Kevin McMaster, The Long Game In Freight

SUMMARY: In this episode of Choppin' It Up, host Will Jenkins sits down with Kevin McMaster, SVP of Sales and Operations at Flock Freight. Kevin shares his story of immigrating to the U.S. and building a standout career in freight, from his early days at Coyote to leading teams at Flock. He opens up about the challenges he faced, the mentors who shaped him, and the mindset that helped him grow into a top performer. Will and Kevin dig into the competitive nature of sales in logistics, the shift from individual contributor to leader, and what it takes to build and scale a freight organization. They also talk about the power of relationships, leadership lessons learned the hard way, and the books that helped shape their perspectives. TAKEAWAYS: Kevin immigrated to the U.S. at 13, an experience that helped build his resilience and independence. He started his career in transportation in 2007 and quickly learned the value of hard work. The competitive, high-performance culture at Coyote played a major role in shaping his career. Mentorship was a key factor in Kevin’s growth—from carrier sales to leadership roles. His time in Europe gave him an early sense of independence and problem-solving. Struggles in school taught him grit and how to push through challenges. Prioritizing customer service became a cornerstone of his sales approach. Kevin’s competitive mindset was clear: “I wanted to emulate number one—and beat number one.” He believes you need to do the job you want before you get the job you want. Building strong, authentic relationships is essential in leadership. Success comes from organizing and executing around what the business truly needs. Some challenges—like the infamous "$10 books"—still persist in the freight world. "If you go and book the volume, the money will come." He was scared to leave Real Time Freight for Coyote, but believed in himself and took the leap. Mistakes are part of the process: “It’s okay to not get it right.” Flock’s success isn’t about one person—it’s about the team and the mission. Belief in himself was a driving force throughout his career. CHAPTERS: 00:00 Introduction to Kevin McMaster 02:53 Kevin's Early Life and Immigration Story 11:26 Educational Journey and Career Beginnings 14:09 Joining Coyote: The Early Days 18:59 Roles and Responsibilities at Coyote 25:25 Transitioning to Leadership and Career Growth 25:53 The Competitive Spirit: Emulating Success 26:43 Leadership Lessons from Coyote 32:57 Transitioning to Flock Freight 41:14 Building a New Organization: The Flock Experience 51:27 Key Takeaways and Influential Books Start your Journey at www.journeydelivers.com EPISODE CREDITS: Host, Will Jenkins Creative Director, Erin Sweeney Edited and mixed by Keenan McCarthy Music licensed through Envato LINKS: Be sure to follow and tag @JourneyDelivers on LinkedIn Instagram Twitter Facebook TikTok YouTube ABOUT THE JOURNEY PODCAST: Welcome to The Journey Podcast, where we talk freight, sales, tech, the market and everything in between. Hosted by Will Jenkins, CEO and Founder of Journey, this show pulls from years of building & scaling freight brokerages along with the work our team does with hundreds of clients. We break down how brokers grow, how teams sell, how leaders hire, and what it takes to perform at a high-level in this industry.