Armchair Attorney® Podcast

Matthew Leffler
  • 5.0 (5)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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. 

  1. 4D AGO

    To Own or Not to Own?

    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 leasing industry. With over 100,000 pieces of power & 85,000 trailers, Dean & the team at NationaLease know a thing or two about helping incredible brands safely deliver freight on time & undamaged.  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 technology, DAT One gives you control over every aspect of moving freight, so that you can run your business with speed & efficiency. This program is also brought to you by our newest sponsor, GenLogs. GenLogs is setting a new standard of care for freight intelligence. Book your demo for GenLogs today at www.genlogs.io today!

    52 min

  2. FEB 3

    GenLogs raises $60M Series B

    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 raise aims to expand GenLogs’ AI-powered Truck Intelligence™ platform, which leverages a nationwide network of roadside sensors, satellites, and diverse data streams to provide unprecedented visibility into U.S. trucking operations. We talk  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 technology, DAT One gives you control over every aspect of moving freight, so that you can run your business with speed & efficiency. This program is also brought to you by our newest sponsor, GenLogs. GenLogs is setting a new standard of care for freight intelligence. Book your demo for GenLogs today at www.genlogs.io today!

    30 min

  3. JAN 28

    Broker Liability: A Who’s Who of Business Organizations

    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.  Now, the Supreme Court will decide. In this episode, we dig into the latest amicus brief.  A Who’s Who of Business Organizations  Nearly as important as the arguments advanced in this amicus brief are the entities that are advancing them.  U.S. Chamber of Commerce Business RoundtableNational Association of Wholesaler-Distributors (NAW) National Federation of Independent Business (NFIB) National Retail Federation (NRF) 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 technology, DAT One gives you control over every aspect of moving freight, so that you can run your business with speed & efficiency. This program is also brought to you by our newest sponsor, GenLogs. GenLogs is setting a new standard of care for freight intelligence. Book your demo for GenLogs today at www.genlogs.io today!

    34 min

  4. JAN 28

    Trucking Digs Out of Winter Storm Fern

    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 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 technology, DAT One gives you control over every aspect of moving freight, so that you can run your business with speed & efficiency. This program is also brought to you by our newest sponsor, GenLogs. GenLogs is setting a new standard of care for freight intelligence. Book your demo for GenLogs today at www.genlogs.io today!

    58 min

  5. 12/18/2025

    The Trailer Podcast

    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 industry, focusing on innovation, & customer solutions. Get ready, theses trailing winds will lift all ships! 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 technology, DAT One gives you control over every aspect of moving freight, so that you can run your business with speed & efficiency. This program is also brought to you by our newest sponsor, GenLogs. GenLogs is setting a new standard of care for freight intelligence. Book your demo for GenLogs today at www.genlogs.io today!

    47 min

  6. 12/16/2025

    Freight Expectations

    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 technology, DAT One gives you control over every aspect of moving freight, so that you can run your business with speed & efficiency. This program is also brought to you by our newest sponsor, GenLogs. GenLogs is setting a new standard of care for freight intelligence. Book your demo for GenLogs today at www.genlogs.io today!

    1h 9m

  7. 12/04/2025

    It's a Family Business.

    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 business of safely delivering freight on time & undamaged is difficult even under the best circumstances, Syfan sets itself apart. We all fall, it's how you get back up that matters most. In this episode we talk about faith, family, & building a world-class team within the most dynamic industry on the planet: logistics.  Let's go! 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 technology, DAT One gives you control over every aspect of moving freight, so that you can run your business with speed & efficiency. This program is also brought to you by our newest sponsor, GenLogs. GenLogs is setting a new standard of care for freight intelligence. Book your demo for GenLogs today at www.genlogs.io today!

    41 min

  8. 11/18/2025

    The Great Freight Debate

    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 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 technology, DAT One gives you control over every aspect of moving freight, so that you can run your business with speed & efficiency. This program is also brought to you by our newest sponsor, GenLogs. GenLogs is setting a new standard of care for freight intelligence. Book your demo for GenLogs today at www.genlogs.io today!

    57 min
See All (123)

5
out of 5
5 Ratings

About

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. 

Information

  • Creator
    Matthew Leffler
  • Years Active
    2022 - 2026
  • Episodes
    123
  • Rating
    Clean
  • Copyright
    © 2026 Armchair Attorney® Podcast
  • Show Website
    Armchair Attorney® Podcast

You Might Also Like