Episode 70 - Bryan Clayton
Tue Jan 27 2026
If you've ever mowed lawns to make extra cash, this episode will hit home. Today, David DeCelle sits down with Brian Clayton, founder and CEO of GreenPal — the lawn care marketplace Entrepreneur Magazine has called "the Uber for lawn care." Brian's story starts with a teenager pushing a mower for $20 a yard to buy soccer cleats… and turns into building and selling a $10M+/year landscaping company before doing it again in tech, creating a platform that connects hundreds of thousands of homeowners with tens of thousands of lawn care pros across the U.S.
In this conversation, Brian breaks down what it really takes to scale a "non-sexy" service business, why sales is the real business behind every business, and how AI + data are changing the future of local services.
Key Topics Covered: How a $20 lawn turned into an entrepreneurial obsession The real lessons lawn mowing teaches (scheduling, customer service, bookkeeping, marketing) The "video game" concept of business growth: each level has a new boss When Brian stopped being a "lawn guy" and realized he was in the sales business The inflection point: from solo operator to crews, to scaling up operations What it's like to sell a company (and why the exit was "chewing glass") The unexpected reality after a big exit: motivation, identity, and momentum Why Brian launched GreenPal — and how early assumptions were wrong Marketplace vs SaaS: why marketplace founders end up building SaaS tools anyway How GreenPal prevents vendors from going "off-platform" (carrot + stick + data) The behind-the-scenes mechanics: property measurement, tax record APIs, aerial imagery, and quote automation The gritty early days: door hangers, Craigslist, calling pros, hand-cranking the first 100 transactions Brian's feedback/triage philosophy for building products that scale Where AI fits: reducing cancellations, improving reliability, and "closing the gap to magic" The book Brian says every entrepreneur should revisit: The 7 Habits of Highly Effective People
Where to Find Brian Clayton
Website: www.GreenPal.com
LinkedIn: www.linkedin.com/in/bryan-clayton-a96b33214
If you like conversations that mix entrepreneurship, real operator stories, and modern growth strategy, make sure to subscribe and share this episode with a friend who's building something.
#BusinessWithTheBoys #BrianClayton #GreenPal #Entrepreneurship #SmallBusiness #Landscaping #LawnCare #HomeServices #Marketplace #StartupStory #Sales #AI #BusinessGrowth #ServiceBusiness #FounderJourney
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Connect with David:
Website: www.businesswiththeboyz.com
LinkedIn: www.linkedin.com/in/daviddecelle
Email: David@businesswiththeboyz.com
Connect with Landon:
Website: www.businesswiththeboyz.com
LinkedIn: www.linkedin.com/in/landon-troyer-837b822b
Email: Landon@businesswiththeboyz.com
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If you've ever mowed lawns to make extra cash, this episode will hit home. Today, David DeCelle sits down with Brian Clayton, founder and CEO of GreenPal — the lawn care marketplace Entrepreneur Magazine has called "the Uber for lawn care." Brian's story starts with a teenager pushing a mower for $20 a yard to buy soccer cleats… and turns into building and selling a $10M+/year landscaping company before doing it again in tech, creating a platform that connects hundreds of thousands of homeowners with tens of thousands of lawn care pros across the U.S. In this conversation, Brian breaks down what it really takes to scale a "non-sexy" service business, why sales is the real business behind every business, and how AI + data are changing the future of local services. Key Topics Covered: How a $20 lawn turned into an entrepreneurial obsession The real lessons lawn mowing teaches (scheduling, customer service, bookkeeping, marketing) The "video game" concept of business growth: each level has a new boss When Brian stopped being a "lawn guy" and realized he was in the sales business The inflection point: from solo operator to crews, to scaling up operations What it's like to sell a company (and why the exit was "chewing glass") The unexpected reality after a big exit: motivation, identity, and momentum Why Brian launched GreenPal — and how early assumptions were wrong Marketplace vs SaaS: why marketplace founders end up building SaaS tools anyway How GreenPal prevents vendors from going "off-platform" (carrot + stick + data) The behind-the-scenes mechanics: property measurement, tax record APIs, aerial imagery, and quote automation The gritty early days: door hangers, Craigslist, calling pros, hand-cranking the first 100 transactions Brian's feedback/triage philosophy for building products that scale Where AI fits: reducing cancellations, improving reliability, and "closing the gap to magic" The book Brian says every entrepreneur should revisit: The 7 Habits of Highly Effective People Where to Find Brian Clayton Website: www.GreenPal.com LinkedIn: www.linkedin.com/in/bryan-clayton-a96b33214 If you like conversations that mix entrepreneurship, real operator stories, and modern growth strategy, make sure to subscribe and share this episode with a friend who's building something. #BusinessWithTheBoys #BrianClayton #GreenPal #Entrepreneurship #SmallBusiness #Landscaping #LawnCare #HomeServices #Marketplace #StartupStory #Sales #AI #BusinessGrowth #ServiceBusiness #FounderJourney ---- Connect with David: Website: www.businesswiththeboyz.com LinkedIn: www.linkedin.com/in/daviddecelle Email: David@businesswiththeboyz.com Connect with Landon: Website: www.businesswiththeboyz.com LinkedIn: www.linkedin.com/in/landon-troyer-837b822b Email: Landon@businesswiththeboyz.com