Jason Lee & Jordan Upcavage
Green Side Up
Welcome to "Green Side Up: Tackling Entrepreneurial Weeds in Landscaping and Tree Care." Join hosts Jason Lee & Jordan Upcavage, a battle-tested landscaper, and a tree whisperer, as they peel back the layers of small business ownership in the green industry. Get ready for raw stories from the trenches, navigating unpredictable weather, managing demanding clients, and conquering the challenges that define entrepreneurial journeys. Whether you're knee-deep in the dirt or just planting your seeds, this podcast is your companion in the uphill climb of entrepreneurial success. Embrace the messy rea...
Author
Jason Lee & Jordan Upcavage
Category
Podcast website
Latest episode
Jul 9, 2026
Where to listen?
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Episodes
Ep 82. Biochar, Rain Delays, and Business Survival: A Candid Conversation 24.07.2025 1:04:41
In this episode of Green Side Up, Jason and Jordan dive deep into the world of tree care, landscaping, and business management. Jordan shares his recent biochar project in Tampa, detailing an innovative soil remediation technique that could revolutionize urban tree care. The duo discusses employee motivation, the challenges of working in tight urban spaces, and strategies for managing business dur...
Ep 81. Big Fish, Small Bream: Learning How to Let Others Lead 17.07.2025 54:58
In this episode of Green Side Up, Jordan dives deep into the art of delegation and managing multiple complex projects simultaneously. From mangrove trimming to root pruning and mulch installation, he shares insights on how to effectively hand off tasks to competent team members while maintaining quality control. The conversation explores the challenges of running a tree service business, the impor...
Ep 80. The CDL Conundrum: Clever Truck Strategies for Green Industry Pros 10.07.2025 58:27
In this episode of the Greenside Up Podcast, we dive deep into the world of commercial trucks and equipment for tree care and landscaping businesses. The hosts discuss their innovative vehicle setups, including custom bucket trucks, tow trucks with lifts and mini loaders, and strategies for maximizing efficiency while minimizing CDL driver requirements. They share insights on truck selection, trai...
Ep 79. Behind the Scenes: Private Equity, Culture, Home Services 03.07.2025 1:09:16
In this episode of Green Side Up, Johnny Furlong joins the crew to dive deep into the world of private equity, home services, and business ownership. The conversation explores the challenges and opportunities facing service-based businesses, from landscaping to plumbing and HVAC. Johnny shares insights from his experience in management, discussing the complexities of private equity acquisitions, t...
Ep 78. Shop Talk: From Weed Control to Employee Walkouts 26.06.2025 47:02
In this episode of Green Side Up, Jason and Jordan dive into a whirlwind of landscaping adventures. They explore Jordan's robotic mower saga, discuss the challenges of mulch distribution, and break down a unique herbicide experiment. The conversation takes unexpected turns, from an employee's abrupt resignation to security concerns after a past break-in. Packed with industry insights, equipment tr...
Ep 77. Make Your Phone Ring: Crush Competitors with Intrigue Media 19.06.2025 1:04:05
In this lively episode of Green Side Up, hosts Jason and Jordan dive deep with Rob and Vanessa from Intrigue Media, exploring the wild journey of a marketing company that specializes in helping landscape and tree service businesses crush their online presence. From humble beginnings of digital signage to becoming a powerhouse marketing agency, Rob and Vanessa share their origin story, trade show a...
Ep 76. Vacations, Taxes, and Flounder Gigging: A Green Industry Escape 12.06.2025 54:39
In this sun-soaked episode of Green Side Up, Jordan and Jason dive into their vacation adventures while keeping it real with industry insights. Jordan's cleaning freshly caught flounder in the Florida Panhandle, while Jason explores the Dominican Republic with his family. They break down a fascinating Trees Florida presentation about urban development, discuss the wild world of tangible property t...
Ep 75. Marketing, Mentorship, and Making Waves 05.06.2025 1:09:04
In this episode of Green Side Up, hosts Jordan and Jason sit down with Jay Worth, who shares his fascinating journey through the Green Industry. From selling eyeglasses to working at SingleOps and now leading marketing at Outdoor Environments Group (OEG), Jay provides insights into industry marketing, collaboration, and the unique culture of Green Industry professionals. He discusses his career ev...
Ep 74. Semper Fi to Arboriculture: A Memorial Day Special 29.05.2025 1:06:47
In this Memorial Day weekend special of Green Side Up Podcast, hosts Jordan and Jason welcome Buck from Omega Tree, a United States Marine veteran turned certified arborist. Buck shares his incredible journey from enlisting in the Marine Corps right after high school to spending 20 years in the infantry, including roles in reconnaissance and as an infantry officer. The episode offers a personal lo...
Ep 73. Dash Cam Diaries: Protection of Your Fleet with No Contract. 22.05.2025 57:55
In this episode of the Green Side Up Podcast, hosts Jordan and Jason dive deep into the world of GPS tracking and dash cameras with Jake from GS Track Me. Learn how this innovative technology can protect your business, prevent fraudulent claims, and improve operational efficiency. Jake shares real-world examples of how dash cameras have saved companies from costly litigation, while Jordan and Jaso...
Ep 72. The $10 Solution: How Customer Insight Now can Revolutionize Your Business 15.05.2025 1:08:52
In this episode of the Green Side Up Podcast, hosts Jason and Jordan sit down with Brant, creator of Customer Insights Now, an innovative app designed to help contractors understand their potential clients' financial capabilities. Brant shares his journey from a small-town Nebraska landscape designer to developing a tool that provides detailed insights into customer spending habits and ability to...
Ep 71. Money Talks: Financing Your Business Growth with JoAnn from Northern Atlantic 08.05.2025 57:17
In this episode of Greenside Up, hosts Jason and Jordan dive deep into the world of equipment financing with JoAnn from Northern Atlantic Financial. Learn how a specialized finance professional can help tree service and landscape businesses acquire essential equipment without breaking the bank. Joanne shares insider tips on building business credit, navigating financing options, and avoiding commo...
Ep 70. Tree Climbing and Southpaw Saws 01.05.2025 54:59
Go behind the scenes of the Florida Chapter Tree Climbing Competition with an in-depth look at how everything works. Our half time show is brought to you by Southpaw Saws. Heather Craig describes the innovative left handed chainsaw she is bringing to market and the safety benefits for operators. Join expert commentators as they break down the techniques, strategies, and skills that make a top-tier...
Ep 69. More Broken Trucks, Easter Parades, Mega Props, and Brace Rods 24.04.2025 1:07:40
Join Jordan and Jason for another rollicking episode of Greenside Up, where landscaping meets mayhem. This week, Jordan and Jason share their latest projects - from rehabilitating sports fields to installing complex tree support systems. Hear about Jordan's wild Easter neighborhood parade, complete with a bucket loader full of kids, and the surprise addition of a new Bahamian street dog to his fam...
Ep 68. Taproots Horticulture: A Journey Beyond the Family Business 17.04.2025 1:06:56
In this episode of Green Side Up, Jordan and Jason sit down with Rayne Gibson, a passionate horticulture professional who transformed his family's small nursery into a coast-to-coast operation before pivoting to consulting. Rayne shares his incredible journey through the green industry, from growing up in Forest Hill, Louisiana - a hidden nursery capital - to navigating complex family business dyn...
Ep 67. Fuel, Frustration, and Funny Business: A Mechanic's Nightmare 10.04.2025 51:50
In this high-octane episode of Green Side Up, Jordan and Jason dive deep into the world of vehicle maintenance mishaps, fuel contamination nightmares, and the importance of having a reliable mechanic. Jordan shares his frustrating saga with Bill Currie Ford, detailing a series of truck repairs that went sideways, while Jason recounts a fuel mix-up that nearly brought their landscaping business to...
Ep 66. Chum the Waters: How to Get Top Dollar for Your Green Industry Business! 03.04.2025 1:05:21
In this episode of Green Side Up, we dive deep into the world of business sales with Jim the Lawn Boss, a 25-year veteran business broker specializing in lawn and landscape companies. Jim shares insider tips on navigating the complex landscape of business sales, revealing how contractors can maximize their business's value and attract the right buyers. Learn about the current industry consolidatio...
Ep 65. Pivot, Profit, and Personal Growth: The Blue Duck Blueprint 27.03.2025 46:01
In this episode of the Green Side Up Podcast, hosts Jason and Jordan sit down with Matt from Blue Duck Lawn Care to dive into an incredible entrepreneurial journey. Matt shares his transformative story of building a successful lawn care business from humble beginnings, pivoting from traditional lawn maintenance to high-profit services like pest control and Christmas light installations. Learn how...
Ep 64. Shed Squatters, Outrigger Injury, and Yard Sign Wars. 20.03.2025 53:34
In this episode of Green Side Up, Jordan and Jason tackle shed squatters, workplace safety, and marketing strategies with their signature humor. From near-miss incidents to innovative yard sign campaigns, they share candid stories and insights from the landscaping world. Join them for a laugh-filled, behind-the-scenes look at running a green industry business. Connect with Jason and Jordan: https:...
Ep 63. Battery Revolution: How Kress is Transforming Outdoor Power Equipment 13.03.2025 45:24
In this episode of Green Side Up, we dive deep into the world of battery-powered outdoor equipment with Todd Zimmerman from Kress. Discover how this innovative German brand is revolutionizing landscaping tools with groundbreaking battery technology that charges in just 8 minutes and lasts 3000 life cycles. From top-handle chainsaws to robotic mowers, Todd breaks down how Kress is solving real-worl...
Ep 62. Masters of the Canopy: Inside the Florida Chapter Tree Climbing Championships 06.03.2025 1:05:34
Here's a podcast description for the episode: Join Jordan and Jason at the Florida Chapter Tree Climbing Competition as they dive deep into the world of professional arboriculture. In this exciting episode, they're live on-site with certified arborist Andrew Bowles, providing an insider's view of the Masters Challenge. Watch as top climbers David Loats and Forrest McCullough showcase their incredi...
Ep 61. Biscuits and Gravy, Discovering New Tree Legislation, and Onboarding New Talent 27.02.2025 55:41
In this episode, Jordan and Jason discuss their upcoming appearance at the Florida Chapter Tree Climbing Competition, where they plan to cook biscuits and gravy for the attendees. They also cover some business updates, including Jordan's recent family ski trip, the onboarding of a new Account Manager at SkyFrog, and the positive lead generation results they've seen from their marketing efforts wit...
Ep 60. Tony Rudolph: From Family Business to Solo Operator 20.02.2025 1:03:43
In this episode, the hosts welcome Tony Rudolph, host of the "Tony's Lawn Care Talk" podcast, for an in-depth discussion about the landscaping industry. Tony shares his background, explaining how he transitioned from his father's larger company to running his own small, maintenance-focused business. He highlights the unique challenges of providing high-end lawn care services in gated communities w...
Ep 59. Yard Signs, Leftover Take Out, and Losing Golf Tournaments 13.02.2025 1:00:41
In this episode, Jordan and Jason discuss their recent adventures at the SYNKD Live trade show, including an epic dinner at Poor Calvin's restaurant and a hilarious podcast recording with Vanessa and Rob from Intrigue Media. They also cover updates on their business operations, including navigating personnel changes, implementing a new yard sign marketing campaign, and targeting real estate agents...
Ep 58. Building Relationships and Delivering Quality: Inside North Georgia Landscape Management's Commercial Approach 06.02.2025 46:01
In this episode, we sit down with Joseph from North Georgia Landscape Management to discuss his journey into the landscape industry. Joseph shares how he transitioned from the automotive industry into landscape design and maintenance, and how he has built a successful career in the Green Industry We dive into the operational structure of NGLM, including their separate maintenance and design/build...
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