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. 6D AGO

    Ep 112. From Fanboy to BDM: Eric's Gravely Journey and Growth Playbook

    In this Valentine's Day episode of the Green Side Up podcast, Jason and Jordan are back in the "bunker of love" with special guest Eric, Business Development Manager for Gravely Commercial Mowers. The trio traces Eric's unlikely journey from a chance airport encounter after the Equip Expo in Louisville to hanging out in the bunker, then dives into the rich, family-owned legacy of Ariens Co. and the Gravely brand—from snow machines and walk‑behind tractors to today's commercial mower lineup. They unpack the realities of the green industry: healthy vs. cutthroat competition, the "race to the bottom" on pricing, and why real business development is more about consistent action than hype from seminars. Eric breaks down his role as a BDM, how to measure the impact of that position, and why landscapers need to decide if they're Taco Bell or Neiman Marcus. The conversation also previews Gravely's Pro-Stance Ultra, 260, HD, and the radio‑controlled OVIS slope mower that will be featured at the upcoming Landscape Rodeo, along with details on the event, competitions, and why this rodeo is all about raising the bar for the industry while still having a ton of fun. 🌱 Prove your skills at the first-ever Landscape Rodeo! Head-to-head challenges like Zero-Turn Barrel Racing and 3-on-3 Backpack Blower Soccer, plus great food and industry camaraderie — all supporting scholarships and training for Florida's green industry. 📍 St. Augustine, FL | 📅 Feb 19–20, 2026 👉 Sign up & learn more: https://thelandscaperodeo.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)

    1h 8m

  2. FEB 12

    Ep 111. Kicking off 2026: Water Main Craters, Lost HOAs, and Marketing ROI

    In this pre-sunrise episode, Jordan and Jason kick off 2026 with a candid look at what's current in their tree and landscape businesses. They recap January's guest lineup, then dive into real-world topics like business development through BNI and apartment associations, HOA speaking gigs, and an emergency job removing a 40" oak after a massive water main blowout. They share how tools like LiveSwitch and AI are leveling up their proposals, how a 10,000-contact email campaign with a real 10% labor discount helped fill the February schedule, and what they're learning about marketing ROI with Intrigue Media. They also unpack losing a long-term HOA contract, dealing with difficult homeowners, and set the stage for the upcoming Landscape Rodeo with equipment competitions, sponsors, and a VIP crawfish-fueled Low Country boil. 🌱 Prove your skills at the first-ever Landscape Rodeo! Head-to-head challenges like Zero-Turn Barrel Racing and 3-on-3 Backpack Blower Soccer, plus great food and industry camaraderie — all supporting scholarships and training for Florida's green industry. 📍 St. Augustine, FL | 📅 Feb 19–20, 2026 👉 Sign up & learn more: https://thelandscaperodeo.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)

    1h 9m

  3. FEB 5

    Ep 110. Blood Serums, Big Pharma & Big Trees: Andrew Fucarino Joins Independent Tree Service

    In this episode of the Green Side Up podcast, Jordan and Jason talk with longtime friend Andrew "Duck Fisherman" Fucarino about his unusual path from family-owned compounding pharmacy to Business Development Manager for Independent Tree Service. Andrew shares how he helped build a niche, cash-pay compounding business (including custom dry eye drops from patients' own blood serum) that was eventually acquired, why burnout pushed him out of healthcare, and how he's now leveraging his Carrollwood network to open doors with HOAs, property managers, and commercial clients. They dig into what real business development looks like in tree care—education, relationships, understanding budgets, and not wasting time on bad-fit work—while mixing in stories about duck hunting, mini-retirement, and reinventing your career in your 40s. 🌱 Prove your skills at the first-ever Landscape Rodeo! Head-to-head challenges like Zero-Turn Barrel Racing and 3-on-3 Backpack Blower Soccer, plus great food and industry camaraderie — all supporting scholarships and training for Florida's green industry. 📍 St. Augustine, FL | 📅 Feb 19–20, 2026 👉 Sign up & learn more: https://thelandscaperodeo.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)

    1h 8m

  4. JAN 29

    Ep 109. Roths, 401(k)s & SIMPLE IRAs: Retirement Game Plan for Blue‑Collar Pros

    In this episode of the Green Side Up Podcast, Jason and Jordan sit down in person with Danny Gutcher of KASE Wealth Advisors for a deep dive into money, retirement, and long‑term planning—through the relatable lens of Danny's baseball journey. Danny shares his path from Tampa high school standout to Division II national champion catcher at the University of Tampa, then explains how he transitioned from molecular biology and CTE research ambitions into a career as a fiduciary financial advisor. The conversation breaks down, in plain language, topics like fee-based vs. commission-based advising, what a fiduciary really is, Roth vs. traditional IRAs, 401(k)s vs. SIMPLE IRAs, company matches, vesting, HSAs, and tax diversification. Jason and Jordan press Danny on how small businesses like landscape and tree service companies can set up retirement plans, use matches as a retention tool, and structure contributions so both owners and employees win. It's a practical, story-driven guide for young professionals, blue‑collar employees, and business owners who want to stop guessing about retirement and start building a real plan. 🌱 Prove your skills at the first-ever Landscape Rodeo! Head-to-head challenges like Zero-Turn Barrel Racing and 3-on-3 Backpack Blower Soccer, plus great food and industry camaraderie — all supporting scholarships and training for Florida's green industry. 📍 St. Augustine, FL | 📅 Feb 19–20, 2026 👉 Sign up & learn more: https://thelandscaperodeo.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)

    1h 14m

  5. JAN 22

    Ep 108. Wheelies, Skid Steers, and Backpack Blowers: The Landscape Rodeo

    In this episode, Jordan and Jason go behind the scenes of the inaugural Landscape Rodeo in St. Augustine, Florida—fresh off the front page of Lawn & Landscape with Yankee Dan doing a wheelie on a Hustler zero-turn. They break down Media Day, key events like zero-turn barrel racing, skid steer challenges, mini-excavator skills, and the evolving three-on-three backpack blower soccer, plus how to register at thelandscaperodeo.com, event pricing, the $1,000 Landscape Decathlon prize, custom belt buckles, and lodging at World Golf Village Renaissance St. Augustine. They also dig into plant health care with MitoGrow booster applications, air spading and root invigoration, and wrap with how they're using LiveSwitch and AI to capture video walkthroughs, speed up proposals, and better communicate with clients and crews. 🌱 Prove your skills at the first-ever Landscape Rodeo! Head-to-head challenges like Zero-Turn Barrel Racing and 3-on-3 Backpack Blower Soccer, plus great food and industry camaraderie — all supporting scholarships and training for Florida's green industry. 📍 St. Augustine, FL | 📅 Feb 19–20, 2026 👉 Sign up & learn more: https://thelandscaperodeo.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)

    1h 14m

  6. JAN 15

    Ep 107. Profit Builder Breakdown: Pricing, Profit & Growth for Tree and Landscape Pros

    Jordan and Jason link up in Tampa to recap a big week in the Green Industry. They share details on the upcoming Landscape Rodeo and Media Day at Ancient City Farmstead in St. Augustine, then break down what they learned at Tony Bass's Profit Builder seminar in Atlanta. From labor burden and overhead recovery to real equipment costs, sales goals, and culling unprofitable accounts, they explain how knowing your numbers changes everything for lawn, landscape, and tree service businesses. They also touch on branding, uniforms, and using video and tools like LiveSwitch to streamline sales and client communication. Important Links: www.superlawntoolkit.com www.superlawntruck.com 🌱 Prove your skills at the first-ever Landscape Rodeo! Head-to-head challenges like Zero-Turn Barrel Racing and 3-on-3 Backpack Blower Soccer, plus great food and industry camaraderie — all supporting scholarships and training for Florida's green industry. 📍 St. Augustine, FL | 📅 Feb 19–20, 2026 👉 Sign up & learn more: https://thelandscaperodeo.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)

    1h 3m

  7. JAN 8

    Ep 106. Granum: Mark Sedgley's Merger of SingleOps, LMN, and Greenius

    In this episode of Green Side Up, hosts Jordan and Jason sit down in Louisville with Mark Sedgley, CEO of Granum (the merger of LMN, SingleOps, and Greenius), to unpack his unconventional path from teaching English in Poland to leading a major software platform for the green industry. Mark shares how he fell in love with small business, what getting fired taught him about leadership, and how he used sales and acquisitions to scale multiple software companies. He explains why he combined SingleOps, LMN, and Greenius, the key differences between tree care and landscape markets, and how owners should think about expansion, delegation, and core values. Packed with real stories and practical takeaways, this episode is a must‑listen for Green industry entrepreneurs thinking about growth and their next chapter. www.granum.com www.singleops.com   🌱 Prove your skills at the first-ever Landscape Rodeo! Head-to-head challenges like Zero-Turn Barrel Racing and 3-on-3 Backpack Blower Soccer, plus great food and industry camaraderie — all supporting scholarships and training for Florida's green industry. 📍 St. Augustine, FL | 📅 Feb 19–20, 2026 👉 Sign up & learn more: https://thelandscaperodeo.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)

    58 min

  8. JAN 1

    Ep 105. From Bushmaster to Baker: Scaling a 300‑Employee Landscape Company

    In this episode of Green Side Up, Jason and Jordan sit down with Ryan Hudson, General Manager of Baker Commercial Landscaping – Tampa, for a candid, funny look at what it really takes to run a serious commercial landscape operation. Ryan shares his journey from mowing for his dad's company Bushmaster Landscape Maintenance as a kid, to grinding through a 10‑year business degree, to managing an 80-person Tampa branch within a 300-employee, two-branch company. They break down how Baker structures its teams (from crews to ops managers to department heads and the GM), the constant tension between sales and production, and how Ryan often plays "cut man" between Trey Rolquin's big sales vision and the operations crews. The conversation hits on Baker's work in Tampa's Water Street district—rooftop landscapes, tricky access, parking tickets, right-of-way drama, and slow-paying big clients—plus the real economics of palm tree trimming and why it often serves as a loss leader to win better work. Ryan also explains how relationship-driven networking (BOMA, CAI, etc.) and a diversified mix of offices, HOAs, condos, shopping centers, and hotels helped them survive COVID. Mixed in are plenty of stories—from trimming at a nudist resort to 3 a.m. bucket-truck work downtown. If you're in landscaping or tree work and want real-world insight on scaling commercial maintenance without racing to the bottom, this one's for you. 🌱 Prove your skills at the first-ever Landscape Rodeo! Head-to-head challenges like Zero-Turn Barrel Racing and 3-on-3 Backpack Blower Soccer, plus great food and industry camaraderie — all supporting scholarships and training for Florida's green industry. 📍 St. Augustine, FL | 📅 Feb 19–20, 2026 👉 Sign up & learn more: https://thelandscaperodeo.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)

    1h 12m
See All (112)

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
    112
  • Rating
    Explicit
  • Copyright
    © 2024
  • Show Website
    Green Side Up

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