Essays

So why do founders chase high valuations? They're tricked by misplaced ambition. They feel they've achieved more if they get a higher valuation. They usually know other founders, and if they get a higher valuation they can say "mine is bigger than yours." But funding is not the real test. The real test is the final outcome for the founder, and getting too high a valuation may just make a good outcome less likely.

The one advantage of a high valuation is that you get less dilution. But there is another less sexy way to achieve that: just take less money.

Ten years ago investors were looking for the next Bill Gates. This was a mistake, because Microsoft was a very anomalous startup. They started almost as a contract programming operation, and the reason they became huge was that IBM happened to drop the PC standard in their lap.

Now all the VCs are looking for the next Larry and Sergey. This is a good trend, because Larry and Sergey are closer to the ideal startup founders.

Historically investors thought it was important for a founder to be an expert in business. So they were willing to fund teams of MBAs who pla

If you're a hacker, it's good news that investors are looking for Larry and Sergey. The bad news is, the only investors who can do it right are the ones who knew them when they were a couple of CS grad students, not the confident media stars they are today. What investors still don't get is how clueless and tentative great founders can seem at the very begi

Investors do more for startups than give them money. They're helpful in doing deals and arranging introductions, and some of the smarter ones, particularly angels, can give good advice about the product.

In fact, I'd say what separates the great investors from the mediocre ones is the quality of their advice. Most investors give advice, but the top ones give good advice.

Whatever help investors give a startup tends to be underestimated. It's to everyone's advantage to let the world think the founders thought of everything. The goal of the investors is for the company to become valuable, and the company seems more valuable if it seems like all the good ideas came from within.

This trend is compounded by the obsession that the press has with founders. In a company founded by two people, 10% of the ideas might come from the first guy they hire. Arguably they've done a bad job of hiring otherwise. And yet this guy will be almost entirely overlooked by the press.

I say this as a founder: the contribution of founders is always overestimated. The danger here is that new founders, looking at existing founders, will think that they're supermen that one couldn't possibly equal oneself. Actually they have a hundred different types of support people just offscreen making the whole show possible. [3]

I've been very surprised to discover how timid most VCs are. They seem to be afraid of looking bad to their partners, and perhaps also to the limited partners—the people whose money they invest.

You can measure this fear in how much less risk VCs are willing to take. You can tell they won't make investments for their fund that they might be willing to make themselves as angels. Though it's not quite accurate to say that VCs are less willing to take risks. They're less willing to do things that might look bad. That's not the same thing.

For example, most VCs would be very reluctant to invest in a startup founded by a pair of 18 year old hackers, no matter how brilliant, because if the startup failed their partners could turn on them and say "What, you invested $x million of our money in a pair of 18 year olds?" Whereas if a VC invested in a startup founded by three former banking executives in their 40s who pla

As a friend of mine said, "Most VCs can't do anything that would sound bad to the kind of doofuses who run pension funds." Angels can take greater risks because they don't have to answer to anyone.

Some founders are quite dejected when they get turned down by investors. They shouldn't take it so much to heart. To start with, investors are often wrong. It's hard to think of a successful startup that wasn't turned down by investors at some point. Lots of VCs rejected Google. So obviously the reaction of investors is not a very meaningful test.

Investors will often reject you for what seem to be superficial reasons. I read of one VC who turned down a startup simply because they'd given away so many little bits of stock that the deal required too many signatures to close. [4] The reason investors can get away with this is that they see so many deals. It doesn't matter if they underestimate you because of some surface imperfection, because the next best deal will be almost as good. Imagine picking out apples at a grocery store. You grab one with a little bruise. Maybe it's just a surface bruise, but why even bother checking when there are so many other unbruised apples to choose from?

Investors would be the first to admit they're often wrong. So when you get rejected by investors, don't think "we suck," but instead ask "do we suck?" Rejection is a question, not an answer.

I've been surprised to discover how emotional investors can be. You'd expect them to be cold and calculating, or at least businesslike, but often they're not. I'm not sure if it's their position of power that makes them this way, or the large sums of money involved, but investment negotiations can easily turn personal. If you offend investors, they'll leave in a huff.

A while ago an eminent VC firm offered a series A round to a startup we'd seed funded. Then they heard a rival VC firm was also interested. They were so afraid that they'd be rejected in favor of this other firm that they gave the startup what's known as an "exploding termsheet." They had, I think, 24 hours to say yes or no, or the deal was off. Exploding termsheets are a somewhat dubious device, but not uncommon. What surprised me was their reaction when I called to talk about it. I asked if they'd still be interested in the startup if the rival VC didn't end up making an offer, and they said no. What rational basis could they have had for saying that? If they thought the startup was worth investing in, what difference should it make what some other VC thought? Surely it was their duty to their limited partners simply to invest in the best opportunities they found; they should be delighted if the other VC said no, because it would mean they'd overlooked a good opportunity. But of course there was no rational basis for their decision. They just couldn't stand the idea of taking this rival firm's rejects.