So you wanna start a business?

The path of the reluctant leader

There’s a dessert shop on a busy walking street near my house.

Every few years, I’ll watch as they shutter their doors, take down their signs, and close up the shop for good. Within weeks, a new dessert shop will spring up in it’s place. You probably have a bar, or restaurant, or shop in your town just like this.

Each time the store is reborn, the new owners will be wide-eyed, and full of certainty. Their concept is unique enough, their marketing dialed in; they have what it takes to finally beat the curse. They believe, deep down, that they know something all those other business owners didn’t.

Two ways to start a business

What I’ve come to learn about entrepreneurship is that there are really only two ways start a business.

The first is from a place of eager ambition. Believing that you have it right, and the rest of the world has it wrong. That everyone is thinking too small, or too narrow. But you’re not like everyone else, you’re perceptive, you’re tenacious, you think big. So with that unique insight, you bring forth something new. Let’s say mochi cupcakes, or vegan doughnuts, or coffee cocktails. Something that no one asked for, including you.

The second way to start a business is—reluctantly. Instead of seeing what others don’t, you simply have a problem. Something that’s a real pain in your side. Maybe you’re a frequent traveler, and carrying your luggage by hand is tiring. So after your hundredth flight of the year, you finally snap, and super glue wheels to the bottom of your bag. And maybe you stop there, satisfied that your life is now slightly better and shoulders slightly less tired. But maybe on your next trip, another exhausted traveler see’s your bag and how easily you’re gliding around the airport, and asks you where you got it. Then another stops you, and another.

The Reluctant Entrepreneur

In 1957, Yvon Chouinardv bought an iron forge, an anvil, a hammer, and a book on blacksmithing.

He had been living out of a backpack, climbing the peaks of Yosemite for some time now. His life was frugal, his meals were small, and his gear was falling apart. At the time, Yvon was using European-made pitons to scale the vertical 7,500 ft. face of El Capitan. These pitons were little metal spikes that climbers would drill into the rock, in order fasten their climbing rope, and to secure their position on the wall.

There was just one downside to the European pitons— they were all single use. This meant that hundreds of little metal spikes littered the mountainsides after climbers would abandon them while climbing. Yvon, living off 50 cents a day, had no room for waste. With the amount of climbing he was doing, he couldn’t afford to simply leave behind gear. So with his second-hand forge, and book on blacksmithing, he got to work.

“I made them for myself” said Yvon, “and they worked so good…then I made some for friends that I was climbing with, and then friends of friends wanted some.” Yvon’s new, hard-steel pitons, were reusable and many times stronger than their predecessors. So he started a new routine. During the early morning hours, he would forge the new pitons, then in the afternoon, he would do what he loved most and climb. Only in the evenings, after the fun of the day was behind him, would he sell his pitons out of the back of his car.

“I never ever wanted to be a businessman”, Yvon recounted 50 years later. “Those were the days when you thought businessmen were grease balls, and that was the last thing you wanted to be.” Despite his initial reluctance, Yvon’s company, Patagonia, is still privately owned. It’s currently valued at over 4.5 billion dollars. Ironically, Patagonia has now become a status symbol for the exact type of eager entrepreneur that Yvon never was.

The Reluctant Leader

In 1787, George Washington was tired. He had been fighting in one war or another for the past 30 years. Now, after leading the US to military victory, and ultimately independence against the British, he could finally rest.

So as he returned to his Mount Vernon estate. Any reasonable person of the time could agree, his retirement was well earned.

Yet, there were whispers in the Electoral College. Whispers that Washington should lead the newly formed nation. And so, the first ever US presidential campaign began. It began not by Washington seeking out presidency, but by the populous, seeking to convince Washington to lead.

A vote was taken and every single elector, from every single state, chose Washington to be President. Riders delivered the news to Washington, and a reluctant dread filled the room. He had no ambitions to lead, no desire for fame or fortune or spotlight. "Let those follow the pursuits of ambition and fame, who have a keener relish for them, or who may have more years, in store, for the enjoyment.” Washington wrote to the Marquis de Lafayette upon hearing the news of his election.

As the realization of his fate crept in, he wrote to another friend of feeling like a “culprit who is going to the place of his execution.”

Much like Yvon, Washington never wanted the fate in which destiny ultimately doled out for him. But once he accepted, he lead with grace. Masterfully organizing this new nation during its most volatile hour—setting a balanced and democratic political precedence that would be emulated for generations to come.

The lies of leadership and ambition

For the longest time, I believed that the best leaders were hard charging, ambitious, and eager to take up the position. That entrepreneurs had to be bold, with a vision of the world that was obfuscated from the rest of us.

When I think of this type of leader—the type that can see a future that the rest of us can’t—I instantly summon the image of Steve Jobs. Yet, Jobs himself was beyond skeptical of this notion; in fact, he outright rejected it. “You know who the best managers are?” he asked an interviewer rhetorically, “They're the great individual contributors who never, ever want to be a manager”. They’re reluctant, rather than eager, leaders.

“If you think you should be a president or a general at seven years old, there’s something wrong with you.” says the stoic writer Ryan Holiday, “You have no evidence that you’re qualified to do that.” And yet, many of us believe that we’d make a great leader, CEO, or entrepreneur, before ever doing the work required to become one. What’s even more insidious is the implication that, if we don’t envision ourselves at the top of the pyramid, there’s something wrong with us. That followers are somehow less valuable than leaders.

A leader that is cajoled into leadership, is a lot like an entrepreneur who is begged into business. The wind is at their backs, they already have buy in, and a firm team of supporters. Instead of playing games, and politics, and marketing themselves as the best for the job, they are called forth, from obscurity, to serve.

Should you become an entrepreneur?

History is filled with reluctant leaders. At 26 years old, Martin Luther King Jr. didn’t eagerly sign up to lead the Montgomery bus boycotts—and, ultimately, the entire civil rights movement. He was chosen by his peers, and he reluctantly accepted.

After decades of military service, Dwight D. Eisenhower wanted nothing more than to retire to a civilian career in academia. But his character, and military acumen, was so admired by both Democrats and Republicans, that both insisted he run for President under their party’s flag. Just like Washington, a political campaign by the people was launched to convince the candidate, rather than the other way around.

The allure of the reluctant leader, is that of humble reserve. It’s the notion that the world might just know better than we do. That instead of being driven by baseless ambition, politics, and public perception, we should focus on the one thing we can control—the quality of our work.

A business that is pulled from obscurity—from a hobby or side project—to the forefront, is without a doubt more robust than the alternative. By having people beg us to take on the responsibility of an entrepreneur, it ensures one thing. That there’s an actual need for what we do, and that we’re the right person to do it.

Derek Sivers, himself a reluctant entrepreneur, sold his first company CD Baby for $22 million. Like Yvon, he never saw himself as a businessman, but rather, a musician. He created CD Baby so that he could sell his music online. His friends in the industry took notice, and asked if he could feature their music on his site as well. “Don’t start a business until people are asking you to”, is Sivers’s advice to fledgling entrepreneurs. “This is not meant to be discouraging. It just means you need to get the ingredients before you turn on the oven.”

I find myself drawn towards the reluctant entrepreneur. Maybe it’s the humility, or maybe it’s the way they approach the world through curiosity and craftsmanship. But more likely, it’s that reluctant entrepreneurship just makes good business sense. It’s the ultimate expression of product-market-founder fit. Not only are there people clamoring for your product, but they’re clamoring for you to bring it to them.

The dichotomy between reluctant and eager leaders suggest one unsettling thing. We are not selecting our leadership on the premise of competence. We are not investing our time—and resources—in businesses that already have demand, and already have clamoring customers. Instead, we’re getting duped by the overly confident seven-year-olds who think they should be president. We’ve fundamentally confused the being of leadership, with the doing of leadership.

The reason the dessert shop on my street keeps going out of business isn’t because their prices are too high, or there isn’t enough foot traffic, or their social media strategy isn’t dialed in. Rather, it’s the simple fact that nobody is asking for another dessert shop.


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