Chester Lenon III
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Chester Lenon was born to be an entrepreneur. Long before starting PoopScoop Troopers, he was the kid always looking for the next opportunity with something he could buy, fix, improve, or sell. Business wasn’t something Chester discovered later in life; it was something he grew up around. Entrepreneurship runs deep in his family. His parents have owned an accounting business for more than 40 years, and Chester grew up watching firsthand what it takes to build and maintain a business. Both of Chester’s grandfathers were also business owners, making entrepreneurship a part of his family for generations. But one of Chester’s biggest influences was his father. From an early age, his dad taught him about business, leadership, hard work, and taking care of people. When Chester came up with another crazy idea to make money, his father didn’t shut it down—he encouraged him to try it. That entrepreneurial mindset followed Chester into adulthood and through his time serving in the U.S. Army. After leaving the military, Chester was ready to build something of his own. In 2010, he saw an opportunity that most people probably would have walked right past or tried not to step in: dog poop!
Chester started PoopScoop Troopers, a professional dog waste removal company, with one truck, a simple idea, and a willingness to do a job most people would say stinks. Sixteen years later, that one truck has grown into a fleet of more than 20 trucks serving homeowners, communities, and parks throughout Virginia, Maryland, and Washington, D.C. For Chester, the bigger story isn't just how many trucks are on the road—it's about building something that lasts.
His father taught him that if you provide a product or service people truly need, work hard, stay honest, treat people fairly, and never take shortcuts, you can build a successful business. Those lessons have stayed with Chester from day one and continue to influence how he leads his company today. Growing up surrounded by entrepreneurs taught Chester what it means to build a business. Now, he's working on building his own legacy, one that his children can watch, learn from, and hopefully carry forward in their own way. After 16 years in the dog waste business, Chester can definitely say one thing for certain: “Who would have thought you could make money with this shit… literally!” Why step in poop? Just call the Troop!
IN THIS EPISODE YOU’LL LEARN:
- How Chester turned an unwanted chore like dog waste removal into a profitable 16-year business.
- Why a simple, unglamorous service business can become a legitimate company through consistency and customer service.
- That recurring revenue and solving problems people hate dealing with can create lasting business success.
- Why trusting your customers and doing your best work keeps them coming back for years.
- How Chester grew PoopScoop Troopers from one truck to a fleet of more than 20 trucks across three regions.
- That you don't need a glamorous idea to build a successful business—just a reliable solution and strong systems.
- Why adapting to changing customer demand, competition, and technology is essential for long-term survival.
- That entrepreneurship requires taking chances, learning from mistakes, and continuing to move forward through ups and downs.
- How Chester's family legacy of business ownership shaped his work ethic and leadership from childhood.
- Why going after your dream is better than never trying, even if you might fail or need to change direction.
about the show
Legacy Makers is an entrepreneur TV series and business documentary experience built around powerful founder stories, leadership lessons, personal branding, and the strategies behind lasting success.
Each episode takes viewers inside the minds of influential entrepreneurs, industry leaders, pro athletes, executives, and business titans to uncover the moments, decisions, challenges, and breakthroughs that shaped their journey.
Through cinematic storytelling and in-depth conversation, Legacy Makers highlights the real experiences behind success, from building a brand and overcoming obstacles to developing expertise, creating impact, and leaving a legacy that reaches beyond business.
