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Organizing the Entrepreneur Podcast, Episode 10: From Stay-at-Home Mom to Law-Changing Entrepreneur: Jen Benningfield's Inspiring Journey

Writer: Janelle Hawk AzarJanelle Hawk Azar

Scott & Jen Benningfield, former owners of Louisville's first pedal bar bike business.
Jen & Scott Benningfield - Former Owners of The Thirsty Pedaler

Ever been stuck in a waiting room, flipping through a magazine, and suddenly, BAM! An idea hits you that changes everything? That's exactly what happened to Jen Benningfield. In Episode 10 of the 'Organizing the Entrepreneur' podcast, we dive into her incredible journey. It all starts with how a simple article about a pedal bar bike turned a stay-at-home mom into an entrepreneurial powerhouse.


But this isn't just another business story. Jen didn't just build something; she reshaped her community and even changed state laws! This is a tale of resilience, real-life hustle, and the sheer power of a single idea. Get ready to be inspired, because Jen's story proves that anyone can turn a dream into reality.



A Family of Entrepreneurs


Growing up, she saw firsthand what it meant to run a business. Jen's father and grandfather were entrepreneurs, teaching her the value of hard work and the, shall we say, complexities of family businesses. Jen's dad ran a tile business along with his brother and father. She saw the physical demands, the dedication, and the behind-the-scenes effort. But she also learned that family businesses can be tricky, navigating relationships and emotions. Jen's stepdad also owned a business with his son, and she witnessed the tensions that could arise. This experience deeply influenced Jen and her husband Scott’s decision to keep family and business separate, except for their partnership.



A Spark of Inspiration


The idea for their pedal bar bike business? It came from a magazine article at the pediatrician's office, of all places! Jen was waiting, like any young mom, and spotted an Entrepreneur Magazine. Inside was an article about a pedal bar bike, something completely foreign to her. She was immediately fascinated. She tracked down the founder, the US distributor for Petal Pub, who gave her some advice but emphasized that she had to figure out the specifics for Kentucky.


"Louisville needs this!" she thought. It took about a year to convince her husband Scott, and they even faced skepticism from family. But Jen was determined. She told Scott, "When you see this bike rolling down the street and we're not part of it, you'll regret it."


The startup cost was manageable, about the price of a car, and they were willing to take the risk.

Jen Benningfield, former owner of The Thirsty Pedaler, driving the pedal bike bar.

Balancing Family Life and Building a Business: The Real Deal


Jen was a stay-at-home mom with two little girls when they started. Scott was in the military, traveling a lot. How did she juggle it all? Honestly, it was a wild ride. They started with one bike, operating on weekends when Scott was home. She brought the kids along whenever she could, made tons of phone calls, and just made it work. "You just figure it out," she said. "Looking back, it's hard to believe we did it. But when you're passionate, you make it work."


She and Scott divided tasks based on their strengths, with Jen handling scheduling and customer service, and Scott taking care of the mechanical side. They set boundaries, too, making sure they had time for family amidst the craziness of running a business.


Jen, a self-described micromanager (or, as we prefer, "detail-oriented"), had to learn to let go a little. They set aside specific times for work, ensuring the rest was dedicated to family. They were all about "fake it till you make it," with fancy shirts, business cards, and that separate phone line to look professional.



Changing Laws and Revitalizing Downtown: A Community Impact


One of Jen's biggest achievements? Changing Kentucky's alcohol laws to allow people to bring their own drinks on the pedal bar bike. It was a long, hard fight, but they didn't give up. They found a state congressman who believed in their cause, hired a lobbyist, and ultimately went directly to the state officials. "They called us 'persistent sons of bitches,'" Jen laughed, "but we didn't give up." They even got to present their case to the state congress!


And it wasn’t just the law change, they really made a difference in their community. Jen said, “We would have bar owners saying, ‘Thank you, thank you. We had to hire more staff because of you.’” Their business brought life back to downtown Louisville, an area that had been struggling. People who hadn’t been downtown in years were having a blast on the bike, then returning to their favorite bars. “It was just a new complete concept of something to do,” Jen said. “It was a fun way to get together with your friends. You're drinking, you're peddling, you're seeing downtown close up.”



The Decision to Sell and New Beginnings: A Shift in Priorities


After 12 years, Jen and Scott decided to sell the business. COVID-19 and civil unrest in Louisville took a toll, and they were ready for a change. “We had to protect our customers to the best of our ability,” Jen said. They were also ready to reclaim their weekends.


They took a DIY approach to selling, listing the business themselves on bizbuysell.com and providing extensive training to the new owners. When it comes to selling your business, “Know your numbers,” Jen emphasized. “Always know your numbers.” They also created a comprehensive Google Drive with all the information the new owners would need to help them know and run the business.


Now, Jen's diving into a new adventure in medical supply sales. "I can build my own team anywhere in the country. And you can make great money if you sell the products and you work when you want to work," she said, her excitement palpable.


She’s selling amniotic membrane skin grafts, a far cry from pedal bar bikes, but she’s loving the flexibility and the chance to help people. “I just don't want to look stupid,” she laughed, admitting she’s out of her comfort zone. But she’s confident she’ll learn and grow.


Lessons Learned and Future Goals: Embracing the Journey


Looking back, Jen wishes she'd embraced social media more. She also emphasized the importance of knowing your strengths and weaknesses, and not being afraid to step outside your comfort zone.


She recommended the book "Discover Your Clifton Strengths," which helps you understand your personality traits. "Being OK with who you are, all your flaws and everything like that. It's OK. You don't have to be perfect," she said.


Her biggest piece of advice? "Just try to be positive. And if you fail, it's OK. Just keep going."


Jen's story is a reminder that you don't have to have it all figured out to make a difference. It's about passion, persistence, and a whole lot of grit.


Jen Benningfield, former owner of the Thirsty Pedaler, Louisville's first pedal bar bike chatting with people on the street.
Jen Benningfield chatting with bystanders about the pedal bike bar.

Tools and Strategies for Success:


  • Grasshopper (Phone System): This service allowed Jen to have a separate business phone number that routed to her personal phone, helping her distinguish between personal and business calls.

  • QuickBooks (Accounting Software): Jen emphasized the importance of knowing your numbers and using QuickBooks to generate financial reports like profit and loss statements.

  • Google Drive (Document Storage): When selling the business, Jen created a comprehensive Google Drive containing all the necessary information, permits, procedures, and training materials. This highlights the value of centralized digital document storage.

  • Automation: The use of automation for booking tours, sending confirmations, and processing payments was mentioned. This shows the value of using technology to streamline processes



Key Insights and Q&A:


  • Know Your Strengths: Figure out who's good at what, and stick to it. Don't try to be good at everything.

  • Prepare for a Sale: If you plan to sell, start cleaning up your financials and processes way ahead of time..

  • Future Goals: Maddy aims to build a team to expand her business and take on more clients.


Conclusion:


Jen's journey isn't just about a pedal bar bike or changing laws. It's about something bigger. It's about how one person, with a bit of vision and a lot of grit, can shape their community, their life, and even the world around them. It's a reminder that we're all capable of more than we think. We can create something meaningful, build something lasting, and make a difference. And it's not always going to be easy, or pretty, or perfectly organized. But it's going to be worth it. So, let Jen's story be a nudge, a spark, a reminder that your ideas matter, your passion matters, and you matter.

Jen Benningfield, former owner of Louisville's first ever pedal bike bar.
Jen Benningfield - Former Owner of The Thirsty Pedaler

What are your thoughts on Jen's journey? Share your experiences and questions in the comments below!


Don't forget to subscribe to the Organizing the Entrepreneur podcast for more inspiring stories and business tips! Interested in being a guest on the show? Connect with us here.


Resources from Jen's Episode:


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Organizing the Entrepreneur podcast with Janelle Azar. Find it on Apple, Spotify, Amazon Music, and more!


 
 

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