Green Side Up

Green Side Up

By Jason Lee & Jordan UpcavageBusinessEntrepreneurship
Download on the App Store

Green Side Up episodes

  • Ep 104. Entrepreneurship Isn't A Fairytale: Lessons From 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 salesβ€”close rates, how much money they're leaving on the table, splitting sales from operations, and why 2026 will be all about sales training and written processes. It's an honest look at how messy, painful, and rewarding entrepreneurship really isβ€”and how they plan to level up their landscape and tree service businesses in 2026.

    Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website πŸ“§ Email: [email protected] πŸ“˜ Facebook: Green Side Up πŸ“Έ @greensideuppodcast on Instagram πŸ“Έ @skyfroglandscape on Instagram

    Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service

    Save with SingleOps: πŸ’Έ Mention Green Side Up or use this link to get $500 off your SingleOps subscription: πŸ‘‰ Get $500 Off SingleOps

    Sponsors & Partners:

    πŸ‘‰ MitoGrow 🌱 πŸŽ₯ Intrigue Media on Instagram (@imintriguemedia) πŸ“ GS TrackMe

    Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

    1 hr 2 min
  • Ep 103. Internet Wizardry, Jambalaya, and Leveling Up Your Business

    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 challengeβ€”mower races, weed eater and edger contests, and this year's backpack blower soccerβ€”and how it boosts culture and retention. Jordan breaks down how he's using LiveSwitch and AI to turn quick video walkthroughs into written job scopes, crew orientation, and even palm fertilizer estimates, while Jason recaps turf results with MitoGrow, plans for new field trials, updates on the Landscape Rodeo date shift, and an upcoming MitoGrow video project. It's a tactical, real‑world look at using tech, culture, and systems to level up a green‑industry business.

    Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website πŸ“§ Email: [email protected] πŸ“˜ Facebook: Green Side Up πŸ“Έ @greensideuppodcast on Instagram πŸ“Έ @skyfroglandscape on Instagram

    Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service

    Save with SingleOps: πŸ’Έ Mention Green Side Up or use this link to get $500 off your SingleOps subscription: πŸ‘‰ Get $500 Off SingleOps

    Sponsors & Partners:

    πŸ‘‰ MitoGrow 🌱 πŸŽ₯ Intrigue Media on Instagram (@imintriguemedia) πŸ“ GS TrackMe

    Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

    1 hr 8 min
  • Ep 102. Busy but Broke: Fixing Your Pricing with the Million Dollar Landscaper

    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 budgeting, overhead, and job costing. He breaks down the differences between SORS, DORS, and MORS overhead recovery systems, explains how to find your true break-even on every job, and shows why "2x material" pricing is the lazy way that often leads to losses. Scott also discusses leaving the family business, becoming a firefighter, and now helping contractors build profitable companies through his Million Dollar Landscaper coaching and podcast.

    IG: Million Dollar Landscaper

    Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website πŸ“§ Email: [email protected] πŸ“˜ Facebook: Green Side Up πŸ“Έ @greensideuppodcast on Instagram πŸ“Έ @skyfroglandscape on Instagram

    Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service

    Save with SingleOps: πŸ’Έ Mention Green Side Up or use this link to get $500 off your SingleOps subscription: πŸ‘‰ Get $500 Off SingleOps

    Sponsors & Partners:

    πŸ‘‰ MitoGrow 🌱 πŸŽ₯ Intrigue Media on Instagram (@imintriguemedia) πŸ“ GS TrackMe

    Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

    1 hr 1 min
  • Ep 101. Landscaping Unfiltered: From Canada to the EQUIP Expo

    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 the power of podcasting for industry networking. Full of industry insights, laughs, and authentic advice for business ownersβ€”tune in for a fun and honest conversation among landscaping pros.

    Important Links: IG- @thelandscapedaddy, @paver_king, @iamahardscaper, @notourfinesthourpodcast Podcast- How to Hardscape and Not Our Finest Hour

    Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website πŸ“§ Email: [email protected] πŸ“˜ Facebook: Green Side Up πŸ“Έ @greensideuppodcast on Instagram πŸ“Έ @skyfroglandscape on Instagram

    Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service

    Save with SingleOps: πŸ’Έ Mention Green Side Up or use this link to get $500 off your SingleOps subscription: πŸ‘‰ Get $500 Off SingleOps

    Sponsors & Partners:

    πŸ‘‰ MitoGrow 🌱 πŸŽ₯ Intrigue Media on Instagram (@imintriguemedia) πŸ“ GS TrackMe

    Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

    1 hr 7 min
  • Ep 100. Shaking Up Success: Craft Cocktails, Tough Jobs, and Hard-Earned Wisdom

    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. Hear behind-the-scenes anecdotes from TV appearances, learn how word-of-mouth and reputation fuel growth, and discover the importance of teamwork, leadership, and adaptability in the ever-changing world of landscaping. Whether you're a seasoned business owner or just starting out, this episode is packed with real talk, lessons learned, and plenty of laughs from the crew that keeps it greenβ€”on and off the air.

    Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website πŸ“§ Email: [email protected] πŸ“˜ Facebook: Green Side Up πŸ“Έ @greensideuppodcast on Instagram πŸ“Έ @skyfroglandscape on Instagram

    Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service

    Save with SingleOps: πŸ’Έ Mention Green Side Up or use this link to get $500 off your SingleOps subscription: πŸ‘‰ Get $500 Off SingleOps

    Sponsors & Partners:

    πŸ‘‰ MitoGrow 🌱 πŸŽ₯ Intrigue Media on Instagram (@imintriguemedia) πŸ“ GS TrackMe

    Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

    1 hr 16 min
  • Ep 99. Winning Is In The Long Game: Current Struggles At SkyFrog And Independent Tree

    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 staff, encourages customer feedback through creative review requests, and upholds top-tier client service. Whether you're a business owner, a fan of industry insights, or just love genuine conversations, this episode offers practical tips and entertaining stories from the front lines.

    Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website πŸ“§ Email: [email protected] πŸ“˜ Facebook: Green Side Up πŸ“Έ @greensideuppodcast on Instagram πŸ“Έ @skyfroglandscape on Instagram

    Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service

    Save with SingleOps: πŸ’Έ Mention Green Side Up or use this link to get $500 off your SingleOps subscription: πŸ‘‰ Get $500 Off SingleOps

    Sponsors & Partners:

    πŸ‘‰ MitoGrow 🌱 πŸŽ₯ Intrigue Media on Instagram (@imintriguemedia) πŸ“ GS TrackMe

    Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

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

    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 profit versus salary, and the critical steps to setting your lawn care or landscaping company on a path to growth.

    Throughout the conversation, Joey dishes out practical financial wisdom, tells memorable stories from the fieldβ€”including gator hunts and blue-collar life in Floridaβ€”and discusses innovative initiatives like the Lawn Care Launch bootcamp and exciting industry events such as the Landscape Rodeo and Equip trade show.

    Whether you're looking to level up your small business or simply enjoy real-talk and laughs from industry insiders, this episode delivers the inspiration and know-how to move your business forward.

    Connect with Joey: www.thelandscapingbookkeeper.com www.lawncarelaunch.com IG-@joeycoberly. @thelandscapingbookkeeper

    Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website πŸ“§ Email: [email protected] πŸ“˜ Facebook: Green Side Up πŸ“Έ @greensideuppodcast on Instagram πŸ“Έ @skyfroglandscape on Instagram

    Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service

    Save with SingleOps: πŸ’Έ Mention Green Side Up or use this link to get $500 off your SingleOps subscription: πŸ‘‰ Get $500 Off SingleOps

    Sponsors & Partners:

    πŸ‘‰ MitoGrow 🌱 πŸŽ₯ Intrigue Media on Instagram (@imintriguemedia) πŸ“ GS TrackMe

    Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

    1 hr 20 min
  • Ep 97. Edutainment in Entrepreneurship: Mark Masseo's Story of Growth and Guidance

    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 from mentors like Tony Bassβ€”along with hands-on lessons in marketing, hiring, and facing adversityβ€”shaped his career. Brimming with personal stories, laughter, and actionable tips, this conversation is a must-listen for aspiring business owners, industry pros, and anyone who loves a good story about grit, growth, and giving back to the community.

    Whether you're here for tales of entrepreneurship, insider insights into the landscaping world, or just some solid business motivation, you'll find it all in this episode!

    Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website πŸ“§ Email: [email protected] πŸ“˜ Facebook: Green Side Up πŸ“Έ @greensideuppodcast on Instagram πŸ“Έ @skyfroglandscape on Instagram

    Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service

    Save with SingleOps: πŸ’Έ Mention Green Side Up or use this link to get $500 off your SingleOps subscription: πŸ‘‰ Get $500 Off SingleOps

    Sponsors & Partners:

    πŸ‘‰ MitoGrow 🌱 πŸŽ₯ Intrigue Media on Instagram (@imintriguemedia) πŸ“ GS TrackMe

    Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

    1 hr 25 min
  • Ep 96. EQUIP Expo Debrief and the $500 Google Review Challenge

    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 interactions, and the relentless work behind building a repeat customer base. They unveil their new systems for crew management and reveal a bold "Green Side Up Google Review Challenge" with a $500 prizeβ€”inviting listeners to step up their online game. Whether you're a landscaper, entrepreneur, or just love a good behind-the-scenes business story, this episode offers inspiration, tactical advice, and plenty of laughs. Tune in and get ready to up your Google review countβ€”and maybe score some cash!

    Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website πŸ“§ Email: [email protected] πŸ“˜ Facebook: Green Side Up πŸ“Έ @greensideuppodcast on Instagram πŸ“Έ @skyfroglandscape on Instagram

    Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service

    Save with SingleOps: πŸ’Έ Mention Green Side Up or use this link to get $500 off your SingleOps subscription: πŸ‘‰ Get $500 Off SingleOps

    Sponsors & Partners:

    πŸ‘‰ MitoGrow 🌱 πŸŽ₯ Intrigue Media on Instagram (@imintriguemedia) πŸ“ GS TrackMe

    Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

    59 min
  • Ep 95. LiveSwitch: Work Smarter, Not Harder

    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 Switchβ€”a platform enabling virtual job assessments, streamlining workflows, and saving businesses time and money. Jason and Jordan join the discussion, bringing real-world questions about adopting tech in complex service environments. From business tips to funny anecdotes, discover how Live Switch can revolutionize your workflow and why now is the time to embrace innovative solutions. Whether you run a landscaping crew, a tree service, or any field business, this episode offers practical advice and inspiration for leveling up your operations.

    LiveSwitch

    πŸ”— [Book a Demo] 🌐 Website 🎯 Start Your Free Trial πŸ’Έ Coupon: Use code Green10 for 10% off at checkout

    About LiveSwitch: LiveSwitch is the world-leading communications platform for small businesses and entrepreneurs. We provide world-class technologies that help small businesses thrive β€” directly saving them money, making them money, saving them time, and helping them serve their customers better. From virtual estimates and on-site documentation to AI built for small businesses, LiveSwitch uses innovative video and photo technologies to make it all happen.

    Connect with Jason and Jordan: 🌐 Green Side Up Podcast Website πŸ“§ Email: [email protected] πŸ“˜ Facebook: Green Side Up πŸ“Έ @greensideuppodcast on Instagram πŸ“Έ @skyfroglandscape on Instagram

    Visit Our Businesses: 🌿 SkyFrog Landscape 🌳 Independent Tree Service

    Save with SingleOps: πŸ’Έ Mention Green Side Up or use this link to get $500 off your SingleOps subscription: πŸ‘‰ Get $500 Off SingleOps

    Sponsors & Partners:

    πŸ‘‰ MitoGrow 🌱 πŸŽ₯ Intrigue Media on Instagram (@imintriguemedia) πŸ“ GS TrackMe

    Podcast Produced by: 🎧 Mr. Producer (@mrproducerusa)

    58 min

About Green Side Up

From the publisher's feed

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.

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