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 32. Building a Profitable Landscaping Business: Lessons from Tony Bass 08.08.2024 1:05:51
In this episode of the Green Side Up podcast, hosts Jason and Jordan are joined by special guest Tony Bass, a true green industry veteran and entrepreneur. They discuss the keys to building a successful landscaping or tree care business, including the importance of developing written policies, procedures, and systems. Tony shares insights from his experience growing a multi-million dollar lawn ser...
Ep 31. Steve Samuels: From Football to Foliage and the Power of Software 01.08.2024 41:01
The Green Side Podcast is a show that features interviews with entrepreneurs and business leaders in the Green Industry. In this episode, the hosts sit down with Tequila Steve, who works with the software company Single Ops. Steve shares his background in the landscape and irrigation industries, and discusses how Single Ops has helped streamline operations and improve efficiency for his customers....
Ep 30. Couch Cushions, PGRs, and the Evolving Green Side Up Podcast 25.07.2024 40:17
In this episode of the Green Side Up Podcast, Jordan discusses his struggles with high blood pressure and caffeine intake while working long hours trimming trees. Jason explains his use of plant growth regulators to maintain hedges and shrubs. Jordan shares an experiment with using PGRs to control growth on his lawn. The hosts talk about Jordan's efforts to launch a new plant healthcare division f...
Ep 29. Quality Over Quantity: Building a Thriving Pest Control Empire 18.07.2024 1:10:21
In this episode of the Green Side Up podcast, hosts Jason and Jordan welcome Chris from Brothers Pest Control. Chris shares insights on growing a successful lawn care and pest control business from the ground up, emphasizing the importance of quality service, hands-on management, and organic growth through referrals. The conversation covers topics such as employee training, chemical application te...
Ep 28. Trees Florida Debrief and Exciting Business Updates 11.07.2024 1:06:16
Jordan and Jason recap their recent trip to the Trees Florida conference, where they networked with arborists and tree care professionals. They discuss the busy schedule of events and interviews they conducted. The hosts also provide updates on their businesses, including new hires and training plans. Jordan talks about bringing on his personal trainer Brian to help employees and take work off his...
Ep 27. US Navy Veteran, Entrepreneur, Civil Servant: Travis Owen 04.07.2024 51:29
In this episode of the Green Side Up podcast, hosts Jordan and Jason welcome special guest Travis Owen, a Navy veteran and entrepreneur. Travis shares his incredible journey from military service to running a successful pawn shop and eventually transitioning into healthcare management. Listeners will hear captivating stories about Navy rescue swimmer training, the gold-buying business, and unconve...
Ep 26. Tree Climbing Tales from the Trade Show Floor 27.06.2024 40:19
On this episode of the Green Side Up Podcast, Jordan and Jason sit down with friend and tree climbing legend Adam Jackson. Adam shares his journey from starting in landscaping in England to running a major tree division for the largest landscape company in the country. They discuss Adam's 13 years leading the annual Florida tree climbing competition and innovations that have advanced safety. Adam...
Ep 25. Addiction, Discipline = Freedom 20.06.2024 54:39
Addiction, Discipline, and Freedom in the Workplace Jordan and Jason sit down with personal trainer and addiction recovery advocate Brian Belling to discuss the challenges of addiction in the tree care and landscape industry. Brian shares his journey of overcoming addiction through a Salvation Army program and how he now helps others. The hosts also explore strategies for identifying employees str...
Ep 24. Branded Bull: Branding, Websites, and More 13.06.2024 41:23
This episode of the Green Side Up podcast features Adam Fullerton, founder of Branded Bull, a branding and marketing agency. Adam discusses the importance of branding for businesses and how to establish a memorable brand identity. He talks about developing logos, websites, and graphic design that represent your business values and solutions. Listeners will learn how to position their company as a...
Ep 23. Treesources: In Collaboration with Nature 06.06.2024 30:19
This episode of the Greenside Up podcast features Ian Wogan of Treesources, a vertically integrated green infrastructure firm that specializes in tree preservation and relocation. Ian discusses the complex process of preparing trees for transplant, including root pruning, irrigation, and using growth regulators. He shares stories of large tree moves, including a 63-inch live oak. Ian talks about t...
Ep 22. Trees Florida: Preparing for Our First Trade Show 30.05.2024 1:03:10
Jordan and Jason discuss adventures in Texas, balancing work and play on vacation. They prepare for an upcoming trade show, at the Trees Florida Conference, by planning podcast interviews and giveaways. The friends get personal, discussing health checks, soil amendments, and a new Flexi-Pave installation project. Jordan shares his forestry mowing job and invasive plant control challenges. Jason pl...
Ep 21. Tom Cruxon, A Tree Man From Across The Pond 23.05.2024 1:08:11
This episode of the Green Side Up podcast features Tom from Sherwood Tree Service as a guest. Tom discusses how he got started in the tree industry after moving to the US from England over 20 years ago. He talks about his experience owning and operating Sherwood Tree Service in Tampa, and the transition he has made towards focusing more on palm tree treatment and care. Tom also shares stories abou...
Ep 20. Worker's Comp, It's Not That Scary! 16.05.2024 57:23
This episode of the Green Side Up podcast discusses workers' compensation insurance in depth with guest Kian Ostovar from Work Comp Specialists. Kian provides an overview of how work comp rates are calculated in Florida and explains options like employee leasing programs. Listeners learn about classification codes, experience modifiers, dividends, and more. The conversation also addresses a costly...
Ep 19. From Carpenter to "Pond Digger": A Veteran Pond Pro and True Fish Freak! 09.05.2024 47:49
Eric "The Pond Digger" Triplet shares his journey of growing a passion-driven pond business over 35+ years. Starting from aquarium maintenance, Eric evolved his one-man operation into a diversified business installing water features and manufacturing products. He discusses rapid early growth installing over 100 ponds annually, then diversifying services in 2008. Eric also details private labeling...
Ep 18. All Things Equipment 02.05.2024 58:59
This episode of the Green Side Up podcast features Jordan and Jason discussing all things equipment used in their landscape and tree businesses. They talk about the two-cycle equipment they use like chainsaws, blowers, and trimmers. They also discuss the brands and models of lawnmowers in their fleet. Jordan and Jason share details about the lifts, compact utility loaders and trucks they rely on....
Ep 17. Vacations and Getting Fired 25.04.2024 1:01:03
This episode of the Greenside Up Podcast explores balancing work and life as an entrepreneur. Jordan shares how he gave responsibility to employees while taking his family on vacation. He also discusses managing a forestry project remotely. The episode then dives into the highs and lows of business ownership. Jordan details receiving an award but unexpectedly losing a major contract. Practical str...
Ep 16. Elevate Sales to New Heights, Without the Overhead. 18.04.2024 40:09
This episode features Cody Stickle of RevHike as he discusses the company's sales process for green industry businesses. Cody explains how RevHike handles lawn care, landscaping, and tree service leads over the phone, focusing on understanding customers to provide customized solutions. Jason and Jordan are impressed by RevHike's ability to eliminate overhead costs associated with sales staff throu...
Ep 15. Poaching, Pathways, and City Hall 11.04.2024 47:14
On this episode of the Green Sideup Podcast, Jordan and Jason discuss recent challenges and successes in their businesses. Jordan talks about dealing with a difficult city code enforcement situation over a customer's tree. He also had equipment issues on a job that caused delays. Jason worked on installing an intricate labyrinth paver kit and discussed how his biggest competitor directly poached e...
Ep 14. Good Friends, Cold Beer, Hard Work 04.04.2024 46:15
Old Friends, New Beginnings - Jordan and Jason reunite on the podcast to share the story of how their friendship and landscape businesses began while in college at the University of Florida over 15 years ago. They discuss how they met through a mutual friend, bonded over their hard work ethic, and decided to live together in Alachua where they started Skyfrog Landscape and Independent Landscape fr...
Ep 13. TCC Master's Challenge with Colin Kelly 28.03.2024 1:02:51
This episode of Green Side Up features a recap of the Florida Chapter International Society of Arboriculture tree climbing competition. Jordan Upcavage and Nick Myers are joined by competitor Colin Kelly. They discuss techniques, mistakes, and close calls from the competition. Colin also shares advice for new climbers and businesses. Tips include getting involved with your local ISA chapter, focus...
Ep 12. Florida ISA Tree Climbing Competition: Master's Challenge 21.03.2024 1:01:48
Join Jason and Jordan at the Florida ISA Tree Climbing Competition as they provide play-by-play commentary of the Masters challenge event. Hear from Nick Meyers, chair of the competition, as he walks through the scoring and setup. Get an inside look at the techniques of climbers Taylor Pansetti and Colin Kelly as they navigate the challenging course. For landscape and tree care entrepreneurs, this...
Ep 11. Commercial Landscape Guru: Trey Rolquin 14.03.2024 59:39
This episode features Trey Rolquin as a guest. Trey shares about his career in commercial landscape maintenance and how he focuses on building relationships with clients. He discusses the challenges of staffing crews and dealing with rising costs. Trey also provides advice to Jordan and Jason about opportunities in the commercial landscape industry and how to find and maintain large commercial cli...
Ep 10. My Business is on Fire, Literally! 07.03.2024 1:09:21
Jason and Jordan discuss the fire that destroyed SkyFrog Landscape's shop in August 2021. Jason details the events leading up to the fire, including issues with improper pricing, high employee turnover, and a toxic second-in-command. He then walks through the night of the fire and the aftermath, including discovering it was arson. Jason shares lessons learned around insurance and reviews. Connect...
Ep 09. BeaterMowersLife: Building a Lawn Care Community 04.03.2024 47:43
This episode of Greenside Up Podcast features a discussion about using social media for landscaping businesses. Chris from BeaterMowersLife shares his experience growing an Instagram community and hosting a "Mowing Madness" lawn care competition. Jordan expresses his disinterest in social media but learns tips for getting started. The hosts also cover annual lawn care competitions, building client...
Ep 08. Commercial Sales: Cults, Tacos, and Property Managers 28.02.2024 39:24
This episode covers strategies for increasing commercial tree and landscaping sales, with a focus on building relationships with property managers. The speakers discuss topics like networking groups, generating commercial leads, dealing with managers who ghost clients, and educating clients. Sales tactics like food deliveries and taking clients to lunch are also covered. Key takeaways include the...
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