Jason Lee & Jordan Upcavage

Green Side Up

Business EN ↓ 149 episodes

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...

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Author

Jason Lee & Jordan Upcavage

Category

Business

Podcast website

sites.libsyn.com

Latest episode

Nov 12, 2026

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Episodes

Ep 149. Builder to Belgard: What's Next in Outdoor Living 12.11.2026

In this episode of Green Side Up, recorded live at Equip Expo, Jason Lee and Jordan Upcavage are joined by Matt Hiner of Hiner Outdoor Living to talk with Joe Raboine from Belgard . Joe shares his journey from hardscape contractor to outdoor-living manufacturer and his current work with Belgard, including how regional preferences shape paver products and design trends. The conversation also explor...

Ep 148. Beyond the Landscape: Mark Masseo on Construction and Company Culture 05.11.2026

On day two of Equip Expo, the Green Side Up Podcast welcomes returning guest Mark Masseo of Masseo Landscape for a conversation recorded from his RV at the Kentucky Exposition Center. Mark shares how his business has grown from landscape work into design-build and construction projects, including pool houses and a custom home, and explains how detailed estimating, progress payments, and strong cli...

Ep 147. Jeffrey Scott on Scaling, Recruiting, and Financial Mastery 29.10.2026

Recorded live at the Equip Expo in Louisville, this episode of The Green Side Up features business coach and industry consultant Jeffrey Scott discussing how landscape companies can scale with focus, strong organizational structure, financial planning, recruiting, and leadership. Jordan shares lessons from running Independent Tree Service, including building a lasting company culture, helping crew...

Ep 146. Making the Shift: Why Adam Cottrell Chose Landscape Maintenance 24.10.2026

On this episode of the Green Side Up Podcast, Jason and Jordan welcome Adam Cottrell of Eco Maintenance , a Vancouver-based landscaping company. Adam shares why he shifted from landscape construction to maintenance, how his team handles snow and ice with homemade brine, and what it takes to grow a business in a rainy climate. The conversation also covers networking and marketing, landscape-industr...

Ep 145. Pricing for Profit: Debris, Fuel, and the Bottom Line 15.10.2026

In this episode of the Green Side Up Podcast, Jordan and Jason dig into the numbers behind debris hauling, including a nine-week cost review that revealed a significant loss and prompted a temporary pricing adjustment while they work toward a more accurate cost-per-load model. They also discuss the challenges of bidding commercial landscape maintenance, a new sliding-scale fuel surcharge, and the...

Ep 144. Rain Delays, Real Numbers, and the Winter Work Puzzle 08.10.2026

On this episode of  Green Side Up , Jordan and Jason talk through the realities of running a landscape and tree-care business—from analyzing debris-hauling costs and tightening up equipment numbers to reshuffling schedules when rainy weather throws the week off course. They preview upcoming industry events, podcast recordings, and a volunteer landscaping project for the National POW/MIA Museum, th...

Ep 143. Making the Schedule Work: Emergency Jobs, Big Contracts, and Busy Seasons 01.10.2026

In this episode, Jason Lee and Jordan catch up on the realities of running tree care and landscape businesses during a busy—and unpredictable—season. They discuss AI-driven leads and Skyfrog Landscape's new website, the challenge of fitting emergency tree work into packed schedules, and strategies for managing large contracts when client budgets or timelines change. They also get into the behind-t...

Ep 142. Trench Talk Tactics: Flat Rate, CRMs, and Social Media That Actually Converts 17.09.2026

In this episode of Green Side Up, Jason and Jordan sit down for part two with Kevin Battistoni of Hunter Irrigation to dig deeper into what it takes to build a profitable, modern service business. Kevin breaks down the shift from traditional time-and-material billing to flat rate, upfront pricing, and how contractors are using this model to increase service margins by 30% while giving homeowners t...

Ep 141. Rising Tides and Real Numbers: Peer Groups, Pricing, and Profit in the Green Industry 10.09.2026

In this episode of the Green Side Up Podcast, Jason and Jordan sit down live at the Landscape Show 2026 in the Hunter Irrigation studio with Kevin from Hunter Industries for a deep dive into where water, technology, and business strategy intersect. Kevin shares his journey as a fourth-generation "dirt surgeon," how he survived the 2008 downturn and COVID by pivoting into digital engagement, and ho...

Ep 140. If You're Not Appearing, You're Disappearing 03.09.2026

In this episode of Green Side Up, Jason and Jordan riff on late-summer grind, momentum, and why "if you're not appearing, you're disappearing" in the Green Industry. Jason shares what's happening at SkyFrog—from plant ID trainings and battling spurge at the Boys & Girls Club to winning the FNGLA Landscape Division State Board seat and helping revive the landscape committee. They dig into how profe...

Ep 139. Get More Customers in Less Time: Marketing and Money Talk with Tony Bass 27.08.2026

In this episode of the Green Side Up podcast, Jason and Jordan sit down with industry veteran  Tony Bass  of Super Lawn Trucks live from the Landscape Show in Orlando. Tony shares hard-won lessons from nearly four decades in the lawn and landscape industry, including why financial literacy is the real foundation of confident pricing and sustainable profit. The conversation then shifts into a maste...

Ep 138. Speed to Lead: How Small Landscape Companies Win with AI and Smart Marketing 20.08.2026

In this live episode of the Green Side Up Podcast from the Landscape Show 2026 inside the Super Lawn Truck Studios, Jason and Jordan sit down with Vanessa McQuade of Intrigue Media and Tyler from Cutz Landscaping Services in Orlando to explore how small but ambitious landscape companies can punch above their weight. Tyler shares his journey from family-operated maintenance work to higher-end hards...

Ep 137. Cease & Desist 13.08.2026

In this episode of the Greenside Up podcast, Jason and Jordan catch up after a hectic summer of family time, vacations, and getting "back in the saddle" at work. They compare how leads are flowing heading into tropical season and unpack how a clunky phone routing setup during vacation likely cost some opportunities. Jordan shares details on the upcoming Tree Care Business webinar series they're ho...

Ep 136. The Stories That Started the Podcast 06.08.2026

This week, we are taking you back to where the Green Side Up Podcast began. In this original first episode, Jason and Jordan introduce themselves, share the vision behind the show, and explain their goal of bringing the landscape and tree care industries closer together through collaboration, relationships, and referrals. They also share their personal origin stories in the green industry. Jason t...

Ep 135. From Popcorn to $42M: Building a Sales Engine with Neal Glatt 30.07.2026

In this episode, Jason and Jordan sit down with Neal Glatt of Neal Glatt Sales and Strategy for a deep dive into what it really takes to build a high-performing sales engine in the green industry. Neal shares his journey from selling Boy Scout popcorn door-to-door to helping grow a snow and landscape company from a single truck to $42M in annual revenue, and how that experience shaped his approach...

Ep 134. How We Approach Commercial Bids and Government Cheese. 23.07.2026

In this episode of the Green Side Up Podcast, Jason and Jordan open with a fun recap of Dollywood—great landscaping, real shade, and a memorable potty-training moment—before announcing a new Tree Care Business Webinar series in partnership with SingleOps and Granum , running August through December. They then dig into how they price big work: Jason breaks down production-based estimating for comme...

Ep 133. Side Hustles, Lawn Care, and Kress Robots 16.07.2026

In this late-night episode of the Green Side Up Podcast, Jason sits down in Orlando with Mike Garvey of the Side Hustle Squad Podcast for a wide-ranging conversation on side hustles, lawn care growth, and the future of robotic mowing. Mike shares how he balanced an 18-year career as a New Jersey State Trooper while building Coastal Fertilization & Weed Control from 10 to over 800 customers, why he...

Ep 132. Bar Graphs, Barge Fireworks, and Building Trust in Your Brand 09.07.2026

In this episode, Jason and Jordan kick things off with post–Fourth of July stories, from eight-inch mortars and a professional fireworks barge to the unexpected lesson in staffing, leadership, and broken promises that came with a canceled show. They pivot into the green industry and dig into how Jason is onboarding virtual assistants (VAs) to help track lead flow, build out data-driven reporting,...

Ep 131. How to Control: Snails, Fungi, and Administrative Tasks 02.07.2026

In this episode of The Green Side Up Podcast, Jason and Jordan cover a full slate of real-world green industry challenges and opportunities. Jason breaks down a Fourth of July–timed median rehab in Alachua, from battling snails in society garlic to testing drift roses in harsh roadway conditions. Jordan shares a profitable roadside removal project and then dives deep into a large-scale plant healt...

Ep 130. From Castrating Cows to Carbon‑Smart Soils: Biochar with Zack Farr 25.06.2026

In this episode of the Greenside Up Podcast, Jordan and Jason sit down with Zack Farr, third-generation citrus grower, redneck entrepreneur, and co-founder of Biotech Applied Research , for a wild, unfiltered ride from castrating calves to carbon-smart soils. Zack walks through his journey from FSU to Miami sales, back home to struggling citrus groves, into industrial hemp, and ultimately to disco...

Ep 129. Selling Knowledge, Not Just Tree Work with Marti Machado 18.06.2026

In this episode of the Greenside Up Podcast, Jordan and the team sit down with ISA Certified Arborist Marti Machado to trace his journey from hustling tree work out of a '72 Toyota dually to becoming one of Hillsborough County's most trusted tree professionals. Marti shares raw, entertaining stories from his early days climbing with a boat anchor line, the career-changing influence of industry leg...

Ep 128. Can You Really Take a Vacation When You Own the Business? 11.06.2026

In this Vacation Edition of the Greenside Up Podcast, Jordan and Jason catch up from the road—Jordan broadcasting from a family beach trip on Florida's Panhandle and Jason checking in from the mountains near Pigeon Forge, Tennessee. They swap stories about night crabbing, offshore fishing, Dollywood, cave tours, and even a behind-the-scenes look at the Bush's Baked Beans factory. Woven through the...

Ep 127. From Pitchford Design to Wilcox Nursery: Zack's Leap from Operator to Owner 04.06.2026

In this episode of Green Side Up, Jordan and Jason sit down with Zack Pitchford, owner of Wilcox Nursery & Landscape in Largo, Florida, to unpack his unconventional journey from high school nursery hand to retail nursery owner and landscape leader. Zack walks through his early days in environmental horticulture at UF, sweating it out on Jordan's maintenance crews, his eye‑opening internship at Val...

Ep 126. The Permaloc Playbook: From Steel to Aluminum 28.05.2026

In this episode of the Green Side Up Podcast, Jason Lee and co-host Jordan Upcavage sit down with Mark Cohen of Permaloc to explore how aluminum edging has reshaped the landscape and hardscape industry. Mark shares the origin story of Permaloc, founded by landscape architect Daniel Zwier as the pioneer of aluminum landscape edging, and explains why aluminum's strength-to-weight ratio, sustainabili...

Ep 125. Family Business to Destination Company: Jeffrey Scott on Building Better Landscape Firms 21.05.2026

In this episode of the Greenside Up Podcast, Jason and Jordan sit down in Tampa with renowned green-industry consultant Jeffrey Scott to unpack his journey from family pool-and-landscape business to leading coach, peer-group facilitator, and host of The Ultimate Landscape CEO. Jeffrey shares stories from growing up in his grandfather's pioneering gunite pool company, scaling a high-margin service...

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