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PODCAST

The Freight Show

The Freight Show brings stories of freight and logistics leaders who’ve shaped the industry. Through in-depth conversations, we explore their journeys, the challenges they’ve overcome, and the insights that have driven their success. Each episode uncovers the lessons, strategies, and wisdom of these freight leaders.

business management

All Episodes

40:44

Phil Shook (Crowley) on CH Robinson's Decentralized...

The Freight Show ·

2026/04/07

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 supply chain wasn't even a college major, joined CH Robinson in 1997 as

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56:25

Jonathan Drouin (WWEX) on Build-vs-Buy for AI in Freight

The Freight Show ·

2026/03/20

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 of this equation. He started as a software developer at 19, moved

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56:22

Terminal Industries CPO Chris Brumett on the Hidden...

The Freight Show ·

2026/03/03

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 Terminal Industries, breaks down how warehouses actually optimize (labor travel time,

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49:33

Price Rite Transport President Will Kerr on How...

The Freight Show ·

2026/02/24

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 mechanics that actually determine who gets freight covered, who absorbs

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54:17

Reliance Partners President Chad Eichelberger on...

The Freight Show ·

2026/02/05

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—helping grow Access America from an early-stage Chattanooga

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54:56

Enterprise Shipper Paul Estrada on Designing a...

The Freight Show ·

2026/01/20

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 two decades leading procurement at scale, and he breaks down what most

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57:10

Evans CEO Ryan Keepman on Becoming a “3.5PL” and...

The Freight Show ·

2026/01/14

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 deregulation era — evolved from a Wisconsin brokerage built on relationships

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52:05

Fura CEO Jeff Dangelo on Why Most Freight...

The Freight Show ·

2026/01/06

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 models break), why most “digital transformation” initiatives stall, and how

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56:40

Bill Driegert (DAT) on the Technology That Actually...

The Freight Show ·

2025/12/16

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 important seat in modern freight: early at Coyote, co-founder of Uber Freight, Head of Trucking

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58:33

A Masterclass in Scaling Freight: The Tech and M&A...

The Freight Show ·

2025/12/10

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, not a job killer.”Doug takes us through the real strategy behind Echo’s rise: building lane

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50:46

The Great Freight Reset: How Smart Data and AI Are...

The Freight Show ·

2025/11/18

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/biannual RFPs, the 50–250 truck carrier sweet spot, and how top carrier reps are now managing 100+

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44:34

Why Most Freight-Tech Projects Fail...

The Freight Show ·

2025/10/27

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 org around strategic sourcing → advanced booking → coverage instead of asking one rep to do it

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47:55

Why Most Brokers Get Freight Pricing Wrong (And How...

The Freight Show ·

2025/10/21

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 planners’ attention. We also talk participation rules, when not to bid, and how to use routing-guide

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53:33

Who’s Really Hauling Your Freight? Rethinking Freight...

The Freight Show ·

2025/10/14

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 compromise Highway’s new Trusted Freight Exchange (TFX)—a secure, identity-verified platform for

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52:31

Mercedes F1 Champion Nico Rosberg on Winning Under...

The Freight Show ·

2025/10/07

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 every week. Nico also shares how he transitioned from the podium to Rosberg Ventures, what he

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42:50

Why AI Won't Replace Freight Brokers (And What...

The Freight Show ·

2025/09/23

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 & ForecastingWhy 2024 spot rate predictions missed the mark (forecast: 13-30% growth, reality: ~0%)The

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39:58

Bootstrapping to $50M: The Power of Reinvestment Over...

The Freight Show ·

2025/09/15

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 investments over a 12-month horizon for proper ROI assessment. Throughout, Ali offers practical

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32:08

Beyond Brokerage: Reimagining Freight Jobs in an...

The Freight Show ·

2025/08/18

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, unstructured data, this conversation highlights the relentless problem-solving and intellectual honesty

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56:42

How Axle Logistics Grew to $1B: Culture, Sales, and...

The Freight Show ·

2025/08/13

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 ops-heavy business can use.Chapters: 00:00 — The hard lessons of first-time leadership 03:30 —

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56:53

From Dispatch to President: How ARL Scales Freight...

The Freight Show ·

2025/08/07

From dispatch trainee to president, Jordan Reber unpacks how ARL Logistics scaled an agent-powered network by pairing offshore talent, selective automation, and a revamped cradle-to-grave model—without losing the relationship-first DNA. We dig into building hybrid teams in Colombia, “train-the-trainer” systems, cleaning messy TMS data, and ARL’s shift toward a revenue-engine sales structure.What We CoverCareer arc: Management trainee → dispatch → brokerage launch → ARL presidencyHybrid

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21 results

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