Driven Too Far: The Truth About Trucking

Most drivers get mesmerized by a shiny, high-rate load—like a $99 per mile offer—and instantly think they've hit the jackpot. But behind that eye-catching number lies a hidden trap that can turn profitable freight into a costly mistake. If you've ever wondered whether to chase the hottest rates or play it smart, this episode will change your perspective.

On this episode of Driven Too Far, Andrew reveals why those outrageously high rates often hide risks—short-term emergencies, bad areas, or companies desperate to offload unwanted freight.

When drivers and safety teams are making crucial decisions without all the facts, it can lead to costly misunderstandings. What if a simple mudflap was mistaken for a leaning trailer, and an unverified opinion could damage trust or derail safety efforts? Andrew Winkler reveals the overlooked power of influence, the importance of facts over assumptions, and how everyone in your organization is an influencer whether you realize it or not.

Most drivers underestimate what it takes to move from behind the wheel to leading the fleet. In this episode, Andrew Naughton shares how he went from flatbed driver to safety manager, and what surprised him most about stepping into the office, from new technology and driver expectations to the mindset shift required for leadership.

He also breaks down the realities of trucking management, including thin profit margins, the role equipment quality plays in retention, and why driver comfort and safety matter. Andrew offers practical advice for making the transition smoothly while staying connected to your roots, making this episode especially useful for drivers considering a move into leadership and managers looking to build stronger driver relationships.

Are you quietly killing your own paycheck?

In this episode of Driven Too Far, host Andrew Winkler breaks down the hidden income leaks that quietly cost truck drivers thousands of dollars every year.

Andrew shares insights from an income simulator he built in-house to help drivers identify where their paychecks are shrinking — and what to do about it. The episode covers common culprits like unnecessary 34-hour resets, late starts after home time, poor maintenance planning, first-come-first-served appointment habits, idling and speed incentive losses, missing paperwork, and broker tracking fines.

The episode drives home a simple truth: small habits add up fast. For some drivers, these leaks amount to $15,000 a year — or about 12 cents per mile in lost earnings.

In this episode of Driven Too Far, host Andrew Winkler breaks down one of the most misunderstood topics in trucking: fuel surcharge programs.

The conversation covers how fuel surcharges work, why they exist, and how they help protect carriers and owner-operators from rising diesel costs. Andrew also explains the difference between contract freight and broker freight, why separating linehaul, accessorials, and fuel surcharge matters, and how transparency helps carriers better understand profitability.

The episode also walks through a real-world fuel surcharge example and shares why Chief Carriers emphasizes education, fairness, and clarity when teaching lease operators how to manage their business.

Why are trucking companies switching to automatic transmissions? A lot of old school drivers prefer and stand by manual transmissions and refuse the ways of automation. Andrew shows us a look behind the scenes as the trucking industry continues to find itself in the midst of a never-ending tug of war between manual and automatic transmissions. He talks about the advantages of automatic transmissions, such as lower operating costs, improved performance, and better fuel efficiency. Would your business benefit from this shift? Tune in for how switching from manual to automatic is a change for the better.

For a fleet that has automatic trucks available visit Chief Carriers.

This podcast is produced by Two Brothers Creative.

Original Air Date: Jan 30, 2023

What's the real cost of changing jobs? The offers out there seem fantastic, but are they worth the move? Making the decision to change jobs is a big one. Not only are there financial considerations to take into account, but other factors such as job satisfaction and stability must be weighed in. Andrew takes an in depth look at these elements that go into the cost of changing jobs. From the risk of losing consistent pay to the reputational cost of job hopping. Check out this episode of Driven Too Far: The Truth About Trucking to learn everything you need to know about the cost of changing jobs.

Want to work for a company that values their tenured drivers? Visit Chief Carriers.

This podcast is produced by Two Brothers Creative.

Original Air Date: Jan 2, 2023

What kind of company do you want to work for? Is your safety department to blame for high driver turnover? Some recent reports say yes, but is that really the whole story? In the episode Andrew takes an in-depth look at the driver turnover problem and some potential solutions to retain top talent and meet safety standards. So tune in and if safety truly is to blame for truck driver turnover.

Learn more about safety and how Chief Carriers is creating a safety culture for their drivers.

This podcast is produced by Two Brothers Creative.

Original Air Date: Jan 09, 2023

How would you like to make a six figure income as a company driver? I'm here today to tell you that you can, if you want, and I can show you how. There are so many things you can do every week to get that paycheck you want. In this episode learn what steps you can take to make six figures as a company driver.

 To learn more about a career in trucking and see how you can make six figures visit Chief Carriers.

This podcast is produced by Two Brothers Creative.

Original Air date: Nov 29, 2022

On this episode, Andrew Winkler is joined by Kent Grisham of the Nebraska Trucking Association (NTA) to discuss how state associations are essential to trucking success. They reveal the aggressive outreach programs, significant scholarship funding (103 scholarships in 2024!), and special programs for farm and ranch workers that are actively bringing the next generation into dynamic careers in driving, diesel tech, and logistics.

Check us out at Chief Carriers. 

This podcast is produced by Two Brothers Creative.