Tyler Harper thought he was signing up for a “big box brokerage” job after ASU. Instead, freight turned into a decade-long obsession, a crash course in carrier sales, and eventually the push that forced him and his co-founders to start Pinnacle Logistics Group, debt-free, on short notice, and with a single book of business.

In this episode, Tyler breaks down the origin story behind Pinnacle, including the moment that changed everything, why the team intentionally leans into “ugly freight” like Mexico, drayage, consolidation, and multi-stop truckload, and how they’ve built a company that’s basically the opposite of the standard brokerage model: roughly 30 people on the team and only 2 sales reps.

The conversation really gets interesting when Tyler explains why LTL is still one of the most underserved modes in freight, how rebuilds, reweighs, and reclasses quietly eat shipper budgets, and how Pinnacle built LTL Flow, a free pre-shipment tool designed to remove human error before the load ever gets booked. Think photos, measurements, documentation, and a dimensioning workflow that cuts down disputes and surprises.

We also talk leadership, how Tyler’s role has shifted from “I’ll do everything myself” to building a culture where speed is king, response time is tracked like a KPI, and offshore teams are treated like a true extension of the company, not a separate branch.