Driven Too Far: The Truth About Trucking with Andrew Winkler

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.