Jason Lee & Jordan Upcavage

Green Side Up

Business EN ↓ 132 episodes

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 rea...

Author

Jason Lee & Jordan Upcavage

Category

Business

Podcast website

sites.libsyn.com

Latest episode

Jul 9, 2026

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Episodes

Ep 107. Profit Builder Breakdown: Pricing, Profit & Growth for Tree and Landscape Pros 15.01.2026

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...

Ep 106. Granum: Mark Sedgley's Merger of SingleOps, LMN, and Greenius 08.01.2026

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 us...

Ep 105. From Bushmaster to Baker: Scaling a 300‑Employee Landscape Company 01.01.2026

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-p...

Ep 104. Entrepreneurship Isn't A Fairytale: Lessons From 2025 25.12.2025

In this Christmas episode of Green Side Up, Jason and Jordan mix holiday banter with a candid year-end business recap. They talk about family trips, zero-turn barrel racing, raccoons in dumpsters, and then get real about 2025: slowdowns, layoffs, experiments with marketing, LiveSwitch video estimates, and dialing in plant health care. The core of the conversation is sales—close rates, how much mon...

Ep 103. Internet Wizardry, Jambalaya, and Leveling Up Your Business 18.12.2025

In this episode of the Green Side Up Podcast, Jason calls in from the SkyFrog shop kitchen while cooking a 10‑gallon pot of jambalaya for the year‑end party, and Jordan shares how his team has tightened up operations with a four‑day workweek and a cleaner, better-organized shop. They talk about SkyFrog's employee skills challenge—mower races, weed eater and edger contests, and this year's backpack...

Ep 102. Busy but Broke: Fixing Your Pricing with the Million Dollar Landscaper 11.12.2025

In this episode of Green Side Up, Jordan and Jason sit down with Scott from the Million Dollar Landscaper podcast to talk about why so many landscape and tree service companies stay busy but barely profit. Scott shares his journey from working in his dad's landscape company in Northwest Indiana to becoming Vice President, realizing the business wasn't making money, and then diving deep into budget...

Ep 101. Landscaping Unfiltered: From Canada to the EQUIP Expo 04.12.2025

Get behind the scenes at Equip Expo with this lively episode recorded in the Super Lawn Truck Studios! Mike and Chad, from Not Our Finest Hour Podcast, join the crew to share stories about growing their landscaping businesses, managing teams, and handling unique challenges like workplace vices, taxes, and HOAs. Dive into real-world discussion on hardscaping, new tech like AI estimating tools, and...

Ep 100. Shaking Up Success: Craft Cocktails, Tough Jobs, and Hard-Earned Wisdom 27.11.2025

Join Jason, Jordan, and Rob Duvall as they sip espresso martinis and dive into a lively, insightful conversation about their journeys in the landscaping industry. Recorded on the eve of the Equip trade show, this episode features stories of friendship kindled in a horticulture club, the challenges and triumphs of starting and growing a business, and practical advice for aspiring entrepreneurs. Hea...

Ep 99. Winning Is In The Long Game: Current Struggles At SkyFrog And Independent Tree 20.11.2025

Join us for a special in-person recording of the Green Side Up podcast, live from the Great Southern Tree Conference at the Hilton! In this episode, your hosts dive into the latest happenings in their business, share exciting updates about their ongoing Google review challenge, and get candid about the real-life complexities of running a service company. Hear first-hand how the team motivates staf...

Ep 98. Scaling Up Smart: Joey Coberly on Building Better Lawn & Landscape Businesses 13.11.2025

Dive into a lively episode of the Green Side Up podcast as hosts Jason and Jordan welcome special guest Joey Coberly, founder of Landscaping Bookkeeper and Lawn Care Launch. Joey shares his journey from leaving the corporate world to building businesses dedicated to empowering small operators in the green industry. Gain valuable insights into the art of bookkeeping, the importance of understanding...

Ep 97. Edutainment in Entrepreneurship: Mark Masseo's Story of Growth and Guidance 06.11.2025

Join us for an inspiring episode of the Green Side Up podcast recorded live from Equip in Louisville, Kentucky! This episode dives deep into the journey of Mark Masseo , a passionate entrepreneur and the "Token Yankee" of the show, as he shares his path from mowing lawns as a teen to building a successful landscaping business. Hear how Mark's early hustle, willingness to learn, and pivotal advice...

Ep 96. EQUIP Expo Debrief and the $500 Google Review Challenge 30.10.2025

Dive into an action-packed episode as Jason and Jordan share their candid debrief of the Equip Expo experience in Louisville, Kentucky. Hear first hand stories about midnight drives, early-morning recording sessions, setting up an engaging trade show booth, and the power of casual networking in the green industry. The hosts reflect on business growth, the importance of authentic client interaction...

Ep 95. LiveSwitch: Work Smarter, Not Harder 23.10.2025

Join us for a lively conversation with James Hatfield, Chief Revenue Officer of Live Switch, as we explore how technology is transforming the Green Industry and home services. James shares his journey from blue-collar entrepreneur to tech innovator, diving into the origins and impact of Live Switch—a platform enabling virtual job assessments, streamlining workflows, and saving businesses time and...

Ep 94. Procrastination, Pickups, and the Pursuit of Growth 16.10.2025

Get ready for a lively, story-packed episode! Join Jason and his co-host as they prepare for the Equip Expo in Louisville and candidly share the pitfalls of travel and late bookings. Listen to the dramatic saga of repeated truck breakdowns, from battery mishaps to DIY roadside fixes—even a helpful push from passing strangers. The hosts dive deep into their landscaping business operations, explorin...

Ep 93. Seasonal Hustle: Surviving Slowdowns, Sagas, and Surprises 09.10.2025

Join Jason and Jordan for an action-packed, early-morning episode recorded in the dark—literally! The guys dive into the ups and downs of running a landscaping and tree service business as the seasons change, sharing real talk about budgeting, staffing, and the unpredictable flow of work. Hear about their latest marketing experiments, from Google Ads to SEO pillar posts, and get a front-row seat t...

Ep 92. Scammed and Slammed: Don't Drink and Drive 02.10.2025

Join Jason and Jordan as they kick off another early-morning episode live from the Sky Frog Kitchen. This week, the Green Side Up Podcast dives into lively tales of alligator hunting adventures, from pre-dawn wake-up calls to boat mishaps and celebrating a record 11-foot, 7-inch catch. The guys share a cautionary tale about falling victim to a sophisticated phone scam—don't miss their essential pu...

Ep 91. Poopin' on the Clock, Bar Golf, and Swamp Stories 25.09.2025

Join Jordan and Jason for a candid, entertaining episode of the Green Side Up Podcast! They tackle the realities of managing a crew (including some hilarious bathroom stories), share wild alligator hunting adventures, and give updates on the upcoming Landscape Rodeo event and new sponsor, Mito Grow. Plus, hear about their charity work, neighborhood antics, and lessons learned from scam calls. Tune...

Ep 90. 5 Marketing Mistakes Green Industry Entrepreneurs are Making 18.09.2025

Unlock the secrets to marketing success in the Green Industry with this insightful episode featuring Rob Murray, co-founder and CEO of Intrigue Media . Recorded live at the Knowledge College session, Rob shares hard-earned lessons from 15+ years of empowering home improvement businesses. Discover the five most common marketing mistakes, why Google reviews are your secret weapon, and how to leverag...

Ep 89. Alligators, Expos, and ICE Deportation 11.09.2025

Join Jason and Jordan for a lively early-morning episode of the Green Side Up Podcast! This week, the duo dives deep into the upcoming Landscape Rodeo event in St. Augustine, sharing behind-the-scenes planning, event highlights, and how you can get involved. They also break down the Equip Expo, reminisce about industry road trips, and debate the impact of Florida's new immigration enforcement on t...

Ep 88. Cultivating Success: The Williams Nursery Story 04.09.2025

Jordan reconnects with his college roommate, Justin Williams, at the Landscape Show in Orlando for a lively and insightful episode of the Green Side Up podcast. Together, they reminisce about their days studying horticulture, share stories from their time as roommates, and dive deep into the evolution of Williams Nursery —a thriving family business in Jacksonville, Florida. Justin discusses the ch...

Ep 87. The Price is Right! 28.08.2025

Join us live from the show floor at the Landscape Show for this week's episode of the Green Side Up Podcast! Hosts Jason and Jordan welcome back Tony Bass , industry veteran and Profit Builder seminar leader, for a deep dive into the real numbers behind running a successful lawn and landscape business. Discover why most companies struggle with low profit, and the three levers every business owner...

Ep 86. Keep your Fleet Fresh 21.08.2025

Welcome back to the Green Side Up Podcast! In this lively, in-person episode recorded live from the trade show floor at the 2024 Landscape Show in Orlando, Jason and Jordan reconnects with Giovanni and Enrique, the innovative founders behind Fleet Fresh —a plant-based deodorizer designed for fleet vehicles and more. Hear the fascinating story of how a background in the marine industry and a knack...

Ep 85. The Landscape Rodeo 14.08.2025

Get ready for a jam-packed episode of the Green Side Up Podcast! Jason and Jordan reunite after a brief hiatus to catch up on company updates, including a new spray technician and the annual company-wide vacation. They dive into the challenges and quirks of landscape maintenance contracts, sharing the story of a major client who might be making a comeback. The highlight of the episode is the offic...

Ep 84. Hiring Made Simple: Team Engine's Approach to Workforce Success 07.08.2025

Join us for this episode of the Green Side Up podcast as we sit down with Carlos, co-founder of Team Engine , to explore the challenges and solutions in recruiting, retaining, and engaging field-based workforces. Carlos shares his personal journey from military service to entrepreneurship, and how his background inspired the creation of Team Engine—a software platform designed to automate and stre...

Ep 83. Tree Preservation in Urban Redevelopment: Challenges and Solutions 31.07.2025

In this compelling episode, veteran arborist Eric Lawyer and industry leader Jordan Upcavage discuss their collaborative approach to tree preservation during a complex 30-acre housing redevelopment project in Tampa. They share insights into navigating city regulations, managing aggressive tree pruning, and implementing innovative root invigoration techniques. Learn how professionals balance urban...

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