From Union Work to Owning the Road | Dante Doss | Ep 7

In this episode of Miles and Mentors, Dante Doss shares his journey from working in the union as a heavy equipment operator to becoming an owner-operator in trucking. With a strong work ethic and a long-term goal of running his own trucking company, Dante discusses the lessons he has learned along the way, the challenges of starting out, and what it takes to succeed in the industry.

Dante’s introduction to trucking started early, inspired by his uncle who spent over 30 years in the industry. While working in the union, he frequently operated trucks, which solidified his interest in pursuing a CDL. When the COVID-19 pandemic disrupted many industries, he saw trucking as a stable career path and decided to make the transition. His ultimate goal was clear from the start—gain experience as a driver and eventually own his own fleet.

One of the biggest lessons Dante shares is the importance of starting as a company driver before jumping into ownership. While many new drivers dream of becoming owner-operators immediately, he stresses that understanding the industry, learning the financial side of trucking, and building experience behind the wheel are crucial before taking on the risks of business ownership. He recommends that drivers save between ten to twenty thousand dollars in emergency funds before making the leap, as unexpected repairs, insurance, and compliance costs can quickly derail an unprepared owner-operator.

Dante highlights the financial realities of trucking—while there is great earning potential, there are also significant expenses. He recalls spending nearly twenty thousand dollars just on tires, emphasizing the importance of financial discipline and planning. Trucking is not just about making money; it is about managing it wisely.

A key factor in Dante’s success has been building strong relationships with dispatchers and brokers. He emphasizes the importance of professionalism, a positive attitude, and reliability. He explains that top-rated drivers get better loads, higher pay, and more consistent work because they prove themselves dependable. Networking and maintaining a good reputation in the industry have been critical to his ability to secure high-paying freight.

Now, Dante is taking his business to the next level by bringing his fiancée into the industry to manage dispatching. This expansion allows him to control more aspects of his operation and optimize his revenue. He stresses that trucking is a long-term game, and those who stay focused, continuously learn, and build a strong foundation will find lasting success.

For those considering trucking, Dante advises taking time to learn from experienced professionals, ask questions, and never stop improving. He strongly recommends obtaining all possible endorsements to increase job opportunities and earning potential.

If you are starting a trucking business or growing your fleet and need expert guidance, reach out to us today—our industry expert partners can help you make the right decisions for long-term success.