Chicago Trucking & Logistics Company, Illinois Freight Operator

$5.5M

Revenue

$957K

SDE

4.0x

Multiple

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Full Editorial Writeup

This is a well-established Chicago-area trucking and logistics operation generating roughly $5.5m in annual revenue with reported cash flow of about $957k, a healthy 17 percent owner-earnings margin for a freight business. It serves a diversified base of large customers, which is the single most important attribute in this space because customer concentration is what kills trucking deals. The asking price of $3.8m implies a 3.97x multiple on cash flow, which is toward the top end of what freight operators typically fetch given the capital intensity and cyclicality of the sector.

Chicago sits at the center of the North American freight network, one of the largest intermodal and logistics hubs in the country. A carrier operating out of this corridor benefits from dense freight lanes, proximity to rail interchange, and steady industrial demand. The business appears to own its fleet, which means the multiple is partly buying hard assets (tractors and trailers) rather than pure goodwill, so a chunk of the enterprise value is collateralizable.

The listing is thin on details around fleet age, contract structure, owner-operator versus company-driver mix, and customer concentration, all of which will drive the real quality of these earnings. Freight is a boring, essential, cash-generative business when run tightly, and the margins here suggest it is being run reasonably well. The open question is how much of that $957k is durable operating profit versus favorable spot-rate timing in a volatile freight market.

Why we like it

Earnings quality looks solid on paper: $957k of cash flow on $5.5m of revenue is a 17 percent margin, well above the thin single-digit margins that plague most asset-heavy carriers. That suggests either strong lane economics, efficient utilization, or a favorable contract mix. The buyer needs to verify how much of this survives a normalized freight-rate environment.
Freight is genuinely essential and recession-resilient at the aggregate level. Goods still need to move in a downturn, and a diversified customer base insulates the operator from any single shipper pulling volume. This is boring, repeatable, cash-generative demand rather than a discretionary or trend-driven revenue stream.
The Chicago location is a real moat feature, not marketing copy. It is one of the densest freight and intermodal hubs in North America, giving the carrier access to deep freight lanes, backhaul opportunities, and a stable industrial shipper base. Geography here reduces empty-mile risk and supports utilization.
The fleet appears to be included, which means part of the 3.97x is buying collateralizable hard assets rather than pure goodwill. That lowers downside risk and improves financeability, since lenders will underwrite against tractors and trailers with clear resale value.

How to improve it

Audit lane profitability and cut the bottom-decile freight within the first 90 days. Most carriers haul a meaningful chunk of loads at break-even or a loss to keep trucks moving, and pruning those while reallocating capacity to high-margin lanes can lift cash flow without adding a single truck.
Build a formal backhaul and load-matching process to attack empty miles. Every deadhead mile is pure cost, and even a few points of improvement in loaded-mile percentage drops directly to the bottom line given the fixed cost of running each tractor.
Lock in more contracted freight versus spot exposure to stabilize revenue. Contract lanes carry lower headline rates but far more predictable volume and margin, which matters both for operating stability and for the exit multiple a future buyer will pay.
Install real telematics and driver-scorecard systems if not already in place. Fuel is the largest variable cost in trucking, and idle reduction, route optimization, and driver behavior monitoring can meaningfully cut per-mile fuel and maintenance spend.
Systematize the maintenance program to extend fleet life and control the single largest capex line. Preventive maintenance schedules and in-house or negotiated shop rates reduce unplanned downtime, which is both a cost and a revenue killer when a truck sits idle.
Diversify and deepen the customer base with formal account management. Even with a diverse base today, adding shippers in complementary industries reduces cyclicality and gives pricing leverage during freight upcycles.

Diligence notes

Scrutinize customer concentration hard. The listing claims a diverse base of large customers, but pull the actual revenue-by-customer breakdown for the last three years. If the top one or two shippers exceed 25 to 30 percent of revenue, the risk profile and the multiple you should pay change dramatically.
Normalize the cash flow against freight-rate cycles. Freight rates were elevated post-2021 and have since softened substantially, so confirm whether the $957k reflects a sustainable run rate or a peak-cycle number. Look at monthly revenue and rate-per-mile trends across at least three years.
Get a full fleet appraisal and capex schedule. Confirm ownership (owned free and clear versus leased or financed), average tractor and trailer age, remaining useful life, and the near-term replacement capex needed. An aging fleet can turn a clean 3.97x into a much worse effective multiple once you fund replacements.
Verify driver structure and DOT compliance. Understand the company-driver versus owner-operator mix, driver turnover, whether workers are properly classified, and the safety/CSA scores. Driver shortages, misclassification liability, and a poor safety record are all live financial and regulatory risks.
Confirm what the $957k cash flow figure actually includes. Determine whether it is true SDE with owner add-backs or a cleaner EBITDA number, and reconcile it to tax returns. Add-backs for owner salary, fuel-hedging gains, or one-time freight surges need to be stripped out to underwrite the deal properly.

Source

Originally listed on DealStream. View original listing →