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PODCAST

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.

business careers

All Episodes

00:15:35

Robert Bain, Freight Tech

The Journey Podcast ·

2026/01/29

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 business lifecycle of a freight brokerage, and knowing when to walk away from the wrong deal. If you

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00:15:00

Daniel Solida, Value Based Selling

The Journey Podcast ·

2026/01/22

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 aligning their approach to outcomes that actually matter to the customer. This episode gets practical fast,

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00:38:38

Matt Fain, Building PopCapacity: The Warehouse Search...

The Journey Podcast ·

2026/01/15

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 platform built to simplify warehouse procurement through technology. The conversation covers real startup

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00:46:00

Cameron Robertson, From Tech Support to CEO

The Journey Podcast ·

2026/01/08

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 the COVID-19 pandemic as a new CEO, and the current trends in freight technology, particularly the role

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00:15:58

Robert Bain, Networking

The Journey Podcast ·

2025/12/18

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 leveraging social media to enhance visibility. The conversation highlights memorable moments from networking

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00:30:59

Special Edition, Two Years In

The Journey Podcast ·

2025/12/04

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 their vision for future growth and partnerships. TAKEAWAYS:The journey of starting a business often

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00:39:16

Megan Masud & Sarah Hanna, Mental Health and Compliance

The Journey Podcast ·

2025/12/04

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 abuse resources. From navigating the healthcare side of trucking to creating safe, judgment-free spaces for

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00:42:58

CJ Johnson, No Shortcuts in This Game

The Journey Podcast ·

2025/12/04

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 at Sears, every step helped prepare him to launch BWS after a failed partnership deal.They dig into how

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00:30:09

Elizabeth Moscoso, A Second-Gen Freight Story

The Journey Podcast ·

2025/12/04

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 challenges of leadership. Elizabeth emphasizes the significance of team retention, problem-solving, and

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00:54:20

Kevin McMaster, The Long Game In Freight

The Journey Podcast ·

2025/12/04

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

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00:31:07

Rob Skelton, Drop the Ego Pick Up the Freight

The Journey Podcast ·

2025/12/04

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 valuable advice for new brokerages. He also shares insights on personal development and the impact of

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00:38:42

Women's History Month #NoGatekeeping

The Journey Podcast ·

2025/12/04

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 advocating for one another, and the trends they hope to see in the freight industry. They celebrate the

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00:30:52

David Bell & Alfonso Quijano, CloneOps at Manifest 2025

The Journey Podcast ·

2025/12/04

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 nature of sales strategies. The conversation highlights the need for businesses to adapt to technological

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00:48:22

The Men of Journey, Black History Month Edition

The Journey Podcast ·

2025/12/04

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, emphasizing the need for community support and understanding. In this conversation, the speakers discuss the

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00:53:13

Marcus Cooksey, DUKE.ai - Automated Freight Invoicing

The Journey Podcast ·

2025/12/03

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 industry, and the development of DUKE.ai, which aims to revolutionize document processing through AI

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00:50:06

Shannon Breen, From Finance to Freight: Building...

The Journey Podcast ·

2025/12/03

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 mergers. He also talks about the founding of FreightVana and the vision behind creating a differentiated

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00:40:59

Special Edition: Journey Turns 1

The Journey Podcast ·

2025/12/03

SUMMARY:Will Jenkins and Erin Sweeney reflect on the first year of Journey, discussing their personal and professional journeys that led to the founding of the company. They explore the importance of mentorship, the evolution of their brand, the significance of training, and the key hires that have shaped their team. The conversation highlights their commitment to authenticity, diversity, and delivering high-quality services to their clients, while also expressing gratitude for the support they've

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00:44:17

Journey & Shipper CRM, Elevating Freight Sales with Tech

The Journey Podcast ·

2025/12/03

SUMMARY: In this special edition of Choppin' It Up, Will Jenkins interviews Krystian Gebis, CEO & Co-Founder of Shipper CRM and Co-Founder of FreightCaviar. They discuss Krystian's Journey from computer engineering to building self-driving trucks and eventually creating Shipper CRM. The conversation covers the evolution of Shipper CRM, its current state, and future aspirations, including the importance of customer feedback and the new investment from Will, and partnership with Journey's sales

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00:41:42

Chadd Olesen, The Power of Automation: AVRL’s Impact...

The Journey Podcast ·

2025/12/03

SUMMARY: In this episode of Choppin' It Up, Will Jenkins interviews Chadd Olesen, CEO of AVRL, discussing his journey from a small-town upbringing to launching a successful voice technology company. Chadd shares insights on work ethic, the evolution of AVRL, and the importance of customer relationships and implementation in the tech industry. He emphasizes the need for innovation and collaboration in transportation technology, highlighting the challenges and successes faced along the

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00:54:24

Michael Horvath, Building Revenova: A Cloud-Based TMS

The Journey Podcast ·

2025/12/03

SUMMARY:In this episode of Choppin' It Up, host Will Jenkins interviews Michael Horvath, Co-Founder and COO of Revenova. Mike shares his journey from a musician to a successful entrepreneur in the tech industry, detailing his experiences in various roles, the founding of Forseva, and the subsequent creation of Revenova. The conversation explores themes of innovation, collaboration, and the importance of maintaining a profitable business model while navigating the challenges of the tech landscape. In

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66 results

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