“Started from the Bottom, Now We’re Here”: Lessons from Musicians-Turned-Entrepreneurs

Have you ever wondered why so many musicians aren’t satisfied to stop at just making music? Everything from clothing and sneaker lines to indie record companies and restaurants, musicians are taking control of their brand and branching out beyond just making music. And the things, many of them have been wildly successful at it.

Keen business minds are in no short supply within the music industry—and I’m not just taking about producers, marketers, and the other obvious candidates. It’s honestly no surprise that most musicians have an entrepreneurial streak. After all, breaking into the music industry is a risky venture onto itself, so the same people who had the courage and the drive to make it big are also naturally savvy when it comes to combining creative talent with commercial awareness.

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The music industry itself is going through a disruptive period, fueled by technology and the common desire of many musicians’ to break from established, often constricting, agencies. In fact, you’ll see that the first step in many musicians’ entrepreneurial journeys is often to create their own record label.

That’s not to say there aren’t a few failures in the mix (and yes, I want to talk about those too), but the music industry has become a sort of ideal training ground for sparking entrepreneurial growth. So, let’s take a look at some of the successes—and failures—of these musicians turned entrepreneurs and see if there are any insights to be gleaned (even for those of us who can’t hold a note).

Successful Musicians-Turned-Entrepreneurs

David Bowie: Early Adopter

Bowie is on this list because he was one of the first musicians to recognize the power of the internet. Always ahead of his time—both in his musical style and in his business ventures, Bowie started a tech company and an internet service provider (BowieNet) in the late 90s. He was also the first artist to sell a song online.

He was also a pioneer for artists looking to take control of their intellectual property. He started his own record label as a way to free himself from the restrictions of the corporate agency model. Extending that freedom to other artists, he launched a website for artists to sell their work outside of the traditional gallery setting. He also created “Bowie Bonds” as a way for fans to share in the ownership of his own creations.

Although BowieNet ultimately didn’t last, Bowie’s keen eye for upcoming trends and technologies made him an inspiring figure in the field of musicians-turned-entrepreneurs.

Gwen Stefani: Branding Expert

SoCal punk singer turned pop star Gwen Stefani first achieved star-status as the frontwoman for No Doubt. Pivoting into the fashion world, Stefani took advantage of her status as a red-carpet trendsetter to launch L.A.M.B., a brand inspired heavily by East Asian and Central American cultures.

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Stefani’s L.A.M.B. clothing line reflects her pop-punk roots.

Over the years, Stefani’s brand has branched out to include accessories, cellphones, and fragrances, transforming L.A.M.B. from a fashion line into a comprehensive lifestyle brand. She has also co-hosted and mentored young musical talents on the hit show, The Voice.

The strength of Stefani’s brand is its adherence to the pop star’s own aesthetic. Everything she does makes sense with the polished, yet punk-inspired image she has cultivated, making it easy to sell the lifestyle that the L.A.M.B. brand offers to fans.

Bono: Ethical Entrepreneur

The U2 frontman’s private equity firm, Elevation Partners, has invested over a billion dollars into various media projects, and he is also the owner of a 5-star Dublin Hotel, The Clarence, which he purchased with bandmate Edge. The Clarence was far from a luxury hotel in 1992 when the bandmates purchased the property, but a successful round of renovations drastically improved the hotel’s reputation.

However, the main focus of Bono’s entrepreneurial endeavors lies in the combination of his passion for helping others with his business acumen. Bono has been a driving force behind the philanthropically-motivated concerts, Band Aid and Live Aid. He also started a clothing line designed to help generate a stable income for impoverished workers in Africa. Although he’s a polarizing figure in his home country, Bono’s entrepreneurial legacy will likely be one of generosity, earning him a great deal of good will and allowing him to make connections with influential figures—including presidents and the pope—around the world.

Sean “Diddy” Combs: Renaissance Man

The list of Sean “Diddy” Combs’ accomplishments is long, and just one of his many business ventures is more than enough to qualify him for this list. The Harvard Business School grad formed Bad Boy Records, home to many big-name artists, including Notorious B.I.G. His clothing line Sean John is worth millions. He’s the CEO of Blue Flame Marketing and Advertising. He created a TV show (Making Da Band) and spearheaded the launch of television network, Revolt. He’s the face of Ciroc Vodka and takes home 50% of its profits. He’s also the owner of multiple New York City restaurants.

Diddy knows how to play the game, and he pays little mind to the people who criticize his rapping abilities, famously saying, “Don’t worry if I write rhymes… I write checks.” Diddy doesn’t mind the haters, and neither should you.

Jay-Z: Empire Builder

“I’m not a businessman. I’m a business, man.”

This line from rapper/producer/entrepreneur Jay-Z is the perfect encapsulation of his wide-ranging career. The music mogul’s record label, Rock-A-Fella, then grew to include a clothing line, an entertainment company, and a sports management firm. The Rock-A-Fella empire is as successful as it is far-reaching.

Jay-Z sold his stake in the company in 2004, after which he became the president and CEO of Def Jam Recordings, owner of a chain of sports bars, and partial owner of the New York Nets. Sports and music are obviously both a huge part of Jay-Z’s life, lending credibility to the saying, “Do what you love, and the money will follow.”

Failures from Musicians-Turned-Entrepreneurs

Those were just five of the many inspiring examples of musicians-turned-entrepreneurs, but now that we’ve talked a little about the successes and the factors that attribute to those accomplishments, let’s look at the duds.

Now, I’m not one for shaming people for taking a risk and failing, but you can often learn just as much (if not more) from the failures as you can the successes.

Although I’ve talked a lot about how the music industry fosters entrepreneurial thinking, not every musician is a natural-born entrepreneur, and it’s clear that some musicians have far more money than they do business sense. Case in point:

Ted Nugent

Before Nugent started his late-life career as a right-wing pundit, he was a failed entrepreneur. While Nugent famously never indulged in the drugs and alcohol like his contemporaries, he seemed to have another vice—bad business ventures.

Although his performances were some of the highest-grossing concerts of his time, that didn’t save him from financial ruin. Nugent went bankrupt in 1980, mostly due to a string of bad investments—including a failed mink farm, a herd of Clydesdales, and a hotel in Flint, Michigan. He did recover by the end of the decade and now prefers to spend his time hunting, running a “Kamp for Kids,” and contemplating a future run for political office (which we can only expect to do about as well as that mink farm).

If there’s a lesson to be learned here, it’s to always have a plan and a focus. If you don’t know anything about mink farming, don’t let someone rope you into investing in a mink farm. Make a real, detailed plan for how you’ll make a profit from your work.

Ja Rule

The ill-fated “Fyre Festival” has been fodder for late-night comedians and documentarians alike. Co-created with Billy McFarland, who already had one sketchy business venture under his belt, Fyre Festival was all smoke and mirrors. Musicals performances were cancelled before they began. Accommodations were more similar to something from The Hunger Games than the luxury resort experience that was promised. Guests were left with nothing to eat besides sad looking “cheese sandwiches.”

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Although he tried to distance himself from this Dumpster Fyre, his efforts backfired. Writing, “I truly apologize as this is NOT MY FAULT… but I’m taking responsibility I’m deeply sorry to everyone who was inconvenienced by this…” Ja Rule’s apology seemed more like an attempt to cover his butt than to make things right. A lesson for would-be entrepreneurs: Don’t lend your name to something if you don’t have the confidence in your product to back it up.

Soulja Boy

In 2018 “Crank That” rapper, Souja Boy, tried his hand at breaking into the crowded gaming hardware industry. Titled “SouljaGame Handheld and SouljaGame Console, the hardware was basically an expensive reskin of classic Nintendo consoles. The consoles came pre-loaded with classic titles and drop shipped from a Chinese company notorious for its sketchy (not to mention IP-infringing) wares. Soulja Boy’s foray into the games industry met its inevitable end just one month after launch when he was forced to pull the consoles from sale due to trademark infringement.

Moral of the Story? Come up with your own ideas, and properly vet your suppliers.


Who’s your favorite musician/entrepreneur? There are many that we didn’t cover here, so let us know in the comments!

Mike Speer Administrator
Chief Marketing Officer Michaels WIlder

Opinions are my own and not the views of my employer.

Chief Marketing Officer at Michaels Wilder and an entrepreneur since before the average person knew what that even meant, Mike has helped countless businesses build effective sales and marketing strategies. His philosophy is, “If you’re not thinking 10 years ahead, you’re already behind.” Mike’s content has appeared in Forbes Magazine, Inc. and Apple News. He has also been featured numerous times as a “Top 10 Writer” worldwide on the Q&A content site, Quora.

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Mike Speer Administrator
Chief Marketing Officer Michaels WIlder

Opinions are my own and not the views of my employer.

Chief Marketing Officer at Michaels Wilder and an entrepreneur since before the average person knew what that even meant, Mike has helped countless businesses build effective sales and marketing strategies. His philosophy is, “If you’re not thinking 10 years ahead, you’re already behind.” Mike’s content has appeared in Forbes Magazine, Inc. and Apple News. He has also been featured numerous times as a “Top 10 Writer” worldwide on the Q&A content site, Quora.

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