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 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!

Green Side Up is a business podcast hosted by Jason Lee & Jordan Upcavage, with 136 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Jason Lee & Jordan Upcavage hosts Green Side Up, a business show with 136 episodes published.

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  Green Side Up

  Ep 137. Cease & Desist

  Aug 13, 202641 min

  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)

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  Green Side Up

  Ep 136. The Stories That Started the Podcast

  Aug 6, 202631 min

  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)

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  Green Side Up

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

  Jul 30, 20261h 7m

  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)

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  Green Side Up

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

  Jul 23, 20261h 16m

  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)

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  Green Side Up

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

  Jul 16, 202656 min

  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)

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