Driven for Success
Driven for Success is a podcast for trucking company owners and executives running 20–80 truck fleets who want to scale without chaos.
Hosted by Mike Ritzema, founder of Superior Trucking Payroll Service, the show focuses on what actually breaks as fleets grow—and how strong operators fix it before constant firefighting takes over.
This isn’t a motivational show and it’s not theory-heavy. Each episode is grounded in real patterns seen across hundreds of trucking companies, covering topics like:
- Where complexity quietly creeps in as you scale
- What to standardize—and what not to
- Why payroll, pay clarity, and systems become retention issues
- How to build infrastructure that supports growth instead of relying on heroics
The goal is simple: give you practical ideas you can apply immediately to run a calmer, more profitable operation.
If you’re building a trucking company that needs to work without you carrying everything on your shoulders, this show is for you.
Episodes
35 episodes
S1 E34 Why Most Trucking Companies Stall at 20–80 Trucks (And How to Fix It)
If you run a trucking company with 20 to 80 trucks and feel like everything still runs through you… you’re not alone.At this stage, many owners hit a point where growth slows down—not because of bad people, but because the business still...
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Season 1
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Episode 34
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12:45
S1 E33 The One Question That Builds Decision-Makers in Your Trucking Company
In growing trucking companies, a pattern quietly takes hold.Every question starts going to the owner.Dispatch asks. Payroll asks. Safety asks. Operations asks.And over time, the company stops buil...
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Season 1
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Episode 33
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13:34
S1 E32 The Hidden Cost of Being the Smartest Person in Your Trucking Company
Early in the life of a trucking company, the owner usually is the smartest person in the room.They know the customers. They know the lanes. They know the drivers. They’ve solved almost every problem befo...
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Season 1
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Episode 32
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14:37
S1 E31 The Escalation Habit That Turns Trucking Owners Into Bottlenecks
As trucking companies grow, something subtle begins to happen inside the business.Dispatch escalates decisions. Payroll escalates questions. Safety escalates problems. Operations escalates anything uncertain.
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Season 1
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Episode 31
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11:56
S1 E30 The System You’re Afraid to Build (Why Owners Become the Bottleneck at 20–80 Trucks)
Most trucking company owners don’t stall because of bad software or bad people.They stall because every “quick question” still lands on their desk.In this episode of Driven for Success, Mike talks about the system most gr...
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Season 1
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Episode 30
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12:47
S1 E29 The First System Every 30–50 Truck Fleet Needs
As trucking fleets grow into the 30–50 truck range, most owners know they need systems — but they don’t know where to start.Should you fix payroll? Dispatch? Hiring? Maintenance?In this episode of Driven for Success, Mike...
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Season 1
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Episode 29
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6:35
S1 E28 What Trucking Fleet Owners Should Stop Measuring (And What Actually Matters Instead)
As trucking fleets grow, owners often track more numbers than ever — revenue, cost per mile, turnover, utilization.But more data doesn’t always mean more control.In this episode of Driven for Success, Mike Ritzema explain...
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Season 1
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Episode 28
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10:45
S1 E27 Why Good People Burn Out in Bad Systems
As trucking fleets grow past 20–50 trucks, many owners start noticing something uncomfortable: good people seem overwhelmed, reactive, or burned out — even though they care and work hard.In this episode of Driven for Success...
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Season 1
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Episode 27
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9:01
S1 E26 What to Fix First When Everything Feels Important
When trucking companies grow into the 30–50 truck range, most owners don’t struggle because they don’t know what needs to change.They struggle because everything feels urgent.Hiring needs work. Pay policies feel me...
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Season 1
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Episode 26
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11:45
S1 E 25 Why Good Systems Feel Rigid (and Why Growing Fleets Actually Need Them)
Somewhere between 25 and 60 trucks, many fleet owners start to feel resistance when new systems are introduced.Not because the systems won’t work — but because they feel rigid, bureaucratic, or “not like us.”In this episode of
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Season 1
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Episode 25
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13:22
S1 E24 What Owners Have to Stop Doing to Scale Past 30–50 Trucks
Somewhere between 30 and 50 trucks, a subtle shift happens for most fleet owners.The business is bigger. Revenue is there. Fewer fires are breaking out day to day. And yet, it still feels like everything depends on you.In...
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Season 1
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Episode 24
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13:02
S1 E23 - Are You Growing — or Just Getting Busier? A Reality Check for Mid-Size Fleets
Most trucking company owners can tell you they’re busy. But somewhere between 20 and 50 trucks, it gets harder to answer a different question:Are we actually growing… or are we just running faster than we used to?Because ...
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Season 1
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Episode 23
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15:46
S1 E22 What Breaks First at 25 Trucks (And Why It’s Not Dispatch, Payroll, or Drivers)
Somewhere between 20 and 30 trucks, running a trucking company starts to feel heavier than it should.You’re busier than ever—but not more confident. And many owners quietly wonder what they missed.In this episode of Driven for...
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Season 1
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Episode 22
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8:40
S1 E21 You’re Not Running a Small Fleet Anymore: A Strategic Reset for 20–80 Truck Companies
Most trucking companies don’t fail.They just keep running the same business at a larger scale — until it finally breaks.If you’re running a fleet with 20 to 80 trucks, you’re no longer in the startup phase. You’ve entered...
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Season 1
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Episode 21
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14:14
S1 E20 The True Cost of Trucking Payroll After You Outgrow Small-Fleet Thinking
Many trucking fleet owners believe payroll “only costs a few hundred dollars a month.”That may feel true at ten trucks. It’s almost never true once you’re running a mid-size fleet.In this episode of Driven for Success...
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Season 1
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Episode 20
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17:54
W-2 vs. 1099 at Scale: Why Mid-Size Trucking Fleets Face Higher Risk
Once you grow past a small fleet, the W-2 vs. 1099 conversation changes — fast.At five trucks, classification mistakes may slide under the radar. At 30, 40, or 80 trucks, the same decisions can trigger audits, penalties, and six...
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Season 1
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Episode 19
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23:47
Why Your Driver Hiring Isn’t Working — And the Mindsets That Fix It
Most fleets think their driver hiring problems come from pay, lanes, or the market. But after working with hundreds of trucking companies — especially in the 30–80 truck range — I can tell you the real truth:Driver hiring is ...
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Season 1
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Episode 18
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33:39
S1 E17 How to Prepare for Year-End: A Simple Checklist for Stress-Free W-2s
Year-end doesn’t have to be chaotic — but for most trucking companies, it is. Not because the work is hard, but because so many small details get overlooked until it’s too late.In this episode, I walk through a clear, practical ...
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Season 1
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Episode 17
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14:55
S1E16 What 300+ Trucking Companies Taught Me: The Habits That Build Trust, Culture, and Long-Term Success
After serving more than 300 trucking companies, you start to see patterns. Not in their freight. Not in their lanes. But in the way they lead, operate, and treat their drivers.In this episode, I share the biggest lesson...
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Season 1
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Episode 16
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26:36
S1 E15 What Really Happens After You Hit ‘Submit Payroll’ (And Why It Matters More Than You Think)
Most people think running payroll ends when you hit “Submit.” But in reality? That’s when the real work begins.Behind that single button press is a whole chain of systems, verifications, bank transfers, tax fil...
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Season 1
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Episode 15
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19:17
S1 E14 Switching Payroll Providers Without the Headache: How to Do It the Right Way
Switching payroll companies feels like it’s going to be painful — like you’re signing up for chaos, late paychecks, angry drivers, and IRS problems. But the truth? It doesn’t have to be hard if you know the timing, the process...
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Season 1
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Episode 14
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20:56
S1 E13 How to Vet a Payroll Provider for Your Trucking Co Like a Pro (Without Getting Burned)
Choosing a payroll provider for your trucking company isn’t just another business decision — it touches everything: your drivers’ trust, your compliance with the IRS, and your ability to focus on growing instead of putting out fires.In t...
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Season 1
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Episode 13
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21:31
S1 E12 QuickBooks Payroll and Trucking: What Works, What Doesn’t
QuickBooks Payroll is everywhere — it’s simple, it’s affordable, and for a lot of small business owners, it feels like the safe choice. And honestly? For many industries, it is. But trucking is a whole different world.In this ep...
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14:27
Top 4 Payroll Services for Trucking Companies (Pros & Cons) + Question of the Week
Let’s be honest — payroll isn’t just numbers on a page. It’s trust, it’s drivers’ livelihoods, it’s whether your business runs smoothly or falls into chaos. And when it comes to choosing who handles it, the decision can feel overwhelming.
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Season 1
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Episode 11
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17:11
S1 E10 Should You Keep Payroll for Your Trucking Company In-House or Use a Service?
Payroll is one of the most important — and stressful — parts of running a trucking company. The big question: should you keep it in-house, or hand it off to a service?In this episode of Driven for Success, Mike breaks down the <...
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Season 1
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Episode 10
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17:58