What happens when your body knows what your mind won't admit? For Matt Keller, it took chest-tightening panic attacks in his corporate office to recognize he was on the wrong path entirely. Despite managing a $250 million budget at Walmart by age 26, something was deeply wrong.
"I used to sit at Sam's home office, looking out the window, thinking if I could, I'd rather be digging a trench than looking at another spreadsheet right now," Matt reveals in this raw conversation with host Sy Kirby. This admission kickstarted a remarkable transformation from corporate executive to landscape business owner.
The journey wasn't without humiliation. Matt shares the gut-wrenching story of a former colleague secretly photographing him mowing lawns, a moment that could have crushed his spirit but instead fueled his determination. "That lit a fire under me," he explains, his voice still carrying the emotion of that day.
Drawing on his horticulture background and corporate skills, Matt methodically built his business by converting one-off jobs into steady contracts, focusing on commercial clients over residential headaches, and leveraging his professional communication abilities to secure apartment complex contracts. His corporate experience, once seen as irrelevant in his new field, became his secret weapon.
This episode offers practical insights for anyone contemplating a career pivot, especially those considering trading white-collar comfort for blue-collar fulfillment. Matt's advice on finding your vision, staying focused, and not diversifying too quickly applies universally to entrepreneurs at any stage. For those staring out office windows dreaming of something different, this conversation might just be the push you need to make your move.
Have you been feeling that same restlessness in your corporate role? Maybe it's time to consider what's on the other side of the window. Subscribe to the Blue Collar Business Podcast for more stories of transformation and practical business advice from those who've done the work.
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More About this Episode
From Corporate Cubicle to Commercial Landscapes: How One Entrepreneur Built a Blue Collar Empire with Purpose
In a world where “success” is often measured by the height of your office window and the size of your spreadsheet, Matt Keller took a bold leap. It was a move that many dream about but few act on. From managing a $250 million budget at Walmart to digging trenches in Arkansas soil, Matt’s story is more than a career change. It’s a blueprint for how faith, grit, and purpose can pave the way to true fulfillment in the blue-collar world.
The White Collar Wake-Up Call
Matt’s journey began like many others in corporate America: with ambition, accolades, and a sense of achievement that should have felt like success. Fresh out of college with a horticulture and turfgrass management degree, Matt traded his green thumb for a corner cubicle at Walmart, then Sam’s Club. He climbed fast. By 26, he was managing massive budgets and meeting with billion-dollar executives.
But somewhere between the board meetings and budget spreadsheets, reality struck. Dizzy spells, a tight chest, a trip to the ER, and the realization that what he was feeling wasn’t a heart attack. It was burnout. That moment was the crack in the dam. He recalls thinking, “I’d rather be digging a trench than looking at another spreadsheet.”
A Crisis That Sparked Change
Like many transitions into blue-collar life, Matt’s shift wasn’t perfectly planned. COVID hit. Corporate job cuts followed. With a newborn at home and job prospects dwindling, he reached a breaking point. Tired of chasing paychecks for work that didn’t inspire him, Matt started asking deeper questions: What would I do if money weren’t the motivator? What would I do that made me feel alive?
His answer was landscaping. Not just mowing lawns, but full-scale property and grounds management. It was a natural fit for a man who spent his formative years maintaining pristine golf courses and noticing which patches of grass stood too tall. He wasn’t just passionate. He had an eye for detail that only years of high-standard maintenance work could develop.
Buying the Business and Rebuilding It
Matt’s leap into business ownership wasn’t a cold start. Through trusted conversations and a bit of financial backing, he acquired an existing landscaping company with around 40 residential and 10 commercial clients. But what he inherited was far from turnkey.
The previous owner, though respected, ran the business on a reactive basis. He would invoice after service, with no contracts and inconsistent cash flow. That model wasn’t going to cut it for Matt. His first winter in business, right after acquiring it in October, forced him to make a critical decision. How could he generate stable income in the off-season?
So he flipped the model. He moved commercial clients to annual contracts, spreading income evenly across 12 months and securing predictable cash flow. Not only did it stabilize his business, but it also positioned him as a true partner to his clients rather than just a service provider.
Losing Clients to Gain Momentum
Matt ended up with none of the original clients within a few years. Instead of seeing that as a failure, he saw it as growth. Many of those long-standing customers were locked into outdated pricing and were resistant to change. He thanked them for helping him start, but recognized they were not aligned with his long-term vision.
By understanding his costs and committing to building a sustainable, value-driven operation, Matt found better clients. These were the ones willing to invest in quality and consistency. Through faith, prayer, and hustle (including knocking on doors at more than 30 apartment complexes in a week), he turned one contract into four in just a few months. The domino effect began.
Scaling the Right Way
Today, Matt runs three full-time landscaping crews, each with three employees. He still handles all the office work himself. Scheduling, invoicing, estimating, and customer relations are all on his plate. It’s a load every blue-collar entrepreneur knows well. But he also understands that level of juggling is temporary.
“I’m not at the point where I need to hire an office person,” he said. “But that day’s coming. Until then, I just keep juggling.” His honesty about the grind resonates with those walking the same path. He’s not glamorizing the hustle. He’s showing what it takes to build something real.
The Power of Saying “No”
One of Matt’s biggest takeaways is learning to say no.
“I’m not a guy who takes on work just to take on work,” he explained. Early on, he said yes to every opportunity. But experience taught him that trying to do everything is a fast track to burnout and thin margins. Today, he focuses on what he does best: commercial landscaping, property management, and turf care.
He also moved away from residential work. The reason? It was too much of a headache. Endless change orders, emotionally driven decisions, and last-minute complaints from homeowners weren’t worth the effort. On the other hand, commercial clients value consistency and professionalism, which matches what Matt delivers.
Lessons for the Guy in the Cubicle
Matt’s story is more than just a career change. It is a message to anyone staring out their office window, daydreaming about a different path. “You’ve got to have vision,” he said. “Know where you want to go, and then do whatever it takes to get there.”
He credits his success to something many overlook: relationships. It was the trust of a mentor and support from family that helped him make the leap. Relationships with property managers fueled growth. Consistency and professionalism keep them coming back.
Staying Profitable in a Seasonal Business
One of the most impressive parts of Matt’s operation is how he manages seasonality, a common challenge in landscaping. By converting clients to annual contracts, he created income during the slower months of January and February. That’s not just smart - it’s sustainable.
He also diversified with snow removal and winter services to maintain momentum. While diversification is key to weathering the off-season, Matt makes an important point. Don’t diversify until your core services are strong. Master the main business before branching out.
What’s Next for Five Star Grounds Management?
Rebranding is underway. Matt is launching his new brand, Five Star Grounds Management, to reflect a broader scope of services. It’s not just turf anymore. It’s total property care. From a new website to enhanced marketing efforts, he is laying the groundwork to become a company that “just popped up” with a strong and polished presence.
Though he isn’t quite ready to hand off his QuickBooks account, he knows that day is coming. Whether through hiring an office assistant or working with fractional professionals, delegation will be the next step for sustainable growth.
If you are stuck, whether in a cubicle or in the same blue-collar job for years, Matt Keller’s story is your sign.
- Have a clear vision
- Learn to say no
- Know your costs
- Build strong systems early
- Lean into relationships
- Let faith guide you
Whether you're wearing a hard hat or business casual, the takeaway is clear. Success isn’t about where you start. It’s about where you’re willing to go and how hard you’re willing to work to get there.
Matt didn’t build Five Star Grounds Management overnight. He built it one job, one lesson, and one moment of faith at a time. If he can, maybe you can too.
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