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. 6H AGO

    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)

    1h 5m

  2. MAR 12

    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)

    1h 4m

  3. MAR 5

    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 min

  4. FEB 26

    Ep 113. The First Annual Landscape Rodeo: A Full Rodeo Recap

    In this episode of the Green Side Up Podcast, Jason and Jordan sit down with guest Erin Alvarez to recap the first annual Landscape Rodeo at Ancient City Farmstead. They walk through what it took to pull off a brand‑new event—from last‑minute insurance and equipment logistics to course design, sponsors, and volunteers—plus highlights like the truck and trailer / Isuzu box truck course, the articulated wheel loader water challenge, a VIP night with an epic low country boil, and a crawfish race. You'll hear how FFA students, owner‑operators, larger landscape companies, UF, and vendors all came together to compete for custom belt buckles and showcase real‑world skills in the green industry, and why one FFA student's comment on local TV proved the event is a real pipeline for the next generation. The episode closes with Jordan sharing the story behind his wife Sydney's new children's book, "Looking for Bunny Flies," a nature‑themed seek‑and‑find inspired by her late father's bedtime stories. Landscape Rodeo: Action News 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 6m

  5. FEB 19

    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

  6. 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

  7. 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

  8. 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
See All (116)

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
    116
  • Rating
    Explicit
  • Copyright
    © 2024
  • Show Website
    Green Side Up

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