In this episode, Dave sits down with Will Jenkins, CEO and founder of Journey, to explore real-world strategies that can help entrepreneurs, small business owners, and startup founders thrive in the freight and logistics industry. Will Jenkins shares his journey scaling a company to a billion dollars in revenue and explains how Journey has built a successful reputation by focusing on niche markets and serving over 160 clients, including 11 of the top 100 industry leaders. You’ll hear firsthand insights on what’s actually working for ambitious founders in 2026, including narrowing in on your ideal customer profile (ICP), the power of bespoke sales strategies, and how technology—especially AI and efficient tech stacks—can make or break small to mid-sized businesses. Will Jenkins opens up about the reality of competition, the essentials of staying focused amid noisy trends, and the simple but critical skill of building genuine relationships with clients and industry peers. Whether you’re in transportation, launching a startup, or looking to make smarter business decisions, this episode delivers honest advice, growth stories, and actionable takeaways you can use to build a resilient, customer-focused business. Connect with Will on LinkedIn: linkedin.com/in/willjenkinswcj/ #freighttech #logistics #entrepreneurship #podcastinsights

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