Smart Hiring Strategies for Trucking Fleets with Rob Carpenter | A Trucking Podcast
Miles and Mentors Trucking Podcast
Release Date: 09/24/2025
Marketing That Actually Works for Owner-Operators with Webster Jorgensen | Ep 57
Miles and Mentors Trucking Podcast
What simple marketing moves put a brand-new carrier ahead of half the competition? In this episode of Miles and Mentors: A Trucking Podcast, Webster Jorgensen shares practical, first-week marketing advice for new carriers and small fleets. Drawing on more than a decade leading digital marketing at Shamrock Trading and now running his own agency, Demand Stack, Webster breaks down what really matters for trucking companies trying to stand out online. From understanding market cycles and building a simple Google Business Profile to creating a basic website and asking for reviews, Webster explains...
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Helping Drivers Think Like Business Owners with Annique Lesage | Ep 56
Miles and Mentors Trucking Podcast
What separates surviving from thriving as an owner-operator or broker? It’s not luck. It’s how you show up. In this episode of Miles and Mentors: A Trucking Podcast, Annique Lesage of Small World Ventures shares how she went from the shipper side of logistics to building her own brokerage—proving that professionalism, mentorship, and mindset matter more than hype. Annique unpacks what brokers often overlook, how to filter real guidance from bad advice, and why drivers need to approach freight with business-owner thinking if they want to grow. Whether you’re just stepping into your own...
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You Signed Up for This with Chris Jolly | Ep 55
Miles and Mentors Trucking Podcast
What does it actually take to build a freight business in today’s market, and why do so many give up too soon? In this episode of Miles and Mentors: A Trucking Podcast, Chris Jolly, founder of Freight Coach Logistics and host of The Freight Coach podcast, breaks down what it means to build with intention, survive the downturns, and create value that lasts in this industry. Chris shares how his father's legacy as a 40-year owner-operator shaped his mindset, what most brokers are still getting wrong, and why mentorship—not hype—is the real path to growth. Whether you're launching a...
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From First Turn to Fleet Wisdom with Chemistry Howard | Ep 54
Miles and Mentors Trucking Podcast
What does it really take to build longevity in trucking, and how do you know who’s worth listening to? In this episode of Miles and Mentors: A Trucking Podcast, Chemistry Howard, better known as The Classy Trucker, shares her story of breaking into a male-dominated industry, going owner-op during the toughest years in trucking, and turning lived experience into mentorship. From making her first right turn to clocking over 3 million miles, Chemistry opens up about the mindset, mistakes, and mentorship that shaped her career. This episode is packed with hard-won truths for anyone looking to...
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Smart Hiring Strategies for Trucking Fleets with Rob Carpenter | A Trucking Podcast
Miles and Mentors Trucking Podcast
What’s the real risk behind a bad hire in trucking, and how do you avoid it? In this episode of Miles and Mentors: A Trucking Podcast, Rob Carpenter of Truck Safe returns with real-world advice for fleet owners navigating the challenges of hiring. From overlooked vetting steps to systems that prevent expensive mistakes, Rob outlines exactly how to build a safer, more reliable team from day one. We get into the shift from solo operator to fleet leader, the red flags that often go unnoticed, and the systems Rob uses to protect reputation, reduce liability, and avoid costly breakdowns both...
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From Dispatcher to Global Strategist with Wolfgang LaMarca | Ep 52
Miles and Mentors Trucking Podcast
What does it look like to rise from the dispatch desk to the top floor of global freight strategy? In this episode of Miles and Mentors: A Trucking Podcast, Wolfgang LaMarca joins us from Hong Kong to share his decades of logistics leadership across Europe, Asia, and the Americas. From his early days in local distribution to advising multibillion-dollar firms and startup founders, Wolfgang has seen it all and brings a rare, holistic view of how freight connects the world. We talk shop about real-world trucking, the evolution of tech like IoT and AI in logistics, and what it means to build both...
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Building a Fleet from Scratch in the U.S. with Bek from Bek Logistics | A Trucking Podcast
Miles and Mentors Trucking Podcast
What does it take to start over in a new country and build a successful trucking company from the ground up? In this episode of Miles and Mentors: A Trucking Podcast, Bek, founder of Bek Logistics and an immigrant from Uzbekistan, shares how he launched and scaled a fleet in the U.S. after starting in agricultural transport overseas. His journey, from exporting produce in Central Asia to running a multi-truck operation in America, is packed with insight, grit, and the kind of hard-earned wisdom every driver-turned-owner-operator should hear. From dealing with border customs abroad to...
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Producing Road-Ready Drivers with Ed Kimes and Darrell Spitzer | A Trucking Podcast
Miles and Mentors Trucking Podcast
What if CDL training wasn’t just about passing a test but preparing drivers for a lifetime on the road? In this episode of Miles and Mentors: A Trucking Podcast, Ed Kimes, CDL Program Director, and Darrell Spitzer, Dean of Workforce Education at Eastern Wyoming College, share how their college-based CDL program is setting a new standard for entry-level driver training. From mechanical foundations to mountain road readiness, Ed and Darrell explain why their students don’t just graduate. They roll out as professionals. This isn’t your typical truck school. With high instructor standards,...
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Building Freight Trust Through Transparency with Ryan Suydam | A Trucking Podcast
Miles and Mentors Trucking Podcast
What if the biggest competitive edge in freight isn’t rates or routes but trust? Too many freight professionals underestimate the power of reputation until it’s too late. In a high-stakes industry plagued by fraud and fragmentation, the ones who win are those who build trust first, transactions second. In this episode of Miles and Mentors: A Trucking Podcast, Ryan Suydam, agency owner at RKC Logistics under Armstrong Transport Group, shares what it means to be known as “The Trusted Freight Guy.” With over two decades of experience, Ryan dives into building resilient broker-carrier...
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Building a Load Board from Scratch with Nisrine Masri | Ep 47
Miles and Mentors Trucking Podcast
What if the most overlooked corner of the logistics industry held your next big opportunity? While most tech innovation in freight focuses on dry van or flatbed operations, Nisrine Masri saw a different gap. One that’s plagued moving and storage for decades: backhauls, fragmented labor sourcing, and outdated tools. With over 20 years in the industry and a passion for solving real problems, she built Movers Dispatch Board from the ground up. No outside funding, just grit and know-how. In this episode of Miles and Mentors: A Trucking Podcast, Nisrine shares how she transitioned from running a...
info_outlineWhat’s the real risk behind a bad hire in trucking, and how do you avoid it?
In this episode of Miles and Mentors: A Trucking Podcast, Rob Carpenter of Truck Safe returns with real-world advice for fleet owners navigating the challenges of hiring. From overlooked vetting steps to systems that prevent expensive mistakes, Rob outlines exactly how to build a safer, more reliable team from day one.
We get into the shift from solo operator to fleet leader, the red flags that often go unnoticed, and the systems Rob uses to protect reputation, reduce liability, and avoid costly breakdowns both mechanical and human.
Like what you hear? Be sure to like, subscribe, and share the show with others in the trucking world.
🎧 Episode Timestamps
📍 00:03:44 – Why hiring is the most overlooked risk for fleet owners
📍 00:04:50 – The hidden cost of bad hires: reputation, litigation, and loss
📍 00:05:12 – A real story that put Rob’s fleet at risk
📍 00:06:13 – The two biggest decisions that shape your business
📍 00:07:46 – How poor hiring ruined a past business venture
📍 00:09:46 – Insurance red flags and vetting that matters
📍 00:10:26 – What small fleets get wrong about risk
📍 00:10:52 – Rob’s “barriers first” approach to low-cost vetting
📍 00:12:18 – Why you must do road tests even if they have a CDL
📍 00:14:17 – Hidden risk: drivers failing other companies’ drug tests
📍 00:15:16 – The difference between PSP and MVR and why it matters
📍 00:17:10 – What violations matter most when screening drivers
📍 00:18:23 – Training or termination and how to judge coachability
📍 00:20:09 – What insurance companies look for in your driver file
📍 00:21:11 – The hidden traps during insurance renewal
📍 00:23:09 – How poor hiring raises costs for everyone
📍 00:24:44 – Will today’s trucking volatility reshape the industry
📍 00:27:58 – Why even old trucks now cost more than ever
📍 00:29:12 – How modern emissions systems kill reliability
📍 00:30:55 – The risks of auto-braking and overloaded electronics
📍 00:32:03 – AI-driven roadside inspections are already here
📍 00:33:35 – The pros and cons of fully automated enforcement
📍 00:35:22 – Can AVs really replace the working driver
📍 00:37:15 – How regulation or the lack of it is changing fleet risk
📍 00:38:00 – The future of enforcement, compliance, and fleet ownership
🎙 About Our Guest
Rob Carpenter is a safety and compliance expert, fleet owner, and founder of Truck Safe, a platform dedicated to helping trucking companies stay compliant and build safer fleets. Through consulting, content, and training, Rob has helped thousands of carriers better understand risk, regulation, and reputation in the modern trucking world.
Learn more at: https://trucksafe.com
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🎤 Want to be a guest or sponsor the show
Miles and Mentors is more than a podcast. It’s a movement of real stories, tactical advice, and mentorship to help the next generation of freight leaders succeed.
Reach out at: milesandmentors@gmail.com