The Gambit

From Totally Broke to Multimillionaire: How Jen Sincero Pivoted from Rock Star to Bestselling Self-Help Author and Success Coach

The author of 'You Are a Badass' used to front multiple rock bands. Now, she aims to teach people to unlock their potential for confidence, wealth and success.
From Totally Broke to Multimillionaire: How Jen Sincero Pivoted from Rock Star to Bestselling Self-Help Author and Success Coach
Image credit: Heather Gildroy
Jen Sincero
Entrepreneur Staff
Associate Editor
14 min read

In this series, The GambitEntrepreneur associate editor Hayden Field explores extraordinary risk, speaking with successful people about how they overcame unusual obstacles to found a company or switched industries entirely in a "career 180."

Jen Sincero felt panicked.

It was August 2011, and she had a book due in about a month. An entire book. Cover to cover. Hundreds of pages.

So far, she’d barely written the introduction.

That’s because she hadn’t yet found her perfect place to write: a glass house on a hill in the countryside, surrounded by nature. Sincero only started to search for her ideal creative haven at the last minute, messaging friends, asking acquaintances and checking Airbnb. Nothing was panning out, and she’d waited so long that most hotels were booked. Panicking, Sincero worried she’d have to admit the ultimate defeat: return to write the book in her old room at -- gasp -- her mother’s house.

But one day, she whipped herself into a more positive mindset with one thought: How ironic is it that I’m about to sit down and write a book on manifesting your desire and believing it into truth, and I don’t believe I can find a place to write it?

Sincero sent one last email to her colleagues asking for help finding somewhere to write, then tried to do what she does best: Manifest it. She imagined she’d already found the property, and she acted how she would if that were true. That night, she treated herself to a celebratory sushi dinner -- and returned home to an email from a friend offering access to a glass house on a hill about an hour east of San Francisco. She says that email made her hair stand on end, and she took it as a motivational kickstart.  

Sincero stayed in the glass house on the hill for two months, kept company only by the horse and two goats living on the property, and wrote about how to change your mindset to change your life. The book, You Are A Badass: How to Stop Doubting Your Greatness and Start Living an Awesome Life, went on to sell millions of copies, was translated in close to thirty languages and become a number-one New York Times bestseller.

But before Sincero cracked open the business of self-help and success with books, speeches and coaching, she was living a much edgier lifestyle -- as a singer in multiple rock bands. Here’s her story.

The Detour

In the 1990s, Sincero remembers the record industry as comparable to the show Mad Men. Mountains of cash were being thrown around. Drugs and prostitutes were sent to label executives in exchange for listening to a band’s record. Women in the industry were few and far between. And a twentysomething Sincero bore witness to it all as a marketing employee at a top record company.

She and a co-worker, Sara Rotman, wondered why no one had written a movie about the glitz and grit of the record industry, so they decided to do it themselves. Their screenplay would center around a fictional band called Crotch, so the next logical move in their minds was to take it upon themselves to make that band a reality. Sincero was no stranger to hard rock and heavy metal -- she created ads for the record company and even worked on a tagline for one of Ozzy Osbourne’s albums -- but she knew just three guitar chords. Nevertheless, she picked up a guitar and enlisted her brother as drummer. They figured they’d see what they could get away with -- and since there weren’t many female-fronted bands in those days, Crotch ended up with more fans than they predicted.

Image credit: Courtesy of Jen Sincero


Rotman wrote a song about dating in New York City called “Sew Me Up, I’ve Had Enough.” Sincero says she wrote an essentially autobiographical song called “No Experience Necessary,” the lyrics being:

“I am busted, I thought for sure

I’ve never done any of this shit before

But they swallowed it whole

They gave me lots of money and my own phone line

They didn’t even check a single reference of mine

Now I’m bigger than you

I’ve got a Cadillac

No experience necessary”

Infighting -- the cause of death for an innumerable amount of many musical groups -- led to Crotch’s disbandment, so Sincero moved on to Albuquerque in 1996, where she started the Jenny Clinkscales Band with a local singer/guitarist. She also launched a solo effort, 60 Foot Queenie -- which she describes as a mix of pop, rock, dance and disco -- with song titles such as “Bomb” and “Dirt Gravel Grass.” Sincero had discovered she was a better songwriter than guitarist, so she gravitated towards being a frontwoman and surrounded herself with “excellent musicians who didn’t want to write music.”

A few years later, the Jenny Clinkscales Band broke up due to another rock ‘n’ roll trope -- a band love story gone wrong. After Sincero ended her relationship with her drummer, she knew she needed a change of scenery. She jumped on a plane from Albuquerque, bought a car in Austin and drove to Los Angeles.

A newly single Sincero arrived in L.A. on Valentine’s Day in the pouring rain, with the key to a tiny studio apartment. She felt completely isolated. I’m 35, she thought. I’ve got to get my shit together.

The Breaking Point

Sincero’s move to L.A. in 2000 triggered a deep depression. She had just broken up with someone she was “deeply in love” with, she had no idea what to do with her life and she was completely and utterly broke. She still wanted to pursue music, but she also needed a significant increase in cash flow. Sincero had experience writing ad copy at the record company, so she began freelancing. Writing was the only thing she knew how to do to make money.

The freelance gigs didn’t pay much, but they did lead to a casual offer for a book deal. At a cocktail party, Sincero met a woman who had started her own small publishing company. She suggested Sincero write a quasi-autobiographical story called Don’t Sleep With Your Drummer and offered her a contract, saying, “If you had an agent, they would tell you not to sign this, but this is all I’ve got.” Sincero accepted. It was her first foray into writing books.

Sincero was as broke as ever. When she calculated her hourly rate for time spent writing, the result was uncomfortably close to zero. Sincero kept taking on more writing gigs, but no matter how much she worked, she seemed to barely break even on her cost of living. The artist and musician in her didn’t want to focus on making money and the “unholy dollar,” but her lack of it meant she thought about money every five minutes.

Is this really the best you can do? Sincero asked herself. So, though she was a staunch skeptic when it came to all things self-help, she begrudgingly decided to give it a shot.

Her first foray into self-help was reading Eckhart Tolle’s The Power of Now. But muddling her way through the text wasn’t easy. Sincero found the words and ideas to be profound but also advanced and confusing. She constantly felt like she had to lie down with her arm over her eyes, and she compares reading the book to “eating a brick.” But she knew she needed to make a change in her mindset, so she forced herself to follow through.

After finishing Tolle’s book, Sincero took on others in the self-help genre. She read about positive thinking, meditation and money. She learned more about the theory that mindset drives people’s experiences, and when she asked experts for proof, they told her to test it out herself.

Sincero was still extremely skeptical, but she kept attending coaching seminars with cheesy titles where she had to wear a nametag, hug her neighbor, shout things and high-five people. Everything she tried felt unbearably cringeworthy at first, but she bit the bullet anyway. What she had done up until then hadn’t worked, and as the old adage states, “Insanity is doing the same thing over and over again and expecting different results.”

Slowly but surely, Sincero started to recognize the lies she told herself daily -- things like the idea that she would never be wealthy, that being broke was the norm, that she wasn’t successful. Once she started committing to the success strategies she learned in the books and meetings, she started to see changes in herself -- and her circumstances. After a while, Sincero realized she had to actively make the decision to start making money and reach success -- otherwise, there was no chance it would happen.

The Turnaround

To truly change her life and increase her bottom line, Sincero felt she’d have to not only step outside her comfort zone -- she’d have to sprint so far from it that she felt like she’d wet her pants from fear. So in 2007, that’s what she did.

Sincero hired a private coach that specialized in helping female entrepreneurs with their finances, charging the woman’s fee -- which was a quarter of Sincero’s annual income at the time -- to her credit card. “[It was] the most terrifying thing I’ve ever done,” she says.

The coaching panned out, and -- by doing everything she was told and “working [her] ass off” -- Sincero says she tripled her income within three months. Since she was a twice-published author and knew how to write and sell a book, she set up an online business coaching women on writing and selling book proposals. She networked at conferences and events and added a sales page for a nonfiction book proposal course to her website. But because Sincero had built up her street cred through fronting multiple bands, she was worried about losing her “cool” factor.

“Isn’t there a cooler way to do this?” Sincero remembers asking her coach.

“Not in online marketing,” she replied. “You have two choices: You can be broke and cool or rich and cheesy right now.”

“All right, rich and cheesy,” Sincero said. “I’m in.”

Slowly but surely, Sincero brought more of her authentic voice and personality into her course, newsletter and writing. She’d already been informally coaching women through a local entrepreneurial think tank, but she started to work as a “success coach” in her own capacity around 2008. Over the next eight years or so, she would go on to work with hundreds of clients -- mostly remote via phone calls -- on how to achieve confidence, wealth and success.

In spring 2011 -- 11 years after Sincero had arrived in L.A. -- the city of angels still hadn’t captured her heart. Plus, her cat had died, so she figured it was as good a time as any to say goodbye to the city for good. She’d been flirting with the idea of a book teaching people how to discover their inner badass; she wanted to use the same authentic, curse-word-heavy, no-bullshit spin she applied to online marketing to upend the self-help industry. So she made another change. Two weeks before a planned family vacation to Italy, she decided to make the trip open-ended and scrambled to make the appropriate arrangements. Sincero says being a “laptop entrepreneur” wasn’t common at the time, and she worried her business would tank. She went for it anyway.

Image credit: Jen Sincero


During her months of nomadic travel, Sincero shopped around her proposal for her book idea. But You Are a Badass received a resounding no from everyone she reached out to -- including past publishing collaborators. The companies argued she wasn’t saying anything new, but Sincero didn’t claim to. What she brought to the table was sharing the ideas in her own unique way.

The Leap

Finally, a publisher called Running Press took on the proposal. Sincero was thrilled at first, but they worked much quicker than most publishers she’d worked with in the past. They gave her eight months to write the first draft, so naturally, she waited until the last month to write it in the glass house on the hill.

Image credit: Jen Sincero


After sending it in, Sincero says she didn’t hear much for three months and then -- the weekend before the book was to go to print -- received a message saying it was good to go with a few tweaks.

“I’m not putting my name on my rough draft,” she remembers telling the company. She says they told her there was no time to rewrite, so she explored her options -- returning her $35,000 book advance, writing a new contract stipulating that she owned the rights to the material or self-publishing.

“Nobody else will publish this book,” Sincero remembers her agent telling her. “If you don’t go with these guys, I can’t get you another publisher.”

No matter what the outcome, Sincero wouldn’t put her name on something she wasn’t proud of. She looked into self-publishing, but she was terrified that she wouldn’t have the discipline to finish the book without a hard-and-fast deadline. “It was the valley of darkness,” she says, but she stuck to her guns.

Finally, she says Running Press came back to her with a new offer: three-and-a-half weeks to make all the changes she’d like. Sincero took it.

You Are a Badass published in April 2013, and its subsequent sales earned the lemon-colored book a new nickname from Sincero: the “yellow snowball.” When she first made the New York Times bestseller list, her agent broke the news over the phone. Sincero, who calls the list the “holy grail” for writers, celebrated by going to see Elvis Costello and Steely Dan play at a casino in New Mexico.

Image credit: Jen Sincero


She continued coaching and wrote another book, published with a green cover this time, which applied her “badass” teachings exclusively to the world of wealth. The idea of changing her money mindset propelled Sincero into the self-help world in the first place, so she felt she owed it its own volume -- plus, as someone who saw herself as “completely committed to poverty” until her 40s, she had a lot more to say on overcoming mental obstacles.

The Next Step

As for Sincero’s current day-to-day? She’s living the good life, dedicating it to spending time with people she loves, “laughing [her] ass off,” collaborating on screenplays and comedy projects, planning a potential online money success course, renovating a home and picking out tile.

She’s also working on a new project called You Are a Badass Every Day, set for release on Dec. 4, 2018. The idea came from her readers: They experience a peak in excitement when they see an inspirational person speak or read a self-help book, but after a while, that motivation wanes. Sincero's new book will have daily strategies for keeping the momentum going and constant reminders of your inner “badass.”

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