Green Side Up
Green Side Up
Jason Lee & Jordan Upcavage
Ep 128. Can You Really Take a Vacation When You Own the Business?
1 hour Posted Jun 11, 2026 at 8:00 am.
0:00
1:00:39
Download MP3
Show notes

In this Vacation Edition of the Greenside Up Podcast, Jordan and Jason catch up from the road—Jordan broadcasting from a family beach trip on Florida's Panhandle and Jason checking in from the mountains near Pigeon Forge, Tennessee. They swap stories about night crabbing, offshore fishing, Dollywood, cave tours, and even a behind-the-scenes look at the Bush's Baked Beans factory. Woven through the vacation highlights is a candid conversation about what it really takes to step away from your business: how Skyfrog Landscape has evolved since the "Siesta Key chaos" days, the impact of hiring and culture on being able to unplug, losing a key office manager, and why owners never fully "clock out." They also touch on industry events like Trees Florida, the Arbor Next youth program, upcoming trade shows, and a surprising win using AI ("Switchy") to diagnose a boat motor issue. It's a relaxed, real-world look at balancing work, leadership, family time, and the never-ending responsibilities of business ownership.

Connect with Jason and Jordan:
🌐 Green Side Up Podcast Website
📧 Email: [email protected]
📘 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)