Chapter 27: 月报

I would like a monthly update from you that includes the key metrics for the business, as well as what you consider the wins and losses since the last email. I would like you to put requests for me and your other investors in the email as well. Every email should have how much cash you have left, your burn rate, and when you will be out of cash so that we can all plan for future raises.

“When you do get a new report, it’s wise to read it fully and send a short follow-up with some positivity for what’s working (“nice work landing that head of sales”) while being understanding about the losses (“Sorry you lost your CTO. Is there a job description I can share on LinkedIn?”). Depending on your related experience, there are always ways for you to be helpful. I like to pose these as questions, as opposed to edicts. For example, consider these two statements: “You need to do Facebook ads.” and “Have you considered doing Facebook ads?”

Chapter 28: 跟投与救急

When founders from strong companies raise another round, they will simply let you know that they’ve found a new investor, hopefully a venture capitalist who also wants to join the board, and tell you “what the new terms are and ask if you want to take your pro rata. You will have a date by which to respond yea or nay to reinvest or get diluted by the new money coming into the company. This doesn’t happen too often, and when it does, you should spend as much time as possible figuring out what this new investor sees in your startup. If new money is willing to pay a higher price, it probably means you picked a winner and you might want to consider putting in another $100,000. If this was a $25,000 bet, you will be quadrupling down, and if you did this as a syndicate for $1,000, you will be, ummm, maybe hundred-upling?! Centupling.

When deciding to give a bridge, you need to have a candid talk with the founders about what the bridge will accomplish, typically by having them present some goals and what the startup will look like when this new tranche of capital comes in. “What you see here is a pattern. Founders believe that one magical event is going to save the startup, be it adding a feature or a team member or a customer. You have to ask yourself two questions when presented with this strategy. First, is it true that this one event will change their trajectory? Second, is it possible to reach that event given these additional resources?

Chapter 29: 心态、策略、成长、长期的眼光

These days, when something blows up, I tend to move pretty quickly from an initial reaction of an “Oh fuck!” to an “Oh well” and then to “Okay, now let’s focus on what’s working.” It sucks to lose, but the more time and energy you put into your losses, the more you will feel like a loser. Instead, you should have been quadrupling down on your winners and spending more time on them.

If you’re constantly learning and working hard—two things that are in your control—good things will happen. This goes equally for founders and investors, which is why my reality show catchphrase is going to be “Do the work.

You don’t need to win every pot. You don’t need to win every day. You do need to win in the long term. Think about angel investing as a decadelong pursuit.

Chapter 30: 退出方式

When an IPO happens, your previously illiquid shares, which lived on a spreadsheet at the company, are magically transferred into your E-Trade, Charles Schwab, or—ideally—Wealthfront account (see chapter 9; I’m an advisor). These shares are typically locked up for the first six months you own them, but after that “lockup period” you can do what you want with them.

A market for selling private company shares emerged. The reasons for this are (1) the perfect storm of private companies not wanting to go public too soon and (2) the availability of massive pools of private funds from private equity and late-stage venture capital firms wanting to own significant positions in those companies.

If you have a winner and it’s surging, it’s tough to sell knowing that your equity is likely to grow. But taking 10 or 20 or 30 percent of your winnings off your table at a high-enough price and putting it back into your portfolio will almost always help you sleep better.

The third, and most common way, an angel makes their money is when a startup is bought. There are three types of M&A (merger and acquisition) deals: acquihires (a.k.a. fire sales), appropriate acquisitions, and premium sales. The term “acquihire” is a combination of “acquisition” and “hire,” and it’s what you call it when a big company buys a smaller company only to hire the entire team without doing a complete end run around the investors. When a startup gets acquihired, shareholders are likely to get back just pennies for every dollar they invested.

Chapter 31: 天使投资策略

Remember, we have more blind spots than we do clear vision, so you must unlearn what you have learned to be a successful angel.

Some angels bet on founders. Some angels want to solve a problem. Some angels bet on delight. Some angels bet on markets.

Chapter 32：和成功者同行and do the work

Soak in what you’ve learned by hitting a home run in your first thirty bets while appreciating the randomness of life. You “didn’t exactly hit the lottery, but you did get lucky because your thirty bets probably weren’t all that different from the bets of people who lost money or broke even. In fact, almost all angels probably have a very similar return profile if you take out their top investment—and the exact same return profile if you take out their top three hits.

Life is random, but luck isn’t. Lucky people surround themselves with the most successful people in the world “and take chances. It isn’t hard or impossible. It just takes work. Do the work. Trust me, just do the work.