Green Side Up

Jason Lee & Jordan Upcavage

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. -5 Ч

    Ep 121. DSL, Drum Circles, and Deep Roots: How Erin Found the Green Industry

    This episode of the Green Side Up Podcast is a lively, story-packed conversation featuring Jordan, Jason, and returning guest Erin Alvarez. The trio starts with weekend plans—kayaking, manatees, race car–themed kids' parties, daddy–daughter dances, and tax woes—before drifting into hilarious side tangents about trolling lettuce for manatees, oversized margaritas, and the realities of squeezing tree crews through tight access. From there, Erin shares her winding journey into the green industry: growing up outdoors, bouncing between zoology, political science, and English at UF, burning out on office life at the student newspaper, rediscovering herself through hands-in-the-dirt yard work, and ultimately finding her home in Environmental Horticulture. They dig into UF horticulture culture—plant ID war stories, cheating (or trying to) in physics, the love–hate relationship with Landscape Architecture, and the birth of Deep South Landscaping (DSL) with all its youthful hustle, tax dodging, and terrible-but-memorable merch. The episode wraps by connecting Erin's past to her current role in business development at SkyFrog Landscape, touching on long-game relationship building, commercial maintenance bidding cycles, and future growth, all while maintaining the loose, funny, and unfiltered vibe that defines the show. 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)

    1 ч. 8 мин.
  2. 16 АПР.

    Ep 120. Sharpen Your Axe!

    In this episode of Green Side Up, Jordan Upcavage and Jason Lee welcome Kristoffer Rasmussen—certified arborist, safety professional, auditor, educator, and all‑around arboriculture lifer—for a rich conversation recorded live from ArborFest in Asheville, North Carolina. Kristoffer shares what makes ArborFest special, from crane‑hung "ninja climbs" to family-friendly vibes and hands-on equipment demos. He then walks us through his unlikely path into tree work, starting on a Wisconsin tree farm, discovering line clearance in Texas, teaching himself to climb, and eventually building municipal urban forestry programs for the City of Dallas. The discussion dives deep into risk management, safety culture, and TCIA accreditation—why third‑party audits matter, how solid processes reduce incidents, and what top-performing companies do differently. Kristoffer and Jordan swap memorable bee and yellow jacket stories, explore the power of "sharpening your axe" through training and events, and break down how prescription pruning (PPQ) is transforming communication between consultants, estimators, and production crews. Whether you're a tree service owner, municipal arborist, or just obsessed with doing tree work the right way, this episode is packed with practical wisdom, career insights, and a fresh way to think about investing in your people and your processes. 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)

    1 ч. 11 мин.
  3. 9 АПР.

    Ep 119. Pounding Trees with Sauce: MitoGrow Boosters That Actually Work

    In this episode, Jordan and Jason share real-world results from high-rate MitoGrow applications on stressed live oaks, sports fields, and problem lawns—including a dramatic turnaround case at the University of Tampa and a residential yard battling take-all root rot. They break down practical application rates and methods, how they're pivoting plant health care programs toward targeted "booster" treatments, and why ethical fertilization matters in tricky sites like sea wall trees. The conversation then shifts to commercial work, where Jordan walks through a detailed 23-tree HOA pruning proposal that stands out against generic bids, and Jason outlines plans to grow commercial maintenance through better content, education, and customer service—backed by a strong spring showing from their plant health care revenue.   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)

    49 мин.
  4. 2 АПР.

    Ep 118. Spring Doesn't Create Operational Problems in Tree Care — It Exposes Them.

    Today's episode captures a Business Solutions webinar hosted by the Tree Care Industry Association (TCIA), featuring insights from landscaping and tree service executives. The discussion focuses on operational readiness for the spring season, emphasizing the transition from winter dormancy to peak demand. Key speakers from Skyfrog Landscaping, Independent Tree, and Lynch Landscape and Tree Service share strategies for managing equipment maintenance, crew scheduling, and workforce training. The participants highlight the importance of integrated software like SingleOps to eliminate communication bottlenecks and improve estimate accuracy. Additionally, the webinar covers contingency planning for emergencies, such as hurricanes, and the necessity of maintaining company culture through delegation and safety protocols. The session concludes with a Q&A addressing niche equipment, hiring standards, and the benefits of standardized service templates. 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)

    1 ч. 6 мин.
  5. 26 МАР.

    Ep 117. Pretzel Pavers, Protected Trees & Process: Building a Smarter Operation

    In this episode, Jordan and Jason dive into real-world production, consulting, and systems work in their green industry businesses. Jordan breaks down a 7,000 sq ft Bellgard turf block install at Blue Springs State Park, then unpacks a six‑figure consulting project tied to the City of Tampa's strict tree protection rules, air spading, and water main replacement work. He also shares how he's using LiveSwitch video proposals (and a simple Do Not Disturb trick) on high-touch residential jobs. Jason walks through using Leanscaper's AI to build a detailed sales‑to‑invoice workflow for SkyFrog Landscape, clarifying roles, triggers, and accountability. They round things out with a Spanish moss spraying project on pecans and live oaks, gear and supplier talk, Jordan's involvement with TCIA and Trees Florida, and a standout example of proactive, photo‑driven plant health care communication that turns good service into smart upsells. 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)

    1 ч. 5 мин.
  6. 19 МАР.

    Ep 116. Work Mullets, Dashcams, and Keeping Your Schedule Sane

    In this episode, Jordan and Jason kick things off with light banter—Spanish greetings, coffee, "Zoom mullets," and Jordan's upcoming New York trip—before diving into real-world business lessons. Jordan shares how a harsh one-star Google review over "bad driving" was completely debunked using dash cam footage, and what that taught them about professionalism and reputation management. They then dig into how they schedule and coordinate tree care and landscape work using SingleOps, from grouping jobs by geography and leaving buffer days to handling maintenance vs. one-off vs. install work, and tightening communication between sales and operations. The episode wraps with how they close out jobs, ask for Google reviews, handle invoicing and collections, and a few project updates—including a turf block job at Blue Springs State Park and Jordan handing off plant health care scheduling so he's not doing it at 2 a.m. If you run a tree care, landscape, or service business, you'll get practical insight on dealing with difficult customers, scheduling smarter, and getting paid on time—delivered with Jordan and Jason's usual humor and honesty. Show notes: TCI Webinar: https://granum.com/events/singleops-tcia-webinar-built-for-spring/   GS Trackme Dash Cam Video https://drive.google.com/file/d/159FfY9cC8sNaGoiFcXPblE7CRJRmHhWN/view?usp=dr   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)

    1 ч. 5 мин.
  7. 12 МАР.

    Ep 115. Selling Smarter: On-Site Sales, SOPs, and Running Lean

    In this episode of the Greenside Up Podcast, Jason and Jordan continue their deep dive into real-world sales processes for landscape and tree care businesses. Jason recaps his trip to the Leanscaper operations intensive and shares how tools like Lana AI, SOPs, and "lean boards" can streamline communication and checklists—along with the real financial and implementation challenges. They talk about tool management, the impact of employees who care (or don't), layoffs, a values-based termination, and what it feels like to run lean with just two days of work on the books. Jason then walks through his design-build sales approach, from pre-visit confirmations and on-site discovery questions to quick visual concepts and aiming to close in the $10–15K range on-site. Jordan follows with his tree-care sales workflow, focusing on education, helping clients choose between prolonging or removing trees, and always ending with a clear, verbal recap of the scope. They wrap by previewing their upcoming TCI / SingleOps webinar and teasing a future episode on business development and growth strategy. 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)

    1 ч. 4 мин.
  8. 5 МАР.

    Ep 114. Scripts, Systems, and Sexy Proposals: Upgrading Your Sales Process

    In this episode of Green Side Up, Jordan and Jason kick off with some laughs and then dive into the real meat: tightening up your landscape sales process from first phone call to booked job. Prompted by listener questions and real scenarios from the field, they walk through using a phone script to vet leads, set project minimums, and talk budget ranges, plus Jordan's nine-step customer journey from inbound call through follow-up and invoicing. They dig into when and how to charge for landscape designs, how to avoid doing free design work for clients who hire someone else, and how tools like LiveSwitch and CompanyCam help create clear work orders and standout proposals. Along the way, Jordan shares a Bayshore Boulevard removal story that shows exactly how to price for complexity and client expectations. If you're a landscaper, hardscaper, or arborist who's tired of tire-kickers and wants a cleaner, more confident sales flow, this one's 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)

    59 мин.
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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!

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