E270: From Landscaping Hustle to Tech Empire: Bryan Clayton’s $90M GreenPal Revolution - Watch Here

About the Guest:

Bryan Clayton is the CEO and co-founder of GreenPal, a tech platform connecting homeowners with lawn care professionals. Before launching GreenPal, Clayton built and sold a successful landscaping business with over 150 employees. He’s an advocate for using technology to modernize service-based businesses and believes AI will dramatically reshape industries in the coming years.

Summary:

In this episode of How2Exit, host Ronald Skelton sits down with Bryan Clayton, CEO and co-founder of GreenPal, a platform often dubbed the "Uber for lawn care." Clayton shares his entrepreneurial journey, from a childhood forced into mowing lawns by his military father to scaling and selling a multimillion-dollar landscaping company. He discusses the challenges of selling a business, the emotional void that follows an exit, and how he transitioned into the tech space to launch GreenPal. The conversation dives deep into automation, AI’s impact on business, and how small service-based companies can leverage technology to scale efficiently.

Key Takeaways:

1. Forced Entrepreneurship Sparks Innovation: Clayton’s first business began out of necessity when his father made him mow lawns as a teenager. That small hustle turned into a multimillion-dollar landscaping business.
2. Scaling a Service Business is a Systematic Process: Building a large-scale landscaping company required Clayton to develop efficient processes, training programs, and a system for hiring and retaining workers.
3. Selling a Business Takes Preparation: It took Clayton two years—one to structure the business properly and another to find a buyer—to successfully sell his landscaping company.
4. The Emotional Impact of an Exit is Real: Clayton struggled with an identity crisis after selling his business, which eventually pushed him to start GreenPal.
5. AI and Automation Are Changing Business Operations: The discussion explores how AI is reshaping everything from customer acquisition to software development, making it easier to run lean and profitable companies.
6. Technology is Now Essential for Service Businesses: Small business owners who fail to adopt tech tools are operating as if it’s still the 1990s, missing opportunities to increase efficiency and profitability.
7. GreenPal Provides a Business-in-a-Box for Lawn Care Providers: The platform handles customer acquisition, scheduling, invoicing, and even upselling additional services for lawn care professionals.
8. Future-Proofing Means Staying Tech-Savvy: Clayton warns that service providers who resist technology will fall behind as AI and automation continue to accelerate business capabilities.

Article:

Lawnmowers, AI, and the Art of the Business Exit

How Bryan Clayton Scaled, Sold, and Reinvented the Lawn Care Industry

Bryan Clayton never planned on being an entrepreneur. In fact, if it weren’t for his father’s no-nonsense military discipline, he might have spent his youth perfecting his Super Mario Kart skills instead of mowing lawns. But as he quickly realized, mowing one lawn led to another, then another, and before he knew it, he had built a landscaping empire. His journey—from reluctant teen worker to CEO of GreenPal, the Uber of lawn care—isn’t just about trimming grass. It’s a masterclass in scaling, selling, and leveraging technology to disrupt an industry.

From Lawns to Leadership

Clayton’s first business began with a simple push mower and a little neighborhood hustle. Over the years, he scaled his landscaping company to 150 employees and over eight figures in revenue. Yet, despite his success, something wasn’t right.

“Every year or two, the business forced me to evolve,” Clayton recalls. “And I loved that. But at a certain point, I hit a plateau—I wasn’t learning, and I wasn’t growing.” This led him to an important realization: it was time to sell.

Selling, however, wasn’t as simple as listing it and waiting for the highest bidder. Clayton spent a full year preparing his business for sale, cleaning up financials, streamlining operations, and making sure the company could run smoothly without him. Even after the sale, he wasn’t prepared for the emotional aftermath.

“When you sell your business, it’s like selling a piece of yourself,” Clayton admits. “I had to figure out who I was without it.”

Reinventing the Lawn Care Industry

Instead of retiring, Clayton saw an opportunity. He knew that the lawn care industry was still operating like it was 1995—manual calls, pen-and-paper scheduling, slow invoicing. What if there was a way to make hiring a lawn care provider as easy as ordering an Uber?

Enter GreenPal, a platform that allows homeowners to find, book, and pay lawn care professionals seamlessly. “We built the business with both sides in mind—the homeowner who wants quick, reliable service, and the service provider who needs an easy way to manage customers, scheduling, and payments,” Clayton explains.

Technology Is No Longer Optional

While GreenPal offers a sophisticated backend for lawn care professionals, many small business owners are still hesitant to embrace tech.

“I see it all the time,” Clayton says. “Business owners running their companies like it’s the 90s, using clipboards, MapQuest printouts, and post-it notes to manage their operations. Meanwhile, technology exists to make all of that seamless.”

His advice? Adopt technology or get left behind. With AI rapidly advancing, even blue-collar businesses like landscaping, pest control, and home services are integrating automation to optimize efficiency.

AI: The Silent Business Partner

The conversation shifts to AI, a tool that both Skelton and Clayton believe is drastically changing the business landscape. Clayton sees AI as the great equalizer—allowing small businesses to scale and operate at a level previously reserved for Fortune 500 companies.

“We used to have to hire people just to handle scheduling, customer follow-ups, and payment processing. Now, AI can do all of that instantly,” Clayton says. Even software development, once the domain of expensive engineers, is being democratized. “When I first learned to code, it took me days to build what AI can generate in seconds.”

Skelton agrees, adding that AI is rapidly replacing mid-level professionals across industries. “If you’re a mid-tier accountant, lawyer, or software engineer, you should be worried. AI is closing the gap between entry-level and expert,” he warns.

Where GreenPal Goes From Here

Despite its success, GreenPal isn’t slowing down. Clayton’s goal? One million weekly users. “There’s so much opportunity in just this one space,” he says. “We’re not looking to expand into pool cleaning or house painting. Lawn care is a $90 billion industry, and we’re just getting started.”

For lawn care providers, GreenPal isn’t just a way to get more customers—it’s a full-fledged business-in-a-box. From automated scheduling to customer acquisition, it takes the heavy lifting out of growing a service business.

Final Thoughts

Bryan Clayton’s story is a testament to the power of grit, adaptability, and the willingness to embrace technology. From mowing his first lawn under duress to disrupting an entire industry with GreenPal, his journey underscores a key takeaway for any entrepreneur: the game is always changing, and those who evolve with it will win.

Whether you're in lawn care, acquisitions, or any service-based business, one thing is clear—technology isn’t coming for you. It’s already here.

That wraps up this week’s podcast review! Want more insights like these? Subscribe to our newsletter for in-depth breakdowns of the best business and acquisition podcasts. 🚀

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Hirschmann stresses the importance of networking with the right intermediaries, such as CPAs, attorneys, and business brokers, to uncover off-market deals. “The best acquisitions happen through relationships,” she says.

For those looking to build deal flow, Hirschmann and Skelton both agree: getting on the right stages—whether digital or physical—can make all the difference.