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Armchair Attorney® Podcast
Armchair Attorney® Podcast
Author: Matthew Leffler
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© 2026 Armchair Attorney® Podcast
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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.
123 Episodes
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To Own or Not to Own? That is the question. And who better to help answer that question than Dean Vicha, President of NationaLease. Who is NationaLease? How about one of the largest full-service commercial truck & trailer leasing organizations in North America? Founded in 1944, it is a member-owned network of over 100 independent businesses operating more than 1,000 service locations across the United States and Canada. As Dean would say, think the Ace Hardware of heavy duty le...
In this lightning installment, we are joined by Ryan Joyce, CEO & Co-Founder of GenLogs. On February 2, 2026, GenLogs announced that it has closed a $60 million Series B funding round. The investment, led by Battery Ventures and including participation from IVP, Cathay Innovation, 9Yards, and existing backers like Venrock, Steel Atlas, HOF Capital, TitletownTech, and Autotech Ventures, brings the company’s total funding to $81 million since its founding in 2023. This latest capital ...
In a big Supreme Court showdown over trucking accidents, major business groups have filed a friend-of-the-court brief supporting freight brokers. The case, Shawn Montgomery v. Caribe Transport II, LLC, et al., stems from a 2018 crash where a trucker hired through broker C.H. Robinson hit Montgomery’s car, causing injuries. Montgomery sued the broker for negligent hiring, claiming CH picked an unsafe carrier. The Seventh Circuit Court said federal law blocks such state lawsuits against brokers...
Experts have warned that Winter Storm Fern, which battered multiple U.S. states over the weekend, could result in a financial fallout exceeding $100 billion. How are the freight markets responding? We go to Ken Adamo of DAT Freight & Analytics to dig in. Or is it dig out? While some schools face cancellation, this fully remote class certainly won't be. This program is brought to you by DAT Freight & Analytics. Since 1978, DAT has helped truckers & brokers discover more avai...
Oh, it's time! It's time! It's Trailer Time! In this installment, I welcome Brent Yeagy, President & CEO of Wabash, the publicly-traded manufacturing company that designs & produces dry freight & refrigerated trailers, truck bodies, & tank trailers. Wabash also provides parts, services, & solutions like "Trailers as a Service" (TaaS). Founded in 1985 & headquartered in Lafayette, Indiana, Wabash National is THE major player in the transportation & logistics ...
That's right, Craig Fuller, Freight Alley himself, joins the podcast where we talk all things supply chain! 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 freight. New users of DAT can save 10% off for the first 12 months by following the link below. Built on the latest tech...
Oh this one was a long time coming! I first met Steve Syfan at DAT's Executive Symposium in the spring of 2025. As one of the founders of Syfan Logistics, a leading 3PL based in Gainesville, GA, Steve lives a life rooted in his Christian faith. As a family business owner, Steve works alongside his father & brother as well as a team of incredible men & women that share a vision of integrity & a commitment to delivering excellence 24 hours a day, 7 days a week. While the busin...
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...
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...
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...
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...



