Green Side Up: Ep. 108 — "Wheelies, Skid Steers, and Backpack Blowers: The Landscape Rodeo"

Date: January 22, 2026
Hosts: Jason Lee & Jordan Upkavage

Episode Overview

This episode is a deep dive into the upcoming inaugural Landscape Rodeo—a unique, hands-on competition for landscape and tree care professionals in Florida. Hosts Jason and Jordan break down the event's creation, preview the events (with lively tales from their media day escapades), and share logistical details, registration tips, and broader industry insights. Along the way, they unpack business strategies, new tech tools, and plant health care advances, all in their unfiltered, on-the-ground style.

Key Discussion Points and Insights

1. Landscape Rodeo Hits the Limelight

• The inspiration for the Landscape Rodeo: turning real-world landscaping skills into competitive, fun challenges.
• The front-page feature of Lawn & Landscape Magazine, with “Yankee Dan” popping a wheelie on a zero-turn mower—an instant viral moment for the event’s buzz.
  • Quote: “That Yankee Dan is popping a wheelie on your hustler Z-turn on the front page of lawnandlandscape.com!” (Jason, 04:23)

2. Event Preview: What’s on Tap at the Rodeo?

[07:00–16:00]

• Competitions include:
  • Zero-turn mower barrel racing
  • Skid steer tire flip
  • Mini skid steer pallet stack challenge
  • Two-person mower relay
  • Backpack blower soccer (with comical struggles finding the “right ball”)
• Challenges in event design:
  • The backpack blower soccer game: Too wild, too hard, too much fun—no one has scored yet.
    • Quote: “The guys just go full, fighting with backpack blowers… But then at the end of it, it’s so hard, like no one scores.” (Jordan, 05:08)
    • Experiments with soccer balls, beach balls, exercise balls, foam balls, and field configurations.
  • Jason’s suggestion to solve the scoring: “What if you just have an end zone instead of a goal?” (Jason, 09:14)

3. Behind the Scenes: Media Day Madness

[10:56–19:23]

• Media Day Recap:
  • Industry friends and sponsors test-drove courses and equipment.
  • Social media content creation—drone footage, stills, meta-glasses videos.
  • Dan’s fearless wheelie becomes the signature image.
  • Quote: “Dan comes down and… pops a wheelie, runs the course, Ric Flair hollering.” (Jordan, 17:31)
• Equipment talk:
  • Range of machines (Gravely, Hustler, Takahoochi, Toro Dingo, Vermeer).

4. Event Logistics: How to Register & What to Expect

[21:00–30:38]

• Event Date & Venue:
  • February 19 (VIP Dinner) & February 20 (Rodeo), Ancient City Farmstead, St. Augustine, FL.
  • Website: thelandscaperodeo.com
• Early bird registration, T-shirts, swag bags, and VIP dinner details.
  • “We are making the events pretty low cost… Our goal now is to get teams signed up and people registered.” (Jordan, 21:05)
• Spectator, dinner, and event tickets are affordable ($10 to attend, $50 VIP dinner, $5 per event).
  • Quote: “If you have not had the life experience… you can potentially break [a mower] for five bucks.” (Jason, 25:41)
• Team and individual sign-up options; accommodations for solo participants.

5. Event Structure & Prizes

[28:00–31:10]

• Over 20 events; $1,000 cash prize for the decathlon winner (lowest average rank across 10 events).
• Belt buckles for individual event winners—real, engraved metal buckles.
• Strategic advice: “If you want to win the thousand bucks, register for as many events as possible to average out your odds.” (Jordan, 30:13)
• Sponsors make the low entry cost possible; shoutouts to key supporters.

6. Lodging & Logistics for Attendees

[34:03–36:49]

• Block rooms at the World Golf Village Renaissance St. Augustine Resort for $149/night (well below market).
• Other affordable local lodging & RV options.
• Step-by-step tips for out-of-towners: where to stay, logistics on arrival day, food trucks, after-hours networking.

7. Business & Plant Healthcare Insights

[41:11–52:24]

• Mitigro plant supplement discussion: lessons from field tests and new application rates.
  • Jason & Jordan share how correct dosing and aggressive applications have started to show results.
  • Use cases for lawns, sports fields, and mature trees.
  • Quote: “I have my eyes opened and I am changing what I am doing.” (Jason, 52:18)

8. Operational Tools: Bringing AI and Video into the Field

[62:57–68:20]

• Leveraging Live Switch: Using video documentation and AI work order generation for client walkthroughs and crew briefings.
  • Detailed workflow: video link in crew notes and client emails.
  • Quote: “My proposals are that much more flashy, sexy, professional and it represents my business even better.” (Jason, 66:09)
• Discussing generational tech shifts and staying ahead of industry automation.

9. Future Guests & Upcoming Episode Teasers

[71:11–73:26]

• Upcoming guest: “Danny,” an ex-employee turned financial advisor, discussing retirement and IRA setup for the industry.
  • “Don’t try to sell it to me one-on-one. Let’s record it. Great info for our listeners.” (Jason, 71:29)
• Upcoming adventures: Bull riding event, Gasparilla Children’s Parade, networking opportunities at the rodeo.

Notable Quotes & Moments

On the energy of the rodeo:

“If you can drive it, cut it, trim it or haul it, it’s time to prove it.” (Announcer Sam, 13:29)

On realistic event creation:

“We are making this up as we go. Like there’s no regulation. There’s no three-on-three backpack blower soccer regulations for us to follow. This isn’t the Ocho!” (Jordan, 10:17)

On business mindset:

“If you want to bet on yourself for $60, you could turn 60 into a grand. You never know.” (Jordan, 30:13)

On staying ahead:

“We used to be the poachers with the typed proposals… But now we’re getting picked off by Gen Z-ers and, soon, alphas, who have ChatGPT and AI as part of their culture.” (Jason, 66:29)

Timestamps for Key Segments

• 00:47–04:55: Icebreaker, cold weather blues, Dan’s media day antics
• 07:00–10:09: Backpack blower soccer saga and brainstorming solutions
• 10:56–19:23: Social media content creation; wild rides and event-planning stories
• 21:00–30:38: Registration walkthrough and behind-the-scenes logistics
• 34:03–36:49: Accommodations and travel tips for attendees
• 41:11–52:24: Mitigro plant health product deep-dive and application lessons
• 62:57–68:20: Adoption of Live Switch AI tools and tech-forward business strategy
• 71:11–73:26: Upcoming guests, rodeo week plans, community-building outlook

Final Thoughts

This episode is a lively, inside look at how industry events are born, the chaos (and comedy) of turning skilled trade into competition, and the evolving business tools helping landscapers and arborists set themselves apart. From hands-on mower stunts to practical advice on plant health and technology, Jason and Jordan’s authenticity and expertise shine through—creating both a valuable resource and a rallying cry for Florida’s green industry.

Actionable takeaway:
Want to participate? Visit thelandscaperodeo.com and sign up—"crazy cheap, unforgettable, and your chance to mix skill, fun, and professional growth in one wild weekend."