Some freight careers start out with a pretty solid plan. Preston’s didn’t. He wasn’t chasing logistics in high school or studying supply chain in college. Instead, he found this industry almost by accident, while he was looking for a sales job that would reward him for the hard work he put into it. Years later, he’s now built a growing agency at Tallgrass with a book of business that keeps climbing alongside a back office he genuinely trusts. Here’s how he got there.
Life Before Tallgrass
When Preston graduated from college, he knew he wanted more than bartending and waiting tables, so he looked for a sales role with real training and real pay. That search landed him at a large 3PL, where he took a pay cut just to get his foot in the door.
The pivot paid off at first. Within a year, Preston had already hit an elite tier for new hires and established a strong base of customers. But about a year and a half in, the commission structure completely shifted under him. Preston was still hitting big numbers — with nothing to show for it.
“It was frustrating,” he admits. “But I’m thankful for it now, because it made me start asking questions my peers never asked, like, is this really what the industry is like? Is this all there is? I knew there had to be something better out there.”
Preston left for an agent-model brokerage in Chicago, where he started from scratch. Within a couple of years, he’d built a team of over 20 people and grown the operation past $6 million in annual revenue. He ran the office — including hiring, managing sales and more — essentially doing everything except owning the book he’d established.
As the company started moving in a different direction from what he envisioned for his career, Preston started to get curious about what was next. “I started thinking to myself, I should probably do this for myself,” he shares. He circled back to an agency program where he crushed it, even earning Rookie of the Year. But some things happened along the way that left a bad taste in his mouth, so Preston found himself wanting more integrity from the back office. He decided to explore other agency programs, this time more carefully.
Where He Landed: Growing with Tallgrass
Word of Tallgrass reached Preston twice in the same week — once through his own research, and once via a former colleague who’d heard an agent rave about the company at a bar in Chicago. “It felt like the world kind of aligned,” he laughs. He got to work: asked around, talked to current Tallgrass agents, researched online and got better feedback than he’d heard about any other program, which sealed the deal for him.
Preston started strategically, bringing on one small customer, then another, building trust in the Tallgrass name and in himself. Within six months, he grew tremendously, prompting him to make his first operations hire. TGF’s onboarding made the transition simple.
He closed his first year well past the Club 250 mark, and picked up another Rookie of the Year title along the way. This year, he’s on pace for roughly 25% more volume and margin than last, which is no small feat, given everything going on in the economy. In under two years, he’s taken his book from nothing to a half-million-dollar business, with his team still growing.
Why Tallgrass?
Preston’s biggest hesitation about making another move? Ensuring history doesn’t repeat itself. The communication gaps, the disconnect — those were the things that had previously worn him down. He made sure to lay it all out for Sean and Jordan, who reassured him that wasn’t how Tallgrass operates. “So far, Tallgrass has exceeded all of my expectations,” he says.
Preston moves a lot of fragile freight, which means claims can be a near-weekly reality. That’s exactly where he says the back office shows up most. “They handle claims like it’s their own account,” he shares, pointing to Alyssa on the claims team, who chases down insurance companies and keeps customers in the loop so he doesn’t have to.
On the credit side, he can go straight to Ryan and make the case for a customer he trusts, rather than getting an automatic no. Knowing his team has it covered means Preston can stay focused on his day-to-day and keep the money coming in, instead of getting pulled into everything himself.
The CRM has been a huge asset for him too. Preston says it keeps his business moving and makes training new hires a breeze. That kind of access, paired with peers who genuinely pull for each other instead of circling each other’s accounts, is what keeps Preston at Tallgrass. “I know everybody by name that I need help from,” he says. “My account matters here. I matter here.”
What’s Stopping You?
Preston’s advice for anyone eyeing a career move is to do your homework. Ask other agents about carrier relationships, pay terms, and how customers view the brokerage. “If it checks all of those boxes for you, that’s probably the place to go,” he says.
If you’re ready to take ownership of your career and build something that’s truly yours, we’d love to talk. Reach out to our team today to learn more about becoming a freight agent with Tallgrass.