What Does it Take to Run a 10 Million Dollar Trucking Company?

September 15, 2022

Join us on The Road Forward this week as we talk with Aaron, who owns Moneypenny trucking and runs a YouTube channel called The Trucking Guy.

He shares with us the story of his success–growing from around 30 to 60 trucks in just a year.

Aaron also discusses some of the special challenges that come with being a motor carrier with a growing business, and how he’s learning to handle them.

About 60% of Aaron’s fleet consists of hotshot trucks pulling 40ft trailers, with the rest being a mix of open deck trailers including flat beds, step decks and a handful of RGN trailers. Around 90% of his drivers are owner-operators, and he’s always looking for more to join the team. 

Here are some issues Aaron has run into as his business continues to grow:

  • Record Keeping and Paperwork

With as much growth as he’s seen in the past year, a big struggle for Aaron’s business has been dispatching and other behind-the-scenes work. This can mean a load of paperwork for things like tolls, especially with trucks running in so many states.

  • Inspections

Unfortunately, while there are many advantages to using hotshots, this also means more inspections and potential run-ins with DOT. Hotshots don’t have as many regulations, so they tend to get more attention from DOT.

  • Insurance

Insurance can make or break your business, and getting the right coverage for the right price has the potential to hold you back.


Aaron shares some of his personal suggestions and what’s helped him get to where he is:

  • Build a brand online

“If you don’t have an audience…nobody’s gonna know who you are.”


Building an online brand is vital to getting your company out there. This includes having a presence on social media, including YouTube, in addition to old-fashioned recruiting. 

  • Keep Learning and Don’t Quit

Trucking is not an easy business to get into, especially when starting out as a new carrier. It may be a cliche, but you’ll have to go through a lot of trial and error, and the key is not to give up.

“We know ten ways not to do it, let’s go see if we can find the way to do it.”


Aaron suggests working for another company first, to see firsthand what works and what doesn’t. You can take that knowledge and put it into starting your own operation.

“You can learn on your dime or learn on somebody else’s dime.”


Something else Aaron has learned when bringing on new owner-operators is to manage expectations. He tries to discern what they are looking for in joining his company, and he prefers to ‘under-promise and over-deliver.’

Looking to lease as an owner-operator? You can reach out to Aaron through his social media; find him on Instagram, TikTok and YouTube.

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