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PODCAST

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

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All Episodes

9:01

S1 E27 Why Good People Burn Out in Bad Systems

Driven for Success ·

2026/02/10

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, Mike Ritzema explains why burnout in growing fleets is rarely a motivation problem — and almost always a systems problem. You’ll learn: Why effort stops working as fleets growHow unclear decisions and expectations quietly exhaust good employeesThe three system gap...

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11:45

S1 E26 What to Fix First When Everything Feels Important

Driven for Success ·

2026/02/03

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 messy. Exceptions keep piling up. And every system seems like it needs attention at once. In this episode, we talk about why trying to fix everything at the same time usually makes things worse — and how to identify the one place to start that restores momentum ins...

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13:22

S1 E 25 Why Good Systems Feel Rigid (and Why Growing...

Driven for Success ·

2026/01/27

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 Driven for Success, we talk about why that discomfort shows up right when a business is ready for its next stage of growth. We explore why flexibility works early, why it becomes exhausting at scale, and why good systems often feel wrong before they start to feel like...

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13:02

S1 E24 What Owners Have to Stop Doing to Scale Past...

Driven for Success ·

2026/01/20

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 this episode, we talk about why that happens — and why it’s usually not a motivation problem, a leadership failure, or a lack of delegation. More often, growth stalls because owners keep doing things the business should have already learned how to do without them: an...

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15:46

S1 E23 - Are You Growing — or Just Getting Busier? A...

Driven for Success ·

2026/01/13

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 those two things can feel exactly the same day to day. In this episode of Driven for Success, we talk about the difference between real growth and what often looks like growth but is really just more activity, more decisions, and more pressure on the owner. You’ll hea...

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8:40

S1 E22 What Breaks First at 25 Trucks (And Why It’s...

Driven for Success ·

2026/01/06

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 Success, Mike Ritzema breaks down what actually starts to break at around 25 trucks—and why it’s rarely dispatch, payroll, drivers, or safety. This isn’t a failure stage. It’s a transition stage. We talk about: Why informal systems stop stretching as fleets growHow de...

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14:14

S1 E21 You’re Not Running a Small Fleet Anymore: A...

Driven for Success ·

2025/12/30

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 the design phase of your business — whether you realize it or not. In this episode of Driven for Success, we step back from day-to-day operations and talk about what really changes as fleets grow: Why your role shifts from doing the work to designing the workWhy strategy i...

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17:54

S1 E20 The True Cost of Trucking Payroll After You...

Driven for Success ·

2025/12/23

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, we break down what trucking payroll really costs once your fleet grows past small-fleet size — and why so many owners dramatically underestimate the impact payroll has on their operation. We talk through: Why the payroll fee is the wrong number to focus onThe hidden lab...

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23:47

W-2 vs. 1099 at Scale: Why Mid-Size Trucking Fleets...

Driven for Success ·

2025/12/16

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-figure exposure. In this episode of Driven for Success, we break down W-2 vs. 1099 specifically for mid-size trucking fleets — without legal jargon, scare tactics, or internet myths. You’ll learn: Why worker classification gets riskier as fleets scaleWhat regul...

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33:39

Why Your Driver Hiring Isn’t Working — And the...

Driven for Success ·

2025/12/09

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 a mindset problem long before it’s a recruiting problem. In this episode, we dig into the culture, beliefs, and expectations that separate the fleets who attract (and keep) great drivers… from the ones who stay stuck in constant turnover. You’ll learn: Why knowing ...

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14:55

S1 E17 How to Prepare for Year-End: A Simple...

Driven for Success ·

2025/12/02

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 year-end checklist that will save you hours of cleanup in January and prevent the most common W-2 mistakes trucking companies face. We’ll cover: Why updating addresses (especially for termed drivers) matters more than you thinkThe one state form almost everyone ...

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26:36

S1E16 What 300+ Trucking Companies Taught Me: The...

Driven for Success ·

2025/11/25

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 lessons I’ve learned watching fleets grow, stall, struggle, and succeed — the real habits that separate the companies who build momentum from the ones who stay stuck in survival mode. We dig into: Why the strongest fleets know exactly who they are — and who they’re notTh...

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19:17

What Really Happens After You Hit ‘Submit Payroll’...

Driven for Success ·

2025/11/18

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 filings, reconciliations, and compliance checks — most of which trucking company owners never see, but all of which matter deeply to paying drivers accurately and keeping the IRS off your back. In this episode, I pull back the curtain and walk you through: What actually happen...

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20:56

S1 E14 Switching Payroll Providers Without the...

Driven for Success ·

2025/11/11

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, and the questions to ask before you make the move. In this episode, I walk through: When to switch — and the one time of year you should absolutely avoidWhat you need to gather before you change providers (so nothing falls through the cracks)Red flags during the ...

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21:31

S1 E13 How to Vet a Payroll Provider for Your...

Driven for Success ·

2025/11/05

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 this episode, I’ll walk you through: The exact questions to ask any payroll provider before you signThe red flags that should make you pauseThe hidden costs beyond the monthly fee (time, stress, and even driver relationships)Why the right partner can save you ...

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14:27

S1 E12 QuickBooks Payroll and Trucking: What Works,...

Driven for Success ·

2025/10/28

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 episode, I’ll break down: What QuickBooks Payroll actually does well for trucking companiesThe common gaps where it just isn’t built for driver payWhy per diem, multi-state compliance, and driver add-ons (like detention and layover) matter so muchThe hidden costs you ma...

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17:11

Top 4 Payroll Services for Trucking Companies (Pros &...

Driven for Success ·

2025/10/21

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. This week, I start with a client’s question about hiring their kids in an S-corp — because real life questions deserve real answers. Then we move into the heart of it: the three payroll options most trucking companies look at. I’ll walk you through ADP, Quic...

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17:58

S1 E10 Should You Keep Payroll for Your Trucking...

Driven for Success ·

2025/10/14

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 real pros and cons of both options and shares a framework to help small fleets decide what’s right for them. You’ll learn: • Why in-house payroll looks cheaper but often costs more • The risks of staff turnover, payroll errors, and data security issues • How ou...

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18:00

S1E9 Trucking Payroll Errors Hidden Costs & How to...

Driven for Success ·

2025/10/07

In this episode of Driven for Success, Mike starts with the September Driver Pay Index update — a look at how driver wages are trending and what it means for small fleets trying to stay competitive. Then we dive into the main topic: why payroll errors cost far more than most trucking companies realize. It’s not just about math mistakes — it’s about trust, compliance, and reputation. You’ll learn: • How payroll mistakes erode driver trust and retention • Why the IRS doesn’t care if...

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17:22

S1 E8 IRS Trucking Audits: Red Flags Every Fleet...

Driven for Success ·

2025/09/30

The IRS is paying closer attention to trucking companies than ever before. In this episode, Mike breaks down the top red flags that trigger IRS audits — from payroll tax deposits and W-2 vs. 1099 misclassification to per diem compliance and sloppy recordkeeping. You’ll learn: • Why trucking companies get audited more often • The most common mistakes fleets make with payroll • How to avoid IRS penalties by tightening your processes now Plus, we cover the latest per diem rate ...

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28 results

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