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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

00:30:59

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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00:41:19

Amado Cruz, National Truck Driver Appreciation Week...

The Journey Podcast ·

2025/12/03

SUMMARY:In this episode of Chopping It Up, host Will Jenkins interviews Amado Cruz, CEO and Founder of Limitless Carriers. Amado shares his journey from being a truck driver to becoming a successful trucking company owner. He discusses the importance of understanding the trucking industry, the challenges faced by drivers, and the strategies he employed to grow his business. Amado emphasizes the significance of customer service, building relationships, and creating a positive company culture to

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00:56:54

Steve Zambo, Growing Up In Freight

The Journey Podcast ·

2025/12/03

SUMMARY:Steve Zambo, CEO and founder of AGL, shares his background and journey in the freight industry. He grew up in a logistics household and interned at a freight forwarding company before exploring other industries like marketing and telecom. Eventually, he decided to start his own company and moved to Los Angeles to open a branch for an IT recruiting organization. During this time, he learned the importance of effective communication and building relationships. He successfully grew the branch

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00:48:56

Kristy Knichel, Building Confidence as a CEO

The Journey Podcast ·

2025/12/03

SUMMARY:In this episode of Choppin' It Up, Will Jenkins interviews Kristy Knichel, President and CEO of Knichel Logistics. Kristy shares her career journey and the growth of her company from a two million dollar business to a hundred million dollar company. She discusses the importance of having a niche and being really good at a few modes and commodities. Kristy also emphasizes the significance of being engaged at the owner and executive level in the sales process. She talks about the challenges

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00:49:37

Kary Jablonski, Lessons Learned as a Leader

The Journey Podcast ·

2025/12/03

SUMMARY: Kary Jablonski, CEO of Trucker Tools, shares her background and career journey in this conversation. She discusses her experience as a certified archery instructor, growing up in Boston with two brothers, and the impact of attending an all-girls summer camp. Kary talks about her college years at Georgetown, where she studied economics and government, and her time working at Deloitte as a consultant. She then shares her transition to Uber, where she worked in various roles, including

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00:39:29

Morgan MacDermaid, Life On Your Own Terms

The Journey Podcast ·

2025/12/03

SUMMARY: Will Jenkins interviews Morgan MacDermaid, previously Sr. Recruiting Advisor at Journey. Morgan shares her career journey, which includes working at Disney World, backpacking around the world, and working odd jobs in different countries. She eventually found her way into the transportation industry and became a successful recruiter. Morgan discusses the importance of taking risks, learning from mistakes, and finding a balance between work and personal life. She also shares her dreams for

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61 results

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