Cook County Transportation - Fleet Owner/Operator

Full Editorial Writeup

This is an asset-heavy transportation company operating 17 Freightliner Cascadia tractors and 20 trailers across Cook County, Illinois. Founded in 2007, the business has built nearly two decades of customer relationships while generating $5 million in annual revenue with $1.2 million in cash flow. The operation employs 23 people including 20 contractor drivers, suggesting an owner-operator model where the company provides equipment and dispatch services to independent drivers.

What makes this deal notable is the debt-free fleet valued at over $2 million, representing roughly one-third of the asking price in hard assets. The business operates with established systems for dispatch, compliance, and customer management, serving what appears to be a mix of regular freight customers. The 24% cash flow margin on $5M revenue indicates solid operational efficiency, though the heavy asset base means this is more of a fleet management play than a pure logistics arbitrage business.

The seller cites pursuing other opportunities as the reason for sale, and the financials show some discrepancies between the headline numbers and detailed breakdown that warrant investigation. With operating authority, customer relationships, and a turnkey fleet, this represents a substantial transportation operation positioned in the Chicago market.