The Journey Podcast

Will Jenkins
  • 5.0 (8)
  • Careers

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.

  1. 5d ago

    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, 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 JourneyCreating clearer processes and business structureGrowing from approximately $35–40M to a projected $70–75MWhy Blackbox tracks loads per repWhat changed through the consulting engagementWill Hopkins’ advice for other freight brokerage leaders  CHAPTERS: 00:00 — Introducing The Journey Podcast00:18 — The story behind the conversation01:46 — Meet Blackbox Logistics02:02 — Why Blackbox brought in Journey02:31 — What changed03:04 — Revenue growth and stronger processes03:35 — Tracking loads per rep04:09 — Advice for other brokerage leaders04:33 — Working with Journey05:02 — Closing   RESOURCES: Blackbox Logistics → shipblbx.comBlackbox Logistics on LinkedIn → LinkedInWill Hopkins on LinkedIn → LinkedIn Start your Journey: journeydelivers.com   TUNE IN: Apple Podcasts → Listen on Apple PodcastsSpotify → Listen on SpotifyYouTube → Journey on YouTubeThe 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 LinkedInInstagramTwitterFacebookTikTokYouTube 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.

  2. Sep 24

    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, 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 LinkedInInstagramTwitterFacebookTikTokYouTube 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.

  3. Sep 17

    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 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 LinkedInInstagramTwitterFacebookTikTokYouTube 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.

  4. Sep 10

    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, 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 transportation05:20 — Why marketing matters in freight10:20 — Rebuilding Grane’s commercial presence18:30 — Bringing The Grane Way to life23:19 — The impact on inbound leads and sales25:55 — From a Google search to trucks on the street27:48 — Grane’s next phase of growth29:17 — 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 LinkedInInstagramTwitterFacebookTikTokYouTube 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.

  5. Sep 3

    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 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 Usher01:04 From dance and entrepreneurship to logistics02:27 Finding recruiting03:47 Internal vs. agency recruiting05:39 What Kelly had to unlearn07:29 Earning trust with clients and candidates09:32 Communication and hiring decisions12:38 Coaching candidates and clients15:30 Managing time across searches19:42 Building trust in freight22:02 Kelly’s experience with the Journey Recruiting team23:34 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 LinkedInInstagramTwitterFacebookTikTokYouTube 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.

  6. Aug 13

    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, Abby Hafenbredl, Kary Jablonski, Ben Bar-Lev, Chadd Olesen, Will Hopkins, Kevin McMaster, and Madison Santo, this episode brings back lessons on freight pricing, sales, leadership, prospecting, automation, cold calling, and building a business for the long game.  Most importantly, it’s a thank you to every guest, listener, and member of the team who helped get us to 100.  TAKEAWAYS: Kevin Miles on using freight bid data to make smarter pricing decisions  Abby Hafenbredl on getting more out of freight conferences through preparation Kary Jablonski on building trust by listening before leading Ben Bar-Lev on finding better freight leads through genuine interests and personal connection Chadd Olesen on why strategy and adoption have to come before automation Will Hopkins on bringing personality and creativity into shipper outreach Kevin McMaster on confidence, taking chances, and playing the long game in freight Madison Santo on getting to the financial impact quickly during a cold call    TIMESTAMPS: 00:19 Celebrating 100 episodes of The Journey Podcast  01:15 Kevin Miles: Freight pricing and getting more from bid data  02:35 Looking back at Episode 1 and Kevin’s return in Episode 95  03:14 Abby Hafenbredl: Preparing for freight conferences  05:10 Kary Jablonski: Listening, trust, and leadership  07:38 Ben Bar-Lev: Finding fresh freight leads  10:18 Chadd Olesen: Strategy before automation  13:30 Will Hopkins: Getting creative with shipper outreach  15:26 Kevin McMaster: Confidence and the long game in freight  17:11 Madison Santo: Getting to the money on cold calls  19:16 What 100 episodes have meant to Will and the team  20:57 Here’s to the next 100    ABOUT THE JOURNEY PODCAST: The Journey Podcast brings together freight leaders, founders, operators, sales professionals, and technology leaders for conversations about freight, sales, tech, the market, and everything in between. Subscribe wherever you listen to podcasts and join us for the next 100.    Start your Journey: www.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 LinkedInInstagramTwitterFacebookTikTokYouTube 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.

  7. Aug 6

    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 FreightVana built shipper trust, grew through a prolonged freight downturn, and created a power-only network that connects more than 50 shippers each week.   TAKEAWAYS: Why FreightVana built its brokerage without commissions What separates a true power-only network from leased trailers How FreightVana grew during a difficult freight market What new freight companies need to do differently   CHAPTERS: 00:00 Meet Shannon Breen02:43 Building FreightVana Differently08:28 Growing Through the Freight Downturn14:20 Why FreightVana Removed Commissions21:16 Finding the Right Shipper Fit27:09 Building a True Power-Only Network30:43 Questions Shippers Should Ask32:35 Starting a Freight Company Today   Listen to the full episode to hear how FreightVana built a different kind of freight brokerage. Subscribe to The Journey Podcast for weekly conversations on freight, sales, technology, and building stronger companies. 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 LinkedInInstagramTwitterFacebookTikTokYouTube 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.

  8. Jul 30

    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 early. He also shares how Wheelhouse found an opening in dry partial truckload and temperature-controlled LTL, two areas many larger brokerages overlook or avoid. The conversation gets into why specialization helps smaller brokerages compete, how operating experience builds trust with shippers, and why strong carrier partners can become a real sales advantage. Travis also shares how Wheelhouse uses LinkedIn to build familiarity, recruit proven people, and earn a seat at the table. Will and Travis close with a conversation about honesty, reputation, and why doing right by people matters in an industry where everyone seems to know everyone.    TAKEAWAYS:  Consistent prospecting remains the foundation of freight sales.  Commission-only sales taught Travis personal accountability and how to bet on himself.  Smaller brokerages can compete by owning freight modes larger companies often overlook.  Dry partial truckload and temperature-controlled LTL became clear points of difference for Wheelhouse.  Deep operating knowledge helps sellers speak with more confidence and earn trust faster.  Founders should stay close to sales while the company is still building.  Strong carrier partners help brokerages win, retain, and grow customer accounts.  A broader customer base reduces the risk of depending too heavily on one shipper.  LinkedIn can build familiarity and credibility before the first conversation.  Honesty, kindness, and doing business the right way carry real value in freight.    CHAPTERS  00:00 Introduction  02:59 From sales jobs to freight brokerage  05:29 Betting on yourself in commission-only sales  10:58 Why consistent prospecting still wins  13:38 Building a freight agency and launching Wheelhouse  17:06 Finding an opening in partial truckload and refrigerated LTL  21:33 How specialization changes the sales conversation  27:21 Why founders still need to sell  30:24 Choosing the right customers and reducing account risk  36:41 Why carrier partners are central to growth  41:33 Building credibility and recruiting through LinkedIn  47:19 Authenticity, reputation, and doing business the right way    Listen to How Wheelhouse Wins Business the Big Brokerages Miss on Apple Podcasts, Spotify, and YouTube.  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 LinkedInInstagramTwitterFacebookTikTokYouTube 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.

See All (105)

5
out of 5
8 Ratings

About

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.

Information

  • Creator
    Will Jenkins
  • Years Active
    2024 - 2026
  • Episodes
    105
  • Rating
    Explicit
  • Copyright
    © Journey Solutions Group, LLC
  • Show Website
    The Journey Podcast