HeyJaredThe Journey Podcast
Welcome to The Journey Podcast, where we talk freight, sales, tech, the market and everything in between.
- Indexed episodes, last 90 days
- 10
- Latest publication
- Sep 24, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 9, 2026
Latest episodes
Mike Riccio, Work the Plan: What Brokerage Owners Miss as They Scale (opens the original)
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Mike Riccio, Founder of More Than Miles Consulting and Co-Founder of Open Road Ventures, joins Will Jenkins to talk about scaling a freight brokerage, building a business plan your team can follow, and preparing for growth or an eventual exit. Mike brings nearly four decades in transportation, including helping build Leonard’s Express and later working directly with brokerage owners through More Than Miles Consulting. He explains why owners sometimes need to slow down before moving faster, defin
Charles Gracey, Pricing, Value and Bringing Solutions (opens the original)
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Charles Gracey, Radio Host of Trucking Sense on SiriusXM, joins Will Jenkins to talk about the freight market, trucking rates, driver recruiting and the standards shaping transportation today. Charles shares what he’s hearing from drivers, executives and regulators, why higher trucking rates do not necessarily mean freight volume has returned, and where he thinks the industry has become too comfortable with lower expectations. They also get into building and selling a recruiting company, pricing
Kyle Engdahl, The Grane Way (opens the original)
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Kyle Engdahl, Vice President at The Grane Companies, joins The Journey Podcast to talk about how a 100-year-old transportation company changed the way it presented its business to the market with the help of Journey's Marketing Consulting & Creative Services. Grane already had the infrastructure, experience, and service offering. The challenge was making it easier for customers to see the full picture. Kyle shares how working with Will & Erin to create new website, sales materials, photography,
Kelly Usher, Why Agency Recruiting Is Sales Through and Through (opens the original)
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Kelly Usher didn’t start out planning to work in recruiting. Her path took her from dance and entrepreneurship into logistics, internal talent acquisition and, eventually, third-party recruiting with the Journey Recruiting team. In this episode, Kelly talks about what changes when you move from recruiting inside one company to representing multiple clients and candidates. She shares why agency recruiting is sales through and through, how she earns trust with different decision-makers, and why so
Celebrating 100 Episodes of The Journey Podcast (opens the original)
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100 episodes. A lot of freight conversations. Even more lessons along the way. For our 100th episode, Will Jenkins goes back through some of his favorite conversations from The Journey Podcast, from the early days of Choppin’ It Up and Sales Bites to the show it is today. Featuring Kevin Miles, Abby Hafenbredl, Kary Jablonski, Ben Bar-Lev, Chadd Olesen, Will Hopkins, Kevin McMaster, and Madison Santo, this episode brings back lessons on freight pricing, sales, leadership, prospecting, automation
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