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.

The Journey Podcast is a business podcast hosted by Will Jenkins, with 105 episodes on record and a Required Pod Score of 80.

Will Jenkins hosts The Journey Podcast, a business show with 105 episodes published.

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  Episode #105

  Will Hopkins, How Blackbox nearly doubled revenue with Journey

  Oct 1, 20266 min

  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, stronger business structure, and better visibility into productivity. Will shares how the work supported Blackbox’s growth from approximately $35–40 million in 2024 revenue to a projected $70–75 million.   IN THIS EPISODE: Why Blackbox brought in Journey Creating clearer processes and business structure Growing from approximately $35–40M to a projected $70–75M Why Blackbox tracks loads per rep What changed through the consulting engagement Will Hopkins’ advice for other freight brokerage leaders   CHAPTERS: 00:00 — Introducing The Journey Podcast 00:18 — The story behind the conversation 01:46 — Meet Blackbox Logistics 02:02 — Why Blackbox brought in Journey 02:31 — What changed 03:04 — Revenue growth and stronger processes 03:35 — Tracking loads per rep 04:09 — Advice for other brokerage leaders 04:33 — Working with Journey 05:02 — Closing   RESOURCES: Blackbox Logistics → shipblbx.com Blackbox Logistics on LinkedIn → LinkedIn Will Hopkins on LinkedIn → LinkedIn Start your Journey: journeydelivers.com   TUNE IN: Apple Podcasts → Listen on Apple Podcasts Spotify → Listen on Spotify YouTube → Journey on YouTube The Journey Podcast → journeydelivers.com/podcasts   EPISODE CREDITS: Host, Will Jenkins Creative Director, Erin Sweeney Edited and mixed by Keenan McCarthy Music licensed through Envato LINKS: Be sure to follow and tag @JourneyDelivers on LinkedIn Instagram Twitter Facebook TikTok YouTube ABOUT 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.

  ListenShow Notes
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  Episode #104

  Mike Riccio, Work the Plan: What Brokerage Owners Miss as They Scale

  Sep 24, 202636 min

  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, including helping build Leonard’s Express and later working directly with brokerage owners through More Than Miles Consulting. He explains why owners sometimes need to slow down before moving faster, define where the business is going, reverse engineer the steps to get there, and stay focused when day-to-day problems start pulling the team off course. They also talk about getting employees connected to the bigger direction of the company, freight brokerage acquisitions through Open Road Ventures, succession planning, business valuation, partial exits, and what owners should think about before selling.   CHAPTERS: 00:00 Meet Mike Riccio 01:05 Nearly 40 years in trucking 04:24 From family business to consulting 06:11 Helping brokerage owners avoid common mistakes 09:30 Why simple processes work 12:50 Setting the vision before scaling 14:42 Control what you can control 16:46 Turning goals into a plan 17:46 Slow down to speed up 19:05 Getting employees connected to the plan 21:39 Open Road Ventures and freight brokerage acquisitions 23:57 How the Open Road Ventures model works 29:48 Finding the right acquisition partner 35:36 Preparing for a partial or full exit   FIND MIKE: Mike Riccio on LinkedIn:   / mike-riccio-5a8a4bb   More Than Miles Consulting: https://www.morethanmilesconsulting.c...   LISTEN TO THE JOURNEY PODCAST: Spotify: https://buff.ly/4aTO9Lu YouTube: https://buff.ly/3UBLjFO Apple Podcasts: https://buff.ly/sEonaKX EPISODE CREDITS: Host, Will Jenkins Creative Director, Erin Sweeney Edited and mixed by Keenan McCarthy Music licensed through Envato LINKS: Be sure to follow and tag @JourneyDelivers on LinkedIn Instagram Twitter Facebook TikTok YouTube ABOUT 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.

  ListenShow Notes
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  Episode #103

  Charles Gracey, Pricing, Value and Bringing Solutions

  Sep 17, 202631 min

  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 not necessarily mean freight volume has returned, and where he thinks the industry has become too comfortable with lower expectations. They also get into building and selling a recruiting company, pricing around customer value, saying no to the wrong business and what stronger driver and carrier partnerships look like.   CHAPTERS: 00:00 Meet Charles Gracey 03:48 Building and selling a trucking recruiting company 06:01 Lessons from building the business 10:32 Leadership and standards in trucking 13:45 Driver recruiting and better opportunities 17:58 Why trucking normalized driver no-shows 22:36 When to say no to business 25:24 Building trust with carriers and drivers 27:56 Pricing around customer value 30:27 Trucking rates vs. freight volume 33:36 What Charles is seeing in the freight market 35:22 Final thoughts   RESOURCES: Charles Gracey on LinkedIn: https://www.linkedin.com/in/charles-gracey/   ABOUT THE JOURNEY PODCAST: The Journey Podcast features conversations with leaders across freight, logistics, trucking, recruiting, sales and transportation. EPISODE CREDITS: Host, Will Jenkins Creative Director, Erin Sweeney Edited and mixed by Keenan McCarthy Music licensed through Envato LINKS: Be sure to follow and tag @JourneyDelivers on LinkedIn Instagram Twitter Facebook TikTok YouTube ABOUT 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.

  ListenShow Notes
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  Episode #102

  Kyle Engdahl, The Grane Way

  Sep 10, 202627 min

  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, experience, and service offering. The challenge was making it easier for customers to see the full picture. Kyle shares how working with Will & Erin to create new website, sales materials, photography, and video helped Grane increase inbound interest, strengthen sales conversations, and create new revenue opportunities.   TAKEAWAYS: Strong marketing gives sales teams proof, not just talking points. Showing customers the full scope of your services can create new revenue from business you already have. Video can help freight companies prove their infrastructure, facilities, and capabilities faster. A stronger website can improve inbound lead volume and bring in higher-value opportunities. Better sales materials can help reps walk into meetings with more confidence. Marketing works best when it helps customers understand why they should trust you. Grane’s growth strategy is still rooted in the same principle that has carried the company for 100 years: serve the customer well and grow with their needs.   CHAPTERS: 00:32 — The Grane Companies and 100 years in transportation 05:20 — Why marketing matters in freight 10:20 — Rebuilding Grane’s commercial presence 18:30 — Bringing The Grane Way to life 23:19 — The impact on inbound leads and sales 25:55 — From a Google search to trucks on the street 27:48 — Grane’s next phase of growth 29:17 — Advice for companies investing in marketing   QUOTES “If you don't think that you need to invest in marketing, you're going to realize that word of mouth can only get you so far.” “There's no smoke and mirrors. It added credibility.” “We don't have stockholders, we have customers.”   Check out Journey's Marketing Consulting & Creative Services: https://www.journeydelivers.com/consulting/creative-services EPISODE CREDITS: Host, Will Jenkins Creative Director, Erin Sweeney Edited and mixed by Keenan McCarthy Music licensed through Envato LINKS: Be sure to follow and tag @JourneyDelivers on LinkedIn Instagram Twitter Facebook TikTok YouTube ABOUT 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.

  ListenShow Notes
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  Episode #101

  Kelly Usher, Why Agency Recruiting Is Sales Through and Through

  Sep 3, 202623 min

  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 recruiting inside one company to representing multiple clients and candidates. She shares why agency recruiting is sales through and through, how she earns trust with different decision-makers, and why some of the skills that worked internally had to be relearned in a third-party setting. Kelly and Will also get into candidate coaching, client communication, managing expectations and knowing where to spend your time when every search is moving at a different pace. If you work in recruiting, lead a team or are hiring in freight, this conversation gives you a look at what strong recruiting work requires on both sides of the table.   TAKEAWAYS: Internal recruiting vs. third-party recruiting Getting to know each hiring decision-maker Building trust with candidates and clients Why recruiting is a sales job Coaching candidates through the hiring process Managing client expectations Knowing when to push and when to give a search time Working efficiently across multiple searches Kelly’s experience with the Journey Recruiting team   CHAPTERS: 00:00 Meet Kelly Usher 01:04 From dance and entrepreneurship to logistics 02:27 Finding recruiting 03:47 Internal vs. agency recruiting 05:39 What Kelly had to unlearn 07:29 Earning trust with clients and candidates 09:32 Communication and hiring decisions 12:38 Coaching candidates and clients 15:30 Managing time across searches 19:42 Building trust in freight 22:02 Kelly’s experience with the Journey Recruiting team 23:34 Closing Connect with Kelly: LinkedIn: https://www.linkedin.com/in/kelly-usher/ Kelly@journeydelivers.com Work with the Journey Recruiting team: journeydelivers.com EPISODE CREDITS: Host, Will Jenkins Creative Director, Erin Sweeney Edited and mixed by Keenan McCarthy Music licensed through Envato LINKS: Be sure to follow and tag @JourneyDelivers on LinkedIn Instagram Twitter Facebook TikTok YouTube ABOUT 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.

  ListenShow Notes

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