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Armchair Attorney® Podcast

Author: Matthew Leffler

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The Armchair Attorney® Podcast is program hosted by the Armchair Attorney® himself, Matthew M. Leffler. Matthew is a real-life attorney with a curious mind and a passion for how things work. From law to supply chain and everything in-between, he bridges the gap between education and entertainment. 

116 Episodes
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What happens when an unstoppable force collides with an immovable object? Thanks to the Traffic Club of Chicago, we found out! On Thursday, November 13th, Craig Fuller, Founder & CEO of Freightwaves & SONAR met Ken Adamo, GM for Shipper & Chief of Analytics for DAT Freight & Analytics. Missed the live event? Here you go! Follow Craig & Ken on x for even spicier takes! This program is brought to you by DAT Freight & Analytics. Since 1978, DAT has helped truc...
We're digging deep this week at the Armchair Attorney® Podcast as we dive into two Supreme Court cases. The first case is Learning Resources, Inc. v Trump. At issue is whether IEEPA authorizes the use of tariffs, and if it does, did Congress unconstitutionally delegate that power to the President? Oral arguments were last week, we'll discuss! The next case is Montgomery v. Caribe Transport II, LLC, which will determine whether federal law preempts state-law claims against freight broke...
For months we've watched this case move through the federal courts at a breakneck speed. Oral arguments for the V.O.S. Selections v. Trump case occurred on November 5, 2025. All roads lead to SCOTUS. Does IEEPA authorize tariffs? If it does, did Congress unconstitutionally delegate that power to the President? We're closer than we've ever been to knowing the answers. For your listening pleasure, here is the oral argument in its entirety. This program is brought to you by DAT Freight &a...
Must ❤️ Trailers

Must ❤️ Trailers

2025-10-3046:16

In this conversation, I am joined by Josh Allen, Chief Commercial Officer at ITS Logistics. Josh drives the company's business growth, customer acquisition, & commercial strategy, leveraging ITS's asset-based model & innovative tools to expand market share & tackle industry challenges. ITS Logistics is a leading third-party logistics (3PL) company founded in 1999 & headquartered in Reno, Nevada. It specializes in end-to-end supply chain management, offering a wide range of s...
Jordan Graft is a man on a mission. As the Founder & CEO of Highway, the Dallas-based technology company focused on the trucking & industry, Highway is making freight more connected and secure. And it all starts with carrier identity. Or is it single sign on? In this episode, we talk faith, collaboration, Jordan's indefatigable drive to build one of the fastest growing technology companies in all transportation & logistics. And with cargo theft & fraud representing a multi-bi...
In this installment, I sit down with Will Fediw, Senior Vice President of the Virginia Maritime Association, as he gears up for VMA 2025. From serving in the coast guard to working in the c-suite, Will knows what it takes to bring an industry together at the VMA. What is the VMA? Glad you asked! The Virginia Maritime Association is a professional trade organization founded in 1920 to promote, protect, & advance international & domestic commerce through Virginia's ports. It serv...
Seven Mondays a Week

Seven Mondays a Week

2025-09-0355:26

Jorden Reber is an incredible person. A natural leader who excels at bringing the best out of people. As the EVP of ARL Network, an agent-based, asset transportation network built on the foundation of partnerships, and providing top-tier customer service throughout the United States. He also loves Mondays. In this episode, we discuss Jordan's journey from the restaurant kitchen to the C-Suite. Out of the frying pan & into the fire. Get ready. This program is brought to you by ...
Once more unto the breach with the incredible, Anne Reinke, President & CEO of the Intermodal Association of North America. With just a couple weeks to go, the Intermodal Expo is gearing up! In this episode, Anne & I discuss our early careers in food service & retail. We also talk about the BNSF & CSX partnership, the end of the de minimus exemption on tariffs, & the latest in IEEPA. Let's go! This program is brought to you by DAT Freight & Analytics. Since 1978, DAT h...
Beth Young is a force of nature. From WyoTech, to the American Trucking Associations, to Velociti, Beth's career has spanned the logistics landscape. In this installment, we sit down to discuss the connected supply chain. The connected everything, really. We talk about solving problems, amplifying the message of skilled trades, & Beth's latest work helping fleets leverage technology to mitigate risk. Gear up, we're exploring the great outdoors of the connected supply chain! This pr...
Should I Panic Yet?

Should I Panic Yet?

2025-08-1101:02:09

Probably not. But if you're looking for a broader recovery in the freight market, you will not find it here. Today I saw down with Ken Adamo, Chief of Analytics at DAT as well as Prof. Jason Miller of Michigan State University's Eli Broad College of Business. Get ready, we get spicy! This program is brought to you by DAT Freight & Analytics. Since 1978, DAT has helped truckers & brokers discover more available loads. Whether you're heading home or looking for your next adventure...
In this episode, I sit down with Pamela Bracher, Deputy General Counsel for the American Trucking Associations. That's right, we're talking law! Pamela's career spans the transportation industry. Not only has she been a professor, but she practiced at Miller & Martin before helping build & lead best in class claims departments for some of the most sophisticated trucking companies in the country, US Xpress & Knight-Swift. We talk law school, legal practice, & the jo...
In this episode, I talk with freight tech legend, Bill Driegert. We talk about his journey in logistics as well as the recent acquisition of the Convoy Platform by DAT. From Coyote to Amazon, to Otto & Uber, Bill has been at the cutting edge of freight. Let's get into it! It's been a year! In less than 12 months, DAT has made some moves, most recently with the acquisition of the Convoy Platform from Flexport for $250 million on July 28, 2025, Outgo in May 2025, & Trucker Tools ...
Since taking office in January, President Trump has leaned heavily on tariffs to address trade deficits & drug trafficking, invoking IEEPA — a 1977 law granting presidents emergency economic powers — to bypass Congress. The Worldwide and Retaliatory Tariffs, rolled out via Executive Order 14257 in April, imposed a 10% duty on all imports, with higher rates (up to 50%) targeting 25 countries, including a tit-for-tat escalation with China peaking at 125% & continue to be a moving target...
In this episode, we welcome Gord Magill, the Canadian-born trucker, writer, & commentator with over 25 years of experience in the trucking industry across four countries, including Canada’s ice roads, Australia’s outback, & New Zealand’s logging routes. He has written extensively on trucking issues & Canadian politics for publications like Newsweek, The American Conservative, & American Affairs Journal, and runs the substack Autonomous Truck(er)s. Magill gained attention for...
In our next installment, we welcome Anne Reinke, the President & CEO of Intermodal Association of North America (IANA). For the past 20 years, Anne has helped navigate corporate, transportation policy & political experience throughout the supply chain. Not only did Anne serve as the President & CEO of the Transportation Intermediaries Association (TIA), but she's held senior roles at both USDOT AND CSX. From one lawyer to another, I am excited for this conversation. Let's go! Sp...
Supply Chain 101

Supply Chain 101

2025-07-0801:11:38

Good afternoon, class. My name is Professor Leffler, and this is my colleague, Professor Schreiber. Today we're going to be discussing how everything moves. Today, we study logistics. Welcome to Supply Chain 101. This program is brought to you by DAT Freight & Analytics. Since 1978, DAT has helped truckers & brokers discover more available loads. Whether you're heading home or looking for your next adventure, DAT is building the most trusted marketplace in freight. New users of DAT c...
We're All In!

We're All In!

2025-06-1301:13:30

It's episode 100 for the Armchair Attorney® Podcast so we're going big! In this installment we sit down with JJ Schickel, founding partner of EVE Partners. Together with his team, JJ has led more than 150 transactions exceeding $11 billion in value, solidifying his reputation as a leader in transportation-focused investments. At Omni Logistics, JJ led company growth from 200 employees to nearly 5,000, with a customer base expanding from 300 to over 7,000 across 25+ countries. This grow...
Law & Supply Chain

Law & Supply Chain

2025-05-2355:56

About two decades ago, I walked the same halls as my next guest, James Sidou, VP & General Counsel at Saddle Creek Logistics. See, Jim & I both attended Michigan State University College of Law. Go Green! In law school, it's about survival. The first year scares you to death, the second year works you to death, & the third year bores you to death. Or so I've heard. Fast forward to 2025 & I find myself next to Jim at the Motor Carrier Insurance Education Foundation (MC...
Freight 360

Freight 360

2025-05-0801:41:34

Oh this is a good one! I had the great privilege to sit down with the team at Freight 360. We dig deep on some of the biggest legal issues facing the supply chain. Broker Liability? We cover it! Nuclear Verdicts? We cover it! Broker Transparency? We cover it! English proficiency? We cover it! You will not want to miss this one, my friends! This program is brought to you by DAT Freight & Analytics. Since 1978, DAT has helped truckers & brokers discover more available loads. Wheth...
It's a simulcast! In our 97th episode, I join my good friend Brandon Wiseman as well as Rob Carpenter, Brian Runnels, & Jack Van Steenburg to discuss President Trump's Executive Order on English Proficiency for CDL holders. Get ready! This program is brought to you by DAT Freight & Analytics. Since 1978, DAT has helped truckers & brokers discover more available loads. Whether you're heading home or looking for your next adventure, DAT is building the most trusted marketplace in fr...
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