Will Wilson

Will Wilson – Rebuilding a Thriving Business With Servant Leadership

Will Wilson is the CEO of Tennessee Cheesecake, which crafts custom desserts for the food service industry. He grew up in the business after his mother founded it in 1981. For over 15 years, Will has led Tennessee Cheesecake from a product-centric to a service-oriented company, focusing on team development and adaptability.

Here's a Glimpse of What You'll Learn

[1:50] Will Wilson shares his background and how his mother started Tennessee Cheesecake
[6:14] Will’s early involvement in Tennessee Cheesecake
[10:55] The decision to address and transform a toxic company culture
[14:45] How EO shaped Will’s leadership development
[16:32] Tennessee Cheesecake’s strategic endeavors, including acquiring a pie company
[23:46] Challenges of managing seasonal demand and maintaining consistent operations year-round
[25:55] Will talks about life before EO and how he discovered his passion for servant leadership

In This Episode

Many entrepreneurs find themselves stuck in chaos juggling growth, operations, and team management without stepping back to assess the emotional pulse of their company. How can you rebuild a thriving business culture when you realize it’s broken, and you might be the reason why?

For second-generation business leader Will Wilson, the turning point in his company came when he recognized that his team was struggling under a culture he didn’t realize had gone sour. He transitioned from a problem-solver to a servant leader focused on empowering others. After navigating a chaotic manufacturing environment, Will built a culture rooted in accountability, improvement, and trust. He credits EO and EOS for helping him prioritize team growth, create strategic clarity, and break seasonal cycles by reinvesting in his people and processes.

Join Robert Hartline in today’s episode of The Decision as he sits down with Will Wilson, CEO of Tennessee Cheesecake, to discuss how he transformed his leadership and company culture. Will talks about developing his team, overcoming burnout cycles, and finding strength through EO.

Quotable Moments:

“The greatest leaders that I know don’t push any rocks; they teach their whole team how to push.”
“You just don’t know what you don’t know, and that happens with all business, right?”
“Be happy for your problems; your problems are an opportunity to improve.”
“Every time I have given, I have always received, and I have taken that to the next level.”
“We just have this incredible improvement culture… everybody’s an improver, and that’s how you get really good.”

Action Steps:

Shift from problem-solving to people development: Focusing on growing your team builds long-term capability and reduces burnout. Empowered employees take ownership and contribute to a healthier, more resilient culture.
Embrace a continuous improvement mindset: Small, consistent improvements compound over time and create meaningful progress. This approach also encourages team engagement and accountability at every level.
Seek out peer networks like EO: Learning from other entrepreneurs provides perspective, accountability, and new ideas you might not discover alone. It also combats the isolation many business owners feel.
Use systems like EOS to align your team: Frameworks like EOS help define priorities, track performance, and create clarity. This structure makes it easier to scale without losing focus or control.
Invest in leadership training and forums: Developing leadership capacity within your organization builds a stronger foundation for sustainable growth. Forums also help leaders build confidence and improve decision-making.