Our history

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Hard Assets


Roy was born in Berane, Montenegro on August 5th, 1969. He moved to the US in 1997 and has lived there ever since.

Mr. Dobrasinovic owns a group of well-established businesses, which address a variety of customer-related needs in the transportation industry. Compass Holding, LLC and Compass Financial Holding Group, LLC have several separate business entities that serve the modern trucking industry.

  • 1997 - Beginning

    In 1997, Roy started working for Roberts Express in Akron, Ohio as a company truck driver. The following year, he purchased his first truck and joined Watkins Motor Lines as an owner and operator.

  • 1999 - Compass Express

    In 1999, Roy had a vision and looked to make an impact on Chicago’s transportation industry. He then opened the trucking company, Compass Express. What started as a small trucking company with only a few trucks turned into a large operation with over 100 trucks. Understanding the importance of safety for a trucking company, Roy provided his drivers with extensive safety training and orientation programs. At its peak, Compass Express operated 250 trucks.

    With a set of sharpened business skills in the transportation industry, Roy purchased a property in McCook, Illinois in 2003 – which he used to build a modern gas and fueling station. With accessibility for large trucks and automobiles, Compass Fuel provides customers with a modern convenience store and a Dunkin Donuts franchise.

  • 2004 - Compass Truck Sales

    In 2004, Roy opened Compass Trucks Sales, LLC, which is a heavy/used truck dealership in the Chicago area. It was built upon the philosophy “buy here, pay here” – Compass Equipment Finance, LLC was then formed to provide flexible in-house financing for customers.

  • 2007 - Compass Lease

    In 2007, Compass Lease, LLC was formed to provide trucking companies with trailer rentals and leasing options.

  • 2008 - Compass Funding

    In 2008, many local start-up trucking companies began to form, most of them facing serious cash flow challenges. Roy took notice of this trend and decided to offer small carriers with a solid financial solution – so Compass Funding Solutions, LLC was formed to provide factoring services. Compass Funding Solutions helps improve cash flow for trucking companies, while helping them build valuable relationships with brokers and shippers.

    In the same year, Roy decided to close Compass Express in an effort to avoid competing with his strong customer base in the transportation industry. He then turned to the insurance market to capitalize on the “one stop shop” philosophy, so Compass Insurance Group was formed, providing a broad assortment of coverages to trucking businesses.

  • 2014 - Compass Truck Rental and Leasing

    In 2014, Compass Truck Rental and Leasing, LLC were formed to lease and rent trucks to trucking companies. The years 2015 and 2017 marked the beginning of several new Compass affiliates: Compass Payment Services LLC, Compass Specialty Insurance Risk Retention Group Inc. and Compass Logistics LLC. The scope of these new companies ranges widely, from providing commercial fuel funding to owner operators and writing commercial liability insurance to arranging the transportation of freight between shippers and carriers.

Over the years, Roy has built a valuable commercial real estate portfolio. As a philanthropist, he supports several charitable events and sporting activities; he has donated much of his time and money to the Shriners Hospital for Children and other recognizable organizations. Roy is held in high regard by his employees and enjoys respect in his local community.

Roy Dobrasinovic is a confident businessman who promotes the power of vision among is employees and management team. One of Roy’s favorite quotes is “Vision empowers you to see beyond and drives you to your preferred destination. Never give up!”