The Freight Show

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 actu...

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 K...

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...

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 i...

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 t...

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...

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...

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. Jonath...

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 Of...

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 ad...

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 throu...

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...

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 stil...

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 (a...

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...

Building a $1B+ multimodal 3PL brokerage in a deregulated, brutally cyclical trucking market doesn’t happen by accident. Doug Waggoner, Chairman & CEO of Echo Global Logistics, walks through one of the most dramatic long-run arcs in transportation — from three-martini LTL sales calls and rolls of quarters for pay phones to cloud-optimized networks, data-driven pricing, and AI as a “task killer...

Freight market pulse + what’s next. Echo Global Logistics EVP Jay Gustafson breaks down why shippers are consolidating carrier networks, how continuous movement & drop-trailer programs create stability, and where AI + email automation will actually move the needle for brokerages and carriers. We cover market conditions (soft but stable demand, high primary acceptance), the return of annual/bia...

Ryan Schreiber—Chief Growth Officer at Metafora—joins The Freight Show to unpack why most freight-tech projects fail before they start, how to reframe “the problem” as an operational one, and why a broker’s goal should be zero inbound calls . We dig into AI’s real promise (natural-language workflows at 3 a.m.), the orchestration mindset (people × process × tech), and how to redesign the carrier or...

Freight analyst ≠ data analyst. In this deep dive, Chadd Olesen , co-founder & CEO of AVRL , explains why averages lie, how “composition scoring” beats lane-by-lane thinking, and what it really takes to make automated spot bidding profitable at scale. We get tactical on separating cost from margin , building region-first strategies, measuring MAPE, and why speed to quote (sub-second!) wins pla...

Freight fraud is evolving — gone are the days of just stolen cargo. Today’s attacks are digital: email hijacks, phone spoofing, “sold MCs,” and identity theft. In this episode, Michael Caney , Chief Commercial Officer at Highway , unveils how fraud works in 2025 and how his team is building the rails to stop it. We dig into: Why fraud attempts spiked 27% in 2024 , led by identity theft and inbox c...

2016 Formula One World Champion Nico Rosberg joins The Freight Show to unpack the mindset, mechanics, and team dynamics behind working with / competing with legends like Lewis Hamilton - and how those lessons now power his work as an entrepreneur and investor. We dig into sports psychology, meditation, micro-improvements, F1 team culture, and the insane logistics of moving a global racing circus e...

In this episode, we sit down with Drew Herpich, a freight industry veteran with nearly two decades of experience scaling brokerages and leading carrier sales teams. Drew brings a wealth of knowledge from the trenches, sharing insights on navigating today's challenging market conditions and what it takes to build successful freight operations. Key Topics Discussed: Market Analysis & Forecasting...

In this episode, Ali Shafi, CEO of SIO Logistics, shares insights on bootstrapping a freight brokerage without outside capital. He emphasizes prioritizing company culture over short-term revenue and discusses how AI is increasing load-to-rep ratios. Ali covers early-stage cash flow management, co-founder dynamics, and the benefits of counter-cyclical hiring. He advocates for evaluating tech invest...

In this episode of The Freight Show , Mike and Jesse, co-founders of Vooma , sit down to discuss how a chance introduction between a strategist and a builder evolved into one of logistics’ most exciting automation platforms. From early experiments—including wild ideas like training crows for last-mile delivery—to killing the wrong projects and zeroing in on freight’s biggest bottleneck, unstructur...

Shawn McLeod, President of Axle Logistics, joins us to share how the Knoxville-based 3PL scaled from $17M to over $1B in revenue. We explore Axle’s “build your empire” culture, their six-week LaunchPad training program, and where they automate without losing the human relationships that drive freight. From hiring and retention to thriving in soft markets, Shawn delivers a playbook any brokerage or...