Ep. #65: Matt O’Mara, CEO & Founder, Whimsy Intermodal

In this episode, Andrew welcomes Matt O’Mara, CEO and founder of Whimsy Intermodal and Whimsy Trucking. Matt’s journey into the transportation industry began in 1994 when he worked as an owner-operator for a trucking company. When that company was acquired and its drivers let go, Matt seized the opportunity to start Whimsy Intermodal in 1996 and hired many of those drivers. Today, Whimsy has about 50 company drivers, 145 owner-operators, and 150 trucks. 

Andrew and Matt also cover:

• Whimsy’s organic business growth and unique capability in handling challenging freight, the importance of finding consistency, and Whimsy’s focus on execution, including how they add value beyond transportation.
• The significant challenges Matt ran into of implementing new TMS systems in a legacy company, the importance of team buy-in, and the eventual success of digitizing and going paperless, including leveraging AI for order entry and real-time driver coaching.
• Treating drivers with respect and providing robust support as the key to retention, highlighting the reason why Whimsy has a waiting list for owner-operators.
• The importance of transparency, leading by example and avoiding hypocrisy, and the critical role of communication, emotional intelligence, and self-awareness in leadership.
• Current market conditions, the lack of impact from Chinese New Year, potential tariff effects, and the critical need for robust infrastructure and processes.