Green Side Up

Hosted by Jason Lee & Jordan Upcavage

Business Entrepreneurship

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Episodes

138

Latest episode

Aug 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

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)

August 6, 202631 min

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)

July 30, 20261 hr 6 min

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

In this episode, Jason and Jordan sit down with Neil Glatt of Neil Glatt Sales and Strategy for a deep dive into what it really takes to build a high-performing sales engine in the green industry. Neil 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 Neil 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 Neil 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)

July 23, 20261 hr 15 min

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)

July 16, 202655 min

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)

July 9, 20261 hr 9 min

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

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, and improve budgeting and cash flow visibility. The conversation gets candid around switching to weekly payroll, the hidden cost of payroll advances, and where to draw the line between supporting employees and becoming "the bank." They compare live answering options like Ruby versus AI-backed tools such as RingCentral, and explore how VAs, phone systems, and SingleOps can work together to tighten operations. Jason shares how he's thinking about social media ROI, content strategy with Sky Palm Studios, and why long-term trust-building may beat pure ad spend. Jordan closes with two powerful branding and values stories: how 25 years of Empire Today ads led him to a no-hesitation buying decision, and how an HOA dust-up over flying the American flag at the community boat ramp turned into a real-world case study in leadership, perception, and standing your ground. 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)

July 2, 20261 hr 6 min

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

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 healthcare bid for a new Wesley Chapel/Zephyrhills community—complete with reclaimed water issues, clay "cereal bowl" planting holes, Phytophthora pressure, and a step-by-step prescription using Hydretain, Quali-Phite F, and Mitigrow. The conversation branches into mangrove trimming under strict regulatory rules, the hidden cost of right-of-way permits on a downtown Tampa project, and how check fraud forced a total banking reset. Jason closes by unpacking his move to Virtual Assistants, leveraging SingleOps, Leanscaper, Google Chat, and GS Track Me to tighten office systems, track crew inefficiencies, and finally get serious about data, SOPs, and content production for the business and the 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)

June 25, 20261 hr 11 min

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

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 discovering the power of biochar after a "holy grail" 15' x 15' patch of supercharged soil changed everything. The conversation dives deep into the realities of Florida agriculture, the collapse of citrus, the politics and economics around hemp, and how biochar is being used for tree restoration, mitigation projects, turf and landscape installs, and large-scale soil remediation. Along the way, they swap stories about a high-spec Tampa tree mitigation job that unknowingly used Zack's product, talk practical application methods, ROI, and why biochar might be the "foundation concrete" of healthy soils rather than just another green-industry fad. If you're in trees, turf, landscape, or ag and want a real-world, boots-on-the-ground look at biochar and regenerative practices in Florida, this episode is for you. 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)

June 18, 20261 hr 5 min

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

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 legend Richard Bailey, and how he evolved from "just cutting branches for a paycheck" to selling knowledge, risk management, and long-term tree health. Along the way, the conversation dives into sales strategy in tree care, how to read customers and ask better questions, building a high-caliber crew and culture at Independent Tree Service, and why showcasing live job sites is their best closing tool. Outside of work, Marti opens up about family life, raising a volleyball standout daughter, and his infamous neighborhood guacamole and margarita showdown, blending humor, heart, and hard-earned wisdom from a lifetime in arboriculture. 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)