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The Question

Bailey Kalesti

On a recent StartUp episode, the team at Gimlet were telling the story of a particular startup in the Bay area that almost failed over and over again. Before eventually selling their company at a ridiculous price, there were many times when they had no idea if the damn thing was even worth all the trouble. There was a lot of stalling and failures before success. Have a listen:

Everyone that goes off on their own will inevitably face the question of "do I push ahead, or do I hang it up?" And rightly so. Even though my small freelancing business is small, I've asked this question over and over again. It's so hard to know when to change direction and when to push on. Because in the moment, both paths feel exactly the same. Those who have been far more successful than I say that the success they did eventually acquire was usually a surprise to them. That is, things were bad for a long time before they were good.

So, is this an immovable wall, or is it just the way of it? I don't know. But I'm going to push on.

Bailey