What does it take to scale a business from 2 locations to 37 while keeping culture, trust, and freedom intact?

In this episode of The TrustBuilt Podcast, host Alan Bennett sits down with Jonathan Brooks, CEO of Warehouse on Wheels, to talk about how he’s built a self-sustaining business that runs without him at the center.

John shares his journey from accounting and private equity to leading a 37,000-trailer rental company, including:

Why owner-dependent businesses kill deals (and how to avoid it).

✅ How to use trust, emotional intelligence, and systems to build culture at scale.

✅ Why Extreme Ownership and Gallup’s Q12 framework anchor his leadership style.

✅ The connection between employee engagement and business value.

✅ What it really looks like to step away while your business thrives.

If you’re an exhausted owner looking for a business that can scale — and sell — without you, this episode is packed with real-world lessons.

🎙️ Subscribe for more conversations on how to build a business that runs without you 👉 www.youtube.com/@trustbuiltpodcast

⏱️ Chapters

00:00 – Why trust matters in private equity and leadership

01:00 – John Brooks’ career path

03:45 – Building Warehouse on Wheels: 2 locations to 37,000 trailers

04:15 – Using Gallup Q12 to measure and improve culture

06:00 – Shifting from data-driven CFO to emotionally intelligent leader

08:00 – Creating a learning & development department for employees

10:00 – Extreme Ownership as a foundation for decision-making

12:00 – Interview questions that reveal motivation and fit

13:00 – Hiring for attitude vs. aptitude

15:00 – What Warehouse on Wheels actually does

16:00 – Ritz-Carlton service at the Hampton Inn price

18:00 – Scaling through acquisitions & greenfield markets

19:15 – Onboarding new hires with culture and ownership

23:15 – Field training exercises & experiential learning

26:00 – Equity & reward structures that drive buy-in

27:30 – Building competency and succession into the business

30:00 – Scaling easier once trust systems are in place

33:40 – Agility and empowering local market CEOs

35:20 – Trust + culture = engaged employees & loyal customers

37:00 – Could the business run without John Brooks? (succession planning)

39:00 – Vision: 100,000 trailers, 100 locations

42:00 – Owner dependence kills deals (and how to avoid it)

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Connect With Jonathan & Warehouse on Wheels

🌐 https://wowtrailers.com/

💻 https://www.linkedin.com/in/jnbrooksiv/

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Are you a business owner who is ready to break free from the day-to-day grind & build a self-sustaining company?

👉 Set up a time to talk to Alan

🔗 https://www.trustbuiltsolutions.com/contact

Do you ever wonder if your business could run without you?

In this episode of The TrustBuilt Podcast, host Alan Bennett interviews Steven Schmitt of Willow Financial, about building a trust-driven business that thrives even when the owner steps away.

Steven shares his real-world experience of going from sleepless nights as a solo founder to creating a team and systems that allow his firm to grow without constant oversight. From how to trust your team, to creating business systems that work, to succession planning and exit strategies, this episode is packed with insights for business owners who want freedom from the daily grind.

Whether you’re looking to scale your company, prepare it for sale, or simply take a real vacation without everything falling apart—this conversation will give you practical strategies to build a self-sufficient, owner-independent business.

🎙️ Subscribe for more conversations on how to build a business that runs without you.

00:00 – Radical Trust: Why Willow Shares a Company Inbox

02:42 – From Solo Founder to Building a Scalable Firm

05:22 – Creating “Light Bulb” Moments for Clients

09:41 – Sleepless Nights and Entrepreneur Pressure

11:26 – Hiring Your First Team Member (and Lessons Learned)

13:05 – Planning for Succession & Exit Strategy

15:02 – Building Trust with Clients and Teams

17:17 – Why Transparency Builds Business Value

21:27 – Onboarding Clients with Clarity

23:24 – Helping Owners Face Estate & Succession Planning

27:21 – What the “Right Client” Looks Like

29:31 – Passion, Purpose & Trust Beyond Yourself

31:17 – What Steven Would Do Differently

32:10 – How Willow Uses AI as a Business Thought Partner

34:53 – How to Connect with Steven

Are you a business owner who is ready to break free from the day-to-day grind & build a self-sustaining company?

👉 Set up a time to talk to Alan

🔗 https://www.trustbuiltsolutions.com/contact

business that runs without you | how to trust your team | business systems and processes | succession planning small business | owner independent business

If you're an entrepreneur craving freedom, purpose, and a team you can trust, this episode is for you.

Jessica Crum, founder of Silverlake Design Studio, shares her incredible journey from the high-pressure world of Los Angeles fashion to building a thriving marketing agency in Arkansas.

In this inspiring conversation Jessica opens up about career pivots, the real struggles behind entrepreneurship, building a mission-driven brand, and stepping away from hustle culture to create a sustainable, impact-driven business.

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🔗 Connect with Jessica & Silverlake Design Studio

🌐 https://silverlakestudio.com/

LinkedIn: https://www.linkedin.com/in/jessica-crum/

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Are you a business owner who is ready to break free from the day-to-day grind & build a self-sustaining company?

👉 Set up a time to talk to Alan

🔗 https://www.trustbuiltsolutions.com/contact