Welcome to This Week In Trucking! In this episode, Caroline sits down with Jamie Hagen, owner of Hellbent Express, for a deep dive into the real numbers and realities of running a trucking business in today’s market. Jamie shares his journey from being a lifelong driver to building a fleet, discusses the challenges of 2020, and breaks down the true costs of operating trucks, including equipment, insurance, fuel, maintenance, payroll, and more. Learn how Jamie navigates tight profit margins, sources and retains great drivers, manages safety and compliance, and adapts to industry changes. 🔴DON’T FORGET TO SUBSCRIBE!🔴 Have questions for Jamie or want to share your own experiences? Drop them in the comments below! Don’t forget to like, subscribe, and hit the bell for more real-world trucking business content. 👉Sign up for This Week In Trucking's FREE newsletter! We break down the hottest freight markets by equipment type, plus interviews with carriers sharing their real cost per mile and PROFITS. ✅ http://www.bobtail.com/newsletter ⏰ Chapters: 00:00 – Introduction & Welcome 00:19 – Jamie’s Background & Hellbent Express Story 01:05 – Starting a Trucking Business in 2020 02:25 – Fleet Size, Equipment, and Freight Types 03:36 – Surviving Market Ups and Downs 05:30 – Cost Breakdown: Trucks, Trailers, and Insurance 07:19 – Recruiting & Retaining Drivers 10:24 – Dispatching, Safety, and Wearing Many Hats 13:31 – Factoring, Payroll, and Owner Compensation 16:00 – Fuel, Maintenance, and Managing Expenses 19:00 – Parking, Compliance, and Hidden Costs 21:36 – Profit Margins & Real Numbers 23:58 – Advice for New Owner-Operators 27:25 – The Importance of Mental Health & Resilience 29:00 – Final Thoughts & How to Ask Jamie Questions GET STARTED 🌍 Our website: https://www.bobtail.com/ 🌍 Sign up for factoring: https://www.bobtail.com/contact-us/ 🌍 Sign up for a fleet card: https://www.bobtail.com/fleet-card/ JOIN OUR COMMUNITY 📸 Instagram: bobtailcapital ABOUT US Bobtail is a financial services company dedicated to helping carriers manage cash flow, fuel expenses, and operations efficiently. Co-founded by Gurvir Singh, Bobtail offers factoring, fuel savings, and load management solutions tailored for small trucking businesses. Caroline Asiala, Bobtail’s marketing manager, hosts in-depth conversations with carriers and industry experts, breaking down real company numbers and sharing valuable insights to help trucking businesses succeed. If you have any questions regarding our services such as factoring or fuel card, please send us an email at hello@bobtail.com #trucking #owneroperator #truckingbusiness #truckingindustry #truckinglife #boxtruckbusiness #hotshottrucking #truckingtips #truckingInsights #freighttrends #dieselprices #diesel #fuelupdate #truckerpodcast #truckingpodcast #podcast #trucker #Transportation #Logistics #HellbentExpress #ThisWeekInTrucking Tune in on YouTube, Apple Podcasts and Spotify!
