The Strongest Man in Logistics with Robert Bain | Ep 49

In this episode of Miles and Mentors, Robert Bain shares the lived experience behind his title as the strongest man in logistics. With two decades of freight industry depth, Bain opens up about how a mix of accidental entry, personal drive, and relentless accountability shaped his career from early brokerage roles to executive leadership and consulting. He reflects on how a sharp eye for detail and a now-infamous $175,000 insurance oversight story kicked off his logistics career in dramatic fashion, proving early on that speaking up and being right can open doors in unexpected ways.

Throughout the episode, Bain weaves together themes of discipline, ownership, and growth, both in business and personal life. He breaks down the origin of his brand and nickname, explaining how a serious injury in 2020 during the pandemic led to a moment of personal reckoning. That setback, paired with a friend’s passing comment, inspired Bain to fully embrace the strongest man in logistics identity and to use it as a platform for leadership and motivation in the freight world.

He walks listeners through his leadership philosophy, emphasizing the importance of leading with empathy, taking full ownership of outcomes, and building systems that support operational resilience. His approach draws heavily from hard-earned experience and thought leadership such as the principles in Jocko Willink’s “Extreme Ownership” and business strategy models drawn from Amazon’s customer-first and cash-flow-focused mentality. Bain underscores that in trucking, being a great driver does not automatically translate into being a great business owner, and he stresses the importance of mentorship, system design, and selecting the right technology stack early to avoid costly mistakes later.

Robert also speaks candidly about personal development, sharing how his pursuit of powerlifting paralleled his business journey. He illustrates how the discipline of training, the audacity to pursue 1000-pound squats, and the mindset of constant process improvement have helped him succeed not only on the platform but in boardrooms. For those trying to scale a small fleet, navigate leadership challenges, or grow into a next-level operator, Bain offers actionable insight and motivation rooted in personal experience.

The episode concludes with a reflection on identity, authenticity, and letting go of others’ expectations. Bain speaks openly about the transformation he went through to become the same person in every room, regardless of whether that room was a gym, a board meeting, or his home. He encourages listeners to embrace their own strength, to accept being misunderstood by some, and to build their businesses and lives with clarity and conviction.