Missing The Forest Through The Trees

At the tail end of the post that I wrote on how USV (me in particular) missed the first round for Airbnb, I wrote:

We made the classic mistake that all investors make. We focused too much on what they were doing at the time and not enough on what they could do, would do, and did do.

But we sometimes get it right when others get it wrong. When Henry Ward, founder and CEO of Carta (then known as eShares) wrote about their Series A round, he said:

I used to try explaining that $20 stock certificates were an entry point into something bigger. It never worked.

Same issue. Most investors looked at the business of selling $20 electronically issued stock certificates and missed that it was simply the entry point to moving the entire private securities market to the cloud.

Investors have figured that out now and Carta is one of the fastest growing SAAS companies out there.

But missing the forest through the trees is a common mistake that early stage investors make. I make it. We make it. Everyone makes it.

My partner Brad Burnham has the best framework for thinking about this issue that I know of. He calls it “finding the narrow point of the wedge.” The analogy is trying to hammer a piece of metal into a block of wood. If the metal is large and flat, you can’t do it. But if it is narrow and thin, you can. And, of course, once you get the narrow point of the wedge into the block of wood, you can hammer it all the way in.

So, that’s what we all have to think about. Is there a large market out there that can be fundamentally changed with technology (like moving the private securities market to the cloud, or turning empty real estate into places to stay when you travel)? And what is the simplest and easiest way to get into it (like selling $20 electronic stock certs or putting air mattresses on living room floors)?

We try to keep Brad’s framework in our heads at USV, but we forget it frequently. And it is often the costliest mistake we make in the VC business. Because high impact companies do not come along that often, and when they do, we have to find a way to say yes.