Ode to Outsiders and Mavericks

It’s the most iconic photo in rock history.

Caught in the chaos of the moment, a musician coils his body, wielding his Fender guitar like an axe, poised to smash it to pieces. Taken at New York City’s Palladium in 1979, the photo is a timeless depiction of rock’s energy, rebellion and power.

True to the punk ethos, the musician in the photo, The Clash’s Paul Simonon, was a novice bass player at best. In fact, most of the band played rudimentarily when they formed.

Like their counterparts in the Sex Pistols, they were musical primitivists and outsiders breathing rebellious life and energy into rock music. The photo became the cover of London Calling, now considered one of the great albums of all time.

The Clash and the Pistols reinvented rock music.

I had the good fortune of seeing The Clash perform live, as well as many of their peers and descendants, from The Damned to Husker Du to The Replacements to Fishbone. Decades later, the Clash’s “do-it-yourself” garage energy still inspires bands to get started.

Similarly, Thelonious Monk and Charlie Parker baffled the jazz world when they emerged on the scene. Monk’s initial albums sold dismally. His piano style was percussive and sparse, emphasizing bold playing that defied conventional smoothness. But there was playfulness and humor lurking beneath the sophistication for those who listened.

Parker’s breakneck pace and jagged harmonies bewildered jazz audiences at first. He played with unprecedented speed and precision. Beneath the deeply technical playing were intense feelings of joy, sadness and mischief. He reshaped jazz into an art form for serious listening.

Monk and Parker were seen as musical misfits. But sophisticated fans and artists realized their brilliance. They created a new style that signaled jazz’s evolution from dance-hall entertainment to a serious art form.

They invented modern jazz.

Jimi Hendrix transformed the rhythms and traditions of blues and rock with feedback, distortion, and pioneering effects. Voodoo Chile, with its thunderous, primordial riffs, is the sound track to a blues apocalypse.

Initially, audiences were not sure what to think of Hendrix’s hippy outfits, flashy showmanship and deep electric blues. But his peers realized he was the future. Hendrix influenced every guitarist who followed. It’s impossible to imagine modern rock music without him.

Jack Kerouac typed his iconic novel, On the Road, on a single, continuous 120-foot reel of paper. Fueled by coffee and Benzedrine, Kerouac worked with almost no sleep for several weeks, writing in a stream-of-consciousness that echoed the spontaneity of life on the road.

Kerouac, from the blue-collar town of Lowell, MA, was perceived as a barbarian at the literary gates. But he was undeterred and went on to inspire generations to come.

I read On the Road as teenager. It felt like a message beamed down from another planet. Like so many, I was transfixed. It inspired me with a lifelong passion to travel and write.

Paul Simonon, Charlie Parker, Jimi Hendrix and Jack Kerouac were ridiculed at first. But they all reinvented their worlds. They’re the kind of mavericks and disruptors I’ve admired my whole life.

We can see these outsiders and innovators across business, government, the arts and sports. Outsiders and rebels who hear a different tune, who view the world differently, who follow their muse even when it leads to ridicule and resistance.

They are not welcomed at first. When they emerge on the scene, the odds are stacked against them. And then they change everything.

An Unfair Game

The movie Moneyball, based on Michael Lewis’s brilliant book, is the story of Oakland A’s General Manager Billy Beane. Beane revolutionized baseball, and all professional sports, by using analytics to identify talent, turning his back on a century of scouting tradition. At first, he was viewed as a misfit and met massive resistance.

In the movie, Boston Red Sox owner John Henry says to Beane:

“The first one through the wall, it always gets bloody, always. It threatens not just their way of doing business, but…their livelihoods…their jobs…the way that they do things. And every time that happens, whether it's the government or a way of doing business or whatever it is, the people holding the reins, with their hands on the switch, they go bat shit crazy.”

Or, as Billy Beane, played by Brad Pitt, says in the movie, summarizing the experience of all outsiders and mavericks: “It’s an unfair game.”

I have seen this again and again in leading transformation. At the outset, the obstacles seem insurmountable.

In the early years of Amazon, it felt like the odds were stacked against us. We were doing something no one understood. We experienced intense resistance from the centuries’ old publishing industry. We were called “Amazon.con” and “Amazon.bomb,” among other things.

Publishers didn’t want to talk to us. They didn’t want to give us a reasonable allocation of inventory. Some of them criticized innovations that customers loved, such as customer reviews or discounted bestsellers. Laying the foundation for digital books was a massive uphill battle.

When I led digital transformation at a large US airline, we were seeking to create a seamless digital experience. But something as simple as building a good mobile app was excruciatingly hard at first.

In those days, it took a month to put out a single software release and it usually broke things. We had no modern microservices. Our server was in our building, subject to power outages and floods. The underlying technology infrastructure supporting the airline industry, such as Sabre, was archaic and overly complex. TSA agents weren’t comfortable or equipped to easily scan mobile boarding passes.

It is an unfair game. But we persisted and changed the game.

When I need inspiration, I think of Simonon’s iconic photo. I think of music stores refusing to sell Monk’s albums. I think of Kerouac typing On the Road, now considered a classic, on a 120-foot roll of paper. I think of Billy Beane being laughed at and criticized as he reinvented professional sports.

In the end, they all changed the game and the world. And we are better for it.