When asked about becoming an entrepreneur, business owners often say that being their own boss and running a business is exciting and freeing, and above all, challenging. Entrepreneurship takes both skill and determination.

For professional owner-operators like those leased to Landstar, it’s not always the most obvious expertise that makes them successful. As they tell it, it’s more of the drive to be a small-business owner than the driving that has put them on a long and winding road to a successful career. For many Landstar business capacity owners (BCOs), it is the journey that brought them to Landstar that best prepared them to be independent owner-operators.

John Babine
Roadstar and Two Million Mile Safe Driver
J&J Trans-Truck LLC
Leased to Landstar in 1998

At 19 years old, John Babine’s first job was being a small-business owner. After high school graduation, Babine bought a fishing boat, then invested time and money into the equipment and tools he would need like fuel, bait, lobster barrels, rope and traps. Then, Babine says, he set sail on his first business adventure, intending to bring some mouthwatering lobster from Maine to market.

The problem? Well, there were many. Babine says he was too young and he didn’t know enough about the business. After all of the necessary expenses to keep his small lobster fishing boat running, he wasn’t making a profit. Eventually, Babine decided to keep the boat just for personal fishing adventures and ended his stint as Captain John. As the Landstar Roadstar® Honoree and Two Million Mile Safe Driver explains, the failure was a great lesson that taught him exactly how to run a business.

What made you decide to change lanes and become a professional truck driver?

"After the lobster boat failed, I started working at Tom’s of Maine® – in its factory. That’s when I started driving a truck to move materials and products for the company. I liked it, so I went to trucking school and got my CDL while I was working there. I never wanted to be cooped up and not be on the move. After I got my CDL, I wanted to be an owner-operator and run my own business – that was something I always knew I wanted to do."

Why did you want to become an entrepreneur and own your own business? 

"I always wanted to be my own boss. I like things my way. Being a business owner would provide a better life than what I had growing up. We weren’t wealthy and couldn’t afford college. I was motivated to work hard for a better and more productive life than I had back then."

How did your previous career prepare you to own your own business as a Landstar BCO?

"I learned on the lobster boat how to run a business  and what needs to be done to be a successful business owner. You have to think about overhead in business, and there were too many expenses on the lobster boat. I didn’t pay attention to my bottom line. One of the first things to determine when you are running a business is the lowest level you can operate – find the margin that is acceptable for you. Then, think about all of the expenses, your budget, include maintenance, and make sure you can make a profit."

Steve Grillo
BCO Fleet Owner
SNL Transport LLC
Leased to Landstar 2014

A BCO fleet owner with four trucks leased to Landstar, Steve Grillo says he wanted to be a truck driver, but promised his parents he would go to college and spend five years working in the field he studied. After earning his bachelor’s degree in accounting and finance, Grillo kept his promise by spending the next eight years working in his field – three years as the controller for a wholesale sports apparel company, then five more as an executive vice president for a construction company. His experience in managing budgets, payroll functions and daily cash/credit transactions pays off now in managing his small fleet of trucks.

What made you decide to change lanes and become a professional truck driver?

"I’m aware of the line most drivers give when asked this question – and it’s true for me. As a kid I always wanted to drive a truck. I didn’t grow up in a traditional trucking family. We lived in downtown Chicago, but my uncle from Mississippi drove a truck. He gave me a tour of his cab, and I absolutely loved it. My parents knew my passion for trucking but urged me to go to college.
After graduation, I made it eight years before I finally decided to hang up my suit and climb into the cab of a truck to get my license. I earned my CDL in 2005, started as a company lease-operator, and ultimately became an owner-operator."

Why did you want to become an entrepreneur and own your own business? 

"I knew early in my career as a professional truck driver that I wanted to own a small fleet of trucks.
I wasn’t exactly sure how to achieve that, but I knew my end goal included owning and managing a fleet. I fantasized about all the freedom I would have as a business owner, though I was also very aware of the responsibility that would come with owning my own business."

How did your previous career prepare you to own your own business as a Landstar BCO?

"The extensive amount of accounting and management earlier in my finance career has played an integral role in my transition to becoming a successful business owner. Some of the most important metrics in trucking are rooted in numbers and the analytics that go with them. I think having a strong background in accounting helped me to be better equipped to understand the numerous data points of fleet ownership and to quickly make the necessary adjustments in the ever-changing dynamics of trucking. Being able to create a budget, track the variances between the budget and actual expenditures, and make changes according to results is very important."

Sara Pingel
Roadstar and Million Mile Safe Driver
Pinklin Express LLC
Team Driver, Leased to Landstar in 2007

Vic Pinkston
Million Mile Safe Driver
Pinklin Express LLC
Team Driver, Leased to Landstar in 2007

Before she became an independent owner-operator, Sara Pingel was a self-professed “jack of all trades, master of none.” After high school, Pingel worked as a crew member aboard a ship turned museum, spent time working in accounting, ran a unit at an autism care facility, was a security guard, a florist, and, finally, a company driver. That’s when the Roadstar Honoree and Million Mile Safe Driver met her business partner, Vic Pinkston, also a Million Mile Safe Driver leased to Landstar.

Pingel says she never intended to own a truck or a business. But after working with Pinkston as company drivers, and learning from his previous business experience as the general manager of a car dealership, Pingel decided it was time to be at the helm of a new business adventure, owning and operating a truck.

What made you decide to change lanes and become a professional truck driver?

"Vic and I both came into the industry to travel and see the country. We met as drivers and ran as a team at another company before we decided to lease to Landstar. I wasn’t looking to own my own business, but I had a desire to travel and see the country. And, Vic wanted to live and work on his own terms and manage a business at his own pace."

Why did you want to become an entrepreneur and own your own business? 

"We both have the motivation and drive that makes us successful business owners. In Vic’s case, his daily responsibilities at the car dealership were to overcome obstacles, customer service and business growth. While working with Vic as a team driver, he taught me a lot and I liked working with him, so I decided to join him on this new adventure of owning our truck and starting a business partnership."

How did your previous career prepare you to own your own business as a Landstar BCO?

"Our combined experiences have made us successful team drivers and helped us thrive in the transportation industry. Vic has a strong background when it comes to ‘Business 101,’ a lot of experience working with budgets, managing overhead and negotiating prices from his days at the car dealership. My experience in customer service and overall patience with difficult situations, coupled with my observation and navigation skills, are an asset to our business. We are looking forward to many more successful miles down the road together."



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