All Episodes

S1 E39 Trucking Owners You’re Delegating the Wrong Decisions (And It’s Costing You Control)

S1 E38 Are You Accidentally Overpaying Your Drivers?

S1 E37 The Real Reason Your Trucking Team Can't Make Decisions (and How to Fix It)

S1 E36 Why Your Trucking Team Doesn’t Follow Your Processes (And What to Do About It)

S1 E35 What Decisions Should You Keep as a Trucking Company Owner?

S1 E34 Why Most Trucking Companies Stall at 20–80 Trucks (And How to Fix It)

S1 E33 The One Question That Builds Decision-Makers in Your Trucking Company

S1 E32 The Hidden Cost of Being the Smartest Person in Your Trucking Company

S1 E31 The Escalation Habit That Turns Trucking Owners Into Bottlenecks

S1 E30 The System You’re Afraid to Build (Why Owners Become the Bottleneck at 20–80 Trucks)

S1 E29 The First System Every 30–50 Truck Fleet Needs

S1 E28 What Trucking Fleet Owners Should Stop Measuring (And What Actually Matters Instead)

S1 E27 Why Good People Burn Out in Bad Systems

S1 E26 What to Fix First When Everything Feels Important

S1 E 25 Why Good Systems Feel Rigid (and Why Growing Fleets Actually Need Them)

S1 E24 What Owners Have to Stop Doing to Scale Past 30–50 Trucks

S1 E23 - Are You Growing — or Just Getting Busier? A Reality Check for Mid-Size Fleets

S1 E22 What Breaks First at 25 Trucks (And Why It’s Not Dispatch, Payroll, or Drivers)

S1 E21 You’re Not Running a Small Fleet Anymore: A Strategic Reset for 20–80 Truck Companies

S1 E20 The True Cost of Trucking Payroll After You Outgrow Small-Fleet Thinking

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

Why Your Driver Hiring Isn’t Working — And the Mindsets That Fix It

S1 E17 How to Prepare for Year-End: A Simple Checklist for Stress-Free W-2s

S1E16 What 300+ Trucking Companies Taught Me: The Habits That Build Trust, Culture, and Long-Term Success

S1 E15 What Really Happens After You Hit ‘Submit Payroll’ (And Why It Matters More Than You Think)

S1 E14 Switching Payroll Providers Without the Headache: How to Do It the Right Way

S1 E13 How to Vet a Payroll Provider for Your Trucking Co Like a Pro (Without Getting Burned)

S1 E12 QuickBooks Payroll and Trucking: What Works, What Doesn’t

Top 4 Payroll Services for Trucking Companies (Pros & Cons) + Question of the Week

S1 E10 Should You Keep Payroll for Your Trucking Company In-House or Use a Service?

S1E9 Trucking Payroll Errors Hidden Costs & How to Avoid Them Plus September DPI update

S1 E8 IRS Trucking Audits: Red Flags Every Fleet Owner Should Know

5 Smart Ways Small Trucking Companies Can Use ChatGPT to Save Time and Run Smoother

S1 E6 Let Drivers Opt Out… But First, Show Them This | Driven for Success Podcast

How to Roll Out Per Diem the Right Way: A Playbook for Trucking Companies

Truck Drivers Love Per Diem — And Here's Why

Per Diem for Trucking Companies: Save Big Money and Keep Drivers Happy

What Trucking Payroll Really Costs (And What You’re Not Seeing)

W-2 vs. 1099 for Truck Drivers: What Every Carrier Should Know

Introducing Driven for Success — A Podcast for Trucking Company Owners