In this episode of OnAir with Airfreight.com, host Kevin Carpenter sits down with John Elliott, founder and executive chairman of Load One, to talk about building one of the country’s leading expedited freight carriers and what it takes to stay competitive in a fast-changing industry.

John walks through his unusual path into trucking, starting with a family legacy in transportation, a college degree in aviation management, and an early career that eventually brought him back to freight. He shares how Load One began as a regional truckload carrier before a series of decisions — including one persistent employee bringing him an expedite opportunity — pushed the company into the expedited freight space.

The conversation covers:

• John’s family history in trucking and how it shaped his career
• Why Load One initially focused on regional freight and low-hanging opportunities
• How a hands-on leadership style helped the company grow
• The role of technology in improving driver experience, operations, and customer service
• Why Load One built its own software instead of relying on standard industry platforms
• How AI and automation are changing trucking operations
• A hard-earned lesson about cargo insurance and subrogation
• John’s perspective on the current state of trucking, freight cycles, and carrier failures
• What it looks like to transition leadership while still staying involved

John also reflects on what matters most after decades in the industry: building the right team, giving back, and helping shape trucking for the long term.

Key takeaways

• Staying close to drivers and staff builds trust and culture.
• Technology can be a major differentiator when service levels are similar.
• Trucking remains cyclical, and strong operators win by managing costs and cash flow.
• Leadership transitions work best when they are intentional and gradual.
• Long-term industry impact includes service, advocacy, and giving back.

Notable moments

• The story of how Load One entered expedited freight
• Why John believes owning software and data creates a strategic advantage
• The insurance lesson that became an expensive but important wake-up call
• John’s view that trucking affects the whole economy

About the guest

John Elliott is the founder and executive chairman of Load One, a major expedited freight carrier based in Taylor, Michigan. He is also a former vice president of the American Trucking Associations and former chairman of the Truckload Carriers Association.

In this episode, Kevin Carpenter hosts Daniel Perry, a private equity expert from Court Square Capital Partners, to explore how investors evaluate transportation companies for scalability and growth. We delve into what makes a transportation business attractive to private equity, the role of sales and marketing, and how AI is transforming sales processes in logistics.

Main Insights:

• Private equity firms like Court Square raise billions to acquire and improve companies, aiming for a 2.4x return over 4–6 years
• Evans Network exemplifies a value-driven, service-based transportation company focusing on owner-operators and small markets
• Key factors for investment include company culture, business model, customer concentration, and contractual relationships
• Evans employs dual sales forces: one for agent partnerships, another for direct customers, utilizing AI to enhance targeting and lead qualification
• The company’s core expertise is in drayage, providing backend support for port-to-warehouse freight, mainly short hauls
• AI tools assist in sales efficiency, lead qualification, and proactive account management, including early warning indicators for agent attrition
• Private equity evaluates potential acquisitions systematically, emphasizing scalability, contract stability, and service-based assets

Timestamps:

00:00 - Introduction to private equity's role in transportation 00:19 - What private equity firms like Court Square do 01:20 - How investments generate returns 02:42 - Notable investors and global reach 03:14 - Private equity exit strategies and company improvements 04:11 - What makes Evans’ model attractive for investment 05:01 - Evans’ focus on small markets and owner-operators 05:27 - Providing backend support as a service business 06:07 - Sales strategies for Evans, including agent and direct sales 07:43 - Explaining Evans' official classification as a 3PL 08:03 - Drayage operations and local freight hauling 09:15 - The agent network and customer base 10:25 - Use of AI in sales prospecting and lead qualification 11:37 - Efficiency improvements with AI and human collaboration 12:10 - Setting sales targets and organization structure 13:14 - Sales process automation and account management 14:02 - Early warning systems for agent retention 15:11 - How AI enhances sales and operations 16:30 - The importance of human touch in customer service 17:08 - Handling non-emergency freight customers 18:36 - Analyzing sales calls with AI for performance insights 19:14 - Key metrics distinguishing top salespeople 20:34 - Providing industry insights to customers as a sales advantage 21:34 - The value of operational expertise in customer interactions 22:26 - Active market assessment and quality criteria for acquisitions 23:50 - Customer concentration and contractual relationships 24:36 - Assets versus services in transportation acquisitions 25:00 - Closing remarks and promotion for airfreight.com