The freight market has trained most brokerages to chase volume, compete on price, and treat service lines like shiny add-ons. Evans Transportation took the opposite approach: build a durable business by leaning into complexity, building culture as a competitive advantage, and diversifying with discipline.

In this episode, Ryan Keepman shares how Evans — one of the rare family-owned brokerages still standing from the deregulation era — evolved from a Wisconsin brokerage built on relationships into a multi-division logistics operator supporting everything from envelopes to excavators. We unpack the real mechanics behind service-line expansion, why the “jack of all trades” strategy kills trust, and how Evans uses intentional culture and in-person connection to keep remote teams aligned as the company scales.

What you’ll learn

• How Evans Transportation survived deregulation and stayed family-owned: Why relationship-driven brokerage and early operational investments helped Evans outlast consolidation.
• The real reason Evans diversified into multiple divisions: Diversification wasn’t a growth gimmick—it was a strategic defense after losing top clients and recognizing weaknesses in truckload execution.
• Truckload procurement vs. traditional brokerage: How Evans built a carrier procurement engine designed to protect managed transportation performance rather than operate as a pure sales brokerage.
• The modern 3PL approach and blind bidding: How Evans structures managed transportation so shippers can keep multiple brokers in the mix while Evans competes fairly without undercutting.
• How managed transportation adoption has changed: Why most shippers are already using 3PLs, how the sales cycle has shifted to CFOs and VPs, and why strategic sponsorship matters.
• Why Evans avoids price wars and “broker poker freight”: Their focus on value, complexity, and long-term trust instead of transactional spot quoting.
• How to build trust by saying no: Why Evans intentionally accepted only 3 of 13 specialized moves to avoid failure and earn long-term credibility.
• The blueprint for launching new service lines: Why face-to-face time, slowing down, and releveling teams matters more than speed when integrating new divisions.
• Evans’ culture operating system: Quarterly in-person rhythms, shared experiences, and a “do life together” philosophy that fuels cohesion across remote leadership.
• AI as a relationship accelerator: How automation reduces noise so brokers can invest in carriers, deepen relationships, and drive better outcomes.

Time-stamped highlights

• (00:00) Introduction to Ryan Keepman and Evans Transportation
• (01:14) The Early Years and Founding Story
• (03:48) Starting Evans with High Risk and Early Challenges
• (07:32) Evolution from Brokerage to Managed Transportation
• (08:16) Early TMS Development and Technology Advantage
• (09:19) Leadership Transition to Ryan
• (10:02) Diversification Strategy and the Truckload Division
• (11:07) Expansion into Mexico, Specialized, Parcel, and Government
• (13:09) Managed Transportation and Truckload Procurement
• (16:28) Modern 3PL Model and Blind Bidding
• (19:55) Shipper Trends and Managed Transportation Adoption
• (24:35) Building a Moat with Parcel and Full-Suite Solutions
• (25:46) New Warehouse Product and Strategic Fit
• (28:28) Avoiding Price Wars and Competing on Complexity
• (32:00) Building Trust Through Gradual Growth and Saying No
• (35:08) Lessons Learned in Launching New Service Lines
• (40:08) Evans Culture and the “Do Life Together” Approach
• (44:16) Leading Distributed Teams with Quarterly In-Person Rhythms
• (48:10) Leadership Growth, Directness, and Personal Reflection

Guest

Ryan Keepman — CEO, Evans Transportation
Ryan Keepman has spent 19+ years at Evans Transportation Services, building his career across key accounts, sales leadership, and executive leadership roles. He became CEO in December 2020 after serving as President (2018–2020) and previously leading growth as Vice President of Logistics Sales (2014–2020) and Vice President of Key Accounts (2007–2020). Under his leadership, Evans has evolved into a diversified logistics partner spanning managed transportation, truckload procurement, Mexico, specialized solutions, parcel, government services, and new warehousing offerings—while maintaining a people-first culture built on trust, accountability, and shared experience.
LinkedIn: https://www.linkedin.com/in/ryan-keepman-75246610/

Links & references

• Evans Transportation: Family-owned logistics provider offering managed transportation and multimodal solutions — https://www.evanstrans.com/
• Strength to Strength (Arthur C. Brooks): A framework for reinvention and sustaining fulfillment through midlife transitions
• Transportation Deregulation (Motor Carrier Act of 1980): The policy shift that reshaped the freight brokerage industry

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