Todd Waldron, Brokerage, Trucking, and Tech All in One Career

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 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: * "How do we differentiate in a commoditized brokerage market?" * "Can technology actually solve freight problems or is it just marketing?" * "What does real innovation look like in logistics?" * "How do I build a team that embraces change instead of resisting it?" 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: * How shared truckload actually works and why it's more than just pooling freight * The routing technology and AI that powers Flock's optimization engine * Why market timing matters when introducing disruptive models * Taking a consultative approach with shippers instead of pitching features * How data and flexibility drive operational excellence * Why Flock focuses exclusively on shared truckload instead of expanding services * Building trust when your business model is unfamiliar to customers * Real differentiation vs. claiming you're different in brokerage * Customer retention strategies when you solve actual problems * How to prepare shippers for the shared truckload transition * Building teams that are energized by change instead of exhausted by it * The future outlook for shared truckload and freight optimization * Why delivering on promises matters more than perfect marketing 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: * 0:00 Introduction: Flock Freight and Shared Truckload * 2:57 The Technology Behind Shared Truckload Routing * 5:57 Market Timing and Why Now for Shared Truckload * 9:09 Consultative Selling in Freight Innovation * 11:58 Data, Flexibility, and Operational Excellence * 14:51 Why Flock Only Does Shared Truckload * 17:57 Building Trust and Delivering on Promises * 20:59 Real Differentiation in Brokerage * 23:59 Customer Retention Through Value Creation * 27:03 Preparing Shippers for Shared Truckload * 30:14 Future Outlook for Flock Freight   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   ⭐ LOVE THE JOURNEY PODCAST? Help us grow! ⭐  → Leave a 5-star review on Apple Podcasts or Spotify  → Subscribe so you never miss an episode  → Share this episode with someone in freight or logistics   LISTEN & SUBSCRIBE: 🎧 Apple Podcasts: https://buff.ly/d9QupIc 🎧 Spotify: https://buff.ly/rm6ZRT0 🎥 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 [https://www.linkedin.com/company/journeydelivers/?viewAsMember=true] * Instagram [https://www.instagram.com/journeydelivers/] * Twitter [https://x.com/journeydelivers?s=11] * Facebook [https://www.facebook.com/profile.php?id=61554001587959] * TikTok [https://www.tiktok.com/@journeydelivers] * YouTube [https://www.youtube.com/@JourneyDelivers]   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.

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 over 1,400 AI practice calls before touching a real prospect. The results? Five weeks later: 27 new customers, $139,000+ in revenue, and 14 out of 17 reps had already landed business. If you've ever thought: * "New reps take forever to ramp." * "We're burning good leads on untrained people." * "I don't have time to role play with everyone." * "Training results are inconsistent." This conversation will give you the solution. Ali and Haley share how Axle uses AI-powered role plays to get reps productive in 90 days instead of 6-12 months.   TAKEAWAYS: * Why traditional training leaves reps unprepared for real calls * The 6-week Launchpad program that gets reps to $139K in 5 weeks * How 1,400+ AI practice calls build confidence before burning real leads * The data that shows exactly where each rep struggles * Why practicing the full sales cycle (cold call to QBR) changes everything * How managers went from 40 hours of role plays to targeted coaching * Getting veteran reps to buy in when they think they don't need practice * Training for capability vs. training for compliance * How to adjust training as market conditions change in real-time Whether you're training brokers, managing a team, or scaling your brokerage, this episode delivers proven results.   ⭐ LOVE THE JOURNEY PODCAST? Help us grow! ⭐ → Leave a 5-star review on Apple Podcasts or Spotify → Subscribe so you never miss an episode → Share this episode with someone in freight or logistics   CHAPTERS: * 0:00 Introduction: AI Training at Axle * 2:29 The 6-Week Launchpad Program * 5:19 Why Axle Invested in AI Training * 11:16 Real Results: 17 Reps, 27 Customers, 5 Weeks * 19:09 Training for Capability Not Compliance * 27:23 Ending Inconsistent Onboarding * 30:49 Data-Driven Coaching * 41:21 Getting Veteran Buy-In   RESOURCES: Axle Logistics - https://axlelogistics.com/ Journey AI Training - https://journeydeliver.com   CONNECT WITH THE AXLE TEAM: Ali Fraley - https://www.linkedin.com/in/alifraley/ Haley Williams - https://www.linkedin.com/in/haley-williams-/   FOLLOW JOURNEY: Instagram: @journeydelivers Twitter/X: @journeydelivers TikTok: @journeydelivers   LISTEN & SUBSCRIBE: 🎧 Apple Podcasts: https://buff.ly/d9QupIc 🎧 Spotify: https://buff.ly/rm6ZRT0 🎥 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 [https://www.linkedin.com/company/journeydelivers/?viewAsMember=true] * Instagram [https://www.instagram.com/journeydelivers/] * Twitter [https://x.com/journeydelivers?s=11] * Facebook [https://www.facebook.com/profile.php?id=61554001587959] * TikTok [https://www.tiktok.com/@journeydelivers] * YouTube [https://www.youtube.com/@JourneyDelivers]   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.

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 high-energy cubicles at CH Robinson, to opening JB Hunt's Minnesota brokerage branch, to transforming a 40-year-old trucking company, to now shaping carrier experience at TruckStop—Todd's 17-year journey proves that great leaders are built through relentless learning and adaptation.   If you've ever thought: * "How do I move from operations to leadership?" * "Can I build tech without being a tech person?" * "How do I create culture when everyone's remote?" * "What does real leadership actually look like?" * "How do I prioritize when everything feels urgent?" This conversation will give you the blueprint.   Todd shares honest insights about: * Why "motion creates emotion" and how to create energy in any team * How trust is built or destroyed in every single interaction * The difference between managing people and leading them * Why asking questions beats making assumptions every time * What it really takes to transform a decades-old company culture   TAKEAWAYS: * Why the energy at CH Robinson shaped Todd's entire leadership philosophy * The sales manager conversation that forever changed how Todd prioritizes time * What Todd learned opening JB Hunt's Minnesota brokerage branch from scratch * Inside look at building JB Hunt 360 marketplace and the tech lessons learned * How Todd transformed Q Carriers' culture in a 40-year-old trucking company * The moment Todd realized great culture starts with how leaders actually listen * What carriers really want from load boards (it's not what brokers think) * Why TruckStop built a Carrier Advisory Board and how it changes product development * The fraud problem hitting the industry and how technology is solving it * Where AI actually helps carriers vs. where it creates more problems * How authority age filters help new carriers cut through the noise * Why "boost loads" might finally solve the duplicate load nightmare * Todd's time management system that reduced chaos and increased productivity * The leadership frameworks from "Good to Great" and "Five Dysfunctions" that actually work in freight   Whether you're in brokerage, running trucks, building tech, leading a team, or just trying to level up your career, this episode is packed with hard-earned wisdom.   ⭐ LOVE THE JOURNEY PODCAST? Help us grow! ⭐ → Leave a 5-star review on Apple Podcasts or Spotify → Subscribe so you never miss an episode → Share this episode with someone in freight or logistics Your support helps others in the industry find these conversations!   CHAPTERS: * 0:00 Introduction: Meet Todd Waldron * 1:32 Career Journey: From CH Robinson to VP at TruckStop * 3:21 Early Brokerage Lessons: Energy, Prioritization & Sales * 5:58 Leadership Philosophy: Trust in Every Interaction * 12:35 JB Hunt Experience: Building Tech & Opening Minnesota Branch * 17:43 Leading Q Carriers: Cultural Transformation of a 40-Year Company * 22:08 The Culture Shift: Employee Engagement & Retention * 23:32 TruckStop Innovation: Building Products Carriers Want * 25:38 Understanding Carrier Needs: The Advisory Board Approach * 28:37 Tech Integration Lessons: What Worked at JB Hunt * 30:27 Market Insights: Cycles, Trends & What's Coming Next * 34:04 Technology Adoption: Getting Carriers to Actually Use It * 37:51 What's Next at TruckStop: Authority Filters, Deduplication & AI * 39:42 Book Recommendations: Leadership & Time Management   RESOURCES: Good to Great by Jim Collins https://www.amazon.com/dp/0066620996   Do More Better by Tim Chalies https://www.amazon.com/dp/1950523774   Five Dysfunctions of a Team by Patrick Lencioni https://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756   TruckStop Platform https://truckstop.com   JB Hunt 360 Marketplace https://www.jbhunt.com/360/   Q Carriers https://qcarriers.com   CONNECT WITH TODD WALDRON: LinkedIn: https://www.linkedin.com/in/todd-w-21897b19/ Website: https://truckstop.com   FOLLOW JOURNEY: Instagram: @journeydelivers Twitter/X: @journeydelivers TikTok: @journeydelivers   LISTEN & SUBSCRIBE: 🎧 Apple Podcasts: https://buff.ly/d9QupIc 🎧 Spotify: https://buff.ly/rm6ZRT0 🎥 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 [https://www.linkedin.com/company/journeydelivers/?viewAsMember=true] * Instagram [https://www.instagram.com/journeydelivers/] * Twitter [https://x.com/journeydelivers?s=11] * Facebook [https://www.facebook.com/profile.php?id=61554001587959] * TikTok [https://www.tiktok.com/@journeydelivers] * YouTube [https://www.youtube.com/@JourneyDelivers]   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.

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 trucking operations to building MySavant.AI, an AI-powered nearshoring platform, Hunter's journey proves that the biggest opportunities often hide in plain sight within the industries we know best.  If you've ever thought:  * "I want to start something but don't know what."  * "AI feels too complicated for my industry."  * "How do I compete with established players?"  * "I'm stuck in the family business mindset."  This conversation will give you a roadmap.  Hunter shares raw, honest insights about:  * How to spot innovation opportunities in traditional industries * The mindset shift from logistics worker to tech entrepreneur * Building AI solutions when you're not a "tech person" * Leadership lessons learned the hard way  * Why nearshoring is the future of workforce optimization    TAKEAWAYS: * The exact moment Hunter realized traditional logistics needed disruption  * How AI is solving workforce challenges most companies ignore * Why you don't need a tech background to build tech solutions * The hardest lessons about team building and company culture * Industry trends that will reshape freight and logistics in the next 5 years * Practical advice for entrepreneurs stuck between family expectations and their own vision * The books and mindsets that shaped Hunter's approach (Think and Grow Rich, The Strangest Secret) * How to hold yourself accountable when no one else will * Why "believing it to achieve it" isn't just motivational it's operational Whether you're in logistics, considering a career shift, exploring AI for your business, or just love hearing how people build companies from scratch, this episode delivers.    ⭐ LOVE THE JOURNEY PODCAST? HELP US GROW! ⭐  * Leave a 5-star review on Apple Podcasts or Spotify  * Subscribe so you never miss an episode  * Share this episode with someone in freight or logistics  Your support helps others in the industry find these conversations!    CHAPTERS:  * 0:00 Meet Hunter Bell  * 1:22 Growing Up in Transportation: The Foundation  * 6:07 Family Business Lessons and Early Entrepreneurship  * 9:35 MySavant Explained: AI-Powered Nearshoring Solutions  * 15:24 Advice for Young Entrepreneurs (What Hunter Wishes He Knew)  * 18:25 Industry Outlook: Where Freight and Logistics Are Headed  * 20:18 Building Teams: Leadership Style and Company Culture  * 22:58 The Future of MySavant: AI Integration and Expansion    EPISODE RESOURCES:  Think and Grow Rich by Napoleon Hill https://www.amazon.com/Think-Grow-Rich-Napoleon-Hill/dp/1934451509  The Strangest Secret by Earl Nightingale https://www.youtube.com/watch?v=7X7X7X7X7X  MySavant AI Platform https://mysavant.ai    CONNECT WITH HUNTER BELL:  LinkedIn: https://www.linkedin.com/in/hunter-bell-0299b4167/  Website: https://mysavant.ai    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 [https://www.linkedin.com/company/journeydelivers/?viewAsMember=true] * Instagram [https://www.instagram.com/journeydelivers/] * Twitter [https://x.com/journeydelivers?s=11] * Facebook [https://www.facebook.com/profile.php?id=61554001587959] * TikTok [https://www.tiktok.com/@journeydelivers] * YouTube [https://www.youtube.com/@JourneyDelivers]   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.

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 approach to sales and marketing. The conversation delves into actionable insights for sales leaders, focusing on optimizing for quick wins and aligning brand messaging with target audiences.   TAKEAWAYS: * Customer segmentation is crucial for effective sales strategies. * Different customer sizes have varying technical requirements. * Revenue bands help in identifying customer segments. * Sales cycles can be shorter with SMBs compared to enterprises. * Aligning sales strategies with customer segmentation is essential. * Brand messaging must resonate with the target audience. * Understanding customer requirements is key for sales success. * Focus on quick wins to drive business growth. * Small wins can accumulate into significant success over time. * Sales leaders should prioritize understanding current performance metrics.   CHAPTERS: * 00:00 Introduction and Setting the Stage * 00:17 Understanding Customer Segmentation * 08:35 The Importance of Technical Requirements * 11:41 Aligning Sales Strategies with Customer Segmentation * 17:21 Actionable Insights for New Sales Leaders       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 [https://www.linkedin.com/company/journeydelivers/?viewAsMember=true] * Instagram [https://www.instagram.com/journeydelivers/] * Twitter [https://x.com/journeydelivers?s=11] * Facebook [https://www.facebook.com/profile.php?id=61554001587959] * TikTok [https://www.tiktok.com/@journeydelivers] * YouTube [https://www.youtube.com/@JourneyDelivers]   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.