Josh Rosenthal Turns Every Challenge Into a Stepping Stone
Josh Rosenthal never intended to become a serial entrepreneur. Growing up in Fort Worth with a father who worked three jobs and was a graduate student, Josh witnessed firsthand what it meant to carry weight. But unlike his father, who traded time for money, Josh chose a different path: one where he, as an everyday athlete, and entrepreneur would become the twin engines he uses for moving his mindset forward.
“My dad worked three jobs and was getting his master’s degree all at the same time,” Josh reflects. “We were very poor, living in inner-city Fort Worth. I saw him doing admirable things, but as a kid, it doesn’t matter if it’s admirable or unethical—my dad wasn’t around.” This early experience shaped Josh’s approach to both entrepreneurship and parenting, driving him to create something that would give his own children more time with their father and a little margin for fun.
The entrepreneurial bug bit early. Josh’s last full-time boss was in 2005, when he was just 22 years old. The firing came with memorable feedback: “You’re the guy I would want in the room if there was a fire. However, you are the worst person to put together a plan if there’s not a fire.” That assessment proved prophetic. Josh thrives in crisis mode but struggles with routine operations. This self-awareness would later become his superpower.
The Eight-Year Cycle and the 18-Month Truth
Josh’s career follows a fascinating pattern: eight-year cycles with critical 18-month decision points. He spent eight years in music, eight years in coffee, and now finds himself deep into his trail running business phase. “I can do anything for 18 months,” he explains. “Unfortunately, I can only do things I like for that long as well.”
At the 18-month mark, Josh faces a choice: pivot away from what’s become mundane, or bring in partners to push through to the eight-year mark. “When I get to that 18-month point, either I pivot or I bring in partners if the business is meant to continue. I’ve learned that if I give up at 18 months, I leave stuff on the table.”
I’ve never considered this 18-month truth or 8-year cycle concept, but it resonates deeply. In Corporate America, my finish line was always 5 years—after that, I’d find myself bored and ready for the next challenge. Run Tri Bike will hit its 5-year concept mark in October 2025 and become a 5-year business in January 2026. Does that mean I’ll pull the plug? Doubtful, but life is unpredictable. I’m considering adopting Josh’s 18-month framework for new Run Tri Bike initiatives—maybe not 18 months exactly, but 3-month tests with specific goals that must be achieved to earn another quarter.
Running as the Ultimate Business Tool
Josh’s relationship with running began in 2010 with his first half marathon, but it wasn’t until 2012, after watching “Unbreakable” featuring ultrarunning legends like Anton Krupicka and Killian Jornet, that he found his calling. Running became his “cheat code to happiness,” completely eliminating the depression that had plagued him.
“Entrepreneurship is about your ability to carry weight,” he explains. “Running became my primary source of distributing that weight.” The metaphor extends beyond stress relief. Josh describes himself as having “the most torque you’ve ever seen from negative one to zero to one”—excellent at starting businesses and creating initial momentum, but unable to maintain a sustainable pace. This insight led him to hire strategically, covering his weaknesses while maintaining control of finances and brand.
I recognized running as a great escape from corporate stress, but I hadn’t considered it as a business tool. The parallels are clear to me now. Five years ago, I would have been devastated by missed workouts or DNFs. Today, I brush them off easily. I’ve realized nothing goes exactly as planned, and the ability to pivot is key to my company’s success—just like in running.
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Building Coffee Culture and Community
Josh’s coffee business phase began in 2012 with a roasting company, eventually growing to include wholesale distribution and four retail locations. The business earned recognition as one of the top 100 fastest-growing inner-city businesses in America, but Josh’s proudest moments came from the relationships he built.
“There wasn’t one thing at Labarba Coffee that I hired out for that I didn’t do myself at one point, except for roasting,” he recalls. This hands-on approach prepared him for the trail running business, another passion industry where people contribute more for love than money. “Coffee is such a passion industry—people making $7.25 an hour saying they’ll do this for the rest of their life because they love it so much. Trail running is that times 10.”
I’ve been hearing about “running culture” constantly, but I’ll be honest—I have no clue what it means beyond shoes, socks, shorts, and putting one foot in front of the other. Nobody owns running culture. There are pros, elites, mid-packers, back-of-the-packers, recreational runners, and everything in between. Imagine telling a recreational runner they’re not a “real runner” unless they wear certain brands or run specific distances? They’d rightfully tell you to get lost. I’m running, therefore I’m a runner. Simple. This mindset is what I bring to Run Tri Bike—building community without gatekeeping, whether someone’s chasing a sub-3 marathon or finishing their first 5K.
Trail Running: Where Passion Meets Purpose
Today, Josh runs Borderlands Trail Running, organizes races, and is developing the Wylder app. His team consists of 6-12 people, most with day jobs who contribute because they love the sport. “I get people who just want to give five hours a week to contribute to the business of trail running because they love it so much,” he explains.
Josh is building this team around what he calls “good hang.” These are people he feels safe with and enjoys working with. “Priority one is that we’ve got to be a good hang,” he says. “I have to look forward to every meeting because when I come around, I’m like a grandpa in the business. I want to hear about your family, have some candy in my backpack.”
The approach works because Josh has learned to match his creative entrepreneurial mindset with the fundamentals of business. “I tend to approach the fundamentals of business like a creative,” he explains. “I’m not a product guy. I’m a creative entrepreneur focused on finding a way forward.”
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The Tension of Running Your Running Business
Running a business centered on your passion creates unexpected challenges. “I don’t feel like I can give myself a season of not running when I’m in the business of running,” Josh admits. The pressure to maintain credibility while focusing on business growth creates constant tension.
He draws a parallel to sports commentary: “There’s never a moment where someone comes to Stephen A. Smith and says, ‘How’s your game?’ Every second that dude’s playing basketball, he’s killing his career. I continue to run because I love it, but to be a great technician, I can’t put in 80-mile weeks.”
This tension reflects a broader challenge for everyday athletes who build businesses around their passions. The sport that once provided escape and clarity becomes intertwined with livelihood and responsibility.
When I started Run Tri Bike, I thought I’d be running constantly. Turns out, I have to be far more flexible with training than I ever imagined. Was it worth trading a set schedule for skipped workouts? Absolutely. I’ve met incredible people who give me energy that compensates for running, cycling, or swimming less. I’m more particular about race registrations now—I don’t want to pay entry fees for races I might not be able to attend or complete. It requires more organization, but it’s worth the trade-off.
Lessons for the Everyday Entrepreneur-Athlete
Josh’s journey offers several key insights for athletes considering entrepreneurship:
Self-awareness is everything. Josh credits personality assessments—Birkman, Enneagram, DISC, Myers-Briggs—with helping him understand his patterns and hire accordingly. “Any business I tried to do totally on my own doesn’t do as well as when I’ve got somebody near me that has a dream,” he explains.
Embrace your natural cycles. Rather than fighting his 18-month attention span, Josh has learned to work with it, either pivoting or bringing in partners when needed. “I hire for my weaknesses, but I never give up oversight of finances or brand,” he says.
Find your weight distribution system. Whether it’s running, meditation, or another outlet, entrepreneurs need ways to manage the mental and emotional weight of decision-making. “Running enabled me to do other things in my life more effectively,” Josh explains.
Build teams around trust and enjoyment. Josh prioritizes “good hang” over pure competency, believing that people who genuinely enjoy working together will solve problems faster and more effectively.
Plant flags along the way. Josh visualizes his progress as planting flags on a mountain climb. “On a bad day, you can look back at these little markers. That flag was my 2025 race, that flag was the day I released Wylder.”
The Full Price Athlete Mindset
Josh’s upcoming podcast concept, “Full Price Athlete,” captures his philosophy perfectly. It’s designed for non-sponsored runners—the everyday athletes who pay full price for their gear and pursue their passion without external support. This mindset applies directly to entrepreneurship.
“Most people see an Amazon or Meta and think it happened overnight,” Josh observes. “The vast majority of businesses are super small and take a lot of work. There’s no overnight success. There are businesses that you all of a sudden heard but they’ve been going hard for 10 years.”
For Josh Rosenthal, every challenge, whether it’s launching a business, training for a 100-mile race, or managing the tension between passion and profit becomes a stepping stone rather than a stumbling block. His journey from the coffee shops of Salt Lake City to the trails of the American West proves that with the right mindset, every ending can become a new beginning.
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