The Miles and Mentors Trucking Podcast

Marketing That Actually Works for Owner-Operators with Webster Jorgensen | Ep 57

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 why marketing doesn't need to be complicated to work. We also talk about when it makes sense to outgrow DIY platforms, how to avoid getting lost in SEO jargon, and why community relationships can be just as valuable as backlinks. Like what you hear? Be sure to like, subscribe, and share the show with others in the trucking world. 🎧 Episode Timestamps 📍 00:01:19 – How Webster got into logistics marketing and grew with Shamrock Trading 📍 00:02:49 – Lessons from building Demand Stack and staying connected to brokerage clients 📍 00:07:15 – Why trucking's market cycles change how marketing performs 📍 00:08:20 – Reading capacity trends before blaming your marketing 📍 00:12:05 – SEO explained simply for new trucking companies 📍 00:13:32 – Two easy wins: claim your Google Business Profile and build a basic website 📍 00:14:59 – Picking a business name people can actually find 📍 00:17:12 – How reviews and responsiveness build trust for referrals 📍 00:18:05 – Why even referrals still Google you 📍 00:21:18 – When it's fine to start with Wix or GoDaddy and when to move on 📍 00:27:31 – The one marketing move every owner-operator should prioritize 📍 00:29:35 – Networking, chambers, and relationships that boost SEO naturally 📍 00:33:54 – Using CRM, ZoomInfo, and automation without overwhelming your team 📍 00:37:51 – Webster's short checklist for small trucking businesses 📍 00:38:37 – Where to find Webster and Demand Stack online 🎙 About Our Guest Webster Jorgensen is a marketing veteran who led digital strategy at Shamrock Trading before founding Demand Stack, a marketing and web design agency that helps carriers and brokers grow smarter. With expertise spanning SEO, paid media, and data-driven sales operations, he continues to guide logistics companies toward measurable growth. Learn more at: https://demandstack.io [https://demandstack.io] 🔗 Follow Miles and Mentors: A Trucking Podcast Website: https://milesandmentorspodcast.com [https://milesandmentorspodcast.com] Facebook: https://www.facebook.com/milesandmentors [https://www.facebook.com/milesandmentors] LinkedIn: https://www.linkedin.com/company/miles-and-mentors-podcast [https://www.linkedin.com/company/miles-and-mentors-podcast] YouTube: https://www.youtube.com/@MilesandMentors [https://www.youtube.com/@MilesandMentors] 🎤 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

Helping Drivers Think Like Business Owners with Annique Lesage | Ep 56

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 authority or looking to sharpen your strategy, this episode delivers no-nonsense insight. If you're serious about turning your trucking experience into a business that lasts, this is a must-listen. 🎧 Episode Timestamps 📍 00:01:13 – From biology degree to logistics: how Annique entered the industry 📍 00:02:06 – Learning customs, LTL, and making the leap to sales 📍 00:03:45 – How transferable skills shape long-term success 📍 00:04:39 – Why most big brokers don't really teach you how to broker 📍 00:05:02 – Mentorship that wasn't soft but changed everything 📍 00:06:38 – Turning a "wasted" degree into entrepreneurial fuel 📍 00:08:22 – Flexibility, relationships, and choosing freight on purpose 📍 00:09:17 – The mindset behind turning unlikely odds into wins 📍 00:12:11 – The difference between mentorship and competition 📍 00:13:00 – Why poor broker training hurts the entire industry 📍 00:14:48 – Training is a perennial, not a one-off 📍 00:16:15 – Use discernment because not everyone wants to see you win 📍 00:18:21 – Look at the whole picture before taking advice 📍 00:19:25 – The biggest misconceptions carriers have about brokers 📍 00:21:31 – Why insulting the shipper's intelligence kills trust 📍 00:22:57 – Entry and exit strategies for new owner-operators 📍 00:24:08 – Drivers must act like business owners, not just show up 📍 00:26:03 – One bad pitch can ruin your company's reputation 📍 00:27:10 – Real prep: attorneys, dispatchers, accountants, and planning 📍 00:30:03 – Specialization beats being a jack of all trades 📍 00:31:15 – Know your lanes, know your profit, and price accordingly 📍 00:32:36 – Reefer, flatbed, and picking the right equipment for your goals 📍 00:35:17 – Why fairness matters more than squeezing the market 🎙 About Our Guest Annique Lesage is the founder and owner of Small World Ventures LLC, a boutique freight brokerage known for combining hands-on service with smart use of technology. With 20 years in the industry, she brings deep experience from both the shipper and broker side. Today, she mentors others in the freight space looking to operate with integrity and strategic focus. 🔗 LinkedIn: https://www.linkedin.com/in/anniquelesage/ [https://www.linkedin.com/in/anniquelesage/] 🔗 Follow Miles and Mentors: A Trucking Podcast Website: https://milesandmentorspodcast.com [https://milesandmentorspodcast.com] Facebook: https://www.facebook.com/milesandmentors [https://www.facebook.com/milesandmentors] LinkedIn: https://www.linkedin.com/company/miles-and-mentors-podcast [https://www.linkedin.com/company/miles-and-mentors-podcast] YouTube: https://www.youtube.com/@MilesandMentors [https://www.youtube.com/@MilesandMentors] 🎤 Want to be a guest or sponsor the show? Miles and Mentors is a platform for real stories, practical guidance, and meaningful mentorship across the trucking industry. 📧 Reach out at: milesandmentors@gmail.com

You Signed Up for This with Chris Jolly | Ep 55

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 brokerage, scaling a fleet, or just trying to keep your business moving, this episode is packed with real-world advice and operational clarity. If you're an owner-operator, aspiring broker, or industry pro trying to get traction, this one delivers. 🎧 Episode Timestamps 📍 00:01:41 – Why Chris launched The Freight Coach and what's broken in freight media 📍 00:02:50 – Growing up in a trucking family and how it shaped his path 📍 00:04:06 – "Work with your brain, not your back" and other dad wisdom 📍 00:06:25 – Why industry change must come from within 📍 00:10:27 – Core values at Freight Coach Logistics: Do the right thing 📍 00:11:55 – Standard operating procedures every broker should follow 📍 00:13:01 – What carriers should expect from a real partnership 📍 00:15:01 – Why brokers must specialize, not generalize 📍 00:17:19 – $60 billion in flatbed and why most are missing the opportunity 📍 00:21:00 – Building long-term carrier relationships during down markets 📍 00:22:37 – Why cash flow is non-negotiable for business survival 📍 00:24:11 – How factoring fits in a real financial strategy 📍 00:28:11 – How to trim expenses when the budget gets tight 📍 00:31:11 – The difference between real mentorship and online noise 📍 00:35:00 – Creating space for voices beyond the top 10 percent 📍 00:36:23 – What good mentorship actually looks like 📍 00:40:45 – Starting a brokerage today: what no one wants to say 📍 00:44:00 – The "add five" mindset that keeps his sales engine running 📍 00:45:01 – Industry outlook for 2026 and why interest rates matter 🎙 About Our Guest Chris Jolly is the founder of Freight Coach Logistics and host of The Freight Coach podcast. With nearly 20 years of experience in transportation and deep roots in a multigenerational trucking family, Chris offers no-nonsense insight into brokerage operations, driver relations, and what it really takes to succeed in freight. 🔗 Connect with Chris Website: https://www.thefreightcoach.com [https://www.thefreightcoach.com] LinkedIn: https://www.linkedin.com/in/chrisjollyfreightcoachhttps://www.linkedin.com/in/chris-jolly-a183aa6a/ 🔗 Follow Miles and Mentors: A Trucking Podcast Website: https://milesandmentorspodcast.com [https://milesandmentorspodcast.com] Facebook: https://www.facebook.com/milesandmentors [https://www.facebook.com/milesandmentors] LinkedIn: https://www.linkedin.com/company/miles-and-mentors-podcast [https://www.linkedin.com/company/miles-and-mentors-podcast] YouTube: https://www.youtube.com/@MilesandMentors [https://www.youtube.com/@MilesandMentors] 🎤 Want to be a guest or sponsor the show? Miles and Mentors is a platform for real stories, practical guidance, and meaningful mentorship across the trucking industry. 📧 Reach out at: milesandmentors@gmail.com

From First Turn to Fleet Wisdom with Chemistry Howard | Ep 54

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 drive smarter, lead with integrity, and stay in the game long term. Like what you hear? Be sure to like, subscribe, and share the show with others in the trucking world. 🎧 Episode Timestamps 📍 00:02:40 – When her trucking dream began: Grandpa, chrome, and a cape 📍 00:05:08 – The moment she knew she could do it: clearing that first right turn 📍 00:06:51 – What 3 million miles have taught her about fear and resilience 📍 00:08:00 – Why trucking is a physical, mental, and spiritual journey 📍 00:09:15 – The 10-year rule for whose advice you should listen to 📍 00:10:21 – A Pepsi dock, a 7-minute back-in, and a silent bet 📍 00:12:50 – The super truckers are gone. The students are still on the road 📍 00:14:06 – How mentorship changed everything 📍 00:15:39 – Driving with humility and the real cost of one bad choice 📍 00:16:55 – Why GPS can't replace an atlas 📍 00:20:17 – From driver to owner-op and facing the business side 📍 00:23:10 – $11K for tires and what people get wrong about owning a truck 📍 00:26:02 – Why relationships are the secret weapon in trucking 📍 00:28:17 – You don't have a business. You have a truck payment 📍 00:30:21 – The pressure to delay maintenance and why it's a bad bet 📍 00:34:14 – What $30K in fuel system damage taught the fleet 📍 00:36:40 – The myth of instant trucking wealth 📍 00:37:32 – Understand your paperwork or prepare to fail 📍 00:39:05 – Why we all take freight for granted and shouldn't 📍 00:40:11 – If it's in your heart and you want to do it, baby, do it 📍 00:40:46 – Her mission behind The Classy Trucker and Velocity 🎙 About Our Guest Chemistry Howard, aka The Classy Trucker, is a veteran driver, speaker, and confidence coach with over a decade on the road. She's driven over 3 million miles, mentored countless new drivers, and now leads The Classy Trucker platform and Velocity, a series spotlighting women thriving in male-dominated industries. Connect with Chemistry: Facebook: https://www.facebook.com/theclassytrucker [https://www.facebook.com/theclassytrucker] TikTok: https://www.tiktok.com/@theclassytrucker [https://www.tiktok.com/@theclassytrucker] YouTube: https://www.youtube.com/@TheClassyTrucker [https://www.youtube.com/@TheClassyTrucker] 🔗 Follow Miles and Mentors: A Trucking Podcast Website: https://milesandmentorspodcast.com [https://milesandmentorspodcast.com] Facebook: https://www.facebook.com/milesandmentors [https://www.facebook.com/milesandmentors] LinkedIn: https://www.linkedin.com/company/miles-and-mentors-podcast [https://www.linkedin.com/company/miles-and-mentors-podcast] YouTube: https://www.youtube.com/@MilesandMentors [https://www.youtube.com/@MilesandMentors] 🎤 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

Smart Hiring Strategies for Trucking Fleets with Rob Carpenter | A 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 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 🔗 Follow Miles and Mentors: A Trucking Podcast Website: https://milesandmentorspodcast.com [https://milesandmentorspodcast.com?utm_source=chatgpt.com] Facebook: https://www.facebook.com/milesandmentors [https://www.facebook.com/milesandmentors] LinkedIn: https://www.linkedin.com/company/miles-and-mentors-podcast [https://www.linkedin.com/company/miles-and-mentors-podcast] YouTube: https://www.youtube.com/@MilesandMentors [https://www.youtube.com/@MilesandMentors] 🎤 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