Green Side Up

Jason Lee & Jordan Upcavage
  • 5.0 (20)
  • Entrepreneurship
  • Updated Weekly

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!

  1. 4d ago

    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)

  2. Aug 27

    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)

  3. Aug 20

    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)

  4. Aug 13

    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)

  5. Aug 6

    Ep 136. The Stories That Started the Podcast

    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 talks about growing up around a cut foliage operation, while Jordan reflects on helping with his family's tree service from an early age. Other topics include: • Learning the value of hard work at a young age • Starting lawn care routes and how pricing has changed over the years • Learning the trades through summer jobs, experience, and mentorship • Handling mistakes and unhappy customers as a business owner • The challenges surrounding palm tree trimming prices in Florida Whether you are a new listener or have been with us from the beginning, this episode offers a great look at the experiences that shaped Jason, Jordan, and the Green Side Up Podcast. 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)

  6. Jul 30

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

    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 to B2B sales, process design, and scalable growth. The conversation covers the difference between B2B and residential sales, why most personality tests fail at predicting sales success, and how Neal uses sales-specific assessments to identify true "all-star" salespeople—including traits like money tolerance, handling rejection, and sales DNA. Jason and Jordan open up about their own businesses' growth spurts and slowdowns—from hurricane-fueled demand and drought-driven slumps to the challenges of hiring sales reps without overloading operations—and Neal unpacks concepts like fractional sales management, designing a compensation structure that doesn't cap top performers, and building a sustainable pipeline through relationships and referrals. Whether you're trying to go from $3M to $6M, hire your first salesperson, or finally get serious about commercial work and sales leadership, this episode gives you a clear, real-world look at how to build a sales system that actually scales. 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)

  7. Jul 23

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

    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 commercial maintenance, including policing trashy sites and structuring man-hours, while Jordan walks through his daily-rate method and a real government bid for invasive plant removal, from OpenGov and pre-bid meetings to MOT, herbicide subs, and building in the right fudge factor. They wrap by teasing future content on autonomous Kress mowers and inviting listeners to catch them at the Landscape Show in Orlando. 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)

  8. Jul 16

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

    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 chose fert and weed control over mowing, and how add-on mosquito and tick services fit into a lean, profitable model. Jason and Mike swap stories on stacking side hustles—from Trash Panda Express dumpsters to becoming a Kress dealer—and break down real-world marketing tactics, including full-court-press branding, reviews, chamber networking, and trade show presence. They dive deep into the business case for robotic mowers on sports fields, HOAs, and campuses, talking labor efficiency, noise complaints, and how early adopters will lock in future contracts. The episode wraps with a look at Pod Row, Pod House, and how industry events, rodeos, and collaborative content can move the green industry forward. Connect with Mike: roped.us www.coastalnj.com www.sidehustlesquadpodcast.com 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)

See All (140)

5
out of 5
20 Ratings

About

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!

Information

  • Creator
    Jason Lee & Jordan Upcavage
  • Years Active
    2024 - 2026
  • Episodes
    140
  • Rating
    Explicit
  • Copyright
    © 2024
  • Show Website
    Green Side Up

You Might Also Like