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.

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:

ABOUT THE JOURNEY PODCAST:

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.

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.

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:

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:

Work with the Journey Recruiting team:

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.

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:

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

• 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.

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:

CHAPTERS:

00:00 Meet Shannon Breen
02:43 Building FreightVana Differently
08:28 Growing Through the Freight Downturn
14:20 Why FreightVana Removed Commissions
21:16 Finding the Right Shipper Fit
27:09 Building a True Power-Only Network
30:43 Questions Shippers Should Ask
32:35 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

• 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.

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: 

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

• 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.

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 booking. He also shares what the company has learned from working across more than 3 million loads. Will and Kevin get into what freight tech companies need to prove in a down market, how the sales message changes when volume returns, and why brokers should be getting more from the people, carriers, and systems they already have. This episode is for freight leaders thinking about where to spend, where to automate, and how to grow without adding headcount too quickly. 

TAKEAWAYS: 

CHAPTERS: 

00:00 Meet Kevin Coomes, CRO at Chain 

01:33 Kevin’s path into freight technology 

05:33 Working in China and speaking Mandarin 

06:22 What is changing in the freight market 

09:16 Selling through different market cycles 

13:17 How Chain got started 

16:31 Automating freight tracking at scale 

18:50 Moving from tracking into booking 

20:40 Why freight experience matters in product development 

22:01 Proving ROI in a down market 

26:34 Helping brokers grow without adding headcount 

32:28 Carrier data and what comes next 37:40 Closing thoughts 

START YOUR JOURNEY: 

http://www.journeydelivers.com

 KEYWORDS: freight tech, freight automation, freight brokerage, freight market, Chain, Kevin Coomes, freight tracking, freight booking, carrier management, freight sales, logistics technology, capacity planning, freight operations, carrier networks, brokerage automation, freight market cycles, product-market fit, logistics software, transportation technology 

RESOURCES: 

Chain: https://trychain.com/

 Kevin Coomes on LinkedIn:https://www.linkedin.com/in/kevin-c-46a8a129/

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.

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 he was 19, scheduling appointments and working directly with carriers. 

Today, he is helping Qued solve that same appointment scheduling problem at scale. Tom explains why sales starts with knowing whether you can genuinely help the buyer. He shares why freight sales teams should stop forcing square pegs into round holes, focus on the problems they understand best, and become specialists rather than trying to sell every possible service. The conversation also covers the role of end-user buy-in when selling freight technology. 

Tom explains why executive approval may get a contract signed, but trust from schedulers and operations teams is what keeps customers engaged. Will and Tom also discuss asking stronger discovery questions, solving problems for the customer’s customer, reading the room during a sales call, and staying true to your own personality rather than copying someone else’s sales style. For freight brokers, logistics sales teams, freight technology companies, and transportation leaders, this episode offers a practical look at building trust, earning referrals, and creating lasting customer value. 

TAKEAWAYS: 

CHAPTERS: 

00:00 Meet Tom Curee, President of Qued 

02:59 Starting in freight at TQL at 19 

05:02 Selling by serving a real customer need 

07:10 Understanding buyer goals and performance measures 

08:59 Knowing when not to make the sale 

09:53 Why Qued stays focused on appointment scheduling 

12:04 Specialists vs. companies that promise everything 

14:19 Understanding the problem before pitching the solution 

15:59 Winning trust from schedulers and end users 

17:32 Executive approval vs. team adoption 

18:14 Sales makes promises. Operations keeps them. 

20:43 How appointments affect freight margins 

23:04 Solving problems for your customer’s customer 

24:05 Asking stronger discovery questions 

26:56 Selling something you truly care about 

27:24 Finding your own sales style 

29:45 Why honesty earns referrals 

32:26 Knowing who you are as a salesperson 

34:27 Reading the room and adapting the call 

36:02 Closing thoughts 

START YOUR JOURNEY: www.journeydelivers.com 

KEYWORDS: recruiting, consulting, training, freight sales, freight technology sales, freight brokerage sales, logistics sales, Qued, Tom Curee, freight appointment scheduling, transportation sales strategy, freight broker training, logistics customer service, freight technology implementation, customer discovery questions, sales trust, freight operations, shipper needs, carrier sales, end-user adoption, logistics software sales

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.

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, including time on the shipper side managing RFPs. In this conversation, he breaks down how policy changes, rising costs, technology, and AI are all hitting brokers at the same time. Will and Kevin also get into one of the biggest questions facing freight leaders today: when the market starts to move, how do you grow without spending too fast, hiring too late, or buying technology that does not solve the actual problem? This episode covers smarter RFP strategy, freight pricing, AI adoption, TMS mistakes, hiring trends, and how brokers can position themselves for the next cycle with more discipline. 

TOPICS: 

TAKEAWAYS:

CHAPTERS: 

00:00 Introduction to The Journey Podcast 

01:00 Kevin Miles returns as the first-ever Journey Podcast guest 

01:18 Kevin’s background and the start of Eureka BI 

03:40 Freight market pressure, policy changes, and technology shifts 

05:01 Where technology implementation breaks down 

07:54 AI adoption, demos, prototypes, and real-world use 

11:23 Building, testing, and improving technology faster 

12:06 Policy changes and the impact on capacity 

13:03 Insurance costs, rate pressure, and RFP changes 

15:07 Healthy growth versus market-driven revenue gains 

18:05 Spending discipline during a market shift 

19:02 Hiring trends across freight brokerages 

21:23 How brokers should approach new RFP opportunities 

23:35 What is next for Eureka BI 

24:18 Closing thoughts 

RESOURCES: 

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.

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 combines multiple LTL shipments into full truckloads using AI-powered optimization. The result? Lower costs for shippers, better rates for carriers, and freight that moves without touching a dock.

If you've ever thought:

This conversation will give you the roadmap.

Kevin shares insights on building technology that actually works, selling differentiation in a skeptical market, and leading teams through constant evolution.

TAKEAWAYS:

Whether you're in brokerage, building freight tech, leading sales teams, or exploring new business models, this episode delivers insights from someone actually doing it.

CHAPTERS:

RESOURCES:

Flock Freight: https://flockfreight.com

CONNECT WITH KEVIN MCMASTER:

LinkedIn: https://www.linkedin.com/in/kevin-mcmaster-25a7237/

FOLLOW JOURNEY:

Instagram: @journeydelivers

Twitter/X: @journeydelivers

TikTok: @journeydelivers

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LISTEN & SUBSCRIBE:

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🎥 YouTube: https://buff.ly/Vf0w739

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.

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.