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Armchair Attorney® Podcast
Matthew Leffler
112 episodes
6 days ago
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...
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All content for Armchair Attorney® Podcast is the property of Matthew Leffler and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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...
Show more...
Entrepreneurship
Business
Episodes (20/112)
Armchair Attorney® Podcast
Blue Skies & An Open Highway
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...
Show more...
1 month ago
56 minutes

Armchair Attorney® Podcast
A Deep Dive with the Virginia Maritime Association
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...
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1 month ago
51 minutes

Armchair Attorney® Podcast
Seven Mondays a Week
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 ...
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2 months ago
55 minutes

Armchair Attorney® Podcast
(Another) Precision Scheduled Podcast
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...
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2 months ago
45 minutes

Armchair Attorney® Podcast
The Connected Everything
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...
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2 months ago
57 minutes

Armchair Attorney® Podcast
Should I Panic Yet?
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...
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2 months ago
1 hour 2 minutes

Armchair Attorney® Podcast
The Law of Logistics - Office Hours
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...
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2 months ago
1 hour 5 minutes

Armchair Attorney® Podcast
DAT Acquires Convoy, A FreightTech Level Up
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 ...
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2 months ago
55 minutes

Armchair Attorney® Podcast
The Most Important Lawsuit in America
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...
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3 months ago
19 minutes

Armchair Attorney® Podcast
Untying Trucking's Gordian Knot.
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...
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3 months ago
1 hour 21 minutes

Armchair Attorney® Podcast
Precision Scheduled Podcast
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...
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3 months ago
56 minutes

Armchair Attorney® Podcast
Supply Chain 101
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...
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3 months ago
1 hour 11 minutes

Armchair Attorney® Podcast
We're All In!
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...
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4 months ago
1 hour 13 minutes

Armchair Attorney® Podcast
Law & Supply Chain
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...
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5 months ago
55 minutes

Armchair Attorney® Podcast
Freight 360
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...
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5 months ago
1 hour 41 minutes

Armchair Attorney® Podcast
Trucksafe LIVE - Episode 48 - English Proficiency
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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6 months ago
1 hour

Armchair Attorney® Podcast
Freight Intelligence
I am excited to welcome Ryan Joyce, CEO & Co-Founder of GenLogs to dig deep in freight intelligence as well as his time with the CIA. In this conversation, we talk about our families as well as the events that led to Ryan serving his country. Finally we look at the technology that is powering GenLogs battle against fraud & theft in the trucking industry. This is a conversation that you will enjoy! To see more of GenLogs, check this out. This program is brought to you by DAT Frei...
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6 months ago
53 minutes

Armchair Attorney® Podcast
Pink Cheetah v. TQL
We are so back! Total Quality Logistics (TQL), the nation’s second-largest freight broker, is under fire in a new federal lawsuit filed on Feb. 25 in the U.S. District Court for the District of Columbia. Pink Cheetah Express LLC, a small Kissimmee, Florida-based motor carrier, alleges that TQL has flouted a 2023 Department of Transportation order mandating compliance with federal broker transparency rules. The suit, which seeks declaratory and injunctive relief, reignites a long-simmering deb...
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6 months ago
46 minutes

Armchair Attorney® Podcast
International Emergency Economic Powers Act of 1977 (IEEPA)
If you're following the tariff discussion, you better understand IEEPA. This post aims to make sense of IEEPA, which is a US federal law enacted in October of 1977, & signed by President Jimmy Carter in December of 1977. It grants the President broad authority to regulate international commerce & economic transactions during a declared national emergency. Let me be clear, this is not intended as a pro or anti Trump post. This is simply how I answer a question I have been getting a lo...
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6 months ago
27 minutes

Armchair Attorney® Podcast
Promises Made, Promises Kept
MyCarrier began a fight with project44 that they could never win. In a closely watched dispute over API services in the logistics industry, the Delaware Court of Chancery has found that MyCarrier likely did breach its contract with project44 both by "building behind" project44 as well as transitioning to an alternative provider, SMC3. Despite the likely breach, the Court determined that project44 failed to show irreparable harm, a key requirement for injunctive relief & denied project...
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8 months ago
21 minutes

Armchair Attorney® Podcast
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...