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Entrepreneurship in America: How a Father-Daughter Motorcycle Project Created a Family “Legend”

Gwen Jessup and “Legend” | 1982 Harley-Davidson FXR

In the summer of 2019, a father and daughter set out to rebuild a 1982 Harley-Davidson FXR. Their project led to a prized industry award and once-in-a-lifetime experience, strengthening their bond, building confidence in her own two hands, and passing on the passion, art, and expertise that lives on in America’s iconic motorcycle culture.

Gwen Jessup’s love of motorcycles began in childhood.

I was six years old the first time I took a long motorcycle ride with my dad. I remember how putting on the helmet changed me instantly. Sitting on the back of the bike, holding on tight, feeling the bike rumble beneath our seat as we picked up speed, and watched town fade into fields and rolling hills — it was incredible. It was like the first time I could really hear my own thoughts. From then on, I’ve been hooked.

Gwen’s immersion into the world of riding and repairing Harley-Davidson motorcycles started with spending time in her dad’s sales and repair shop which she refers to simply as, “the shop.” The shop is a no-frills kind of place — a huge warehouse in an industrial neighborhood, hot in the summer, and cold in the winter, protected by a chain-link fence. The shop’s business name is Team Dream Rides, headquartered in Stockton, California.

By age 15, school was not an activity Gwen enjoyed nearly as much as motorcycles. With her parents as the primary support system for igniting hopes, dreams, and aspirations she reached an inflection point. Last summer, she and her dad, John Jessup, had a heart-to-heart about school and her future. Together they set goals that work within the context of their unique household. Her dad proposed a project they could do together — rebuilding an old Harley-Davidson motorcycle. The project became a lesson in design, mechanics, and entrepreneurship. With curiosity and encouragement to experiment, Gwen found a match between spending time with her dad, a desire to learn the trade of motorcycle mechanics, and developing skills she could leverage in the future.

Schools in Gwen’s hometown have little to offer in the way of high-quality STEM experiences. Enrichment programs are few and far between. The City of Stockton survived bankruptcy and has struggled to rejuvenate civic life following decades of setbacks and a reputation for gang-related violent crime. Time Magazine identified Stockton as one of the hardest-hit American cities in the Great Recession[1]. Stockton is not the kind of place where girls expect to win a major award in a competitive, male-dominated industry and then ride off into the sunset. Far from the sparkle and shine of Silicon Valley’s wealthy tech suburbs, stories of long-term unemployment are more common in Stockton than stories of entrepreneurial success. Gwen is part of a generation of youth creating a new definition of success by taking creative action to build and innovate, designing for durability, as well as maintenance and repair.

Role models for innovation and entrepreneurship
The Jessup family business revolves around Harley-Davidson motorcycles. From an early age, Gwen experienced the joys of motorcycle touring and witnessed the awe-inspiring freedom of the open road from the back of her dad’s bike.

“My favorite ride was through the Great Smoky Mountains in Tennessee. It is lush and breathtakingly beautiful,” said Gwen.

As an entrepreneur, Gwen’s dad is always on the lookout for ways to integrate artistic nuances into his work as a custom motorcycle builder and mechanic. Striving to be the best at whatever he does, he’s become one of the most highly regarded builders in the industry, traveling all over the country, including a work trip to Tennessee, where he brought Gwen along. With an artist’s eye for design, he builds finely tuned, mechanically sound bikes that fetch top dollar and are frequently awarded high praise from peers in the motorcycle community. Gwen is no stranger to reframing problems in unexpected ways and seeing opportunities where others see difficulty, a trait she seems to have adopted from a lifetime of watching her dad at work.

Entrepreneurs succeed with a drive and passion to see their ideas through
“To me, old and rare is like new and expensive for most people,” said Gwen as she explained the story of how she and her dad acquired their project bike, a 1982 Harley-Davidson FXR. “My dad found her on eBay and paid one of his buddies to pick her up and deliver her to us. She was mostly stock and hadn’t run in 20 years. She was just sitting collecting dust in an elderly man’s garage.”

Restoring a bike to top performance riding-condition is no small undertaking. Just ask the community of riders and tinkerers. Restoring a motorcycle takes patience, skill, and even then, the task can feel overwhelming.

For several weeks, 15-year-old Gwen woke at 4:30 am to arrive at the repair shop early with her dad, before business hours. They worked for a few hours each day, sometimes both morning and night, after business hours to complete the project. She was up for the hard work and long hours, “it wasn’t until after we finished that I learned it usually takes about a year to rebuild a bike.”

Gwen describes the process of restoring the bike with equal parts anguish and enthusiasm. “We stripped everything off the bike. We took it right down to the frame. The only parts we salvaged were the carburetor, the engine cases, the tin set cases, and an OEM seat. Everything else was bought new.”

An old Harley-Davidson motorcycle being restored by a father-daughter design team in Stockton, California.

Gwen thought through every detail of the project, from handlebars to wheels. The rebuild process gave her a better understanding of practical design principles, and differences between products. She focuses on craftsmanship and quality. “While we were building, I felt like I was constantly thinking. Rebuilding is complicated. There are so many parts and decisions to make,” said Gwen. “My dad would ask me questions about things like handlebars and wheels. Did I want T-bars, straight, or with forward bends? Did I want to customize it for fit, or performance? I had to really think over the options. I spent a lot of time thinking about rims. Ultimately, I went with 90’s performance rims that are light and look good. They were ‘the thing’ before carbon fiber rims today.”

Listening to Gwen talk about tires and rival brands is like hearing a coach describe aspects of their favorite equipment. “For good tires, you typically have a choice of high mileage or high performance. I choose something in-between. They’re designed for mileage and performance. Good tires are essential.” She’s a persuasive communicator, using relatable, concrete examples combined with a lot of enthusiasm.

There were stages of the rebuild that involved advanced technical skills. Gwen and her dad shared the task. He would handle critical components while she spent time polishing, cleaning, and detailing the parts right by his side.

“When I walked away from the project at the end of the day, I’d find myself looking toward the future. I was so eager to finish the bike. It’s so much work to put it together, but even when it’s a quarter finished or half-finished and you see the progress you’ve made, it’s such a relief to see that your work makes a difference. It makes things seem more achievable. The payoff comes later and that’s ok. But when you finish, it’s like this thing, this creation, has a piece of your soul, it’s a part of you and you’re a part of it.”

“When we started, I had no idea what we were doing,” said Gwen. “When my dad said we were going to rebuild a bike in a month, I wasn’t really sure what to think. All I knew was this was something he really wanted to do with me, and he was super excited for us to get the bike ready for the annual Sturgis Rally.” His positive attitude and enthusiasm gave Gwen the confidence she needed to trust in the process and work toward achieving their goal.

Entrepreneurs understand what their communities value
The Sturgis Motorcycle Rally is a longstanding American motorcycle event held annually in Sturgis, South Dakota. The event spans ten days starting the first Friday in August. In 2019, Sturgis attracted 490,000 people. The first rally was organized in August 1938. It’s been held every year, with the exception of one year during World War II due to gasoline rationing. Today, many of the attendees bring along their families, driving campers towing motorcycle trailers across the country. Among a half million people, Gwen and her dad found a way to stand out from the crowd. Their project bike won a “Best of Show” award at the Sturgis V-Twin Visionary Performance Bike Show.

Gwen met a family friend at the rally who commended her for joining the event. The woman made a passing remark that Gwen would be one of the youngest riders, and with her bike, she is “sure to become a legend.” This stuck with Gwen. At 15, she was not old enough to join in the ride, and instead seized the idea of legendary by naming her bike, Legend.

Her ambition and enthusiasm for Legend are palpable, “This bike is Legendary! One of my favorite details is the gold pinstriping brushstrokes done in 1983. All of those details are original. Out of all the Harley’s in the world, there’s nothing like mine,” said Gwen.

Entrepreneurs can be teachers, sharing skills and knowledge
“What I like most about working on bikes is that it’s like a puzzle, and you can always improve,” said Gwen. “I think I like working on bikes almost as much, or more than I like riding them.”

Restoring a motorcycle to its former glory with durable enhancements gave Gwen an opportunity to practice solving a complex problem, overcome fears about the limits of her abilities, and to accept disappointments and frustrations as part of the process. It strengthened her positive, “can-do” mindset. Spending time with her dad, working toward creating something unique aligned their purpose. The results are lasting memories and an experience she can build on for her future.

“I am beyond grateful not only for this “best of show” plaque but more so for the best father in the world who tirelessly worked with me to make this bike the coolest, best, baddest bike I will ever see,” said Gwen.

Entrepreneurship is a path for girls to become game changers
Gwen started going to the shop when she was two and has spent countless hours there after school, on weekends and during the summer. She describes it as her second home. The experience has offered a way to avoid a common adolescent trap of comparing herself to others or focusing on what she doesn’t have. Instead, she’s focused on her goals, which include graduating early and starting college next year while working for the family business.

Working with her dad on a big project changed Gwen’s perspective about him. “I learned my dad is a perfectionist. I learned that my dad expects the highest standards and even when I met those standards he expects more,” said Gwen, eager to rise to the challenge.

Questioning the status quo, existing societal norms, and expectations are family values
Managing expectations is a delicate art form. Father-daughter relationships are complex, dynamic, and multidimensional. Research suggests the best outcomes happen when parent expectations evolve to meet a daughter’s needs for personal growth and are buoyed by supportive interactions[2]. This is no small achievement when combined with the needs and demands of time and attention for other members of a family and work obligations.

Teens are charged with managing expectations for socially constructed roles, behaviors, and activities that society considers appropriate for boys and men, or girls and women. It’s hard to know where you fit when your age is somewhere between childhood and adulthood. Girls are often directed toward what they should do rather than what they should not do[3]. The opposite applies to boys. Gwen and her family have carved out a space for her in a biking culture that has traditionally been a male space. Gwen has found a way to break down social barriers and explore new territories. She’s making it work in her favor.

Entrepreneurship and innovation are a foundation for the future
Gwen’s story shows the infinite learning possibilities beyond the walls of a traditional classroom. She applies the experience as a life lesson in navigating uncertainty — what to do when you don’t know what to do is a scenario people face repeatedly throughout a lifetime. While some are paralyzed by uncertainty, others dig-in, and focus on what matters to them. Gwen and her family set about creating something with the skills and resources available, regardless of cultural norms or what others might think or say. The opportunity to acquire hands-on life experience, use critical thinking, and apply reasoning principles, results in remarkable outcomes, creating a long-lasting positive ripple effect.

Educators, schools, parents, and companies can create entrepreneurial learning environments for youth to lead and develop necessary skills for their future
The world of work is changing fast. Gwen’s experience is an example of how to engage youth in areas where STEM programs and the workforce may not be equal to other parts of the country. Her story shows how trusting young people to take responsibility and a leadership role leads to ideas and innovation, developing the skills and capacities needed to succeed in the world at large.

[1] Time Magazine: America’s Most Miserable City Emerges from Bankruptcy

[2] Parenting Matters: Supporting Parents of Children Ages 0–8

[3] Comparing Prescriptive and Descriptive Gender Stereotypes About Children, Adults, and the Elderly




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Joanne Gouaux

Joanne Gouaux

Social Entrepreneur. Advocate. Doer. Fan of all things neuroscience. Promoter of thoughtful reflection. Believer in synchronicity.

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