Jason Lee & Jordan Upcavage
Green Side Up
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...
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Autor
Jason Lee & Jordan Upcavage
Kategorie
Podcast-Website
Neueste Folge
12. Nov 2026
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Ep 99. Winning Is In The Long Game: Current Struggles At SkyFrog And Independent Tree 20.11.2025 59:15
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 1:19:49
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 1:24:59
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 58:40
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 57:45
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 59:20
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 1:02:43
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 1:05:54
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 1:03:09
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 1:11:36
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 58:59
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 39:12
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 1:10:55
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 27:29
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 52:28
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 56:01
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 47:29
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...
Ep 82. Biochar, Rain Delays, and Business Survival: A Candid Conversation 24.07.2025 1:04:41
In this episode of Green Side Up, Jason and Jordan dive deep into the world of tree care, landscaping, and business management. Jordan shares his recent biochar project in Tampa, detailing an innovative soil remediation technique that could revolutionize urban tree care. The duo discusses employee motivation, the challenges of working in tight urban spaces, and strategies for managing business dur...
Ep 81. Big Fish, Small Bream: Learning How to Let Others Lead 17.07.2025 54:58
In this episode of Green Side Up, Jordan dives deep into the art of delegation and managing multiple complex projects simultaneously. From mangrove trimming to root pruning and mulch installation, he shares insights on how to effectively hand off tasks to competent team members while maintaining quality control. The conversation explores the challenges of running a tree service business, the impor...
Ep 80. The CDL Conundrum: Clever Truck Strategies for Green Industry Pros 10.07.2025 58:27
In this episode of the Greenside Up Podcast, we dive deep into the world of commercial trucks and equipment for tree care and landscaping businesses. The hosts discuss their innovative vehicle setups, including custom bucket trucks, tow trucks with lifts and mini loaders, and strategies for maximizing efficiency while minimizing CDL driver requirements. They share insights on truck selection, trai...
Ep 79. Behind the Scenes: Private Equity, Culture, Home Services 03.07.2025 1:09:16
In this episode of Green Side Up, Johnny Furlong joins the crew to dive deep into the world of private equity, home services, and business ownership. The conversation explores the challenges and opportunities facing service-based businesses, from landscaping to plumbing and HVAC. Johnny shares insights from his experience in management, discussing the complexities of private equity acquisitions, t...
Ep 78. Shop Talk: From Weed Control to Employee Walkouts 26.06.2025 47:02
In this episode of Green Side Up, Jason and Jordan dive into a whirlwind of landscaping adventures. They explore Jordan's robotic mower saga, discuss the challenges of mulch distribution, and break down a unique herbicide experiment. The conversation takes unexpected turns, from an employee's abrupt resignation to security concerns after a past break-in. Packed with industry insights, equipment tr...
Ep 77. Make Your Phone Ring: Crush Competitors with Intrigue Media 19.06.2025 1:04:05
In this lively episode of Green Side Up, hosts Jason and Jordan dive deep with Rob and Vanessa from Intrigue Media, exploring the wild journey of a marketing company that specializes in helping landscape and tree service businesses crush their online presence. From humble beginnings of digital signage to becoming a powerhouse marketing agency, Rob and Vanessa share their origin story, trade show a...
Ep 76. Vacations, Taxes, and Flounder Gigging: A Green Industry Escape 12.06.2025 54:39
In this sun-soaked episode of Green Side Up, Jordan and Jason dive into their vacation adventures while keeping it real with industry insights. Jordan's cleaning freshly caught flounder in the Florida Panhandle, while Jason explores the Dominican Republic with his family. They break down a fascinating Trees Florida presentation about urban development, discuss the wild world of tangible property t...
Ep 75. Marketing, Mentorship, and Making Waves 05.06.2025 1:09:04
In this episode of Green Side Up, hosts Jordan and Jason sit down with Jay Worth, who shares his fascinating journey through the Green Industry. From selling eyeglasses to working at SingleOps and now leading marketing at Outdoor Environments Group (OEG), Jay provides insights into industry marketing, collaboration, and the unique culture of Green Industry professionals. He discusses his career ev...
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