The Journey Podcast
by Will Jenkins
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.
Episodes
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Brad Guinane, What Makes Changing Worth It for Your Customer?
Your customer can keep running their business without your product. So why should they change the way they work? In this episode of The Journey Podcast, Will Jenkins sits down with Brad Guinane, President, Supply Chain Solutions at Blue Book, to discuss what it takes to make customers see the…
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Ricky Gonzalez, The Hidden Risks of Chasing the Wrong Freight Opportunities
Ricky Gonzalez, CEO and Co-Founder of Tabi Connect, joins Will to talk entrepreneurship, scaling freight businesses, and why chasing the next big opportunity can do more harm than good. Ricky shares how he went from building and selling a freight brokerage to co-founding Hubtek and launching Tabi...
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Joe Hurst, The Cost of Getting Freight Compliance Wrong
Joe Hurst, President and Co-Founder of Veroot, joins Will to talk TSA, CTPAT, carrier compliance, and why freight companies may need to start thinking about compliance as a technology and data problem. Joe shares how Veroot grew from a simple TSA carrier directory into a platform supporting...
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Will Hopkins, How Blackbox nearly doubled revenue with Journey
Will Hopkins, Co-Founder of Blackbox Logistics, joins Will Jenkins to talk about what changed when Blackbox brought in Journey for freight brokerage consulting. Blackbox was already working hard in a difficult freight market. The goal was to get more from that effort through clearer processes,...
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Mike Riccio, Work the Plan: What Brokerage Owners Miss as They Scale
Mike Riccio, Founder of More Than Miles Consulting and Co-Founder of Open Road Ventures, joins Will Jenkins to talk about scaling a freight brokerage, building a business plan your team can follow, and preparing for growth or an eventual exit. Mike brings nearly four decades in transportation,...
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Charles Gracey, Pricing, Value and Bringing Solutions
Charles Gracey, Radio Host of Trucking Sense on SiriusXM, joins Will Jenkins to talk about the freight market, trucking rates, driver recruiting and the standards shaping transportation today. Charles shares what he’s hearing from drivers, executives and regulators, why higher trucking rates do…
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Kyle Engdahl, The Grane Way
Kyle Engdahl, Vice President at The Grane Companies, joins The Journey Podcast to talk about how a 100-year-old transportation company changed the way it presented its business to the market with the help of Journey's Marketing Consulting & Creative Services. Grane already had the infrastructure,...
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Kelly Usher, Why Agency Recruiting Is Sales Through and Through
Kelly Usher didn’t start out planning to work in recruiting. Her path took her from dance and entrepreneurship into logistics, internal talent acquisition and, eventually, third-party recruiting with the Journey Recruiting team. In this episode, Kelly talks about what changes when you move from...
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Celebrating 100 Episodes of The Journey Podcast
100 episodes. A lot of freight conversations. Even more lessons along the way. For our 100th episode, Will Jenkins goes back through some of his favorite conversations from The Journey Podcast, from the early days of Choppin’ It Up and Sales Bites to the show it is today. Featuring Kevin Miles,...
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Shannon Breen, How FreightVana Climbed Into the Top 100 in a Down Market
What happens when you remove commissions from freight brokerage? Shannon Breen, Founder and CEO of FreightVana, joins Will Jenkins to explain how the company grew into a top 100 brokerage with a non-commissioned operating model and an equipment-backed power-only network. Shannon shares how...
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Travis Dodge, How Wheelhouse Wins Business the Big Brokerages Miss
Travis Dodge, Founder of Wheelhouse Logistics, joins Will Jenkins to share how he went from a commission-only freight agent to building a brokerage of his own. Travis explains why consistent prospecting remains the foundation of freight sales and why founders cannot step away from selling too...
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Kevin Coomes, How Chain Built Freight Tech Brokers Depend On
SUMMARY: Kevin Coomes, CRO at Chain, joins Will Jenkins to talk about where the freight market is headed and how brokers should be thinking about automation as capacity tightens. Kevin breaks down how Chain is helping brokerages reduce manual work across tracking, exception management, and…
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Tom Curee, Ask Better Questions. Win More Business.
SUMMARY: What separates a trusted freight sales professional from someone simply chasing the next deal? Tom Curee, President of Qued, joins Will Jenkins to share lessons from 20 years in freight brokerage, transportation, and freight technology sales. Tom began his freight experience at TQL when…
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Kevin Miles, The RFP Game Is Changing
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…
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Kevin McMaster, Flock Freight on Shared Truckload, Shipper Success, and the Tech Behind the Model
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...
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How Axle Logistics Uses AI to Upskill Reps Faster
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...
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Todd Waldron, Brokerage, Trucking, and Tech All in One Career
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...
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Hunter Bell, The Power of Relationships in Business Success
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…
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Justin Turner, Account Segmentation
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...
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Will Jenkins and Justin Turner, Black History Month Edition 2026
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...
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Justin Turner, The New Revenue Playbook
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…
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Tyler Harper, A Modern Approach to LTL Shipping
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...
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Robert Bain, Freight Tech
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...
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Daniel Solida, Value Based Selling
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...
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Matt Fain, Building PopCapacity: The Warehouse Search Platform
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...
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Cameron Robertson, From Tech Support to CEO
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...
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Robert Bain, Networking
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...
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Special Edition, Two Years In
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…
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Megan Masud & Sarah Hanna, Mental Health and Compliance
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...
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CJ Johnson, No Shortcuts in This Game
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...
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Elizabeth Moscoso, A Second-Gen Freight Story
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...
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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...
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Rob Skelton, Drop the Ego Pick Up the Freight
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....
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Women's History Month #NoGatekeeping
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...
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David Bell & Alfonso Quijano, CloneOps at Manifest 2025
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...
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The Men of Journey, Black History Month Edition
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...
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Marcus Cooksey, DUKE.ai - Automated Freight Invoicing
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....
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Shannon Breen, From Finance to Freight: Building FreightVana
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…
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Special Edition: Journey Turns 1
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...
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Journey & Shipper CRM, Elevating Freight Sales with Tech
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...
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Chadd Olesen, The Power of Automation: AVRL’s Impact on Logistics
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...
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Michael Horvath, Building Revenova: A Cloud-Based TMS
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...
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Amado Cruz, National Truck Driver Appreciation Week Edition
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...
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Steve Zambo, Growing Up In Freight
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…
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Kristy Knichel, Building Confidence as a CEO
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…
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Kary Jablonski, Lessons Learned as a Leader
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...
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Morgan MacDermaid, Life On Your Own Terms
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…
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Sebastian Pedraza, Entrepreneurship, Ambition, & Automation
SUMMARY: Sebastian Pedraza, Co-Founder and Chief Revenue officer of Oko, takes us on a journey through his career journey. From his formative years in Colombia, where his fascination with math & science took root, to his collegiate days balancing football & school, Sebastian shares how these...
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Joy Stephens, Finding Your Authentic Path to Success
SUMMARY: Joy Stephens, Chief Consultant at New Heights Academic and Leadership Consulting, shares her career journey and the pivotal moments that led her to her current role. She discusses her early aspirations to be an actress, her background in engineering, and her transition into sales and...
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The Women of Journey, Women's History Month Edition
SUMMARY: Erin Sweeney, Maya Quijada, Nicki Childers and Morgan MacDermaid discuss their career journeys as women in & out of the transportation industry in honor of Women's History Month. They share their experiences of being the only woman in the room, facing stereotypes and objectification, and...
About this show
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.
Hosted by
Will Jenkins
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