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In this solo, highly personal episode of To The Point Home Services, Chris gets real about one of the most defining seasons of his entrepreneurial journey: what it truly feels like to shift from playing offense to playing defense after selling your business.
This episode is raw, reflective, and deeply relevant for founders, operators, and leaders at any stage, especially those who have sold (or are considering selling) part or all of their company. Chris breaks down the emotional, strategic, and cultural realities of private equity, leadership transitions, and what happens when control, identity, and energy collide.
Whether you are building, scaling, exiting, or questioning your next move, this conversation will challenge how you think about growth, leadership, and what it really means to win in business.
Offense vs. Defense: The Founder Shift No One Warns You About
Chris opens the episode by defining what “playing offense” has always meant to him as a founder. Offense is forward motion. It is creativity, opportunity, momentum, and the constant pursuit of growth. He admits he has never been the stereotypical operations-focused leader. His strength has always been driving the business forward, understanding how customers buy, staying competitive, and building something that wins in the marketplace.
Offense is being able to move at your own speed. It is building relationships, creating new opportunities, showing up on stages, working relentlessly, and pushing the company into the future. That energy is what made his company what it became, but everything changed after the private equity deal.
The decision to partner with private equity was not about cashing out. It was about scaling. Chris and Anna spent 14 months searching for the right partner. They believed in the leadership at the time and respected the CEO who helped earn their trust. But what Chris did not anticipate was how quickly leadership could shift, and how much that shift could change everything.
Playing defense, in Chris’s words, “sucked.”
Instead of building, he felt like he was protecting. Instead of accelerating, he felt like he was bracing for impact. Chris describes defense as the moment when new development stops. When your instinct is no longer to create, but to shield what already exists. That was the hardest part.
- What “playing offense” means as a founder
- What playing defense feels like in a PE-owned company
- Losing control, leadership shifts, and gut instincts
- Culture vs efficiency and leadership misalignment
- Identity, energy, and weekly life on offense vs defense
- Culture, employees, and why people matter most
- What founders are most naïve about when selling
- Navigating private equity partnerships: expectations vs reality
- And more!
Chris and Anna never built the company with dollar signs as the motivator. The driver was always doing right by the customer, and just as importantly, taking exceptional care of employees. Chris makes the point clearly: you cannot scale without your people. In fact, they are more important than the customers. If you lose your integrity in how you treat your team, you lose the foundation of everything.
Get Back On Offense
Chris believes most founders underestimate themselves, but also misunderstand what it takes to reach the next stage. He knew he was built for the early stages. He and Anna had built a machine. They knew the levers. They were ahead of the market. The clients were happy. The business worked. But beyond that? The jump from 50 to 100 felt unclear at the time.
Today, Chris says it is crystal clear. And the biggest blessing of the last two and a half years has been the education. Seeing how massive businesses scale, building relationships with leaders further ahead, gaining perspective through peer groups, and understanding what real growth requires. The lesson is not that private equity is always wrong. There are plenty of success stories. The lesson is that if you cannot see what is ahead, you need help, mentorship, and proximity to people who have done it before.
If you’re feeling like you’re always on defense, find a way to get back on offense as quickly as possible. Sometimes cutting the cord is worth the cost because in the end, how you make your money matters more than how much you make. That is integrity. And it is not something you can afford to lose.
Until next time…NO. ZERO. DAYS.
