The Freight Show

Forty-one years is a long time to run one software company. Tom McLeod started McLeod Software in 1985, five years after deregulation blew open an industry that had been run like a public utility, and he's still at the helm today with 550 employees, no outside investors, and a product line that just went through a complete revamp. In the mid-80s, dozens of small software companies were all trying to build the operations platform fo...

Every broker on the phone is pitching service. Jacob Benbenek has a harder proof point than most: Magna has never had a fraud incident in 14 years of business, and his carrier reps get paid on loads that lose money exactly as if they made a hundred dollars. Ask him how a small team stays disciplined on a hard-to-cover load at 4:30 on a Friday, and the answer starts with how people get paid, not with a compliance tool.

Jacob spent te...

Most brokerages that stall in the $40-50M range never get out. The math is unforgiving: growing means hiring, onboarding, and training faster than the volume arrives, but staffing ahead of volume burns cash you don't have yet. American Diamond Logistics sat at $44-45M for three straight years. Then, in a matter of months, its run rate jumped to nearly $100M.

Steve Wineriter has been in freight since 2002, when he joined his dad's 3P...

Going into the Montgomery case, everyone expected the brokers to win. The FMCSA and the Department of Transportation both filed on the brokers' side. Matthew Leffler, a supply chain attorney and law professor, called it for the brokers too. The Supreme Court came back unanimous, against them, and wiped out a presumption the entire brokered freight model was built on: that when a motor carrier has a catastrophic accident, the broker...

Look at a freight brokerage P&L the way most investors do and you'll see a 10 to 20% gross margin, a 3 to 8% EBITDA margin, and a business at the mercy of the freight cycle. Brandon Wolfe looks at the same numbers and sees one of the most underestimated business models in the country. The catch, he says, is that the best brokerages stay private, so almost nobody gets to see what the model actually produces.

Brandon is Co-founder...

For decades, brokerage has run on two assumptions: pay your reps on commission, and stay asset-light. Shannon Breen built FreightVana by breaking both. What happens when you strip commissions out of a brokerage entirely and own the trailers instead of the trucks?

Shannon spent his corporate career inside a large public truckload carrier, where he helped stand up the power-only business after the Knight-Swift merger in 2017. He saw t...

or three years, asset-based carriers got beaten on price by capacity that hauled freight for half of what a real truck needed to break even. Now the cycle has turned, and the shippers who spent those years chasing the cheapest option are calling back. Harman Cheema is in a rare seat to see all of it: he runs 500 trucks and 2,000 trailers at Cheema Freightlines, plus a brokerage at Cheema Logistics approaching $100M in revenue. He's...

Most freight founders start with a plan. Will Hopkins started by getting fired right before Christmas, then spent a year on the carrier side dispatching loads off truck stops before he was legally allowed to broker again. He calls it the best thing that ever happened to his career.

Will Hopkins co-founded BlackBox out of his business partner's living room in Birmingham during COVID and has built it into a $70M flatbed brokerage. He ...

Starting a brokerage from scratch is hard. Starting one at 55, after a 30-year career running brokerage at Schneider, OHL, Redwood, and ITS Logistics, is a different kind of bet — and doing it 18 months before the market collapses into a multi-year freight recession is something else entirely.

Greg Sanders has lived all of it. He grew up in the family business, an intermodal company his dad sold to Landstar in 1994. He spe...

Most freight M&A deals look great on paper—but execution is where they succeed or fall apart. So what actually matters when you’re integrating teams, systems, culture, and operations while the market is turning against you? 

Jordan Strawn has lived every phase of that journey. He joined Reed Transport Services in 2015 when it was a $70M Tampa-based brokerage and helped scale it to $400M before Werner acquired th...

How does a 3PL evolve from a collection of entrepreneurial fiefdoms competing against each other to a unified, technology-enabled powerhouse? And what does it actually take to build exceptional operations in an industry where the basics—moving freight from A to B—haven't changed, but everything around it has?

Phil Shook has lived through every major transformation in modern freight. He started at Hub Group in 1994 when s...

Most freight brokerages are drowning in AI pilots that never make it to production. The gap between a working demo and a system processing thousands of loads per week is not technical — it is organizational.

It comes down to setting clear KPIs up front, running biweekly AI steering committees with full leadership visibility, and being ruthlessly honest about what is working and what is not.

Jonathan Drouin has lived both sides ...

Freight doesn’t slow down at the dock. It slows down in the yard, at the gate, and in the messy handoff between facility ops and transportation. Chris has spent decades inside that “supply chain execution” layer, and he’s now building a modern yard operating system at Terminal Industries to remove the friction most networks have learned to tolerate.

In this episode, Chris Brumett, Chief Product Officer at Ter...

The freight market looks very different depending on which side of the phone you sit on. Will Kerr has lived both sides deeply, first as a carrier sales operator and brokerage founder who scaled Edge Logistics to $10M in its first year and over $160M in revenue, then as a trucking executive navigating today’s broker-driven freight environment. His perspective cuts through a lot of surface-level advice by unpacking the mechani...

Freight companies that scale well usually share one thing in common: they obsess over the operating details that keep the business from breaking as headcount, customers, and complexity explode. Reliance Partners President Chad Eichelberger has built his career inside that reality, from early-stage brokerage growth to enterprise-scale execution and risk management.

In this episode, Chad walks through two rare zero-to-scale runs&mdash...

If you sell into enterprise shippers, here’s the uncomfortable truth: your differentiator isn’t your pitch deck, your coverage story, or even your rate. It’s whether you can deliver predictable service and predictable economics inside a network built to eliminate volatility.

This episode pulls back the curtain on how a large enterprise shipper actually runs transportation procurement. Paul Estrada has spent nearly ...

The freight market has trained most brokerages to chase volume, compete on price, and treat service lines like shiny add-ons. Evans Transportation took the opposite approach: build a durable business by leaning into complexity, building culture as a competitive advantage, and diversifying with discipline.

In this episode, Ryan Keepman shares how Evans — one of the rare family-owned brokerages still standing from the deregulati...

The real bottleneck in freight technology isn’t innovation — it’s adoption, misaligned incentives, and the absence of ownership over cultural change. Jeff Dangelo has lived every side of that problem: early at TQL, helping scale MegaCorp Logistics, founding the freight collaboration platform Turvo, and now leading Fura as CEO.

In this episode, Jeff breaks down what really makes brokerages scale (and where common mo...

Freight tech hype cycles come and go, but what actually sticks inside brokerages, carrier ops, and shipper TMS screens? The “Steve Jobs of freight,” Bill Driegert, traces the real arc of innovation in trucking – from American Backhaulers and the “Chicago model” to Uber-for-Freight experiments, digital freight matching, AI dispatchers, and the Convoy acquisition by DAT.

Bill has sat in almost every impor...