Skid Steer Nation

Ryan Deemer
  • 4.9 (52)
  • Entrepreneurship
  • Updated Weekly

Join the Skid Steer Nation podcast to discover how excavation and land service business owners are finding innovative solutions to grow their businesses. Our in-depth interviews provide valuable tips on everything from customer acquisition, sales and marketing, to employee recruitment and management, all while being entertained by our dynamic host. Don't miss out on this exciting opportunity to take your business to the next level!

  1. 3d ago

    Matt Study: Build a Business That Fits Your Life—Not One That Owns It

    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

  2. Aug 5

    Shelby Akio Howland: Why the Best Operators Say "No" More Than They Say "Yes"

    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

  3. Jul 29

    Ryan Deemer: Why I Had to Step Away

    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

  4. Apr 22

    Christian Lefley: 77th of 77 — Now Running the Same School’s Contracts

    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

  5. Apr 1

    Daniel Snell: The $4,000 Mistake That Taught Him How Commercial Work Really Works

    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/

  6. Mar 25

    Cody Cocas: Why “Nice Customers” Almost Cost Him His Business

    He was mowing customers’ lawns… after finishing their job. Not charging for extras… because he liked them. That mindset almost killed his margins—until he flipped to utilities. Cody Cocas went from small residential jobs to multi-million dollar utility contracts in under 18 months—but not the way most guys think. The turning point wasn’t more leads or better equipment. It was realizing that being “a good guy” in residential work was costing him real money—and forcing a hard pivot into contract-based utility work that actually scales. Takeaways: ✅ Stop “liking your way” out of profit – Cody admits he gave away work just because he liked customers, and it crushed margins early on ✅ Utilities = boundaries – Contract work (stormwater, drainage, energy) removed emotion and made pricing, scope, and payment predictable ✅ Relationships beat luck – His biggest opportunity came from a connection he helped years earlier that came back around when he needed it most ✅ You don’t need to know everything – Your job as an owner is removing roadblocks, not being the best operator or estimator ✅ Fix one problem at a time – Trying to clean up everything in your business at once leads to doing nothing well Why It Matters: If you’re stuck doing low-margin residential work or struggling to scale your dirt work business, this shows what it takes to move into real contract work that grows. Links: ➡️ Visit TSF Construction’s website – Follow Cody Cocas’ excavation journey. ⁠https://thesavagefarm.com/ ➡️ 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://www.getthrottledup.com⁠⁠

  7. Mar 4

    John Seaman: The Day He Fired His Entire Crew (And Rebuilt a Stronger Company)

    Most contractors complain about employees.John Seaman fired his entire crew in one day.What he built after that changed how his excavation company runs forever. Running excavation crews in the mountains of North Carolina means steep slopes, landslides, and million-dollar homes sitting on unstable ground. John Seaman built his company around solving the jobs nobody else wants to touch. But the real turning point in his business wasn’t a project — it was the day he fired his entire crew and rebuilt the culture from scratch. In this episode, John breaks down how transparency with numbers, accountability in the field, and smarter scaling helped him grow a site development company that now handles complex projects across multiple states. Takeaways: ✅ The Day He Fired EveryoneAfter coming back from a trip and realizing his crew had shut down work on their own, John fired the entire team and rebuilt the company culture from the ground up. ✅ Why Most Contractors Scale Too FastAdding a second crew before the first one runs independently can lose money on both crews. ✅ Saving Million-Dollar Homes on LandslidesJohn’s team is known for emergency slope stabilization projects — including saving a $23M home with a million-dollar retaining wall. ✅ Transparency With Numbers Changes EverythingEvery employee in his company knows what a job sells for, what it costs, and whether the company made money. ✅ The System Most Contractors IgnoreTracking time and knowing your real daily overhead can make or break an excavation company. Why It Matters: If you run an excavation, land clearing, or site work business, this episode shows how culture, systems, and financial discipline determine whether your company scales—or collapses. Links: ➡️ Visit JC Property Professionals’ website – Follow John Seamans excavation journey. www.jcpropertyprofessionals.com ➡️ Shop Attachments at Skid Steer Nation: ⁠https://skidsteernation.com/ – “Build your business with the right attachments.” ➡️ Marketing Help at Throttled Up: ⁠⁠https://www.getthrottledup.com⁠⁠ – “Marketing built for contractors.

  8. Feb 25

    Jack Eso: The $4M Move Most Contractors Are Afraid to Make

    He went from renting a skid steer on weekends to landing $4 million in work in 60 days.But the real shift wasn’t equipment — it was systems.And the biggest lesson? Stop racing to the bottom on price. Jack Eso of RoseBrooke Site Development breaks down how he scaled from a side hustle to a 10-man operation doing site work, utilities, concrete, and full residential packages in North Carolina. This episode isn’t about hype — it’s about margins, structure, and building a company that doesn’t fall apart when you step away. If you’re tired of guessing at numbers, chasing every job, and feeling buried in your own business… this one hits home. Takeaways: ✅ 50% Gross Profit Rule (Residential): Jack stopped chasing the “going rate” and built his pricing around what his business actually needs — not what competitors charge. ✅ $300K–$350K Revenue Per Employee: He tracks revenue per team member to know exactly when it makes sense to hire. ✅ Automated Sales Follow-Up: Email, voicemail drops, and video walkthroughs of estimates increased professionalism — and conversions. ✅ Outsourced Estimating = Time Freedom: Hiring a commercial estimating firm helped him land $4M in projects without becoming the bottleneck. ✅ Say No Early: Fiberglass pools? Done. If it doesn’t fit the system, it’s not worth the lesson. Why It Matters: If you're running crews, bidding bigger jobs, or trying to stop undercharging — this episode shows how to build real structure without losing control. Links: ➡️ Visit Rosebrooke Site Development’s website – Follow his Jack Eso’s excavation journey.https://rosebrookelh.com/ ➡️ Shop Attachments at Skid Steer Nation: ⁠https://www.skidsteernation.com⁠ – “Build your business with the right attachments.” ➡️ Marketing Help at Throttled Up: ⁠https://www.getthrottledup.com⁠ – “Marketing built for contractors.”

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4.9
out of 5
52 Ratings

About

Join the Skid Steer Nation podcast to discover how excavation and land service business owners are finding innovative solutions to grow their businesses. Our in-depth interviews provide valuable tips on everything from customer acquisition, sales and marketing, to employee recruitment and management, all while being entertained by our dynamic host. Don't miss out on this exciting opportunity to take your business to the next level!

Information

  • Creator
    Ryan Deemer
  • Years Active
    2022 - 2026
  • Episodes
    131
  • Rating
    Explicit
  • Copyright
    © Ryan Deemer
  • Show Website
    Skid Steer Nation

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