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. 2d ago

    Ep 127. From Pitchford Design to Wilcox Nursery: Zack's Leap from Operator to Owner

    In this episode of Green Side Up, Jordan and Jason sit down with Zack Pitchford, owner of Wilcox Nursery & Landscape in Largo, Florida, to unpack his unconventional journey from high school nursery hand to retail nursery owner and landscape leader. Zack walks through his early days in environmental horticulture at UF, sweating it out on Jordan's maintenance crews, his eye‑opening internship at Valley Crest, and the multiple times he launched (and quit) Pitchford Design & Landscape before ultimately acquiring the historic Wilcox Nursery. He shares how he navigated the numbers, financing, and risk of buying a land-heavy business, rebuilt the team and hierarchy from the inside, and grew both the retail and services divisions. The conversation dives into leadership development, promoting from within, marketing strategy (Google Ads, SEO, email, and video content), and what he's seeing in today's softer design/install market. Zack also breaks down his water-conscious irrigation approach and lawn philosophy, talks about the rise of native plant demand and fine gardening maintenance, and reflects on building a business that can run without him while still serving his community and family. Connect with Zack: 🌐 Wilcox Nursery Website 📸 @wilcoxnursery on Instagram 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

  2. May 28

    Ep 126. The Permaloc Playbook: From Steel to Aluminum

    In this episode of the Green Side Up Podcast, Jason Lee and co-host Jordan Upcavage sit down with Mark Cohen of Permaloc to explore how aluminum edging has reshaped the landscape and hardscape industry. Mark shares the origin story of Permaloc, founded by landscape architect Daniel Zwier as the pioneer of aluminum landscape edging, and explains why aluminum's strength-to-weight ratio, sustainability, and longevity make it a superior alternative to steel and plastic. The conversation digs into spec-driven selling, how educating landscape architects fuels national distribution, and the role of trade shows, ASLA/CSLA partnerships, and student events like Labash and NCLC in influencing the next generation of professionals. Jason and Jordan add real-world contractor perspective—contrasting plastic and concrete edging with aluminum, discussing paver restraint practices in Florida, and talking through evolving applications like resin-bound aggregate and tree ring surfacing. Along the way, Mark highlights iconic projects featuring Permaloc, from the Lady Diana Memorial Fountain to major civic and cultural sites, illustrating how a "niche" product quietly defines and protects some of the most recognizable landscapes in the world. Learn More: https://permaloc.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 6m

  3. May 21

    Ep 125. Family Business to Destination Company: Jeffrey Scott on Building Better Landscape Firms

    In this episode of the Greenside Up Podcast, Jason and Jordan sit down in Tampa with renowned green-industry consultant Jeffrey Scott to unpack his journey from family pool-and-landscape business to leading coach, peer-group facilitator, and host of The Ultimate Landscape CEO. Jeffrey shares stories from growing up in his grandfather's pioneering gunite pool company, scaling a high-margin service division, and navigating the challenges of a crowded family business before launching his consulting practice. The conversation dives into the power of peer groups, why charging for estimates transformed Jordan's tree service, and how setting higher standards for employees and clients creates a "Destination Company." The trio also explores Lean management in practical, jobsite terms—from tool placement to shop organization—plus real-world challenges around sales slumps, weather, hurricanes, and cash flow, and how business owners can respond with better marketing, business development, and strategic experiments. They wrap with a look at mergers and acquisitions reshaping the landscape industry, the upcoming Summer Growth Summit in Detroit, and Jeffrey's framework for helping owners fix, scale, or exit their companies. 🌱 Connect with Jeffrey Scott Consulting 🌐 Website: www.jeffreyscott.biz 📲 Instagram: @jeffreymarkscott ☀️ Summer Growth Summit https://jeffreyscott.biz/summer-growth-summit-26/ 🎟️ Summer Growth Summit Discount Code / Registration Link: www.eventbrite.com/e/1983544708619/?discount=GreenSideUpPodcast 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 7m

  4. May 14

    Ep 124. Big Bids, Busy Seasons: Navigating Growth in the Green Industry

    In this episode, Jason and Jordan catch up on a busy season in the landscape business, comparing lead flow, close rates, and what's really driving sales in different markets. They swap stories about big opportunities—including a major 5,600-foot roadway bid in Kissimmee and a high-profile renovation at Queen of Peace Catholic Church in Gainesville—and break down how they think about strategic bidding for profitable commercial work. Along the way, Jordan spotlights his wife's children's book "Looking for Bunny Flies," now available on major platforms, and the two reflect on the challenge of growing a landscape company while staying smart about risk, equipment investment, and market positioning. 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)

    40 min

  5. May 7

    Ep 123. Partnership Done Right: Luke & Justin's Blueprint for Sky Palm Studios

    In this episode of the Green Side Up podcast, Jason andJordan hit the road to Gainesville, Florida to record at the impressive new home of Sky Palm Studios with co-founders Luke Lower and Justin Short. They dive into Luke and Justin's journey from running separate media companies—one focused on drone and aerial work, the other on video production—to recognizing they were better together and dissolving both businesses to form a new joint venture. The conversation covers how they met, why they chose a partnership despite all the horror stories, how they divided roles as CEO/COO, the impact of faith and family on their decisions, and the hard lessons learned from past failed partnerships, including Luke's front-row seat to his dad's physical therapy clinic struggles. Along the way, they talk burnout, retainer vs one‑off work, building out a beautiful studio space (complete with "sound reverberation walls"), the realities of S corps, K‑1s, and buying houses as young business owners, and what it takes to create a resilient, trust-based partnership in business. If you're a contractor, landscaper, or small business owner thinking about teaming up with a partner—or just wanting a peek behind the scenes of a growing creative agency—this episode is packed with stories and takeaways you'll recognize in your own journey. Connect with Sky Palm Studios: https://skypalmstudios.com/ https://www.instagram.com/skypalmstudios/ https://www.facebook.com/skypalmstudios/ 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 30m

  6. Apr 30

    Ep 122. Soil, Sprouts, and Moonlighting in Cedar Key

    In this episode of Welcome to Green Sign Up, Jordan and Jason start with some early-morning banter about The Curse of Oak Island before diving into real-world tree and landscape work in Florida. Jordan previews his meeting with "Mangrove Alan" on a new waterfront development, while Jason talks through lighting and landscape projects in Cedar Key. They then shift into plant health care operations with insights from certified arborist Ken Miller, covering audits for compliance, smarter use of polyphosphite and  MitoGrow, and adjusting soil pH with sulfur and lime based on University of Florida soil tests. The episode wraps up at the University of Tampa, where they compare treated and untreated trees and foxtail ferns, exploring how their plant health care strategies are showing up in canopy density, new shoot growth, and overall vigor. 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)

    53 min

  7. Apr 23

    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)

    1h 8m

  8. Apr 16

    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)

    1h 11m
See All (127)

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
    127
  • Rating
    Explicit
  • Copyright
    © 2024
  • Show Website
    Green Side Up

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