The Journey Podcast

SUMMARY:  Kevin Miles, CEO of Eureeka BI, returns to The Journey Podcast to talk with Will Jenkins about the current freight market, where brokerages are feeling pressure, and how leaders should be thinking about growth right now. Kevin brings more than 20 years of supply chain experience, including time on the shipper side managing RFPs. In this conversation, he breaks down how policy changes, ri...

If you've ever wondered how technology is actually transforming freight beyond buzzwords and hype, this episode will show you what's possible. Kevin McMaster, SVP of Sales and Operations at Flock Freight, didn't just talk about innovation, he built it. Flock Freight's shared truckload model combines multiple LTL shipments into full truckloads using AI-powered optimization. The result? Lower costs...

If you've ever watched new sales reps struggle for months before landing their first customer, this episode will change how you think about training. Ali Fraley and Haley Williams from Axle Logistics didn't just adopt AI for training, they proved it works. Their January class of 17 reps completed over 1,400 AI practice calls before touching a real prospect. The results? Five weeks later: 27 new cu...

If you've ever wondered how someone goes from brokering freight to leading tech innovation at one of the industry's biggest platforms, this episode will change how you think about career growth in transportation. Todd Waldron didn't just work in logistics—he mastered every level of it. From the high-energy cubicles at CH Robinson, to opening JB Hunt's Minnesota brokerage branch, to transforming a...

If you've ever wondered how traditional industries can transform into AI-powered innovation engines, this episode will change how you think about entrepreneurship.  Hunter Bell didn't just grow up in the transportation and logistics world, he revolutionized it.  From watching his family run trucking operations to building MySavant. AI, an AI-powered nearshoring platform, Hunter's journey proves th...

SUMMARY: In this episode of the Journey Podcast, Will Jenkins and Justin Turner discuss the critical importance of customer and account segmentation in sales strategy. They explore how different customer segments behave based on size and technical requirements, emphasizing the need for a tailored approach to sales and marketing. The conversation delves into actionable insights for sales leaders, f...

SUMMARY: What does Black History Month mean inside corporate America? In this episode of The Journey Podcast, Will Jenkins and Justin Turner share personal stories about growing up in the South, navigating executive leadership roles, and building careers in the logistics industry as Black professionals. They discuss: • The importance of representation in corporate leadership • Why diversity in log...

SUMMARY: In this episode of the Journey podcast, Will Jenkins sits down with Justin Turner to unpack how modern revenue teams must operate in today’s market. They break down why precision now matters more than volume, how ideal customer profiles drive faster sales cycles, and why smaller teams are being held to higher revenue expectations than ever before. The conversation covers top-of-funnel str...

SUMMARY: In this episode, host Will Jenkins sits down with Tyler Harper, Co-Founder and Chief Revenue Officer of Pinnacle Logistics Group, to break down a modern approach to LTL shipping, carrier relationships, and building a freight brokerage in a competitive market. Tyler shares how Pinnacle Logistics Group was built from the ground up, lessons from the first year in business, and why trust, con...

SUMMARY:  In this episode of the Journey Podcast, Will Jenkins sits down with Robert Bain to talk through what actually drives success in Freight Tech sales. They break down why deep product knowledge matters, how to sell technology without overselling, and why live demos outperform polished recordings every time. The conversation covers diagnosing real customer pain points, understanding the full...

SUMMARY: In this episode of the Journey Podcast, host Will Jenkins sits down with Daniel Solida to break down value-based selling in the freight and logistics industry. Daniel shares his path from interning at Coyote Logistics to closing deals at MoLo and now working at Journey. The conversation focuses on how strong sales reps win by identifying a buyer’s core needs, listening closely, and aligni...

SUMMARY:  In this episode of The Journey Podcast, host Will Jenkins sits down with Matt Fain, CEO and founder of Pop Capacity, to talk warehousing, logistics technology, and where the supply chain is headed next. Matt shares how his background in electrical distribution led him into logistics and why he saw a clear gap in how companies source warehouse space. That insight became Pop Capacity, a pl...

SUMMARY: In this episode of The Journey Podcast, host Will Jenkins speaks with Cameron Robertson, CEO of 3PL Systems, about his journey from a tech support role to leading a freight technology company. Cameron shares insights into his early life, career decisions, and the importance of curiosity and mentorship in professional growth. He discusses the challenges of rebuilding BrokerWare, navigating...

SUMMARY: In this episode of The Journey Podcast, host Will Jenkins and guest Robert Bain discuss the significance of networking in the logistics industry. They explore how building relationships without expectations can lead to valuable connections and opportunities. Robert shares his experiences and strategies for effective networking, including the importance of listening to understand and lever...

SUMMARY:  In this episode of The Journey Podcast, hosts Will Jenkins and Erin Sweeney reflect on the two-year journey of their company, Journey. They discuss the evolution of their services from recruiting to consulting, the importance of building relationships with clients, and the impact they have made in the industry. They also share success stories, celebrate their team dynamics, and outline t...

SUMMARY: In this episode, host Will Jenkins sits down with Megan Masud and Sarah Hanna, Co-Founders of Competum Collective LLC, to share their entrepreneurial story and mission to improve the lives of drivers in the logistics industry. They break down how Competum Collective is tackling critical gaps with mental health support, compliance education, affordable healthcare options, and substance abu...

SUMMARY: In this episode of Choppin’ It Up, Will Jenkins sits down with CJ Johnson, founder of BWS Logistics, a 3PL known for handling the tough stuff, like fragile freight, complex consolidation, last-minute loads, with ease. CJ shares how growing up in Chicago and handing out pizza flyers laid the groundwork for his entrepreneurial grit. From switching majors in college to honing his sales game...

SUMMARY: In this episode of Choppin' It Up, Will Jenkins interviews Elizabeth Moscoso, President of Moscoso Express, a trucking company specializing in air freight. Elizabeth shares her journey from childhood involvement in the family business to leading the second generation of the company. The conversation explores the evolution of the trucking industry, the importance of technology, and the cha...

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 int...

SUMMARY: Rob Skelton, CEO of Third Coast Logistics, shares his journey from the military to the freight industry. He discusses the challenges he faced while starting his business, the importance of leadership and team building, and how he navigated financial management during tough market cycles. Rob emphasizes the significance of building strong relationships in the freight industry and offers va...

SUMMARY: In this special Women's History Month edition, the conversation revolves around the importance of mentorship, the challenges women face in a male-dominated industry, and the leadership lessons learned throughout their careers. Erin Sweeney, Maya Quijada and Nicki Bottan share personal stories with Will Jenkins of how mentorship has shaped their professional journeys, the significance of a...

SUMMARY: In this episode of Choppin' It Up, host Will Jenkins joins David Bell, CEO & Founder of CloneOps.ai, and Alfonso Quijano, CTO of Lean Solutions Group, to discuss their experiences in the logistics industry, focusing on the integration of AI and technology in business operations. They emphasize the importance of building relationships, understanding the logistics space, and the evolving na...

SUMMARY: In this special edition of Choppin' It Up for Black History Month 2025, host Will Jenkins is joined by Justin Turner and Calvin Blackmon to discuss their personal journeys, the importance of advocacy in professional spaces, and the ongoing challenges faced by professionals of color. They share insights on mentorship, the freight industry, and the impact of racism in today's society, empha...

SUMMARY: In this episode of Choppin' It Up , Marcus Cooksey, CEO and founder of DUKE.ai, shares his journey with Will Jenkins from a challenging upbringing to becoming a successful entrepreneur. He discusses his early education, cultural influences, and the pivotal moments that shaped his career. Marcus reflects on his experiences at Texas Instruments, his entrepreneurial ventures in the trucking...

SUMMARY: In this episode of Choppin' It Up, Will Jenkins interviews Shannon Breen, Co-CEO and Founder of FreightVana. They discuss Shannon's journey from growing up in Oregon to his career in finance and ultimately to the freight industry. Shannon shares insights on the importance of relationships in freight, lessons learned from his time in transportation, and the challenges faced during the merg...