Conversations with the Operators who move the Industry

#24 Harman Cheema on Why Shippers Are Flooding Back to Asset Carriers | The Freight Show

Harman Cheema runs 500 trucks at Cheema Freightlines and a brokerage approaching $100M at Cheema Logistics. He breaks down the zombie capacity that broke freight rates, the broker liability ruling, and why shippers who chased cheap capacity are calling him back.

#23 How Will Hopkins (BlackBox Logistics) Got Fired Right Before His Biggest Opportunity | The Freight Show

Will Hopkins got fired right before starting BlackBox Logistics. A year dispatching for owner-operators on the carrier side gave him the perspective that shaped how BlackBox built its carrier relationships and grew to $70M in annual revenue.

#22 Greg Sanders (RDS Capacity Solutions) on Building a Brokerage Where Carriers Actually Want to Work | The Freight Show

Greg Sanders, President of RDS Capacity Solutions, shares three decades of lessons from Landstar, Schneider, OHL, Redwood, and ITS Logistics before founding his own brokerage at 55 — including his pod model, field general philosophy, and views on the broker liability case heading through the courts.

#21 Jordan Strawn (Werner) on Building a $400M Brokerage and What Incumbents Miss About Technology | The Freight Show

Jordan Strawn, SVP of Logistics at Werner, explains how he helped scale Reed Transport Services from $70M to $400M before its 2022 acquisition, what made the business attractive to Werner, and why process discipline is the actual driver of operational performance at scale.

#20 Phil Shook (Crowley) on CH Robinson's Decentralized Empire and What Brokers Get Wrong About Scale | The Freight Show

Phil Shook, VP of North America Land Transportation at Crowley, recounts 23 years at CH Robinson including the Backhaulers acquisition that reshaped the industry, explains the intermodal business model, and makes the case that relationship depth in brokerage is an operational advantage technology hasn't replaced.

#19 Jonathan Drouin (WWEX) on Build-vs-Buy for AI in Freight | The Freight Show

Jonathan Drouin, VP of Product Strategy at WWEX, explains how the $5 billion multimodal freight company evaluates AI initiatives against three hard metrics, why the prototype-to-production gap is larger than most companies expect, and why they shifted from internal builds to vendor partnerships in 2025.

#18 Terminal Industries CPO Chris Brumett on the Hidden Cost of Freight Data Silos | The Freight Show

Chris Brumett, CPO of Terminal Industries, explains how warehouses actually optimize, why carrier appointment compliance protects labor plans rather than punishing carriers, and how fragmented data across yard operations creates hidden costs that are larger than most facilities realize.

#17 Price Rite Transport President Will Kerr on How Carrier Density Beats Rate Shopping | The Freight Show

Will Kerr, President of Price Rite Transport, explains how carrier density beats rate shopping at every level of the market and why a broker-centric carrier strategy can outperform direct shipper sales.

#16 Reliance Partners President Chad Eichelberger on Freight Risk, Insurance, and Carrier Vetting | The Freight Show

Chad Eichelberger, President of Reliance Partners, traces two zero-to-scale runs in freight — Access America from seven employees to a $675M run rate, then Reliance Partners into the largest trucking insurance agency in the country.

#15 Enterprise Shipper Paul Estrada on Designing a Low-Cost-to-Serve Freight Operation | The Freight Show

Paul Estrada, Director of Procurement at Niagara Bottling, explains how a large enterprise shipper designs a low-cost-to-serve freight operation — from radical data transparency with carriers, to shrinking a provider network from 150 to 65 while tripling volume, to the standard any AI pitch must meet to earn attention in a procurement meeting.

#14 Evans CEO Ryan Keepman on Becoming a 3.5PL and Scaling From Regional to National | The Freight Show

Ryan Keepman, CEO of Evans Transportation, explains how a family-owned brokerage founded during deregulation survived consolidation by leaning into complexity, building disciplined service-line expansions, and developing culture as a competitive advantage.

#13 Fura CEO Jeff Dangelo on Why Most Freight Transformations Break | The Freight Show

Jeff Dangelo, CEO of Fura, shares hard-earned lessons on scaling brokerages, why digital transformations fail, and how AI can shrink the adoption problem by running in parallel with people.

#12 Bill Driegert (DAT) on the Technology That Actually Sticks in Freight | The Freight Show

Bill Driegert traces the real arc of freight technology from post-deregulation brokerage through digital freight matching and the DAT + Convoy combination, and explains why pure-play digital brokers hit a ceiling and where AI automation is actually headed.

#11 A Masterclass in Scaling Freight: The Tech and M&A Blueprint — Doug Waggoner, Echo Global Logistics | The Freight Show

Doug Waggoner, Chairman and CEO of Echo Global Logistics, walks through one of the most dramatic careers in modern freight — from the deregulation era and three-martini lunches to building a $1B+ multimodal brokerage through 30 acquisitions, an IPO, and a return to private ownership.

#10 The Great Freight Reset: How Smart Data and AI Are Transforming the Industry — Jay Gustafson, Echo Global Logistics | The Freight Show

Jay Gustafson, EVP of Brokerage Operations at Echo Global Logistics, gives a frank read on Q4 2025 freight market conditions, explains why shippers are consolidating carrier networks after the COVID boom, and makes the case for agentic AI in email as the missing link in carrier booking automation.

#9 Why Most Freight-Tech Projects Fail Before They Even Start — Ryan Schreiber, Metafora | The Freight Show

Ryan Schreiber, Chief Growth Officer at Metafora, explains why most freight-tech initiatives fail before they start, why zero inbound calls should be a broker's north star, and how to redesign the carrier org around strategic sourcing, advanced booking, and coverage as three distinct functions.

#8 Why Most Brokers Get Freight Pricing Wrong — Chadd Olesen, AVRL | The Freight Show

Chadd Olesen, CEO and Co-founder of AVRL, explains why freight pricing averages are systematically misleading, how composition scoring by market region beats lane-level thinking, and what it actually takes to make automated spot bidding profitable at scale.

#7 Who's Really Hauling Your Freight? Rethinking Freight Security and Carrier Vetting — Michael Caney, Highway | The Freight Show

Michael Caney, co-founder and CRO of Highway, explains how freight fraud exploded when the industry digitized a high-trust network without verifying who was on it, and what banking-grade carrier identity checks can do about it.

#6 Nico Rosberg on Winning Under Pressure, Building a Venture Fund, and the Future of Mobility | The Freight Show

Mercedes F1 World Champion Nico Rosberg on the mental framework behind the 2016 title, building Rosberg Ventures toward $200M AUM, and the lessons racing teaches founders.

#5 Why AI Won't Replace Freight Brokers (And What Actually Will) | The Freight Show

Drew Herpich, an eighteen-year freight industry veteran, explains why AI will handle scheduling and repetitive carrier interactions but can't replicate the five-year relationship that turns a Fortune 500 shipper into a 10-loads-per-day account.

#4 Bootstrapping to $50M: The Power of Reinvestment Over Outside Capital | The Freight Show

Ali Shafi, co-founder of SIO Logistics, explains how he bootstrapped a freight brokerage from a Corvette sale to nearly 50 employees without ever raising outside capital, and why staying debt-free lets SIO hire counter-cyclically during soft freight markets.

#3 Beyond Brokerage: Reimagining Freight Jobs in an AI-Powered Future | The Freight Show

Mike Carter and Jesse Buckingham, co-founders of Vooma, trace the origin of the company from failed final-mile robotics to an AI platform that automates unstructured data entry for freight brokerages, and share their vision for AI co-workers handling the repetitive grind so brokers can focus on judgment and relationships.

#2 How Shawn McLeod Grew Axle Logistics to $1B | The Freight Show

Shawn McLeod, President of Axle Logistics, explains how the Knoxville-based brokerage grew from $17M to $1B+ in revenue by treating culture as the primary growth strategy, building a structured six-week Launchpad training program, and automating repetitive back-office work while protecting customer relationships.

#1 Jordan Reber (ARL Logistics) on Building a Freight Brokerage with Offshore Talent, Automation, and an Agent Network | The Freight Show

Jordan Reber, President of ARL Logistics, explains how ARL built a hybrid brokerage by moving back-office operations to Colombia before automating them, and why he believes the cradle-to-grave broker model has a structural ceiling.