Green Side Up

Hosted by Jason Lee & Jordan Upcavage

Business Entrepreneurship

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Episodes

145

Latest episode

Oct 2026

Language

EN-GB

About the show

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 reality, find solace in shared struggles, and glean insights to thrive in the wild terrain of landscaping and tree care business. It's not always a walk in the park, but with "Green Side Up," you'll learn to thrive amid the chaos of entrepreneurship. Let's tackle those weeds together!

Listen to episodes

60 recent

October 24, 202651 min

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

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-industry software, vehicle cameras and liability, workplace safety, and the highs and lows of entrepreneurship. Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website 📧 Email: greensideuppodcast@gmail.com 📘 Facebook: Green Side Up 📸 @greensideuppodcast on Instagram 📸 @skyfroglandscape on Instagram Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service Save with SingleOps: 💸 Mention Green Side Up or use this link to get $500 off your SingleOps subscription: 👉 Get $500 Off SingleOps Sponsors & Partners: 👉 MitoGrow 🌱 🎥 Intrigue Media on Instagram (@imintriguemedia) 📍 GS TrackMe Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

October 15, 202649 min

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

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 realities of preparing budgets and pricing jobs in a competitive market. Along the way, they share plans for the Equip trade show, the upcoming POW/MIA Memorial Landscape project, and an October 27 webinar on tree care business finances and pricing. Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website 📧 Email: greensideuppodcast@gmail.com 📘 Facebook: Green Side Up 📸 @greensideuppodcast on Instagram 📸 @skyfroglandscape on Instagram Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service Save with SingleOps: 💸 Mention Green Side Up or use this link to get $500 off your SingleOps subscription: 👉 Get $500 Off SingleOps Sponsors & Partners: 👉 MitoGrow 🌱 🎥 Intrigue Media on Instagram (@imintriguemedia) 📍 GS TrackMe Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

October 8, 202653 min

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

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, then discuss winter workload ideas, including offering Christmas-light installation and exploring an AI voice agent to handle incoming calls. Along the way, they share stories from the field, compare notes on keeping crews productive, and look ahead to what's next for their businesses and the industry. Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website 📧 Email: greensideuppodcast@gmail.com 📘 Facebook: Green Side Up 📸 @greensideuppodcast on Instagram 📸 @skyfroglandscape on Instagram Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service Save with SingleOps: 💸 Mention Green Side Up or use this link to get $500 off your SingleOps subscription: 👉 Get $500 Off SingleOps Sponsors & Partners: 👉 MitoGrow 🌱 🎥 Intrigue Media on Instagram (@imintriguemedia) 📍 GS TrackMe Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

October 1, 202653 min

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

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-the-scenes work of plant healthcare, including billing audits and chasing unpaid invoices, and preview an upcoming conversation with Tim Walters on knowing your true job costs and pricing work profitably before winter. Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website 📧 Email: greensideuppodcast@gmail.com 📘 Facebook: Green Side Up 📸 @greensideuppodcast on Instagram 📸 @skyfroglandscape on Instagram Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service Save with SingleOps: 💸 Mention Green Side Up or use this link to get $500 off your SingleOps subscription: 👉 Get $500 Off SingleOps Sponsors & Partners: 👉 MitoGrow 🌱 🎥 Intrigue Media on Instagram (@imintriguemedia) 📍 GS TrackMe Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

September 17, 202659 min

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

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 true cost certainty. They explore tiered "good, better, best" options, performance-based pay that lets top technicians earn six figures, and how smart use of CRMs eliminates missed materials and back-office rework. The conversation then shifts to social media as a serious lead engine, not a vanity metric game—covering Trench Talk's peer-to-peer content strategy, three core weekly content types contractors should post, and how to leverage tools like AI and simple time-lapse videos to stay top of mind without huge production budgets. Along the way, they wrestle with the tension between tech addiction, family life, and using these same platforms to grow a business and elevate the green industry as a true trade. Show Notes: IG: @kevin_battistoni_from_ hunter FB: @kevinbattistoni Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website 📧 Email: greensideuppodcast@gmail.com 📘 Facebook: Green Side Up 📸 @greensideuppodcast on Instagram 📸 @skyfroglandscape on Instagram Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service Save with SingleOps: 💸 Mention Green Side Up or use this link to get $500 off your SingleOps subscription: 👉 Get $500 Off SingleOps Sponsors & Partners: 👉 MitoGrow 🌱 🎥 Intrigue Media on Instagram (@imintriguemedia) 📍 GS TrackMe Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

September 10, 202651 min

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

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 how tools like Hydrawise and advanced monitoring turn irrigation systems into profit-driving, proactive service platforms. Jason and Jordan open up about building SkyFrog and their Tree Service brands, navigating hurricanes, drought, layoffs, and creative marketing to keep their companies healthy. The conversation then shifts into the power of peer groups, pricing smarter instead of just chasing top-line revenue, and Jason's vision for bringing real peer-to-peer learning into FNGLA across Florida. They wrap by teeing up a part-two episode on social media, digital engagement, and "Trench Talk"—how contractors can turn their everyday work and stories into real business results. Show Notes: IG: @kevin_battistoni_from_ hunter FB: @kevinbattistoni Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website 📧 Email: greensideuppodcast@gmail.com 📘 Facebook: Green Side Up 📸 @greensideuppodcast on Instagram 📸 @skyfroglandscape on Instagram Tree Care Business Webinars: 🌿 A Healthy Bottom Line - Sept. 15, 2026 Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service Save with SingleOps: 💸 Mention Green Side Up or use this link to get $500 off your SingleOps subscription: 👉 Get $500 Off SingleOps Sponsors & Partners: 👉 MitoGrow 🌱 🎥 Intrigue Media on Instagram (@imintriguemedia) 📍 GS TrackMe Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

September 3, 202646 min

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

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 professional organizations like FNGLA and the ISA Florida Chapter elevate the industry through certification, consumer education, and real networking (not just letters after your name). The conversation then shifts to building recurring revenue with plant health care, the upcoming Granum Tree Care Business Webinar on PHC operations, and regional certification events in North Florida. They wrap by highlighting local FNGLA chapter meetings, the POW MIA Memorial service project, and Saluting Branches, reflecting on why giving back, showing up, and surrounding yourself with motivated peers pays off in both business and life. Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website 📧 Email: greensideuppodcast@gmail.com 📘 Facebook: Green Side Up 📸 @greensideuppodcast on Instagram 📸 @skyfroglandscape on Instagram Tree Care Business Webinars: 🌿 A Healthy Bottom Line - Sept. 15, 2026 Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service Save with SingleOps: 💸 Mention Green Side Up or use this link to get $500 off your SingleOps subscription: 👉 Get $500 Off SingleOps Sponsors & Partners: 👉 MitoGrow 🌱 🎥 Intrigue Media on Instagram (@imintriguemedia) 📍 GS TrackMe Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

August 27, 20261 hr 3 min

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

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 masterclass on modern marketing for contractors: using problem-focused truck signage, QR codes, and video-driven landing pages to generate higher-quality leads in a world where AI is reshaping search. Tony walks through his "scale-ready" formula for turning truck signs into automated sales funnels, from headlines like "Is your tree sick?" to online scheduling and even paid consultations. They also dig into the growing influence of private equity in the green industry, why being a local, independent contractor is becoming a powerful differentiator, and preview Tony's upcoming book, The Proud Landscaper . This episode is a practical, high-energy playbook for landscape and tree service owners who want to sharpen their numbers, upgrade their marketing, and protect the soul of independent business. Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website 📧 Email: greensideuppodcast@gmail.com 📘 Facebook: Green Side Up 📸 @greensideuppodcast on Instagram 📸 @skyfroglandscape on Instagram Tree Care Business Webinars: 🌿 A Healthy Bottom Line - Sept. 15, 2026 Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service Save with SingleOps: 💸 Mention Green Side Up or use this link to get $500 off your SingleOps subscription: 👉 Get $500 Off SingleOps Sponsors & Partners: 👉 MitoGrow 🌱 🎥 Intrigue Media on Instagram (@imintriguemedia) 📍 GS TrackMe Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

August 20, 202641 min

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

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 hardscape and outdoor living projects—powered by training with Amish craftsmen and a modern CRM (SynkedUp). Vanessa breaks down practical ways to plug AI into marketing, sales, and phone answering so owners can move faster without losing the human touch, from Google Business optimization and automations to AI-powered answering services and nurture sequences. The group digs into real numbers, growth from $450K to $530K, review-getting tactics that actually work in the field, and how to build a marketing engine that turns ideal clients into long-term maintenance and install relationships—all with plenty of on-the-truck banter and real-world examples landscapers can copy on Monday morning. Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website 📧 Email: greensideuppodcast@gmail.com 📘 Facebook: Green Side Up 📸 @greensideuppodcast on Instagram 📸 @skyfroglandscape on Instagram Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service Save with SingleOps: 💸 Mention Green Side Up or use this link to get $500 off your SingleOps subscription: 👉 Get $500 Off SingleOps Sponsors & Partners: 👉 MitoGrow 🌱 🎥 Intrigue Media on Instagram (@imintriguemedia) 📍 GS TrackMe Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

August 13, 202641 min

Ep 137. Cease & Desist

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 hosting with SingleOps and Granum, while Jason recaps a recent meetup with Pablo the Black Sheep and plugs the FNGLA Landscape Show and fall travel plans to Equip Expo and Pod Row. The conversation then turns serious as Jason opens up about receiving a cease and desist over a non-compete tied to his salesperson Clayton, walking through what the clause says, how it impacts day-to-day operations, and how they're choosing to respond without losing momentum. Along the way, they talk equipment maintenance, late-paying customers, big municipal bids, and Jason's run for the FNGLA state board landscape division seat—all framed as real-world examples of the challenges and opportunities landscapers face while growing a business. Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website 📧 Email: greensideuppodcast@gmail.com 📘 Facebook: Green Side Up 📸 @greensideuppodcast on Instagram 📸 @skyfroglandscape on Instagram Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service Save with SingleOps: 💸 Mention Green Side Up or use this link to get $500 off your SingleOps subscription: 👉 Get $500 Off SingleOps Sponsors & Partners: 👉 MitoGrow 🌱 🎥 Intrigue Media on Instagram (@imintriguemedia) 📍 GS TrackMe Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)