Three Keys to Willie Nelson’s Status as American Icon and Fearless Brand

Willie Nelson

Willie Nelson on stage

When looking for the definition of a fearless brand, one need look no further than American icon, Willie Nelson, one of the most recognizable faces, voices, and talents in all of music. There are thousands of performers in the music industry – so what is it that makes Willie such an icon?

Is it the more than 130 albums he’s recorded – either solo or in collaboration? His music is absolutely an essential component of his legend. That’s especially true when taking into account the hundreds of songs he’s written, many made famous by other artists. Perhaps it’s his trademark bandanna, blue jeans, t-shirt, beard and long ponytail. Yes, it’s partly his look. His legacy is emboldened by his actions – he was on the cutting edge of ‘outlaw country’ music, Willie helped to start Farm-Aid to help America’s family farmers, his July 4th BBQ’s are infamous, as are his ‘dealings’ with the Internal Revenue Service.

Everything listed certainly combines to establish him as an American icon – but all of those accomplishments are the result of Willie Nelson being a fearless brand. Three traits are at the core of Willie Nelson’s success – of him being a fearless brand – passion, purpose and persistence. 

It’s those three characteristics which allowed Willie to transform from a youngster raised by his grandparents, to the clean-cut wannabe country singer as a young man and ultimately to the genuine superstar and icon he’s become.

Shortly after Willie was born in Abbott, Texas in August of 1933, his parents divorced and went their separate ways. Willie and his two-year-older sister, Bobbie, went to live with their paternal grandparents. At the age of six, Willie’s grandfather gave him a guitar and taught him a few chords. That was the spark that would light the flames of Willie’s passion for music. He wrote his first song when just seven. He played at church with his sister (who was quickly becoming a talented pianist), with a local polka band – wherever he could.

As his love for writing and performing grew, he also began to find a purpose for his music. His family, along with most of the locals, would pick cotton to earn money – a job Willie really didn’t like. He found that playing music allowed him to earn enough money to avoid having to work in the fields. He felt his music could become his career. Over time, his purpose would evolve and expand. One purpose was self-fulfilling – writing and performing music fed his soul. Yet there was an even greater purpose. Nelson wanted to share his music, to entertain people, to honor the many performers who influenced his music and his life, and to tell stories. 

Passion and purpose are essential to finding success – to building a personal brand – yet, those attributes are rarely sufficient by themselves. Overnight success – instant success – is very much the exception rather than the rule. The third ingredient of success is persistence. Persistence is something that Willie Nelson has plenty of.

Nelson enlisted in the Air Force, only to be honorably discharged due to chronic back issues. He enrolled at Baylor University and quickly realized that was not his path. From selling encyclopedias door-to-door to working as a radio disc jockey – Willie did what was necessary to support his musical pursuits. Following stints in Vancouver, Washington, Springfield, Missouri and Ft. Worth, Texas – Nelson, married with a child by then, moved to Houston, Texas.

It was there that he first sold one of the songs he had written. Family Bible earned Willie $50.00 – the song would end up becoming a hit for Claude Gray. With that seed money, Willie moved to Nashville. It was 1960.  Nelson spent his time writing, recording and performing – committed to a life of music. He gained notice mainly as a songwriter with several of his songs becoming major hits for other performers. Most famous of them all was the song Crazy performed by Patsy Cline, which would become the biggest jukebox hit of all time.

After a decade in Nashville, things weren’t turning out the way Willie had envisioned. Record companies attempted to shape Nelson in the mold of others. He performed in suit and tie sporting the short hair style of the day. Discouraged, Willie decided to head back to Texas – the tipping point being that his house caught fire. 

Willie Nelson moved to Austin, Texas, a town with a growing music presence and a large population of hippies. Finally – almost by accident – Willie Nelson began to discover his true self. Living and performing in a more relaxed setting, he let his hair grow, wore jeans and a t-shirt, sneakers and a bandanna – with or without a cowboy hat. More than his appearance was changing. Nelson’s music became more honest, the stories more raw.

Little did Nelson know that he was one of several artists leading the charge into a new music genre – outlaw country.

In 1972, Nelson started what would become Willie Nelson’s Fourth of July picnic – a sort of country-hippie answer to Woodstock (2017 saw the 44th edition of this event). 1975 saw the debut of what would become Nelson’s most iconic album – Red Headed Stranger. Finally, Nelson published an album over which he had 100% creative control. Called a ‘country opera’, the album established Willie Nelson – and his music – as a commercial success.

Over the next forty plus years, Willie Nelson has written and performed across a wide variety of musical genres, with dozens of superstar performers, selling over 400 million albums. Yet Willie Nelson hasn’t changed a bit from the country boy whose passion was music.

Fearless Brands are built with passion, purpose and persistence

Willie Nelson is unique in so many ways, beginning with his combination of humility and generosity. He begins every show by simply walking onto the stage – without fanfare and starts to play. He’s given money, jobs, living quarters and more to countless people, merely because they were in need. 

Nelson’s voice is absolutely one of a kind. No one – literally no one – can replicate his unique sound. His writing is also uniquely his own. Nelson uses phrasing and timing which are distinctively Willie. Lastly, he has played the same guitar – literally the same guitar – since 1969. The base guitar is a Martin N-20, but it was fitted with the pickup from his Baldwin guitar which had been smashed when tripped over by a drunk. Trigger, named after Roy Rogers’ horse, has a gaping hole in the top which Nelson will not allow to be repaired. Yet as shown in this video, Trigger, receives the finest care possible.

When his Nashville house was burning to the ground, Willie ran into the flames to save two guitar cases – one contained Trigger, the other held two pounds of Colombian weed. Yes, Willie Nelson, smokes marijuana, a lot. He’s had his brushes with the law and he’s rumored to have smoked a joint on the roof of the White House. It’s part of who he is.

He also had his dealings with the IRS. Bad investment advice, bad accounting and Willie’s notorious generosity led to an enormous unpaid tax bill – $32,000,000. In 1990, the IRS took physical possession of every one of Nelson’s assets in partial payment of his debt. Every asset except for Trigger, which Willie had shipped to Hawaii having caught wind of the impending raid. Nelson’s debt was finally worked off by his producing and selling an album titled The IRS Tapes: Who’ll Buy My Memories?.

Yes, Willie Nelson is without a doubt an American icon – perhaps the most famous and most loved icon of our time. While he never thought of it in these terms – he achieved the success he’s enjoyed and lived the life he’s chosen because he became a fearless brand. Nelson is a truly gifted entertainer and artist. He fueled his talent with passion, was driven by purpose, and endured through persistence. 

Chances are none of us reading this will become nearly the icon that Willie Nelson has become. However, every one of us can become a fearless brand and achieve our life’s ambitions by following Willie Nelson’s example. Expand your talent, fuel your purpose with passion and be persistent. 


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Coach, International Speaker and Thought Partner - Bill’s mission is to add value to the world – one brand at a time. Bill guides individuals and companies alike in building what he refers to as a ‘fearless brand’. This is the process of discovering, embracing and delivering their greatest value – which allows them to realize greater profit. Read More

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