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 very term “bootstrapping” itself comes from a myth of a Baron who found himself drowning in a swamp and was able to grab his own boots an lift himself to safety- a physically impossible feat! Arguably though, bootstrapping a company from nothing is an equally “physics-defying” task.

So is there a repeatable formula for cracking a chicken & egg-style problem?

I used to back in the day. It was my first summer job while I was in college. The trouble with selling anything for the first time though is that it’s obvious when you’ve never sold before- your confidence as a salesperson comes only from making sales. Once you’ve sold even once, 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 real job at that point (let alone a sales position) I was pretty green. I lucked out with some quick initial wins though in pitching wealthy neighbors that either happened to need a new set of $700 knives or were just sympathetic to how crappy I was at sales and bought out of sheer pity. Whatever the reason, I went on to sell over $3k of cutlery in my first week driven purely by the confidence that 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 as a pancake and require that you expand them and close the flaps at one end to make the floor of the box. The flaps, however, all lay together in an impossible interlocking arrangement. If you’re like me you flounder 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, eureka! it all falls together. At some point though, you just have to bend one of the flaps and make it work.

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

In the case of your first job: physically go to the place of your ideal job, confess you know very little but exude energy, convince them they need an intern. Once you’re working there for free, sponge everything, prove your value until you become inexpendable and demonstrate through achievements it’s in their best interest to put you on salary.

In the case of the new product dilemma: go to five people you know and ask them to beta test your product as a favor. Respond to their feedback, iterate the product incorporating good changes, thank them profusely, publicize their input and your response, give them a free account for life, rinse and repeat.

In the case of the investors: scrape something together that’s good enough where you would invest in it yourself if you had the money. Then take a loan, get a credit card or go hold a bake sale and then put your money where your mouth is. Tell your friends what you’re up to and why they’re missing out if they don’t do the same with a small chunk of their spare change. Point to the gradual early testimonials from your beta users.

The point is: in all 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 I had to identify one trait that was consistent across all the founders 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 had enough irrational exuberance that they could suspend disbelief long enough to bend one of the flaps just right so the interlocking pieces came together. And once the flaps got past the initial lock, their pressure actually worked to the entrepreneur’s advantage.

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?