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.

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⏰ 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

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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 

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