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

Founders also love angel syndicates because they exist as only one entity on their cap table: the SPV. This means they don’t have to collect dozens of investor signatures when doing future deals. Instead, they just need to get one signature from the syndicate lead who legally represents all of the other investors in the group.

Having good and bad experiences as an angel or advisor helps you improve your ability to pick great founders—and avoid the bad, immature, or clueless ones.

When you spend time in a role, whether it’s being a pilot, an EMT, or an investor, you’re going to develop strong habits. To be successful, it’s important that you develop good habits and be aware of the bad ones.

In month two, you are going to meet with twenty-five founders. You’re going to listen to their pitches and ask lots of short questions and write long notes about their answers. When they ask you if you’re in, you’re going to tell them that you need some time to come to a decision. Again, never say yes in a meeting. Let them know that you need to do

Carry is short for “carried interest,” and it’s defined as the share of profits that go to the fund manager—in this case called the syndicate lead. The term dates back to the sixteenth century, according to the Wikipedia entry, where captains of ships would charge merchants 20 percent of the profits from cargo that they took the risk and effort to

Those founders don’t need you, they don’t need your money, and they are not going to meet with you. You need to find founders who will become the next Mark Pincus and Evan Williams. The only way you’ll get into a hot deal early on is if you are invited into one or you get lucky. When you first start investing, you should meet with as many people as

If you are managing your bankroll properly, you’re going to have a much easier time enjoying angel investing. As we’ve outlined in this book, I believe that angel investing 5 or 10 percent of your net worth is a worthwhile pursuit, perhaps even 20 percent if you’re a younger person with a steady income stream. The key is to deploy it intelligently.

The more you listen to the partner, and really take in what they are saying, the greater conversationalist you will be. Sure, I’ve given you important questions to ask in this book (see chapter 18), but those questions are not as important as your ability to listen. Being present and keeping your mouth shut is something that does not come naturally

How to allocate your finite time and energy efficiently is something you constantly have to revisit as an investor, founder, parent, and human being. The cost of not revisiting your allocation of time is great, leading to massive regret at having spent too much time on a startup, marriage, friendship, or investment that is destined to disappoint yo

Why now? This question has been floating around the Valley for a while, and the first time I heard it was from my friend, Sequoia Capital’s Roelof Botha—the venture capitalist who convinced me to become a “Scout” for their firm, which led to my two greatest investments to date: Uber and Thumbtack. If you unpack this question, you’re really asking,