IM Landscape Growth Podcast

Running a $4M Tree Biz with Humor, Hustle & Big Nuts – Jordan Upcavage


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“If you’re not making enough money—just charge more.” — Jordan Upcavage

Resources Mentioned in This Episode:

GS TrackMe – GPS and camera tracking system for fleet safety, driver accountability, and insurance protection.
SingleOps – CRM and operations software used to track leads, job progress, and client communication.
Jeffrey Scott Roundtable – Where Jordan first heard the idea of charging consult fees—and implemented it immediately.
ISA (International Society of Arboriculture) – Arborist association behind events like Trees Florida.
Green Side Up Podcast – Jordan and Jason’s industry podcast—raw, real, and ridiculously entertaining.
Independent Tree Service – Jordan’s Tampa-based, $4M tree care company. Website: independenttreeservice.com

Topics Discussed:

[00:00] Meet Jordan Upcavage of Independent Tree Service
How Jordan rebuilt a family business after a total team meltdown—and scaled it to 5 crews and 10 arborists.

[10:33] Engineering Trees & Bracing Systems
Cabling, lightning protection, and propping up 50-foot trees with zinc rods—Jordan doesn’t do ordinary.

[12:25] The Real Growth Constraint: You
It’s not the labor pool or cash. It’s the owner's fear of trying something new—and doing the hard stuff.

[26:35] The $80 Lesson That Changed Everything
Jordan shares how undercharging as a young landscaper taught him the value of his time and knowledge.

[30:12] Charging for Consults Changed the Game
How a $50 consult fee filters tire-kickers, increases trust, and improves close rates—all without hurting leads.

[39:36] How Jordan Stays Sharp as the Business Grows
Investing in team development keeps him focused—and future-proofs the business.

[44:32] Don’t Fear Competition—Build It
Jordan’s philosophy on training people who might leave: good for them, good for the industry, good for you.

[45:46] The Triple-Tap Google Review Strategy
In-person ask, follow-up call, and invoice reminder—how Jordan’s team generated 595+ five-star reviews.

[50:00] Launching a Website in Under 10 Days
Jordan dishes on why his new site went live fast (and what other companies are doing wrong).

[52:18] Favorite Wisdom: Keep It Simple
“If you’re not making enough money—just charge more.” Timeless advice from Jordan’s dad.

Actionable Key Takeaways:

The #1 growth constraint is you. Business owners who don’t try new things or take risks stay stuck.

Charge for consults. A $50 fee weeds out low-quality leads and boosts respect for your time.

Undervaluing yourself is expensive. Know what your expertise is worth—and price accordingly.

Build a team of killers. Jordan trains his crew to become certified arborists and future leaders.

Get reviews the human way. Ask in person, follow up by phone, and include it in the invoice.

Referrals > Ads. Delivering a stellar customer experience leads to word-of-mouth that can’t be bought.

Let people leave better than they came. Training someone who eventually starts their own business is a win—not a loss.

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IM Landscape Growth PodcastBy Intrigue Media