A 23-year-old with a pager, a bag phone, and a point to prove—Chris O’Brien takes us from apologizing for not owning trucks in the early days of his C.H. Robinson career, to shaping one of the most influential commercial engines in logistics, then into a new play: One Armada. We dig into the early days of brokerage at Robinson when check calls ruled and service meant relentless follow-up, and we unpack the moment that rewired Chris’s approach—working on-site at a shipper and learning to think...
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A 23-year-old with a pager, a bag phone, and a point to prove—Chris O’Brien takes us from apologizing for not owning trucks in the early days of his C.H. Robinson career, to shaping one of the most influential commercial engines in logistics, then into a new play: One Armada. We dig into the early days of brokerage at Robinson when check calls ruled and service meant relentless follow-up, and we unpack the moment that rewired Chris’s approach—working on-site at a shipper and learning to think...
Ep. #65: Matt O’Mara, CEO & Founder, Whimsy Intermodal
The Freight Pod
1 hour 26 minutes
6 months ago
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: Whims...
The Freight Pod
A 23-year-old with a pager, a bag phone, and a point to prove—Chris O’Brien takes us from apologizing for not owning trucks in the early days of his C.H. Robinson career, to shaping one of the most influential commercial engines in logistics, then into a new play: One Armada. We dig into the early days of brokerage at Robinson when check calls ruled and service meant relentless follow-up, and we unpack the moment that rewired Chris’s approach—working on-site at a shipper and learning to think...
