How I Went From A $75 Push Mower To A 7 Figure Landscaping Business

When we launched The Good Soil Strategies Podcast, the goal was to have honest conversations with people who are actually doing the work in landscaping, lawn care, and tree service—people trying to build strong local businesses that last.

In the first episode, I sat down with my co-host Matt Penchuk, founder of Search Strategy Marketing, and we decided to start at the beginning: my story. Not the polished version, but the real one—what worked, what didn’t, and what nearly broke the business more than once.

I’m the owner of Anthony’s Lawn Care & Landscaping in Bloomington, Indiana, but that company didn’t start as anything impressive. It started with a single refurbished mower, a minivan, and a lot of improvising.

Starting With Practically Nothing

I started landscaping back in 2011, right after college. My setup was about as basic as it gets:

• a refurbished $75 push mower
• a minivan
• no weed eater
• no blower

To clean up, I used a broom on sidewalks and driveways. For trimming, I used garden shears—around trees, mailboxes, and even fence lines. If you’ve ever tried trimming a chain-link fence with hand shears, you know how bad that is.

At the time, most of my early clients were professors in Bloomington. The pace was a little slower, and people were patient. They didn’t care that I didn’t look like a “real” company yet. They cared that I showed up, did what I said I’d do, and treated their property with respect.

I’d be embarrassed to show up like that today, but back then, it worked. And more importantly, it got momentum started.

How I Got My First Clients With Zero Ad Spend

My very first client came from a free Craigslist post. That client happened to be a doctor who later moved his practice to Terre Haute, but early on, he kept me busy with work at both his home and office. We hit it off, and he found things for me to do constantly for months.

From there, I relied on two things because I had no money for marketing:

1. Free classified platforms
2. The ability to write decent ads

I studied film, television, and advertising at Indiana University, so when I wrote Craigslist ads or university classified ads, I didn’t just wing it. I treated them like real advertisements. Clear offers, clear language, and sometimes small incentives.

The IU classifieds were especially effective because only students and recent graduates could post, and professors actively browsed them. That second summer, I picked up around 30 professor clients, almost entirely from those free posts.

I spent zero dollars on ads, and then word of mouth started kicking in because I actually did a good job.

Door Knocking, Flyers, And Doing Whatever Paid The Bills

In the early days, I did just about everything:

• door knocking (which nobody enjoys)
• posting flyers
• trying direct outreach however I could
• handyman work
• painting
• small moving jobs for students
• even building a tiny cleaning business with my wife on weekends

At one point, I printed flyers at FedEx Office and illegally put them in mailboxes. The post office warned me, didn’t fine me, and I switched to door hangers instead.

None of this was glamorous. It was just survival.

The key thing was avoiding debt and keeping expenses as low as possible so the business could breathe.

Why Living Minimally Bought Me Time

For nearly a decade, my wife and I lived very simply:

• cheap apartments early on
• later, a very modest house with a low mortgage
• old vehicles
• no lifestyle inflation
• no unnecessary payments

That wasn’t accidental. It gave us flexibility. When revenue dipped or equipment broke, we weren’t instantly underwater.

This is something I still believe strongly: the lower your personal expenses, the more room you have to figure the business out.

Stepping Away (And Why It Helped)

Eventually, I stepped away from full-time landscaping and took a “normal” job working in auto body shops. On paper, it looked like a detour, but it ended up shaping how I run my company today.

In the body shop world, I learned:

• how to handle angry, stressed customers
• how to set expectations without overpromising
• how to communicate delays honestly
• how reviews actually get earned
• how customer service directly impacts revenue
• how accounts receivable can quietly kill a business

I was the first point of contact for people who had just wrecked their cars. That environment forced me to learn professionalism, empathy, and structure very quickly.

When I came back to landscaping full-time, I was far better at sales conversations, customer communication, and experience design than I ever was before.

The Pricing Mistake That Almost Killed The Business

One of the biggest lessons I shared in Episode 1 is about true job costing.

Early on, I made the mistake a lot of owners make: pricing jobs too low once employees enter the picture.

A lawn that works financially when you mow it can become a loss when:

• you send two employees
• you factor payroll taxes
• drive time
• fuel
• insurance
• overhead
• non-billable hours

You can literally lose money faster the more you grow.

It took me years to really dial in:

• profit and loss statements
• true costs per job
• break-even pricing

But once I did, it saved the company.

Wanting To Quit (More Than Once)

I’ll say this plainly: I wanted to quit many times.

Even after taking on loans, buying equipment, building a basic WordPress site, and running ads, there were years where I worked 80–100 hours a week and barely made anything personally.

There were stretches where:

• employees were paid
• the business stayed afloat
• but I took home almost nothing

At one point, I tried to sell the company just to escape the debt.

What changed wasn’t one big breakthrough, it was a combination finally lining up:

• better pricing
• better marketing
• better delivery
• better people
• better systems

The Role Of People And Ownership Thinking

The real breakout didn’t happen until we focused heavily on people.

Over the years, I’ve been incredibly fortunate to work with strong employees and partners who brought experience I didn’t have. One of the biggest shifts was creating a deal structure where top employees could grow as the company grew.

I believe strongly in the idea that:

• your top 20% of people drive most of your results
• treating them like replaceable labor is short-sighted
• stability comes from alignment, not squeezing margins

I’ve always wanted crew leaders and key staff to feel like owners within the business, not literally owning it, but thinking that way. When people feel invested, customer service improves, operations tighten, and the company becomes resilient.

What I’d Tell Someone Starting Today

If I had to distill this entire episode into practical advice:

• Start with what you have, but finish jobs professionally.
• Use free channels early, but treat every lead seriously.
• Write clear, honest ads—no gimmicks.
• Keep your personal expenses low while you learn.
• Learn customer service like it’s a trade.
• Know your numbers before scaling crews.
• Build a fair deal for your best people.

Closing Thoughts

Episode 1 of The Good Soil Strategies Podcast sets the foundation for everything that follows. It’s about the messy early years, the financial pressure, the mistakes, and the slow process of turning effort into something sustainable.

This wasn’t an overnight success story. It was a decade of learning, adjusting, and sticking with it long enough for the pieces to finally fit.

If you want to watch or listen to the full episode, you can find it on The Good Soil Strategies Podcast.