The Freight Pod
The Freight Pod
Andrew Silver
Ep. #65: Matt O’Mara, CEO & Founder, Whimsy Intermodal
1 hour 26 minutes Posted May 6, 2025 at 9:00 am.
Sponsor message and Andrew’s introduction
Matt’s accidental start in trucking
Digitizing a legacy trucking company
Retaining drivers through support, training, and process
This business has always been about communication”
On leadership and avoiding hypocrisy
Tariff talk and a market update
Communication and operational strategy in a potential downturn
“Building riches in niches” and Whimsy’s approach to specialized freight
Finding purpose as a CEO and founder
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Show notes
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: Whims...