Working on a startup is a balancing act: being crazy enough to believe your idea can take off, but not crazy enough to miss the signs when it’s clearly not going to.
Why Instagram Worked
Mike Krieger
2K10

I wonder then about Airbnb. Their entire story is about the most desperate kind of desperation I’ve heard in a minute; struggling to pay bills, user count stagnating, selling cereal— it’s a startup nightmare, really.

In a sense, everything was wrong with Airbnb, and I’m sure there’s no shortage of experts who, back then, would have said, “Yeah guys, this is clearly not working out. Part of being an entrepreneur is knowing when to quit, ya know.”

One might say, “well there’s always an exception”, but looking at the scrappyness and hustle of those founders, I can’t accept that. There are worse ideas that get funded every day.

Really, people, how are we entrepreneurs supposed to be able to tell when to hold-em and when to fold-em?

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