Who We Are

Working on the family farm, Brent learned the value of hard work and determination. Upon his graduation from Eastern Kentucky University in 1989, earning a Bachelor of Science in Technical Agriculture with a minor in Business Management, Brent obtained his CDL. Working as a driver for a local fertilizer plant he was quickly promoted to management. He has many years of experience of business, trucking, and management.

Carla earned a Bachelor of Science in Elementary Education in 1988, a Master of Arts in Education in 1991, a Rank 1 in 1993, and her National Board Certification in 2012. During the inception of Oakland Farms she worked full-time as an educator. Now retired from teaching, she dedicates countless hours in and out of the office to making sure everything is running smoothly. You won’t see her go anywhere without her laptop.

Amy was the first person to join our office team in 2020. She's a Western Kentucky University Graduate who obtained her Associate's Degree in Office Management and a Bachelor's in Human Resource Management. Amy currently resides in Richmond with her husband Chad, and their two beautiful children, Uriah and Alena Grace. Living alongside her human children are her three kitties. 

Inside the office you'll see her working her magic on all things documentation and reports. She has an eye for detail that is unmatched and speaks fluent Excel. She takes paperwork and turns it into data that is easy to read and vital to our daily operations. 

Outside of the office Amy has a busy life! But she makes time for her high school interest, scrapbooking. A hobby she’s had since her Junior year, she takes an annual weekend trip dedicated to the art of scrapbooking.

Haley, a Richmond native, joined our team in 2020 after working in Sports Rehab administration. She helps to manage our office, HR and DOT compliance.

Inside the office you’ll catch her bookkeeping, writing long emails to the drivers, keeping driver files up to date… and building awesome websites like this one

Outside the office she has three dogs and an indoor jungle she tends to in her spare time. She enjoys playing videos games, going to Renaissance Festivals, or reading! You’ll probably catch her listening to an audiobook in her kitchen or playing Fornite with her boyfriend, Benton, and his two daughters.

Kayla, another Richmond native, has been helping as needed since Jan 2021 and officially joined our team in Sept 2022. She is an integral part of keeping our digital office streamlined and organized!

When she’s not working for the family business, you’ll find her skillfully pouring Diet Cokes 30,000 feet in the air as a flight attendant, or showing houses around Central KY as a licensed Realtor.

When she’s not working one of her three jobs you can probably find her reading, cooking, or preparing for Christmas (not matter the time of year). She currently lives in Lexington with her fiance, Matt, and their three furry friends: Oliver, Luna, and Willie.

Chris grew up working in his family’s auto body shop and towing. He obtained his CDL when he was 18, and worked for his family for 17 years. Before working in OTR heavy haul, Chris worked in heavy haul recovery in towing. He went on to work as a professional mechanic with his ASE Master Certification on heavy equipment. He has worked for four different municipalities and obtained multiple certifications working on various heavy equipment. He worked as a CDL tester for the state of Florida for two years, and trained while working in towing and recovery.

He is a motorcycle enthusiast. His wife, Tiffany, has coined his 9 member riding group as the “Wild Hog Group.” Together they take annual trips. In 2016 they covered 7800 miles from Florida to South Dakota, and all over the western United States, in the course of two weeks.

Tiffany and Chris have a beautiful blended family. He is grateful to them for the support of his job and what we do as a company, and so are we! We are so lucky to have Chris with us. He has a diverse background in the industry that encompasses all aspects of life on the road. You'd be hard pressed to find someone who is as knowledgeable and professional as he is

Pat started trucking part-time in 1977, and bought his first truck in 1982 (a 24ft box truck) delivering freight in Long Island, NY. He sold his first truck and purchased his first Peterbilt and went on to haul gasoline on Long Island. He moved to California and started his own business hauling glass recycling for 6 years. Pat moved to Florida and started a new career doing OTR heavy-haul. His next venture was in Texas working as an end dump driver, before starting a career working for the oil fields transporting frac sand to the wells.

Pat took a few months off to help care for his mother before she passed in December of 2020. When he was ready to re-enter the workforce in February 2021, we were lucky that he chose to work for our team. Pat has 30 years, and 3 million miles of driving experience.

Pat says he feels like he's found his home with Oakland Farms. He is incredibly knowledgeable, professional and has a great work ethic. We hope you get the chance to meet him and see why we love him!

Welcome Chad!

Chad joined our team in May 2023. We are excited to bring him into the Oakland Farms family and look forward to updating this section with information about him and his career!

Trenton is a Richmond native who has experience working in various industries. He has family members who drive, and always liked seeing nice big trucks. One day, he had an epiphany that he wanted to pursue a career in driving and went on to obtain his CDL in 2016! 

Trenton has known one of our other drivers, Mike, since he was in high school. While working on the pipeline Trenton got a call from Mike asking him if he knew anyone that would be interested in working with him at Oakland Farms in Spring 2021… and the rest is history.

Trenton currently resides in Richmond with his wife Tiffany and their two children - Elliana and Kayson. We are so appreciative to his family for their support of his career with our company, and are proud that Trenton has chosen to become a part of our team. 

Trenton is highly motivated, friendly and a fast learner. He’s very professional and fun to talk to. We hope you get the chance to meet him in the field!

Brennon is another Richmond native, and the son of our owners Brent and Carla! Growing up with family in the industry, Brennon has helped us here at Oakland many times. He made the decision to join our team full-time in 2025 as our designated Pilot Car Driver.

We are so excited to have him as part of our team!

Mike has been driving since 2001,  a career decision easily made with multiple family members in the industry as well. While he has over 20 years of driving experience, he is a jack of all trades with a versatile skillset after working in many different facets such as plumbing, roofing and construction. 

Mike is a Kentucky native, and lives locally with his family. He has three children, and two grandsons. He has been with his wife Helena for 26 years. When he is home they enjoy spending time outside, whether they are off-roading or working on his property, they are not the kind to sit still! 

Mike was the first driver hired at Oakland Farms. He is an incredibly hard worker, and a wonderful asset to our team. We are grateful to his family for their continued support, and to Mike for his unwavering dedication.