If you ask a founder how her startup is going, the answer is almost always some version of “Great!”
There is a huge amount of pressure as a founder to never show weakness and to be the cheerleader in all internal and external situations. The world can be falling down around you—and most of the time when you’re running a company, it is—and you have to be the strong, confident, and optimistic. Failing is terrifying, and so is looking stupid.
Founders end up with a lot of weight on their shoulders—their employees and their families, their customers, their investors, etc. Founders usually feel a responsibility to make everyone happy, even though interests are often opposed. And it’s lonely in a way that’s difficult to explain, even with a cofounder (one of the things that works about organizations like Y Combinator is that you have a peer group you can lean on for support).
So a lot of founders end up pretty depressed at one point or another, and they generally don’t talk to anyone about it. Often companies don’t survive these dark times.
Failing sucks—there is no way to sugarcoat that. But startups are not life-and-death matters—it’s just work.
Most of the founders I know have had seriously dark times, and usually felt like there was no one they could turn to. For whatever it’s worth, you’re not alone, and you shouldn’t be ashamed.
You’ll be surprised how much better you feel just by talking to people about the struggles you’re facing instead of saying “we’re crushing it”. You’ll also be surprised how much you find other founders are willing to listen.