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

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.
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.”
At the core of being a great founder is the unrelenting desire to see your vision—or version—of the world realized. When you meet with founders as often as an angel should, you’re going to very quickly be able to sense if their startup matters enough to them. What you need to figure out is if this founder will quit when things get hard.
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,
... See moreThird, I set the tone that monthly updates are something I like to see before I give the founder my money. Life is one giant test, and interacting with investors is one of those tests. Seeing a person execute on their plan over time is the best way to decide if you should invest.
The biggest leak in my early years was that I frequently assumed that if I, or my very qualified friends, could execute on a plan, then my investments could, too. I assumed that all founders were dogged and die-hard, but I learned the hard way—after a half-dozen startups gave up and gave their investors five to fifty cents on the dollar back—that
... See moreThe best deals are typically not on platforms like AngelList or at incubators like Y Combinator or 500 Startups. The best deals never see the light of day. They’re quickly filled by insiders who are sharing deal flow, and by elite founders with killer startups tapping their existing network. This is why it is critical that you build a deal-sharing
... See moreThe more concise and professional the updates, the greater the chances that angels will be able to help you, including investing more money and introducing you to their friends as a responsible founder who’s a delight to work with. Angels want to feel needed, and founders who don’t make their angels feel needed have lost their most likely source of
... See moreThere are a number of sites offering angel syndicates here in the United States including AngelList, SeedInvest, and Funders Club. At these sites, successful angel investors create an investment group, or syndicate, where they explain what they typically invest in, what they’ve already invested in (their track record), how much they typically
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