How Jonathan Brooks Built a 37,000-Asset Business with Trust-Driven Teams
Most business owners I talk to want the same thing: growth, freedom, and a team they can actually count on. But too often, they end up stuck as the hub of the wheel—every decision, every fire, every problem runs through them. It’s exhausting, and it’s not sustainable.
That’s why my conversation on The TrustBuilt Podcast with Jonathan Brooks, CEO of Warehouse on Wheels, was so powerful. Jonathan has scaled his company from two locations to 37, with 37,000 trailers in operation, and he did it by focusing on people, culture, and trust as much as he focused on the numbers.
So, how does someone go from “recovering CFO” to running a nationwide, self-sustaining business? Here are some of the best lessons from our conversation.
1. Trust Is the Real Growth Engine
John started in accounting and private equity, where the numbers always come first. But over time, he realized data isn’t enough. If you want a business to scale, you have to invest in trust and culture with the same intensity you put into financial performance.
At Warehouse on Wheels, John surveys employees twice a year using Gallup’s Q12 framework, asks them for their best ideas, and—this part is key—responds to every single comment. That level of engagement creates buy-in at scale.
2. Hire for Attitude, Not Just Aptitude
John shared two interview questions he asks every candidate:
What’s a day in the last 90 days you went home saying, “This is why I do this”?
What’s a day you went home saying, “I hate this”?
The answers reveal more than a resume ever could. He’s looking for motivation and fit, not just technical skills. Pair that with tools like the Birkman assessment, and you get teams who actually want to be there—and stay.
3. Train Leaders to Own the Mission
John grounds his company’s leadership style in Extreme Ownership, the book by Jocko Willink and Leif Babin. Every new manager reads it, discusses it, and even trains on it. He takes leaders through experiential field exercises that force them to apply the principles under pressure.
Why? Because when you’ve practiced leading in high-stakes scenarios, handling a client crisis or a tough decision at work doesn’t rattle you. The result? Local market “CEOs” who are empowered to run their branches with autonomy, accountability, and buy-in without waiting on orders from the top.
4. Give People a Stake in the Outcome
Jonathan believes that everyone on his team should feel the upside of success. That’s why every employee has a form of equity in the business.
When the company wins, everyone wins. That shared reward structure is what turns employees into teammates—and teammates into owners of the mission.
5. A Self-Sustaining Business Starts with Strong Teams
Here’s the kicker: Jonathan has built a business that would keep running even if he stepped away. And that’s not an accident.
By empowering leaders, engaging employees, and embedding culture at every level, he’s created a structure that’s bigger than one person.
Why This Matters for Your Business
If you’ve ever felt stuck in the weeds, unable to trust your team to carry the load, Jonathan’s story is proof that it doesn’t have to be that way.
The path to freedom, growth, and, yes—eventually — a more valuable business starts with building teams that take ownership.
Listen to the full episode with Jonathan Brooks here and learn how to start building a team you can trust to step up—not let you down.
Want to build a trust-driven team of your own? Let’s talk.
That’s what we do every day at TrustBuilt—helping owners build businesses that thrive because their teams are engaged, empowered, and ready to take the lead.
