Green Side Up – Ep 113: "The First Annual Landscape Rodeo: A Full Rodeo Recap"

Overview

In this lively recap episode, hosts Jason Lee and Jordan Upcavage are joined by guest Aaron Alvarez to break down their experience organizing and hosting the very first “Landscape Rodeo” in St. Augustine, Florida. The trio share behind-the-scenes stories, lessons learned, memorable moments, and practical wisdom for entrepreneurs in the landscaping and tree care industry. Listen in for tales of teamwork, fostering the next generation, hands-on competitions (including wheelbarrow races and crawfish boils), and a profound sense of community within the green industry.

Key Topics & Highlights

1. Bringing the Landscape Rodeo to Life

• Event Genesis & Organization

  • Months of preparation with Aaron and FNGLA Front Runners as co-organizers ([03:57]).
  • Securing insurance coverage right up to the last moment:
    "There's nothing like sending that [insurance paperwork] down to the last minute as equipment's landing on site…” – Jason ([03:57]).
  • Lesson: Find an experienced insurance broker early on; it saves stress and money ([04:30]).

• Logistics & Set Up

  • Equipment began arriving two days before the event ([05:56]).
  • Volunteers and vendors helped create event courses, some of which were being conceptualized for the first time.

• Publicity

  • Aaron shared about last-minute PR efforts: radio spots, a feature on NPR​’s “First Coast Connect,” and local morning shows ([07:09]).

2. Pre-Event Festivities – Exhibitor Dinner & Crawfish Boil

• VIP Crawfish Boil
  • “Charcuterie table and fixings” lauded as “epic ... beyond whatever the next step over charcuterie is” – Aaron ([13:48]).
  • Jordan describes meticulous engineering of the crawfish race board, improvising with dental floss and a pocketknife:
    “You gotta pony up five bucks, you pick your crawdaddy … when it’s go time, we lift the bucket and there’s a pile of crawfish in the middle.” ([14:22]).
  • The spirit of camaraderie:
    “Next thing I know, I got five dudes sitting around me sucking heads and eating food … If I’m going to be on death row and have a last meal, it’s a low country boil.” – Jordan ([20:34]).

3. The Big Day: Landscape Rodeo Competitions

• Opening Ceremony

  • Aaron takes over the mic as Jason loses his voice after a week of prep.
    “We’ve been planning this for over a year … it was the culmination of everything.” – Aaron ([25:14]).

• Key Events & Winners

  • Truck and Trailer Course, Wheelbarrow Races, Backpack Blower Soccer, Pallet Stacking, Articulating Loader, Zero-Turn Relay, and more ([08:15], [30:40], [41:41]).
  • Jordan’s pride:
    “Your boy took first place. Took gold medal right here. … There’s a wheelbarrow and there’s some grit, and there’s a contest. Who can put this heavy thing in that and push it over there the fastest? I’m gonna win.” ([30:40]).
  • Sky Frog’s Keith wins the decathlon with a multi-event strategy ([41:41], [52:35]).

• Precision Over Speed

  • The message of the day:
    “As Aaron told us … this is a game of precision. Precision will prevail. And time is merely a tiebreaker of precision. And my haste dinged me into second place.” – Jordan ([11:13]).

• Hands-on Equipment Demos

  • Participants test-drove Gravely and Hustler Zero Turns, Bobcats, Avant loaders, Fox Loaders, Super Lawn Truck box trucks, etc.
    “I’d never driven an Isuzu box truck … and I did pretty damn good!” – Jordan ([11:40]).

• Owner-Operators, Students, and Next Generation

  • School FFA chapters compete; Oak Leaf dominates backpack blower soccer ([26:13]).
  • University of Florida sends a strong team ([28:45]).
  • Range of participants from small owner-operators, large companies, and municipalities.
  • Notable “cowboy hat assassin” – a standout, skilled (and stylish) competitor ([26:57]).

4. Impact & Takeaways

• Fostering Industry Passion

  • Media highlight:
    Student: “I wasn’t thinking about landscaping … but after seeing the money in it and all the equipment, I’m actually really interested.” (quoted news segment, [42:14]).

  • Jason:
    “How do we get new employees in this industry that everyone bitches about? Bam. Just cracked the code. Landscape Rodeo.” ([43:14]).

• Hands-on Networking

  • Real, in-person dialogue between industry vets and the next generation:
    “It’s a great way to network for their future.” – News clip ([42:10]).

• Best Aspects & Lessons Learned

  • Tremendous teamwork and volunteer support:
    “What worked the best is that we pulled it off … The greatest takeaway is that we hit the metrics we were looking for and set the bones for the future.” – Jason ([36:00])

  • Areas for growth:

    • More volunteers for smoother schedules, more open-ended event participation ([45:57]).
    • Improved event flow and demo area layout, apologizing to vendors who ended up “on an island” ([47:19]).
    • Hopes for broader municipality involvement.

5. Memorable Quotes & Moments

• On the Event’s Essence
  “The energy was so wonderful. Everyone coming … and as we were up … in Dan’s office doing our little ticky tacky, getting ready for the day, I get the radio call, people are here. It’s like, oh, it’s registration time. We got to go down there and make it happen.” – Aaron ([25:14])

• Precision Over Speed
  “Precision will prevail. And time is merely a tiebreaker of precision.” – Aaron (Quoting himself at opening), ([11:13])

• Lessons in Leadership
  “It’s identifying what you have to do and then figuring out how you’re going to do it and accomplish it and then doing it within the time frame you have to do it … Then you find a thousand other things that you have to do that manipulate and change the things you have already identified.” – Jason ([36:30])

• Jordan’s Reflection on Camaraderie
  “I feel like I have succeeded and done a little bit of my part to … embolden the guy that’s going behind you and see if he can beat you. … You put a hand out to give a hand up.” ([51:04])

6. Touching Close: “Looking for Bunny Flies”

• Jordan celebrates his wife Sidney’s accomplishment as a children’s book author, sharing the heartfelt story behind “Looking for Bunny Flies.” ([57:29])
  • “You may not have known that you’ve seen a bunny fly today, but I saw one, and it’s happening right now. I am looking at two bunny flies through this computer. … That’s a bunny fly I’m looking at right now.” – Jordan ([61:07])

7. Key Timestamps (MM:SS)

• Event prep & insurance: 03:57–05:56
• PR & media: 06:58–07:21
• Course building: 08:11–12:50
• Exhibitor dinner & crawfish race: 13:39–22:16
• Opening ceremonies & student engagement: 24:35–26:03
• News clip with students: 40:37–43:14
• Lessons learned: 36:00–38:04; 45:57–49:02
• Awards & closing stories: 52:35–55:44
• “Looking for Bunny Flies” segment: 57:29–61:22
• Closing thanks: 61:27–64:58

Summary & Next Steps

This episode is a masterclass in community spirit, grassroots event organizing, and the value of hands-on engagement in the landscaping and tree care industries. Jason, Jordan, and Aaron’s storytelling brings the colorful chaos, learning curves, victories, and celebrations of the first Landscape Rodeo to life—leaving listeners inspired by the “messy reality” and camaraderie of entrepreneurship.

Stay tuned for next year’s event; follow the Landscape Rodeo on Instagram, Facebook, TikTok, and YouTube. If you attended, tag your posts so the community can share in your memories!

Notable Sponsors Thanked:

Super Lawn Truck, Hustler Turf, Gravely Lawn Mowers, Dynamic Equipment Group, Alta Equipment, Crystal Tractor, Box Loaders

Memorable Final Words:

"As you continue your journey toward entrepreneurial success, let Jason and Jordan be your trusted companions ... keep working hard so you can play even harder and keep the green side up." ([65:08])