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The Journey Podcast
The Journey Podcast episodes
- 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 Connect, a freight pricing automation platform. Along the way, he learned some expensive lessons about taking risks, building businesses, and knowing when to change direction. They get into the challenges of breaking through growth plateaus, hiring the right people, and finding opportunities to use technology to eliminate bottlenecks. Ricky also explains why freight companies need to look past the AI hype and focus on technology that delivers real results. The conversation also covers standing out in a crowded freight tech market, getting teams to adopt new technology, and why staying focused on solving one problem can be the difference between growing and getting stuck.
TAKEAWAYS:
- Lessons from building and selling a freight brokerage
- Why chasing too many opportunities can hurt growth
- How Tabi Connect evolved from staffing and automation into freight pricing technology
- Breaking through growth plateaus with the right people
- Why scaling requires delegation and stronger leadership
- Finding a niche and building technology that solves a real problem
- How to stand out in a crowded freight technology market
- Why implementing AI requires more than buying new software
- The importance of focus, mindset, and long-term vision
CHAPTERS:
- 00:00 Introduction to Ricky Gonzalez
- 01:06 Building a career and businesses in logistics
- 06:10 Entrepreneurship, risk, and lessons learned
- 08:04 Mindset, vision, and staying focused
- 14:25 Solving freight pricing bottlenecks through automation
- 17:55 Finding the right product and market opportunity
- 20:35 Why chasing shiny objects holds businesses back
- 23:49 Building teams that can scale
- 27:03 Breaking through growth plateaus
- 28:53 Standing out in freight technology
- 30:58 Technology adoption and change management
- 33:15 AI innovation and new partnerships at Tabi Connect
CONNECT WITH RICKY:
- Website: https://tabiconnect.com/
- LinkedIn: https://www.linkedin.com/in/ricardo-gonzalez-tabi/
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
- 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.
37 min - 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 thousands of carriers, air freight providers, brokers, and companies managing increasingly complex security requirements.
They get into the Montgomery ruling, FMCSA data, TSA requirements, carrier documentation, and the financial risk that comes with a scattered compliance process. Joe also explains why certifications like CTPAT can do more than protect a business.They can help companies compete for freight they otherwise could not access.
The conversation also gets into building Veroot with his brother, surviving multiple freight cycles, finding product-market fit, and why Joe still believes in making 30 meaningful sales calls a day.
TAKEAWAYS:
- How TSA air freight and indirect air carriers work
- Why carrier and driver data has to stay current
- The impact of the Montgomery ruling on freight companies
- Why Joe sees compliance as a technology and data problem
- How CTPAT certification can open new business opportunities
- Building Veroot from a directory into a larger compliance platform
- Lessons from 15+ years building a freight technology company
- Why early-stage companies need compliance built into their operating costs
- Joe’s approach to sales, customer trust, and product-market fit
CHAPTERS:00:00 Introduction to Joe Hurst
02:11 Growing up around transportation and freight
05:32 TSA air forwarders and indirect air carriers
08:06 How Veroot got started
09:52 Keeping carrier and driver data current
13:12 The Montgomery ruling and rising compliance risk
15:19 Why compliance starts with better data
20:04 Using technology to manage TSA and CTPAT requirements
22:27 Building Veroot over 15+ years23:43 Advice for early-stage freight entrepreneurs
27:43 Sales, trust, and winning customers
30:29 Product-market fit and surviving freight cycles
32:57 Why CTPAT is becoming more valuable
36:18 How to connect with Joe
CONNECT WITH JOE:
Website: veroot.comLinkedIn: https://www.linkedin.com/in/joe-hurst-753b544/
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
- 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.
37 min - 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 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 — ClosingRESOURCES:
Blackbox Logistics → shipblbx.com
Blackbox Logistics on LinkedIn → LinkedIn
Will Hopkins on LinkedIn → LinkedInStart 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/podcastsEPISODE 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
- 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.
6 min - 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/3UBLjFOApple Podcasts: https://buff.ly/sEonaKXEPISODE 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
- 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.
36 min - 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
- 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.
31 min - 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 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 marketingQUOTES
“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
- 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.
28 min - 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 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 ClosingConnect with Kelly:
LinkedIn: https://www.linkedin.com/in/kelly-usher/
[email protected]Work with the Journey Recruiting team:
journeydelivers.comEPISODE 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
- 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.
23 min - 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
- 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.
22 min - 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 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 TodayListen 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
- 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.
37 min - 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
- 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.
51 min
About The Journey Podcast
From the publisher's feed
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.