in sha

While many angels and venture capitalists resisted the idea of letting founders cash out early, they quickly learned that allowing them to sell off $5 million or $10 million’s worth of their equity took a great deal of pressure off these broke, first-time management teams. A person with $10,000 in their bank account and a $10,000-a-month nut is in

I always tell folks that I don’t need to figure out if your product will succeed, I just need to know if you will succeed. If I have a gift in this angel investing game, it’s that I’m good at reading people and figuring out how meaningful winning will be to them.

That’s why you don’t see any books on angel investing or meet many career angel investors. In fact, there have only been a handful of people who have done angel investing for a complete decade and I am on a first-name basis with all of them: Esther Dyson, Mark Cuban, Stewart Alsop, Mitch Kapor, and Ron Conway top my list of angels who just won’t st

If you’re exhausted from angel investing but you are addicted to startups, you’ll have a nice track record with founders that will allow you to join a venture capital firm with a $500,000 starting salary, making this a fantastic investment similar to getting your undergrad and graduate degrees!

If you come to Silicon Valley and invest in thirty startups over two years and make this your half-time or full-time job, reflecting on the wins and losses, spending time with other investors and founders, you’re going to learn a ton. If you’re smart, you will read this book before you start investing, after you invest in ten startups, and again wh

There are some investors who feel it’s the market that makes the startup. They will look at the size of the insurance, food, or transportation industries and say, “Technology is going to massively impact these industries—let’s find startups who are innovating in this market.”