Willie Nelson is your new entrepreneurial hero

By Sarah Lacy , written on July 1, 2015

From The Lessons from the Trenches Desk

“Getting stoned on the roof of the White House, you can’t help but turn inward. Certain philosophical questions come to mind, like…

How the fuck did I get here?”

That statement could only be written by the great Willie Nelson. I just finished his new autobiography, “It’s a Long Story: My Life.” That's an apt title because it’s nearly 400 pages, and it reads with the same folksy story-telling vibe you’re used to if you are a fan of his songs. The book reads like you had a long dinner with Willie and he just unfolded his life to you.

What surprised me is how relevant the book is for entrepreneurs -- especially, but not only, those in the music industry.

Nelson’s story is one about refusing to be bucketed. He isn’t country, he isn’t folk, he isn’t blues, he isn’t R&B… although he was at times accepted and rejected by each of those genres. He kept being told he had to fit somewhere, and he kept refusing. As he found his voice, and these music genres naturally bled into one another, he finally found huge success by sticking to his gut.

It’s a story about never giving up. As he says in the opening, talking about the early 1990s when the IRS came after him:

Everyone was saying that I had reached the end. Everyone was saying it was over. The IRS had come down with the hammer. And those sons of bitches came down mighty fuckin’ hard.

How hard? $32 million in back taxes hard. His ill-advised solution? Fight them rather than file bankruptcy and have the IRS take everything for the rest of his career. As he joked at the time:

What’s the difference between an IRS agent and a whore? A whore will quit fucking you after you’re dead.

His is a story about never rolling over and playing dead. He’s 82 years old. In just the last two years he’s written several dozen new songs, recorded five albums, and played over three hundred live shows.

His is a story about taking stands. Nelson was an advocate for marijuana legalization for decades, and it’s finally happening. He supported pro-legalization candidates when they were getting single-digit percentages of the vote. As long as they got a little more each time, that was good enough for Willie. It meant progress.

His is a story about never forgetting your roots. One of my favorite stories from the book was when Nelson moved back to Abbott, Texas-- the small town where he was born -- to feel centered.  

He was chagrined to see a billboard erected declaring “Abbott, home of Willie Nelson.” He was in his fifties with kids and in the sunset of his third marriage. He didn’t want his anonymity blown. He was playing poker with his old friend Zeke who used to get him in trouble in his youth, bitching about the billboard.

Zeke said, “Well, what do you think we should do about it?”

“Burn the fucker down!” I said.

Zeke didn’t blink. “Good idea.”

I won’t spoil the rest of it, but on the next page Willie and Zeke are dragging a huge can of gas to the freeway.

Some of the best parts of the book are about the record industry over the seven decades or so that Nelson has been part of it.

He has little love for the labels. They constantly tried to force him into molds he didn’t fit, and early on his career stagnated as a result. An early argument over “Yesterday’s Wine” was typical. He was asked to defend his work, and he just stayed silent.

"Well, if you can’t explain your goddamn music to me, how the hell do you expect me to explain it to my sales force?"

“I don’t expect you to explain shit,” I said. “These are my songs. I like ‘em. I’m proud of ‘em. And that’s it.”

That album bombed. And it was the same story on some of his most successful albums. It was only when Nelson met Atlantic Records vice president Jerry Wexler that he started to thrive. When Nelson proposed a gospel album, he asked Wexler, “You’re not worried that it’s not commercial?”

Wexler said, “Fuck commerce. You’re going for art. You’re going for truth. And when the art is truthful, sales will follow.”

They did, and it was clear that he’d been right about what his audience wanted from him all along.

Later with Columbia, Nelson pushed for a contract that guaranteed his artistic freedom. When he produced Red Headed Stranger the label said he’d be “shooting himself in the foot” releasing it.

Nelson responded:

“Maybe so, but the contract couldn’t be plainer. I turn in the music I want to turn in. Your job is to sell it.”

“You’re making our job impossible.”

“Well let’s see what the public has to say”

The public loved it.

The next time it happened he said it only confirmed what he’d always known: “The label really didn’t know shit.”

After making Columbia millions, they eventually dropped him when country artists like Garth Brooks started to surge. When told the news, Nelson’s manager, Mark Rothbaum, actually lunged at the studio exec and had to be restrained. Said Nelson:

I appreciate his passion, but this was one instance when i didn’t share it. To be honest, I didn’t really give a shit.

“It’s outrageous,” said Mark. “Especially in light of the fact that you’ve made these people millions.”...

“No need to preach to the choir. And no need to be all that surprised. I knew this was a cold-blooded business back forty years ago when I recorded for Pappy Daily down in Houston. With these big corporations, it’s only gotten colder."

“At the very least they owe you respect.”

“The only thing those bean counters respect is beans.”

So given that anecote, it's no surprise that Nelson hasn’t shed many tears for what digital music has done to the labels.

Nelson rarely met a cause he didn’t want to play a benefit for, and recently a friend asked why he was so angry about so many things in the world but not the state of the music industry. His answer is long and thoughtful, and I hope he doesn’t mind me quoting so much of it.

The question made me stop and think. Among my peers, and the younger musicians, I hear lots of groaning. Many of the complaints are justified. Record sales are in the toilet. Technology has made it harder for artists to get our fair share of revenue. In the old days you had to buy a piece of sheet music, a 78 shellac record, a 45 or 331/2 rpm vinyl record, a cassette, an eight-track, or a compact disc. Now, in the digital age, you don’t have to buy a thing. With streaming subscription services like spotify, you can listen to anything you want, whenever you want, and on whatever digital device you want. As a result artists’ and songwriters’ royalties have been drastically downsized.

In short, high tech has made music accessible in ways we never could have imagined. It’s something of a free for all.

Does this anger me? Does this alarm me?

I’d have to say no, and here’s why. I like the idea that it’s easier than ever for fans to get hold of the music they love. It’s good that there’s more music on more media outlets than at any time in the history of the world. Some of those outlets have been especially friendly to me. . . . and even if the royalty payout isn’t what it was compared to back in the day, I can live with this new reality-- but it would be nice for artists to get their fair share.

I can live with it because my approach to making my living hasn’t changed since I started out back in the dark ages. My approach is that the wandering minstrel makes his living from wandering-- from playing joints and dives, dance halls and clubs and country fairs. I’ve never counted on income from radio play or record sales -- not then and not now. I’ve always assumed that whatever I got would be watered down by the radio stations and the record companies doing the auditing.

Back in the fifties, the system was rigged against artists getting their fair share of airplay money and record sales. Today it’s a different system, but the result is the same.

I put my faith in one thing and one thing alone: my ability to perform for people. I see records as advertisements for my shows. The only money I’ve ever counted on is the money I make when you buy a ticket to my show. and if hearing my record on your laptop or your smartphone motivates you to come see me, I’m a happy man.