• Inland Distribution
  • September 29 - October 1, 2025 | The Westin Chicago River North

Matthew M. Leffler

Armchair Attorney LLC

Managing Member

Matthew Leffler is the Managing Member of Armchair Attorney, LLC, and a 3rd generation supply chain executive with over fifteen years of experience in safety, compliance, & labor. Matthew provides legal commentary on various supply chain issues & operates a popular industry podcast, Leffler’s Show. In addition, Matthew has served as a senior leader with some of the nation’s most admired maintenance, repair, & leasing companies. Matthew entered the industry as an attorney defending trucking companies in civil litigation in 2010, but cut his teeth helping build & later selling his family’s maintenance firm, Outsource Fleet Services, Inc.

Matthew earned his J.D. from Michigan State University College of Law, Magna Cum Laude, and his B.A. from the University of Illinois Urbana-Champaign. He is licensed to practice law in the State of Illinois; U.S. District Court, Northern District of Illinois; & 7th Circuit Court of Appeals. Matthew is the proud father of Michael, Rowan, Elise, & Elijah & has been happily married to his wife, Holly, since 2008.

Sessions With Matthew M. Leffler

Monday, 30 September

  • 10:05am - 10:50am (CST) / 30/sep/2024 03:05 pm - 30/sep/2024 03:50 pm

    Inland Academy: The Armchair Attorney's Guide to Non-Competes

    More than 30 million workers — at least 18% of the US workforce — are required to sign non-competes as a condition of employment. And yet less than 10% of workers negotiate these clauses. These include a wide range of workers, from supply chain executives to sandwich makers to manufacturers. This session will discuss:

    • What is a post-employment restrictive covenant?

    • The prevalence of non-competes in the United States.

    • Factors that influence the enforceability of a non-compete.

    • How non-competes are enforced and how courts exercise discretion to partially enforce or even rewrite overly broad non-competes.

    • The disproportionate impact of non-competes on women and people of color.

    • The push for regulation on non-competes.