Driven for Success

Send us Fan Mail 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...

Send us Fan Mail 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...

Send us Fan Mail 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 abo...

Send us Fan Mail 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 payr...

Send us Fan Mail 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, sc...

Send us Fan Mail 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 at...

Send us Fan Mail 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 upda...

Send us Fan Mail 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 i...

Send us Fan Mail 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 th...

Send us Fan Mail 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 avoid...

Send us Fan Mail 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 sign The red flags that should make you pause The...

Send us Fan Mail 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 companies The common gaps where it just isn’t built for driver pay Why pe...

Send us Fan Mail 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 mov...

Send us Fan Mail 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 c...

Send us Fan Mail 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 reputati...

Send us Fan Mail 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  • H...

Send us Fan Mail Think AI tools like ChatGPT are just for big companies? Think again. In this episode of Driven for Success , Mike Ritzema shares six practical ways small trucking companies can use ChatGPT right now to save time, reduce stress, and run their back office more professionally. You’ll discover how ChatGPT can: Draft and polish emails and driver texts 🚛 Build checklists and SOPs for p...

Send us Fan Mail Should truck drivers be allowed to opt out of per diem pay programs? Absolutely — but it doesn’t mean they should. In this clip from the Driven for Success Podcast , we explain the smart way to handle driver objections, why some drivers just won’t get it, and how to communicate the value of per diem without forcing it. Plus, hear the analogy that hits harder than a flat tire at sc...

Send us Fan Mail Thinking about offering per diem pay to your truck drivers? Rolling it out wrong can lead to driver confusion, compliance headaches, and missed savings. In this episode of Driven for Success , we give you a step-by-step guide to implementing an IRS-compliant per diem program that your drivers will actually appreciate. You’ll learn: What not to do when setting up per diem (like pay...

Send us Fan Mail Per diem isn’t just a tax strategy — it’s a powerful recruiting and retention tool. In this episode, we break down why truck drivers love per diem , how it increases their take-home pay , and why trucking companies should proudly feature it on their recruiting pages. Plus, we take a look back at how per diem used to work before 2018, and what changed with the Tax Cuts and Jobs Act...

Send us Fan Mail Think you know what you’re paying for payroll? Think again. In this episode of Driven for Success , we break down: The hidden costs of DIY payroll What most carriers miss when pricing services How paying your drivers the wrong way can drive up taxes and insurance Why “cheap payroll” usually isn’t cheap at all We even cover little-known fees like charging drivers for extra direct d...

Send us Fan Mail In this episode of Driven for Success , you’ll learn: What per diem actually is (and how it works in trucking) How it helps trucking companies save thousands in payroll taxes and insurance Why drivers love it — and how it can boost recruiting and retention Common mistakes fleets make (like paying per diem by the mile or percent) How to structure a compliant, high-impact per diem p...

Send us Fan Mail Confused about whether your drivers should be W-2 employees or 1099 contractors? You're not alone — and getting it wrong can cost you big in audits, penalties, and lost drivers. In this episode of Driven for Success , we break down: The key legal and IRS tests for driver classification Why “just calling them 1099” doesn’t protect you How insurance and workers’ comp are affect...

Send us Fan Mail Welcome to Driven for Success — the podcast for small trucking company owners who want to run a smarter, more profitable business. In this quick trailer, I’ll share who this show is for, what we’ll cover, and what you can expect from future episodes. Subscribe now so you don’t miss an episode — and let’s get rolling. Also posted on youtube at youtube.com/truckingpayroll