Business Lessons From Rock Legends

Did you ever think that we could turn to rock and roll stars for lessons on how to conduct ourselves in a business setting? We sure can. Here are some lessons from three of my favorite artists.

1) Stevie Ray Vaughan

Fail magnificently. You never know where it might take you.

The first time Stevie Ray Vaughan played the Montreaux Jazz Festival in 1982, it did not go well.

You can hear the audience booing at the beginning of this clip, and quite often during the rest of the show. But he plowed through the set, head down; smoking; determined; focused. This set was typically impressive, but make no mistake about it. The band was booed during the performance and as they left the stage. You don’t need to be a music critic to know that Mr. Vaughan and Double Trouble were getting the heck out of town after the festival wrapped.

But this story has a happy and fitting ending, given Stevie Ray’s formidable guitar skills. David Bowie and Jackson Browne both saw Stevie Ray play at various times during the festival. Jackson Browne offered Vaughan free recording time at his studio, during which time Stevie Ray & Double Trouble recorded their debut album, “Texas Flood”. Bowie invited Stevie Ray to play on his “Let’s Dance” album. That’s him playing on “Modern Love”, “China Girl”, and “Let’s Dance”.

One could argue that this “failure” – this very performance – took Stevie Ray Vaughan’s career to the next level. Was it not for this concert, would Stevie Ray Vaughan have become STEVIE RAY VAUGHAN, or would he have toiled forever in regional obscurity as a lone Texas bluesman? We’ll never know, and fortunately we’ll never have to ask.

The lesson: Failure can take you to great places.

2) Elvis Presley

Image: It’s never too late to re-invent yourself.

In his exhaustive and exceptional Elvis Presley biography, “Careless Love” [], Peter Guralnick explains that by the late 1960’s, Elvis’s music career needed a bit of a reboot. As the 1960s shifted from grey suits and picket fences to free love and war protests, Elvis was still cranking out those B movies, appearing in a total of 27 during the 1960s alone.

But in 1968, Elvis staged a most magnificent comeback, sparked by the success of a TV special we now know as the “’68 Comeback Special”. This show launched the beginning of what – in my humble opinion – became the richest and most exciting period of The King’s career. This stretch included residences at the International Hotel in Las Vegas, documented in “That’s the Way it Is”, as well as the “Aloha From Hawaii” (the first globally satellite broadcast live rock concert with a single performer), and “Elvis on Tour”, a dizzying and haunting documentary. Elvis was so on top of his game during this time that his rehearsals were performances, and those rehearsals came with costume changes.

The Vegas concerts at the International Hotel always had “A Listers” in attendance, and his extraordinary band included the legendary James Burton on guitar. Live shows from 1969 onward were sold-out events and not to be missed.

The lesson: It’s never too late to change your image and turn your career around.

3) Bruce Springsteen

Humility: Even the Boss looks up to someone.

By 1987, Bruce Springsteen was an enormously successful rock star. He had already released “Born to Run”, “The River”, and “Born in the USA”. His concerts typically began something like this:

Few were bigger than Bruce at the time. But in September of that year, when he had the chance to perform in a Roy Orbison concert at the Coconut Grove nightclub in Los Angeles, Bruce wasn’t about to miss out.

You can see him in this clip, sitting in the background, quietly playing rhythm guitar and admiring his hero.

He wasn’t alone. Other members of the backup band included Elvis Costello, Tom Waits, James Burton, and the rest of Elvis Presley’s legendary “Taking Care of Business” band. They also managed to cobble together some backup singers for the show (Jackson Browne, Bonnie Raitt, k.d. lang, and J. D. Souther, among others). Here they are:

All of these artists respected Orbison’s tremendous songwriting and performing abilities, and were happy to play alongside him. Everyone on stage was a successful star at the time. But I would imagine that they jumped at the chance to perform with Orbison as a way of acknowledging the influence he had on them, and on rock music. The all-star band’s attendance may also say something about Orbison’s character.

The lesson: No matter how successful you become, stay humble, because there will always be someone to admire.

But don’t take it from me. Listen to the Boss.

“It’s not every day that you get to sing harmony with Roy Orbison and play guitar next to James Burton. That’s a dream.” – Bruce Springsteen, backstage following the Black & White concert.

For reference:

Stevie Ray Vaughan

Elvis Presley

Bruce Springsteen + Roy Orbison

  • Many clips are available on YouTube, but this show is one to own and revisit often. Here’s where you can purchase the beautifully shot and recorded DVD:

Daniel D’Ordine, CFP® is the owner of DDO Advisory Services, LLC, a full service financial planning and investment advisory firm in New York City and Rhinebeck, NY.  He is a recovering musician.
Follow @DDOadvisory.

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