Most people get into trucking and fall in love with the truck. Timothy Maddox, CEO of Haul of Duty Inc., fell in love with the business — and that's why he now runs a 23-truck fleet out of one of the hardest places in the country to operate one: New York City.
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From the city streets to the dispatch desk
Maddox started behind the wheel, and he started in traffic that humbles most drivers. But the real shift in his trajectory wasn't a new truck — it was the move from driver to dispatcher. Once he understood that finding and managing freight was the skill that actually paid, the truck became a tool instead of the whole job.
Scaling without losing the wheels
Growth in trucking is easy to fake and hard to sustain. Maddox's approach was unglamorous and durable: build consistent, dedicated routes so drivers have a reason to stay, then keep buying carefully — he talks about sourcing trucks off Facebook Marketplace and being disciplined about money rather than spending to look successful. Driver retention, in his telling, isn't a soft HR concern. It's a growth strategy. Every driver who leaves is a route you have to rebuild.
The relationships that fund the fleet
The other engine is broker relationships. A 23-truck fleet needs reliable freight, and reliable freight comes from being the carrier brokers trust with their loads. Maddox built a hybrid fleet and leaned into dedicated freight to smooth out the volatility that kills small fleets.
The lesson for any operator watching: the truck gets you in the door. What scales you is everything around it — the dispatch knowledge, the driver relationships, the broker trust, and the discipline to grow within your means.
Guest: Timothy Maddox, CEO of Haul of Duty Inc. (@state_to_state89).