SUMMARY:

In this episode, host Will Jenkins sits down with Tyler Harper, Co-Founder and Chief Revenue Officer of Pinnacle Logistics Group, to break down a modern approach to LTL shipping, carrier relationships, and building a freight brokerage in a competitive market. Tyler shares how Pinnacle Logistics Group was built from the ground up, lessons from the first year in business, and why trust, consistency, and clear market positioning matter in freight entrepreneurship. The conversation covers LTL freight strategy, complex shipments, carrier sales, marketing fundamentals, and how Pinnacle delivers enterprise-level logistics solutions to mid-market shippers. This episode is packed with real-world insights for freight brokers, logistics professionals, sales leaders, and anyone interested in entrepreneurship within transportation and supply chain. 

TAKEAWAYS: 

• Tyler Harper brings a multi-disciplinary mindset to freight leadership 
• Trust with carriers is foundational to long-term brokerage success 
• Pinnacle Logistics Group specializes in complex freight, including furniture and LTL shipments 
• The first year of entrepreneurship brings both pressure and momentum 
• Pinnacle expanded from multi-stop consolidation into cross-border logistics 
• Strong market positioning helps mid-market shippers access enterprise-grade solutions 
• Consistency matters more than short-term wins in business growth 
• Team structure and shared ownership drive internal performance 
• Marketing works best when the ideal customer profile is clearly defined 
• A recent rebrand helped Pinnacle sharpen its message and presence 

CHAPTERS: 

00:00 – Introduction 

02:59 – Tyler Harper’s Background and Entry Into Freight 

06:01 – Building Pinnacle Logistics Group 

09:02 – First-Year Challenges and Early Wins 

12:06 – LTL and Complex Freight Services 

14:57 – Market Positioning and Differentiation 

18:12 – Managing Market Volatility 

21:06 – Advice for Freight Entrepreneurs 

24:03 – Team Structure and Leadership 

27:14 – Marketing Strategy in Logistics 

29:48 – What’s Next for Pinnacle Logistics Group 

WHERE TO LISTEN: 

🎥 Watch on YouTube 

🎧 Listen on Spotify 

🎙️ Listen on Apple Podcasts 

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EPISODE CREDITS:

Host, Will Jenkins

Creative Director, Erin Sweeney

Edited and mixed by Keenan McCarthy

Music licensed through Envato

LINKS:

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