OUTTA THE WEEDS
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⁄ ⁄ Episodes
Recent Episodes
Nate Morello: Why “More Equipment” Isn’t the Same as a Better Business
Most excavation and heavy civil contractors don’t fail because of bad work—they fail because of poor cash flow, bad equipment decisions, and...
Richard Piendak: The Exit Strategy Most Contractors Never Prepare For
Richard Piendak didn’t just survive five decades in paving—he built, scaled, sold, and then kept working anyway. In this episode, Richard breaks...
Caley Stecker: The Quote Is the Quote — Stop Guessing & Start Getting Paid
You’ve probably underbid a job, got halfway through, and realized you’re working for free. Caley Stecker from C & C Land Management (Holden,...
Jeremy Whitson: Why Too Much Work Nearly Broke His Excavation Business
He walked away from a VP position with 208 employees.Bought one excavator. No real plan.Then learned the hard way that “booked out” doesn’t mean...
Sheldon Gould: What 25+ Years in a Small-Market Contractiong Business Really Teaches You
If you’ve ever felt stuck in a small market, surrounded by undercutters, wondering if you should just shut it down — this one’s for you.Twenty-plus...
⁄ ⁄ Your Host
Meet Ryan Deemer
I’ve worked with hundreds of trades contractors over the past decade. Same story, different truck. Guy starts a business because he’s good at the work. Three years later he’s making less per hour than his employees, hasn’t taken a real vacation since he filed the LLC, and his wife stopped asking when things would get better.
The answer was always “soon.” But soon is too slow.
I know the pattern because I lived it. And I’ve watched enough contractors break out of it to know the path works. The ones who build real structure – systems that carry the weight instead of their willpower—they get their evenings back. They sit through their kid’s soccer game without checking their phone. They take home what the work is actually worth.
That’s what we talk about here. How to build a business that doesn’t need you white-knuckling it every single day.
⁄ ⁄ Echoes in numbers
From Shop Talk to National Audience
What started as conversations between a few contractors turned into a regular part of how people in the industry learn, compare notes, and keep up with how others are running their businesses.






