Paul Graham on Fundraising

The reason raising money destroys so many startups’ morale is not simply that it’s hard, but that it’s so much harder than they expected. What kills you is the disappointment. And the lower your expectations, the harder it is to be disappointed.

Startup founders tend to be optimistic. This can work well in technology, at least some of the time, but it’s the wrong way to approach raising money. Better to assume investors will always let you down. Acquirers too, while we’re at it. At YC one of our secondary mantras is “Deals fall through.” No matter what deal you have going on, assume it will fall through. The predictive power of this simple rule is amazing.

There will be a tendency, as a deal progresses, to start to believe it will happen, and then to depend on it happening. You must resist this. Tie yourself to the mast. This is what kills you. Deals do not have a trajectory like most other human interactions, where shared plans solidify linearly over time. Deals often fall through at the last moment. Often the other party doesn’t really think about what they want till the last moment. So you can’t use your everyday intuitions about shared plans as a guide. When it comes to deals, you have to consciously turn them off and become pathologically cynical.

This is harder to do than it sounds. It’s very flattering when eminent investors seem interested in funding you. It’s easy to start to believe that raising money will be quick and straightforward. But it hardly ever is.

(Source: paulgraham.com)