From 23 Jobs to CEO: Derrick Roe’s Bold Journey
By Mat Torres | Host of the Bold Moves Podcast
What happens when a restless spirit meets the confines of conventional work? For Derrick Roe, the answer wasn't overnight success—it was a long and winding path paved with lessons, breakdowns, and breakthroughs. Today, Derrick is the CEO of Allure Infinite Beauty Med Spa in Tempe, Arizona. But the road to entrepreneurship was anything but smooth. This is his story of grit, transformation, and the bold decisions that made all the difference.
(image generated via artificial intelligence)
Derrick Roe’s breaking point came on the side of a freeway after missing his son's soccer game for work.
The Early Struggles: 23 Jobs by Age 20
By the time Derrick turned 20, he had cycled through 23 jobs—none lasting longer than two weeks. “I thought I was lazy,” he said. But the truth was more nuanced. He was a visionary in environments that demanded conformity. He wasn’t unmotivated—he was unemployable by conventional standards.
Eventually, he settled into a linen delivery job with one goal in mind: to keep it just long enough to secure health insurance for his newborn. That short-term solution turned into a 12-year grind of 14-hour days, mental exhaustion, and missed family milestones.
The Breaking Point
One evening, after a brutal workday, Derrick sat at his son’s soccer game when his phone rang. His boss demanded he leave immediately to service a client. Derrick stood up, walked away from the field—and never forgot how that felt. “I felt imprisoned,” he recalled. Later that night, alone in his truck, Derrick made the decision that would redefine his life: he quit the next morning without a plan.
“That was the moment I said, ‘I can’t live like this anymore.’”
Unlocking Confidence: Toastmasters and Transformation
Public speaking terrified Derrick. But joining Toastmasters changed everything. Within four months, he was promoted three times at work. More importantly, he learned to communicate, connect, and lead. “Toastmasters was the catalyst that unlocked everything,” he says.
From Tattoos to Med Spa: Taking the Leap
Derrick first dipped his toes into entrepreneurship by working in permanent makeup and tattooing with his father. It was enough to spark a bigger dream. Partnering with his wife, a skilled esthetician, they acquired her parents’ modest skincare business and transformed it into a premier med spa.
Allure Infinite Beauty Med Spa now brings in over $100,000 in monthly revenue.
“We grew it from $21,000 a month to over $100,000 in just two years,” Derrick shared. But the climb wasn’t easy. They took out loans for laser equipment, learned to manage a growing team, and made bold, high-stakes decisions with little room for error.
Lessons in Failure and Forward Motion
For Derrick, failure isn’t the opposite of success—it’s part of the process. “Failure and success are the same path,” he says. “Until you learn the lesson, life keeps repeating it.” That shift in mindset allowed him to see each obstacle as an opportunity for growth rather than a reason to quit.
One of his favorite mantras comes from the show Brooklyn Nine-Nine: “I’m excited to see what life throws at me next.” That sense of openness to experience defines how Derrick now approaches every challenge.
Key Takeaways from Derrick Roe’s Journey
- Failure is a teacher: Learn from it, don’t fear it.
- Take bold action: Sometimes all it takes is 15 seconds of courage.
- Invest in yourself: Toastmasters, books, mentors—they change everything.
- Serve others: Help people get what they want, and you’ll get what you need.
- Just start: Don’t wait for a perfect plan. Take the first step.
Final Thoughts: Make Your Bold Move
Derrick’s story reminds us that transformation is available to anyone willing to act. You don’t need it all figured out. You just need to start. As he puts it: “Most people never do—they just think. But it’s in the doing that change happens.”
So what’s the bold move you’ve been putting off?
Connect with Derrick Roe
Follow Derrick and Allure Infinite Beauty Med Spa on Instagram:
Visit the spa in Tempe for advanced treatments and consultations. Their bold motto says it best: “Come to our place, we’ll fix your face.”
This article was adapted from a full episode of the Bold Moves Podcast hosted by Mat Torres. Listen to the full interview wherever you stream podcasts.
Mat Torres
Strategic Growth Advisor
Hi, I’m Mat Torres. I help people in business and growing their network—whether it’s protecting what matters or making meaningful connections. As a military veteran, Arizona native, and lifelong problem solver, I take a personal approach to guiding people through life’s big decisions. Outside of work, you’ll probably find me geeking out over sci-fi shows, playing the trumpet, acting, or tinkering with a software project. I also love watching Shark Tank because it inspires me to think outside the box.
