Spotlight: Dylan Colwell on Growing a Team-First Tree Care Operation in St. Petersburg

The Indian Shores Busboy to Tree Service Business Owner Journey

Justin: Dylan, last time we spent our one-on-one talking mostly about my side of the platform, but today I want to focus on you. If a homeowner is reading about E & D Trees and trying to decide who to hire, what is the story behind how you got into the business?

Dylan: Honestly, it was a wild start. Back in 2016, I was working as a busboy at a pub on Indian Shores. Hurricane Irma hit, and a buddy of mine who had a truck came up to me and said, "Dylan, go buy this trailer, we'll go make money." I bought the trailer, and we started working together under a company called All Around Trees. But to be completely honest, we failed miserably.

the business setup was a mess. I was always owed thousands of dollars. We'd do a job, get paid, and then he'd need to borrow money just to cover the next job. I kept thinking, this is not how business is supposed to work. We're supposed to be profitable, not constantly playing catch-up.

Fast forward to COVID in 2020. I went to go file my taxes and found out he had taken me off the LLC. It was a mess, but I realized it was my chance to do things right. I took the truck and decided to haul butt on my own.

Justin: That is a tough transition, especially with a partnership ending like that. How did you get the wheels moving on E & D Trees?

Dylan: I was at a gas station with my truck shortly after the split, and this guy walked up to me and said, "Hey, I'm a climber." I took his number. Almost immediately after, tree leads started flooding my phone. I didn't want to leave money on the table, so I called that climber, Seth. He came out that very first day and ran circles around everybody. He was incredible, and it was the coolest thing to watch.

Me and Seth ended up working together for four years straight. We did hurricane work, removals, everything. But the key was that I did everything opposite of how my first partner did it. I focused on profit, organization, and treating people right. Today, E & D Trees has grown from a guy with a truck and trailer into a full operation: four full-time employees, two work vehicles, a dump trailer, a 60-foot lift, and both a big and small skid steer.

Emergency Services & The Ethics of Tree Work

Justin: You've travelled for storm work too, right? That's a completely different level of intensity.

Dylan: Oh, yeah. I've done about six named storms now. We actually travel to the storm zones, camp out, and work for two weeks straight doing emergency services. We take massive trees off houses, structures, and vehicles. We have access to cranes and heavy equipment—there's literally not a tree too big or too small for us.

Justin: But it's not just about cutting everything down. In our previous chats, you mentioned having a strong environmental ethic.

Dylan: Exactly. I have three kids, and I don't want to cut all the trees down. If I do that, what's left for them? Trees are alive living organisms. I try to tell my customers that if we have to remove a massive hardwood, like a 50-year-old live oak, we should plant another tree back. You took something from the earth, so you need to put something back.

Homeowners also need to know that you can't just cut oak trees down on a whim. The city and county have strict laws. If you cut down a protected tree without a permit, both the homeowner and the tree company get heavily fined. The professional is expected to know better. Even pruning has strict rules—you can't cut off too much foliage because it shocks the tree. It’s like cutting off a human limb and telling them to just deal with it without a doctor.

What Sets E & D Trees Apart

Justin: Besides the equipment and the ethics, what sets you apart when you show up to a home in St. Pete or Tampa?

Dylan: Two things: cleanup and my crew.

A lot of tree services will tear a whole yard up and leave a massive mess. We use ground protection mats on every job to protect the grass from ruts. We also offer what I call a "no-mess" price option. For these jobs, we bring a crane in to lift the limbs over the house directly to the street. We won't have a single machine on your lawn, and we leave the property so pristine you won't even find a single track or leaf out of place.

As for my crew, they aren't random people hired off the street. They have families they go home to, and they are trained professionals. My lead guy has been with me for five years, and my bucket operator has been with us for a year. We operate like a family. Teamwork is everything.

Just yesterday, a neighbor came up to me while we were working and asked if I was the boss. When I said yes, he told me, "I just want to let you know your crew works like a fine, oil-tuned machine." That made me so happy, because that’s the definition of being a business owner—when you can step away to do sales and the team runs flawlessly without you.

Justin: Trust is everything in this industry. How do you maintain that client relationship?

Dylan: I'm on the property for every single job. I start my guys out in the morning, get them going, and then I go handle my sales and evaluations. The customer knows that when they hire me, I'm personally involved.

We also focus on honesty. A lot of tree companies scare people into thinking a perfectly healthy tree is going to crush their house just to secure a high-priced removal. We don't do that. If a tree is healthy, I'll tell you. It might just need a structural trim—like a haircut. Our honesty and cleanup are why we've built over 135 five-star Google reviews and why we get so many repeat clients.

We also partner with other great local businesses. If we clear out a backyard and the homeowner wants beautiful landscaping put in, I refer them to Alex Metcalfe at Dreams Into Reality. It makes us look great because our clients get verified, high-quality work from people we trust.