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 grow
• How decision consistency quietly becomes the real bottleneck
• Why many owners become the bottleneck by trying to be helpful
• A simple way to identify the one decision you shouldn’t be carrying alone anymore

If you’re running a mid-size fleet and things feel harder than they used to—without a clear reason—this episode will help you put language to what’s happening and decide where to focus next.

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 work
• Why strategy isn’t a plan — it’s a set of decisions
• How complexity quietly creeps in and starts draining margin and morale
• Why the best-run mid-size fleets intentionally make things boring
• How to move from firefighter to executive without losing control

This episode isn’t about payroll, dispatch, or compliance specifically.

It’s about asking the question most growing fleet owners never slow down enough to ask:

What are we actually building?

If you want a trucking company that:

• runs without heroics
• survives scrutiny
• attracts good people
• and doesn’t rely on you holding everything together

this conversation is for you.

🎧 Driven for Success is the podcast for owners and executives of mid-size trucking fleets who want fewer headaches, better drivers, cleaner systems, and a whole lot less chaos in their business.

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 on
• The hidden labor costs that never show up on a payroll invoice
• How payroll errors and rework quietly drain time and focus
• The cash-flow chaos that comes from unpredictable payroll timing
• Why many recruiting and retention problems are actually payroll problems
• What well-run mid-size fleets do differently to keep payroll boring — and profitable

You’ll also hear why many “payroll providers” are really software platforms, and why software alone stops being enough as fleets scale. At this stage, payroll isn’t a task — it’s infrastructure.

If you’re an owner or executive running a growing trucking fleet and payroll feels heavier, more chaotic, or more fragile than it used to, this episode will help you understand why — and what to do about it.

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 scale
• What regulators actually look at (and what they ignore)
• The most common misclassification myths that trip up growing fleets
• Where mid-size fleets go wrong in real-world operations
• The true cost of getting this wrong once you’re more visible
• What a clean, scalable classification setup looks like

We also mention a free self-assessment tool you can use to pressure-test your current setup.
If you’re unsure whether your drivers should be paid W-2 or 1099, you can take the quiz here:

👉 https://www.truckingpayroll.com/1099-vs-w2-quiz/

This isn’t about fear.
It’s about understanding how running a 20–80 truck fleet is fundamentally different than running five trucks — and building systems that hold up as you grow.

If you’re an owner or executive who wants clarity instead of gray areas, this episode is for you.

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 exactly who you are — and who you’re not — changes everything
• How chaos in the back office shows up as frustration in the cab
• Why the right drivers are drawn to mindset and mission, not CPM
• The expectations you must set before a driver ever applies
• How culture becomes your most powerful screening tool
• The interview questions that reveal habits, not just experience

If you’re running 30–80 trucks, you’re in that middle ground where culture matters as much as compensation — because drivers want trust, consistency, and clarity.

This episode will help you attract the right drivers and protect the team you already have.

🎧 Listen now and start hiring with confidence — not hope.

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 think
• The one state form almost everyone forgets to send their payroll provider
• How to confirm names and Social Security numbers before they become a problem
• What taxable fringe benefits must be added before year-end
• How to audit per diem, detention, layovers, and other trucking-specific pay codes
• The silent issues that pop up with ghost employees and closed accounts
• How to set up your first payroll of the new year so everything runs clean

We also start with our Question of the Week:
“Do I need to issue a W-2 for someone who quit early in the year?”
(Short answer: yes — and I explain why.)

If you want your year-end to be smooth, predictable, and free of surprises, this episode gives you everything you need to get ahead.

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 not
• The single most important factor in driver retention (it’s not pay)
• How forward-thinking companies avoid constant crisis mode
• Why a clean, simple back office creates a calmer, more profitable operation
• The numbers successful fleets always know
• And why payroll is a non-negotiable trust builder, not just a task

You’ll also hear our Question of the Week:
Instead of a question, we offer our sincere thanks to everyone giving up their Thanksgiving holiday to keep the trucks moving.

If you’ve ever wondered what really makes a trucking company succeed — beyond freight rates, fuel prices, or luck — this episode shines a light on the habits that matter most.

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 happens the moment you submit payroll
• Why your payroll provider needs your info before payday
• How the banking system moves money long before drivers get paid
• All the hidden validations that protect you from errors and tax notices
• What great payroll companies do behind the scenes that average ones don’t

We also start with our Question of the Week:
“Why do I have to submit payroll before Friday if payday is on Friday?”
(Short answer: because the ACH system isn’t magic — and your drivers deserve on-time pay.)

If you’ve ever wondered what your payroll provider really does after that button is pressed — or you’ve felt in the dark about the process — this episode will give you the clarity you’ve been missing.