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Journey Podcast

100 Episodes of Freight Sales and Leadership Lessons From The Journey Podcast

Will Jenkins, founder and CEO of Journey, behind a chessboard.

Episode 100: Celebrating 100 Episodes of The Journey Podcast

Released on
August 13, 2026

The Journey Podcast has reached 100 episodes. To mark it, Will Jenkins pulled together favorite moments from past guests, the people who have shaped how freight leaders think about sales, operations, and growth.

Kevin Miles talks about using bid data to price freight. Abby Hafenbredl shares how to prepare for a conference so the trip pays off. Kary Jablonski covers listening, trust, and leadership, and Ben Bar-Lev explains why fresh leads matter. Chadd Olesen makes the case for strategy and team adoption before automation.

Will Hopkins of Blackbox Logistics shares creative ways to reach shippers. Kevin McMaster talks about confidence and playing the long game. Madison Santo explains why reps should get to the financial impact in the first few seconds of a cold call.

The episode closes with a look at the next 100. If one of these lessons hits home, the full episodes are on the podcast page. Reps can practice cold calls and pricing talks in the AI Sales Coach, and leaders working on strategy and adoption can talk to Journey about freight brokerage consulting.

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