No idea is too crazy

In this first-person look inside the world of entrepreneurship, Square co-founder Jim McKelvey details how to build a world-changing company

Published a year ago on Apr 04, 2020 4 minutes Read

Before stalking got such a bad reputation, I was pretty good at it. My target was always the same: some famous businessperson. Entrepreneurship was not taught in school at the time, so I had to invent a way to get instruction. My technique was simple: I would wait until some famous entrepreneur came to St. Louis to give a speech. After the speech I would catch the speaker as he or she left the stage and offer a ride to the airport.

It was a good offer. Ride sharing was twenty years' in the future and St. Louis taxis were run by a cabal of incompetent crooks, as if the grandchildren of the Three Stooges had joined organized crime.Cabs would routinely miss pickups or take the scenic route. I got the speakers to their flights with a minimum of pine scent, and all they had to do was share some knowledge. My technique worked every time except once.

I learned a lot about business on those rides, but never what I wanted to learn. Every time I asked a question about some significant problem I was confronting, the answer would be a variant of either "You can't do that" or "Find someone who has already done it and work for them for a decade." None of these successful people knew how to do anything that had not already been done. I wanted to meet a different type of person, I just didn't know what to ask for.

The Right Word

The English language currently has no word for our subject, but it used to. Like tattoos, the word entrepreneur has lost its shock value through sheer overuse. I no longer recoil when the babysitter has an angry-looking reptile crawling out of his collar or calls himself a "child-care entrepreneur." So called entrepreneurs are everywhere today, from the local dry cleaner to the freelance designer to the kids selling lemonade on the corner-who, thanks to Square, now take credit cards.

It wasn't always this way. When the word entrepreneur first puttered across the Atlantic by steamship in the late nineteenth century, it described a special type of person: a risk taker who reshaped an industry through innovation. Joseph Schumpeter, the economist who popularized its use, described entrepreneurs as revolutionaries and "wild spirits." They were outcasts living on the edge of civilization, doing things that hadn't been done.

But today all businesspeople are considered entrepreneurs, which is like calling all tourists explorers. The problem is not just semantic, because when I talk about entrepreneurship, I mean something very specific.

Let me explain with an analogy. On April 22, 2011, a terrible storm hit my hometown. The wind ripped roofs off people's homes. When I use the word wind, you may think you understand what I am describing, but you probably don't. The wind in this storm was oddly selective. It obliterated two adjacent houses, skipped the next seven, and then trashed five more.

Describing a tornado without using the word wind is nearly impossible. But as soon as you say wind, people immediately assume a bunch of things that aren't true about tornadoes. Wind moves linearly, but tornadoes drop from the sky at random. Wind doesn't suddenly multiply its power, but tornadoes curl back into themselves, becoming strong enough to toss a truck onto a roof or a roof onto a truck. Most places on earth don't get tornadoes, so we lack the words to properly describe them. Imagine the difficulty of trying to explain a tornado to someone living where wind only moves in a straight line. If I say the phrase strong wind you don't picture an airborne cow.

Using the terms of business to describe entrepreneurship is like calling a tornado a strong wind. Yes, both the entrepreneur and the businessperson build companies, but businesses are everywhere while entrepreneurship is as rare as a flying cow. The language of business doesn't work when discussing entrepreneurship; the words are already too laden with other meanings.

In this book, when you read the word entrepreneur, I want you to think of rebels, explorers, and people driven by more than just profit or even common sense. I want you to experience the nervousness that comes from trying something that might not work. I want you to feel a bit crazy. In fact, a good way to understand the original meaning of the word entrepreneur is to substitute the word crazy. Calling someone crazy is generally not a compliment, and neither was calling someone an entrepreneur in Schumpeter's day.

This is an extract from Jim McKelvey's The Innovation Stack published by Portfolio