Why (and How) a Serial Entrepreneur Dropped His Lucrative Businesses to Pursue Music

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By Cynthia Johnson

From the moment we are old enough to speak, it seems that we are being pushed to pursue a career that can bring us financial stability. We live in a world where happiness comes second to income, or is completely dependent on it. I am guilty of this myself.

It is so easy to be constantly busy and to forget about what we really care about. Meeting and working with people that have taken a leap to pursue their dreams against the odds (and leaving success behind to do so) has always inspired me to take risks in my own life. A friend of mine, Dane Maxwell, did just that when he left his successful businesses to build a career that was truly calling to him.

A few years ago, Maxwell started The Foundation, an entrepreneurial lifestyle movement that helps students grow successful software businesses. Before that, he created seven software products and nine other businesses. One of his most successful was Paperless Pipeline, a real estate transaction and commission management system.

"I thought making lots of money would make me feel valuable, so I got really good at it," he said, reminiscing about a record week in 2010 when he made $40,000. I am sure this is a feeling that most of us can relate to.

Pursuing a Passion

Now, Maxwell has decided to walk away from his thriving businesses to pursue his true passion: music. Ironically, the principles he used to build six- and seven-figure businesses are the same he used to break away from.

"It was fun for the first eight years, but then I felt like I was dying in business," he said. "Sure, I made money while I wasn't working. But I got great at something I cared little about."

The transition from entrepreneurship to music has not been easy, but like many entrepreneurs and artists, Maxwell isn't afraid to wear his heart on his sleeve. "[Making music] has felt impossible this entire time," he said. "I woke up every morning for eight months feeling hopeless. I cried for maybe an hour a day just to get through the overwhelm, but thankfully I got my heart back in the process."

Music is something that followed him throughout his life but always lurked somewhere in the shadows. His first seven-track EP was released in October, and talks about the fear of following your dreams and finding value in yourself and the spark inside of you. Though he jokes each song on his first EP is "terrible" and that he "just wanted to get the first one out of the way," reception has been positive and his next album is due for a February release.

Understanding Internal Limitations

Maxwell believes success is limited by a subconscious lack of self-confidence and inherent fear of defeat. In the food chain of prosperity, success grows from failure: Failure leads to experience, experience leads to progress, and progress leads to success. Maxwell wears his own failures like a badge of honor. One of his biggest mistakes was an impulsive $12,000 website purchase that Google AdSense shut down within weeks. This left him with $123 in his bank account and a desire to flip his fate.

Through trial and error, he found a way to predict the success of his companies before building the product. These are the principles The Foundation was founded upon. It teaches others how to break out of their comfort zone, eliminate insecurities, realize their full potential and focus on offering a product that solves a specific issue. "If I could do it, and I'm not really built for business, then I think anyone can," said Maxwell. During the six-month program, students learn to build a lucrative software business that, upon completion, has at least 10 paying customers.

His segue from business to music was a calculated one, and he had to surpass personal limitations before taking action. He participated in a music program at the Berklee College of Music in Boston, where he found inspiration in the musicians around him. Unlike business, creating art wasn't outcome-oriented nor was it measurable. This was a challenging change of pace. Here, students practiced for the sake of practicing and for the love of the craft, not to get something.

Getting Good to Ensure Long-Term Success

"There's a difference between being passionate about something and being good at something," he says. "I'm passionate about music; I'm good at creating businesses." This is the crux of what his EP is about -- finding room to breathe in a cluttered, result-driven industry. For Maxwell, the days of wanting nothing more than a passive income are gone. Now, his results are measured (or not) on how deeply happy he is doing work that he loves.

The fate of The Foundation and his other businesses are in the hands of their successors, but Maxwell believes he's built well-oiled machines that will continue to succeed long after he's gone.

"People were very encouraging with my desire to pursue music, largely due to my success with my businesses," he says. "When I was 22 and just starting out, things were much different as many people were telling me to quit what I was doing and get a job. These days, I've proven to those people (and more importantly to myself) I can achieve whatever I put my mind to. So people encourage whatever I'm doing now."

Cynthia Johnson is co-founder at Ipseity Media, previously managing partner at RankLab (acquired by AAC Holdings, Inc. in 2015).