Green Side Up — Ep 111. "Kicking off 2026: Water Main Craters, Lost HOAs, and Marketing ROI"

Date: February 12, 2026
Hosts: Jason Lee & Jordan Upcavage

Episode Overview

In this high-energy episode, Jason and Jordan dive into the realities of running and growing landscaping and tree care businesses as they start their 2026 adventure. The duo swap tales from the trenches, dissect recent emergencies (including a literal water main crater), grapple with marketing ROI, and confront the loss (and reclaiming) of tricky HOA contracts. Listeners get an unfiltered glimpse into the ups and downs of entrepreneurial life in the green industry, with plenty of wit, wisdom, and raw honesty.

Key Discussion Points & Insights

1. Reflecting on January & Guest Highlights

[03:40–06:21]

• January was packed with quality guests, from a money expert (Danny) to a pharmacy entrepreneur ("Eyedrop Andrew", who infamously shipped a surprising volume of "dick injections"):
  • “The volume of dick injections that Andrew had shipped out was remarkable.” — Jordan [04:39]
• Recap of appearances on the "Million Dollar Landscaper" podcast discussing hiring practices.

2. Current Business Activities — Growth & Challenges

[06:48–13:47]

• Jason shares efforts to restart business development activities, especially getting more involved with local associations and targeting HOAs for speaking opportunities.

• The push to get Aaron back into business dev roles despite time constraints caused by planning the upcoming Landscape Rodeo.

• Lead flow is steady for both hosts’ companies; strategies for more efficient sales and same-day estimates are yielding results for landscape jobs.

• Prepping for spring with ongoing paver projects. Winter has slowed growth and “browned out” lawns, but expectations are high for a vigorous comeback.

  “I maintain the place also. It’s like, this is perfect. This grass isn’t going to grow for another 30 days. But when it does, it’s going to come back with vengeance.” — Jason [13:13]

3. Emergency Water Main Explosion & Tree Rescue

[13:47–20:09]

• Jordan details responding to an emergency call: a water main explosion in Tampa that destroyed part of a road and left a massive crater threatening a grand 40-inch oak tree.

• Logistics challenge: Crater size, damaged infrastructure, and tricky machinery placement without disrupting traffic or property.

• Unique, high-stakes projects keep things engaging:

  “I hate cutting trees down, but this is, in a way, kind of fun because it’s unique. I don’t get to see water explosions under trees every day.” — Jordan [19:59]

4. Tech Tools: Live Switch Shout-Out

[20:09–23:48]

• Jordan’s positive update: Listeners from Alfieri Tree Care (Massachusetts) heard about Live Switch on the podcast and signed up.

• Testimony on how video-based job documentation has upped the company’s professionalism, set him apart from competitors, and made communications easier:

  “My bid presentation was more professional, easier to understand, and was just sexier. And I think Live Switch played a pretty damn well.” — Jordan [22:59]

5. Marketing & Promotions — ROI Real Talk

[25:00–44:17]

• Both hosts dig into their work with Intrigue Media, a marketing firm handling email campaigns, search optimization, and blogging.

• Jordan details a highly effective 10% discount winter promotion blasted to 10,000+ clients; significant spikes in inquiries and jobs resulted.

• Pricing transparency: Discounts applied to labor only to keep things “not flim-flammy.”

  • “It’s legitimate and real. And it’s not all flim flammy, right?” — Jordan [30:03]

• Numbers coming in are very promising — click-through rates and open rates impress both the hosts and their marketing partners.

• Discussion on measuring true marketing ROI:

  • How do you separate organic leads from those generated by the marketing company?
  • Is it even possible, or is it all just part of the business DNA now?
  • Jason reports their marketing dollars are now returning 7–8x, with hopes for greater than 10x as systems mature.

  “It’s the most talked about thing that no one understands...and no one knows what the return should be. And it’s okay not to know, but if you’re spending a bunch of money and you don’t feel like you’re getting a return, then don’t do it.” — Jason [41:33]

• Both reflect that the true test will be a complete annual cycle with the same systems and partners in place.

6. Losing, Leaving, and Winning Back HOAs

[48:00–56:44]

• Jason candidly shares the gut-punch of losing a 12-year, $100-150K annual contract with a large HOA, probably due to price pressures and property management turnover.

• Strategic optimism: leaving the property in immaculate shape with hopes to be the first call when discontent sets in.

• The gritty truth: The green industry is full of “crazy” HOA boards, client churn, and management shakeups.

  “12-year relationship is now gone. And I don't know if that is solely on...price. The irrigation in the neighborhood is a natural born catastrophe.” — Jason [51:25]

• Story of another HOA: after seven months with a budget provider, the property deteriorated and Sky Frog was called back.

7. Dealing with Difficult Customers: The HOA Wildcards

[56:44–61:40]

• Tales of residents resistant to services, special requests, and even police being called over fertilizer applications.
• Jordan: “You have 10 or 15 change orders and special order omelets that you have to juggle.” [56:44]
• Solution: Block problem callers, document everything, and focus on legal compliance.

8. Landscape Rodeo Final Countdown

[61:40–67:28]

• The first Landscape Rodeo (Feb 19–20) — a festival of landscaping skill competitions — is almost here.
  • Major sponsors (Hustler Turf, Gravely, Super Lawn Trucks).
  • Competitions include decathlon events, paver and mowing challenges, and a VIP dinner (Lowcountry Boil — Jordan's estimating 80–800 lbs of crawfish!)
• Strong encouragement to register early for events and the dinner.
• Major prize: $1000 for the decathlon winner (“lowest average ranking across 10 events”).
  • “With my intrigue math, that's 20 times return on investment...” — Jordan [66:32]

Notable Quotes & Memorable Moments

• On adapting marketing strategy:
  “That campaign goes over several days until we've liquidated 10,035 emails.” — Jordan [31:27]
• On business setbacks:
  “It’s a kick in the pants as we’re trying to grow our budget, you know, grow by a million plus. Yes, I'm losing 10% off the top of my growth plan.” — Jason [50:44]
• On HOAs:
  “And the amount of crazy people that live in HOAs… it’s gotta be at least 10%, right?” — Jason [56:09]
• On the unpredictability of entrepreneurship:
  “Let’s have fun 2026. Way to kick it off. Let's have fun this year.” — Jordan [03:27, paraphrased]

Important Timestamps

• Reflections on January, guest highlights: [03:40–06:21]
• Business dev, bidding work, spring prep: [06:48–13:47]
• Water main explosion emergency & tree: [13:47–20:09]
• Live Switch tool praised: [20:09–23:48]
• Marketing, email campaigns, ROI: [25:00–44:17]
• Losing major HOAs & customer churn: [48:00–56:44]
• HOA crazy stories & compliance: [56:44–61:40]
• Landscape Rodeo details & call to action: [61:40–67:28]

Closing Notes

• The episode offers unvarnished entrepreneurial realities: weathering business losses, negotiating customer quirks, celebrating marketing wins, and prepping for high-stakes industry events.
• The hosts’ camaraderie and candor help listeners see that struggling with turnovers, ROI debates, and customer outbursts is all “part of the ride.”
• Listeners are urged to sign up for the Landscape Rodeo and stay tuned for future episodes exploring business managers, growth, and all things green industry.

Contact the show: greensideuppodcast@gmail.com
Landscape Rodeo info: thelandscaperodeo.com

Keep working hard, play harder, and keep the green side up!