Ten years ago, Jesse McGrath had a backpack, a pair of cowboy boots, and nowhere to live. Today, he owns Compass Cleanup & Excavation—but building a bigger company was never the finish line.

Jesse built the business to get something back that money can’t replace: time with his kids, his wife, and his dad. Along the way, that meant learning some expensive lessons, including a cleanup job that cost him roughly $30,000, figuring out which customers actually fit his company, and realizing that more employees don’t automatically solve a bad job.

Jesse also gets into the part of his story most people would hide. Addiction, homelessness, felony convictions, recovery, and the police officer who told him, “I can tell just by looking at you that you’re better than this.” Years later, that same officer sends him work.

Takeaways:

✅ One relationship can change your workload. Jesse says roughly 90% of his work comes through the network he’s built with contractors, real estate developers, salespeople, and other local businesses.

✅ Understand the customer's vision before giving them a number. Jesse refuses to price a job without seeing the site and figuring out what the customer is actually trying to accomplish.

✅ More labor can make a bad job worse. After underestimating a massive cleanup, Jesse tried throwing more people at it. Payroll and equipment rental kept climbing until he finally finished the project himself—about a $30,000 lesson.

✅ Don't build past the life you actually want. Jesse isn't chasing 50 employees. He wants a profitable excavation business that gives him the freedom to hunt with his dad, work alongside his daughter, and be present with his family.

✅ Your past doesn't have to set your ceiling. Jesse openly carries his history into his work today, including helping other guys in recovery get back on their feet.

Why It Matters:

A skid steer, mini excavator, bigger jobs, and more revenue can build a company—but Jesse’s story is a reminder to decide what you want that company to give you before growth starts taking it away.

Links:

➡️ Connect with Jesse on Facebook: https://www.facebook.com/jesse.mcgrath.399

➡️ Get Ryan’s book “Outta The Weeds” on Amazon: ⁠https://a.co/d/0gWFpM0F

➡️ Shop Attachments — Skid Steer Nation: ⁠⁠⁠⁠⁠⁠https://skidsteernation.com/

➡️ Create estimates, track jobs, and stay organized with Tulboxx: ⁠⁠⁠⁠https://www.tulboxx.com/

➡️ Grow your business — Throttled Up Marketing: ⁠⁠⁠ https://throttledupmarketing.com/

Mitchell Roberts was sitting in a Domino’s parking lot, broke and wondering how he’d make his truck payment. A few years later, his lawn and landscape company did $160,000 in a single month. But the number Mitchell cares about now isn’t revenue. It’s how long the business can run without him.

Mitchell started mowing lawns when he was nine and kept the business alive while working on power lines. When his only mowing employee quit in 2021, he had to decide whether to keep one foot in each world or bet on No Mow Worries Lawn Care & Landscape.

Today, the company is doing seven figures with multiple crews—but Mitchell’s biggest lessons aren’t about buying more equipment or chasing more work.

He breaks down the systems that helped him get off the jobsite, why he’s become more careful about hiring, and his simple “peanut butter and jelly” method for teaching SOPs so employees actually understand what “done right” looks like.

Takeaways:

✅ Make SOPs simple enough to use — Mitchell trains his crew using a “peanut butter and jelly” approach: break the job down step by step, physically walk through it, and make sure everyone understands the same standard.

✅ Hire for what you can’t easily teach — Landscaping experience isn't always Mitchell's first priority. He looks for people who can handle chaos, solve problems, work hard, and take ownership instead of making excuses.

✅ Your problems grow with the company — The problem can quickly change from “How do I find enough work?” to “How do we possibly get all this work done?” Growth doesn't eliminate problems. It requires better systems to handle them.

✅ Develop people outside the jobsite — During 90-day reviews, Mitchell asks employees about personal goals like buying a house, then helps them figure out actual steps to get there.

✅ Freedom is becoming the real test — Mitchell's next milestone isn't just another revenue number. He wants to take a two-week vacation without constantly calling back, checking on jobs, or putting out fires.

Why It Matters:

If you're trying to grow a lawn care, landscaping, excavation, or other service business, Mitchell shows why adding revenue and crews only works when you’re also building the people and systems that can eventually replace you in the day-to-day.

Links:

➡️ Connect with Mitchell on Facebook: ⁠https://www.facebook.com/mitchell.roberts.9699/

➡️ Visit No Mow Worries website: https://nomowworrieslawn.com/

➡️ Get Ryan’s book “Outta The Weeds” on Amazon: https://a.co/d/0bDS7Bap

➡️ Shop Attachments — Skid Steer Nation: ⁠⁠⁠⁠⁠https://skidsteernation.com/⁠⁠⁠⁠⁠

➡️ Create estimates, track jobs, and stay organized with Tulboxx: ⁠⁠⁠https://www.tulboxx.com/⁠⁠⁠

➡️ Grow your business — Throttled Up Marketing: ⁠⁠⁠⁠⁠https://www.throttledupmarketing.com

Jerod Condit didn’t wait until retirement to figure out what came next.

He started seven years early.

Now he’s preparing to leave the military with a land clearing business that already runs jobs without him.

After more than 22 years in the military, Jerod is closing in on retirement. But Ironwood Land Solution wasn’t something he threw together at the last minute. He spent years building it on weekends, leave days, and whatever time he could find around his military career and family.

What started with a dump trailer eventually grew into skid steer work, land clearing, mulching, employees, and a business capable of working Monday through Friday while Jerod is still at his day job.

That creates an interesting challenge as retirement gets closer: What happens when the owner suddenly has more time to be in a business that learned how to operate without him?

Jerod gets into the trust it took to turn employees loose on jobs, why he’ll accept slower production while someone learns, and how more than two decades of military leadership shaped the way he trains and communicates with his crew.

One of the biggest shifts came after he crushed an annual revenue goal. Instead of immediately chasing a bigger number, he focused on processes, organization, and making jobs run smoother. The following year brought in less gross revenue—and Jerod still considered it progress.

Takeaways:

✅ Start Before You Have To — Jerod started planning roughly seven years before military retirement, giving himself room to learn the land clearing business without needing it to immediately replace his paycheck.

✅ Let Your Guys Learn Without Hovering — When Jerod couldn't be on a job, his crew had to make decisions. He gave them manageable projects, let them work through problems, and accepted that training sometimes meant a job took longer than he would have taken.

✅ Hire Character, Then Teach the Machine — Jerod looks for people who show up, have the right attitude, and share the right values. He can teach someone to operate a skid steer or stump grinder. A bad attitude is a different problem.

✅ A Better Year Doesn't Always Mean More Revenue — After hitting his financial goal, Jerod shifted his attention toward processes and smoother jobs. Gross revenue dropped the following year, but the business got better.

✅ The Owner Doesn't Have to Be the Operator — As retirement approaches, Jerod is thinking carefully about where he fits into a crew that already has its own rhythm instead of assuming he needs to jump into a machine 40 hours a week.

Why It Matters:

If you're building a skid steer, excavation, or land clearing business around another full-time job, Jerod shows what can happen when you use those years to build the crew and systems you'll need later—not just buy more equipment.

Links:

➡️ Reach out to Jerod Condit — Ironwood Land Solutions: https://www.facebook.com/ironwoodlandsolutions

➡️ Get Ryan’s book “Outta The Weeds” on Amazon: ⁠⁠https://a.co/d/02o1DRKf⁠⁠

➡️ Shop Attachments — Skid Steer Nation: ⁠⁠⁠⁠https://skidsteernation.com/⁠⁠⁠⁠

➡️ Create estimates, track jobs, and stay organized with Tulboxx: ⁠⁠https://www.tulboxx.com/⁠⁠

➡️ Grow your business — Throttled Up Marketing: ⁠⁠⁠⁠https://www.throttledupmarketing.com

He hired more guys, bought more equipment, and got busier. He was also miserable. So JR Laborie started cutting—and his profit got better.

JR built Laborie Land Works from one skid steer into land clearing, excavation, underground utilities, and hydro excavation. But instead of chasing a bigger company, he eventually stripped away low-profit work, lowered his overhead, and built around the jobs he actually wanted.

Today, JR keeps room in his schedule for high-profit emergency utility work, usually avoids projects that tie him up longer than four or five days, and regularly checks which services are actually putting money in his pocket.

Takeaways:

✅ More Equipment Didn’t Mean More Profit – JR realized the trucks and equipment bringing in revenue were also eating tires, time, and money. He started looking at what was actually left after the job.

✅ Keep Capacity Open for Better Jobs – Instead of filling every day months ahead, JR keeps a loose schedule so he can jump on profitable emergency utility work when the phone rings.

✅ Fire the Work That Doesn’t Fit – He cut lower-profit services and became more selective about customers instead of chasing gross revenue for the sake of being busy.

✅ Partner Instead of Adding Payroll – JR works with other small contractors so each company handles what it does best. That lets him scale up for a job without carrying the overhead year-round.

✅ Your Support Tools Matter – A skid steer or excavator is only part of the setup. Hydro excavation equipment, cable locators, breakers, software, and good systems can make a small contractor far more efficient.

Why It Matters:

For small excavation, land clearing, and utility contractors, JR makes a strong case that the goal isn’t owning the most iron or staying busy seven days a week—it’s building a company that produces profit without owning your life.

Links:

➡️ Reach out to JR Laborie — Laborie Land Works LLC: https://www.facebook.com/laborielandworks

➡️ Get Ryan’s book “Outta The Weeds” on Amazon: ⁠https://a.co/d/02o1DRKf⁠

➡️ Shop Attachments — Skid Steer Nation: ⁠⁠⁠https://skidsteernation.com/⁠⁠⁠

➡️ Create estimates, track jobs, and stay organized with Tulboxx: ⁠https://www.tulboxx.com/⁠

➡️ Contractor Marketing — Throttled Up: ⁠⁠⁠https://www.throttledupmarketing.com

Most contractors build a business… then spend years trying to escape it. Matt Study says that's backwards. If your company can't survive while you're gone, you don't own a business—you own a job.

Matt Study of Sapphire Construction Services has grown from running a mini excavator to managing commercial civil projects, but this episode isn't about getting bigger. It's about building a company that supports the life you actually want to live.

Ryan and Matt dig into the trap many contractors fall into—working more hours, missing family milestones, and wearing burnout like a badge of honor. Instead, they talk about building systems, trusting your people, and defining your non-negotiables before your business defines them for you.

Takeaways:

✅ Build your life first—then build the business around it. Ryan explains how writing down his non-negotiables changed the way he built Skid Steer Nation, and why every business decision should support the life you want to live.

✅ If you can't leave for a week, you don't own a business. Matt shares how surrounding himself with the right people finally allowed him to step away without everything falling apart.

✅ Don't sacrifice your family for "the grind." Matt refuses to be the employer who makes someone miss their kid's ballgame because he believes businesses should serve people—not the other way around.

✅ Burnout is usually a systems problem. Instead of accepting endless 60-hour weeks, Matt explains why burnout should be a signal to change the way the business operates.

✅ Keep coming back to your non-negotiables. As business gets busy, it's easy to lose sight of what matters most. Matt shares why regularly stepping back keeps him focused on building the life he set out to create.

Why It Matters:

Whether you run a skid steer, excavation, land clearing, or site work business, this episode will challenge you to build systems that create freedom—not just another full-time job.

Links:

➡️ Reach out to Matt Study — Sapphire Construction Services: https://www.facebook.com/sapphirecsmt

➡️ Get Ryan’s book “Outta The Weeds” on Amazon: https://a.co/d/02o1DRKf

➡️ Shop Attachments — Skid Steer Nation: ⁠⁠https://skidsteernation.com/⁠⁠

➡️ Create estimates, track jobs, and stay organized with Tulboxx: https://www.tulboxx.com/

➡️ Contractor Marketing — Throttled Up: ⁠⁠https://www.throttledupmarketing.com

Working more doesn't always make you more money.Shelby explains why turning down jobs made his excavation business stronger—and why the right technology lets one operator outperform a whole crew.

Shelby Howland doesn't fit the typical excavation story. He went from farming, blacksmithing, and tech to building an excavation business that's obsessed with efficiency—not just working harder.

In this episode of the Skid Steer Nation Podcast, Shelby explains why saying no to the wrong jobs creates more opportunity, how tiltrotators and grade control transformed his business, and why solving problems beats blaming people every time.

What You'll Learn:

✅ Why saying "no" to bad jobs can make your business more profitable

✅ How tiltrotators and grade control let one operator do the work of multiple people

✅ Why hourly pricing limits growth—and why fixed bids reward efficiency

✅ The hiring lesson that cost him years of profit

✅ How technology helps small excavation companies compete with much larger contractors

Why This Episode Matters:

If you're running an excavation, land clearing, or site work business, this episode challenges the idea that success comes from working longer hours—and shows how smarter systems create better profits.

Links:

➡️ Reach out to Shelby Howland — Village Earthwright: https://www.instagram.com/village_earthwright/

➡️ Shop Attachments — Skid Steer Nation: ⁠https://skidsteernation.com/⁠

➡️ Contractor Marketing — Throttled Up: ⁠https://www.getthrottledup.com

It's been a while since I sat down behind this microphone.A lot has happened over the last few months.I figured I owed you an honest conversation before we jump back into interviews.

This week's episode is a little different. Instead of sitting down with a guest, it's just me sharing where I've been, what I've been working on, and why the podcast took an unexpected pause.

I'm pulling back the curtain on the last few months—the highs, the challenges, and a few lessons I wasn't expecting to learn along the way. More than anything, I wanted to thank everyone who reached out, checked in, and wondered when the next episode was coming. Your messages meant more than you know, and I truly appreciate everyone who stuck around while I took the time I needed.

Next week, we're back to our regular lineup of conversations with contractors, business owners, and operators. But before we do, I wanted you to hear this story directly from me.

Links:

➡️ Check out my book, “Outta The Weeds” on amazon: https://a.co/d/02o1DRKf

➡️ Shop Attachments — Skid Steer Nation: ⁠https://skidsteernation.com/⁠

➡️ Contractor Marketing — Throttled Up: ⁠https://www.getthrottledup.com

Try TULBOXX Free — AI estimating & invoicing for contractors. First 5 estimates free, no credit card: www.tulboxx.com

Graduated dead last…

Now he’s paid by the same school…

And built a business off word of mouth.

Christian Lefley finished 77th out of 77 in his class—and now does paid work for that same school district. This episode isn’t about motivation—it’s about what actually matters when you’re running a skid steer, answering nonstop calls, and figuring things out the hard way. From burying a rented excavator to turning down big jobs, this is real contractor life.

Takeaways:

✅ Dead last doesn’t mean dead end: School didn’t click—but business did

✅ Your punishment can turn into profit: What got him in trouble now pays him every year

✅ You don’t need perfect systems to start: Most of it is learned under pressure

✅ Missed calls = missed money: If you can’t respond, you’re losing jobs—simple

✅ Good work builds everything: Word of mouth still beats chasing leads

Why it Matters:

If you’re in excavation, skid steer work, or property maintenance, this shows you don’t need a perfect start—you need to execute and stick with it.

LINKS:

Try TULBOXX Free — First 5 estimates free, no credit card: www.tulboxx.com

➡️ Reach out to Christtian — Windwood Property Services: https://www.instagram.com/christian_lefley/

➡️ Shop Attachments — Skid Steer Nation: https://skidsteernation.com/

➡️ Contractor Marketing — Throttled Up: https://www.getthrottledup.com

Try TULBOXX Free — AI estimating & invoicing for contractors. First 5 estimates free, no credit card: www.tulboxx.com

Nicholas White grew up around excavation.

His father has been in the dirt business his entire life.

He waited until he was almost 40 to join him — and it took a vaccine mandate to finally make it happen.

Most guys in excavation started young. Nicholas took the long way around — machinist, CDL trucker, Coca-Cola driver, nuclear journeyman machinist at a US Navy shipyard, engineering technician. Then COVID hit, the shipyard issued the mandate, and the decision he'd been putting off for 25 years got made for him.

He bought a John Deere 200D, called his dad, and they built WPM Excavation in southern Maine from the ground up.

TAKEAWAYS:

✅ The Career Nobody Expected — Nuclear journeyman machinist. Engineering technician. COVID mandate. That's what it took to finally get Nicholas into the excavator full time.

✅ Working With Your Father — His dad is 70, still putting in 10-12 hour days, and owns four of the six excavators. The dynamic took years to get right.

✅ The Job He Should've Walked Away From — He tried to make bad materials work on a pond job. Customer was unhappy. Here's what he learned and what he does differently now.

✅ "I Trained My Competition" — The 17-year-old he hired, developed, and eventually lost to the GC across the street.

✅ Low Overhead as a Moat — In a saturated local market, keeping costs lean is the strategy that lets you outlast the guys who overborrowed.

LINKS:

Try TULBOXX Free — First 5 estimates free, no credit card: www.tulboxx.com

➡️ Follow Nicholas — WPM Excavation: www.wpmexcavation.com

➡️ Shop Attachments — Skid Steer Nation: https://skidsteernation.com/

➡️ Contractor Marketing — Throttled Up: https://www.getthrottledup.com

He lost $4K over one line of missing wording. Not bad work. Not bad equipment. Just one mistake in a contract.

Daniel jumped into excavation young with “$10K and a dream”… but commercial work hit him hard. One missed detail in a bid cost him thousands—and that was just the start. This episode is about what actually happens when you move into commercial site work: slow pay, tight margins, and contracts that can bury you if you’re not careful.

Takeaways:

✅ You’re not losing money on dirt, you’re losing it on wording. One missing “budgetary” note cost him $4,000. Contracts matter more than the machine.

✅ Commercial jobs don’t pay fast, plan for it. 45-day waits with $50K–$80K floating out there will choke you if you’re not ready.

✅ Your reputation gets you in, your paperwork keeps you alive. Word of mouth got him commercial jobs. Contracts almost took him out.

✅ Give customers 3 options and stop getting shopped. Good / Better / Best pricing helped him close more residential jobs without competing on price.

✅ Being a great operator won’t scale your business. The real test = can your company run without you? He calls it the “2-week test.”

Why it Matters: If you’re moving into commercial excavation or site work, this is the stuff that decides if you stay in business.

Links:

➡️ Visit DMS Excavation’s Facebook Page – Follow Daniel Snell’s excavation journey. https://www.facebook.com/dmsexcavation

➡️ Build your business with the right attachments. Shop Attachments at Skid Steer Nation: https://skidsteernation.com/

➡️ Marketing built for contractors. Marketing Help at Throttled Up: ⁠⁠⁠⁠https://getthrottledup.com/