Episode 4 of the Miles and Mentors Podcast features Rob McCutcheon, Vice President of Strategy and Growth at TAFS, a company specializing in transportation factoring and support for small and mid-sized carriers. Rob entered the industry with a background in college athletics and marketing—hardly the traditional route into logistics—but over the last eight years, he has become a trusted voice in trucking finance and mentorship. His journey gives him a unique perspective that resonates with both first-time owner-operators and established fleet owners trying to scale responsibly.
What follows are the core business and mentorship lessons Rob offered during the episode, expanded into practical advice for trucking entrepreneurs. These insights are drawn directly from the episode and validated against top-performing organic search content to ensure this blog can stand out in a competitive SEO landscape.
Surround Yourself with Mentors or Prepare to Learn the Hard Way
Rob didn’t mince words about how important mentorship is to surviving the trucking business. He emphasized that while most new trucking business owners know how to drive, few are prepared to run a business. Without guidance, they quickly face a wall of challenges—financial, operational, regulatory—that can derail even the most motivated entrepreneurs.
“If you don’t surround yourself with people who have done this before… the failure rate is just so high.”
Rob’s advice mirrors what’s found in leading trucking mentorship articles: mentors shorten the learning curve, help new owners avoid costly mistakes, and can offer practical shortcuts in areas like equipment decisions, compliance, and negotiating freight.
For your blog, this positions you to target keywords like trucking business startup help, trucking mentorship program, and how to start a trucking company successfully.
Factoring Is Not Just About Cash Flow—It’s About Business Resilience
Rob offered a detailed breakdown of how factoring works, but what stood out wasn’t just the financial mechanism—it was how factoring companies like TAFS acts as strategic partners.
He explained that waiting 30–90 days to get paid for a load can cripple a small carrier, especially when fixed costs like fuel and insurance stack up weekly. But beyond solving the cash gap, factoring companies can give carriers access to consultants, compliance experts, and fuel discounts that help them grow faster and avoid pitfalls.
“Our goal as a factoring company is to help with that piece and be a sounding board… to help somebody get to the next level.”
When written as a lesson, this shifts factoring from being a misunderstood cost to a form of mentorship and infrastructure for small carriers. It allows us to target trucking finance, factoring for trucking, and cash flow tips for owner operators.
You’re Not Just a Driver Anymore—You’re Building a Brand
Rob’s background in marketing really came through when he spoke about branding in trucking. His perspective was a reminder that every owner-operator is not just delivering freight—they’re representing a business. He covered everything from phone etiquette to dressing professionally at shippers’ docks to having a logo on your cab.
“Even simple things like the way you answer your phone—‘Hey, this is Alex from ABC Trucking’—that’s your brand.”
This is a critical mindset shift for drivers transitioning into business ownership. Rob explained how these small moments build trust and credibility, especially when brokers and shippers are deciding who to work with again. There’s an opportunity here to produce content that competes well with owner operator marketing tips, how to build a trucking brand, and professionalism in trucking.
Build a Business Plan and Know Your Numbers
Many new carriers jump into the business with passion but no plan. Rob recommended starting with a real business plan—even if it’s simple. He emphasized the importance of understanding both fixed and variable costs, identifying your ideal customer, and knowing what makes your business different.
“Some small things you can think about… what is it that makes me unique? What are you going to provide that they’re not going to get from someone else?”
Incorporating this lesson will let you rank for keywords like trucking business plan, starting a trucking company, trucking startup costs, and how to be profitable as an owner operator.
Use Your Resources Wisely and Ask Every Question
One of Rob’s final points may seem simple, but it’s often missed: ask questions before you sign anything. Whether it’s a factoring agreement, lease, or contract with a broker, he urges business owners to make sure they truly understand the fine print. He described how many new carriers accidentally waive rights or sign into agreements they don’t fully grasp—because they didn’t feel empowered to ask.
“Make sure you ask as many questions as you possibly can… so you understand the nuances of it.”
This positions you to create a practical resource around contracts in trucking, understanding factoring agreements, or even questions to ask before you haul for a broker.
Want Help from Experienced Trucking Mentors?
Rob’s episode is proof that mentorship comes in many forms—from one-on-one relationships to vendor partnerships that offer more than just a service. If you’re building your trucking business and looking for a network of experienced professionals to learn from, we’re here to connect you.
