Essays

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Investors will tell you the company is worth more. And they may be right. But that doesn't mean it's wrong to sell. Any financial advisor who put all his client's assets in the stock of a single, private company would probably lose his license for it.

More and more, investors are letting founders cash out partially. That should correct the problem. Most founders have such low standards that they'll feel rich with a sum that doesn't seem huge to investors. But this custom is spreading too slowly, because VCs are afraid of seeming irresponsible. No one wants to be the first VC to give someone fuck-you money and then actually get told "fuck you." But until this does start to happen, we know VCs are being too conservative.

19. Investors vary greatly.

Back when I was a founder I used to think all VCs were the same. And in fact they do all look the same. They're all what hackers call "suits." But since I've been dealing with VCs more I've learned that some suits are smarter than others.

They're also in a business where winners tend to keep winning and losers to keep losing. When a VC firm has been successful in the past, everyone wants funding from them, so they get the pick of all the new deals. The self-reinforcing nature of the venture funding market means that the top ten firms live in a completely different world from, say, the hundredth. As well as being smarter, they tend to be calmer and more upstanding; they don't need to do iffy things to get an edge, and don't want to because they have more brand to protect.

There are only two kinds of VCs you want to take money from, if you have the luxury of choosing: the "top tier" VCs, meaning about the top 20 or so firms, plus a few new ones that are not among the top 20 only because they haven't been around long enough.

It's particularly important to raise money from a top firm if you're a hacker, because they're more confident. That means they're less likely to stick you with a business guy as CEO, like VCs used to do in the 90s. If you seem smart and want to do it, they'll let you run the company.

20. Investors don't realize how much it costs to raise money from them.

Raising money is a huge time suck at just the point where startups can least afford it. It's not unusual for it to take five or six months to close a funding round. Six weeks is fast. And raising money is not just something you can leave running as a background process. When you're raising money, it's inevitably the main focus of the company. Which means building the product isn't.

Suppose a Y Combinator company starts talking to VCs after demo day, and is successful in raising money from them, closing the deal after a comparatively short 8 weeks. Since demo day occurs after 10 weeks, the company is now 18 weeks old. Raising money, rather than working on the product, has been the company's main focus for 44% of its existence. And mind you, this an example where things turned out well.

When a startup does return to working on the product after a funding round finally closes, it's as if they were returning to work after a months-long illness. They've lost most of their momentum.

Investors have no idea how much they damage the companies they invest in by taking so long to do it. But companies do. So there is a big opportunity here for a new kind of venture fund that invests smaller amounts at lower valuations, but promises to either close or say no very quickly. If there were such a firm, I'd recommend it to startups in preference to any other, no matter how prestigious. Startups live on speed and momentum.

21. Investors don't like to say no.

The reason funding deals take so long to close is mainly that investors can't make up their minds. VCs are not big companies; they can do a deal in 24 hours if they need to. But they usually let the initial meetings stretch out over a couple weeks. The reason is the selection algorithm I mentioned earlier. Most don't try to predict whether a startup will win, but to notice quickly that it already is winning. They care what the market thinks of you and what other VCs think of you, and they can't judge those just from meeting you.

Because they're investing in things that (a) change fast and (b) they don't understand, a lot of investors will reject you in a way that can later be claimed not to have been a rejection. Unless you know this world, you may not even realize you've been rejected. Here's a VC saying no:


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