3. Why now?

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

Once you have the phrase “angel investor” on your online profiles, you will have instant deal flow. It will be an ugly and desperate deal flow at the start, since no one knows you and how brilliant you are, but it will be your deal flow—and that means something because everyone in this industry starts as an outsider.

In some ways, “Why now?” is the most important question about the business you can ask because there are so many folks constantly trying the same ideas over and over again in our business.

For the angel who paid $100,000 of their own money for their one million shares, getting back $1 million would be a fantastic and compelling outcome—$900,000 in profit! They also might consider selling half their shares to investors in a new round ($500,000 worth) as “idiot insurance” in case the company eventually fails, while letting the other ha

But what if you don’t have money? Is there a way to get on the cap table? As we discussed in chapter 4, there is a group of folks known as advisors who trade some combination of their networks and knowledge—and sometimes freelance work—in exchange for shares in a company. Advising startups is often a great stepping-stone to becoming an angel.

The 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

Everyone wants to be a founder, but they don’t understand exactly what that means. Being the leader sucks because you’re ultimately responsible not only for your performance but also for the performance of your entire team, the market, your investors, your competitors, and even your customers. Most people calling themselves founders today are just

As we discussed in the previous chapter, investing in angel syndicates is a wildly effective hack as you start your angel investing journey. Every month, dozens of startups are syndicated on AngelList, SeedInvest, and Funders Club. As an angel investor, you are going to need to invest in fifty startups (diversification!) in Silicon Valley (location