A strange title, I know. Let me explain.

The interesting problems are the ones where a precondition for solving the problem is some level of sucess in already having solved it. Commonly known as “chicken and egg” problems, some examples are:

How do you get hired for a job without experience?
How do you gain experience without having a job?

How do you get users to beta test your product until it’s popular?
How do you make it good enough to become popular before you have beta testers?

How do you raise money to build your product before proving to investors that it will make money?
How do you execute without having money to fund product development?

These paradoxical problems are seemingly unsolvable at first glance because (like one of those weird M.C. Escher paintings) they are inextricably deadlocked with themselves. Startups by nature are a fertile ground for these types of problems; we encounter new challenges like these daily with JumpBox, where the solution demands resources that only become available after some part of the solution is achieved. The term “bootstrapping” itself comes from a myth of a guy who found himself drowning in the sea and was able to grab his own boots an lift himself out of the water to safety- a physically impossible feat! Arguably though, bootstrapping a company from zero resources is an equally “physics-defying” task. So how does one crack a chicken & egg-style problem?

I used to sell cutlery. It was my first job one summer while I was in college. The trouble with selling anything for the first time is that it’s obvious when you’ve never sold anything- confidence comes only from making sales. Once you’ve sold, it becomes infinitely easier to sell again, but getting that first sale is the hardest thing ever. I’d say 70% of the people that were in our group dropped out without getting a single sale. Having never held a job at that point (let alone a sales position) I was not confident. But I was fortunate in that I lucked out with quick initial wins in pitching wealthy people that either happened to need a new set of $700 knives or people that were just sympathetic with how green I was and bought out of sheer pity for my pitch. Whatever the reason for those first couple sales, I went on to sell over $3k of cutlery in my first week driven by the confidence I could sell. And I’m convinced that the secret sauce to that whole equation was a simple bit of advice from my sales manager, Don Gerould: “Fake it until you make it.” Not “fake it” in the sense of “mislead others” but mentally trick yourself into believing you have successfully sold before until you have actually done it and the feeling becomes substantiated by reality.

Here’s another example: you know those cardboard boxes that require assembly? They arrive perfectly flat and require that you expand them and then close the flaps at one end to make a box. The flaps, however, all lay together in an impossible interlocking arrangement such that one lays on another, lays on another, lays on another, lays under the first. If you’re like me you flounder around with it for five minutes cursing the cardboard until you manage to wrangle it just close enough where you can cram one of the flaps underneath the other and then all comes together. At some point though, you just have to bend one of the flaps and make it work.

So the flap-bending tactics for the examples above are:

The point is: in all the problems that have solutions which are inherently deadlocked with themselves, there is some way to eek into it and bend one of the flaps and force it into place. Looking across the thirty-two stories in the book Founders At Work, if you had to identify one trait that was consistent across all the entrepreneurs featured in the book, it could be distilled to this “flap-bending” essence. They understood that in theory what they were doing defied physics and yet they knew that if they could suspend disbelief long enough to bend one of the flaps, the interlocking pieces would eventually come together.

So what’s your biggest chicken & egg problem? What are the interlocking components that are seemingly deadlocked with one another? Which one can be most easily bent into place?