Building a company mirrors the complexities of a relationship. Through selling my first company and navigating a divorce, I’ve discovered profound lessons about how your first business—like your first marriage—shapes and prepares you for the next chapter.
But let me be clear: I’m not advocating for divorce—in life or business. These comparisons are meant to highlight lessons learned and provide insights for first-time CEOs, founders, and employees about the unique challenges and opportunities that come with different stages of entrepreneurship.
Your First Marriage: Falling in Love and Finding Yourself
Your first marriage is often about discovery and experimentation. You fall in love, build a life together, and immerse yourself in family activities—PTA meetings, sports, and milestones. It’s exciting, but it’s also where you figure out who you are.
The same applies to your first company:
Brand Love: You’re passionate about building the company’s image, sponsoring community events, and creating a name that resonates. I remember the pride of sponsoring my kids’ games under my company’s name—it felt like a milestone.
All-In Culture: Your company feels like an extension of your family. It’s personal, emotional, and all-encompassing.
Workplace Therapy: This is where I coined the term Workplace Therapy.
Coining Workplace Therapy
In a first company, the culture often prioritizes the emotional needs of employees over the operational needs of the business. As a founder, you act as a therapist—solving team dynamics, fostering emotional support, and making the workplace feel like a second home.
Here’s the challenge: Workplace Therapy prioritizes employees over the CEO and the company itself. It becomes a liability when scaling because founders often struggle to make tough decisions that prioritize long-term goals over short-term harmony.
Scaling requires clarity and operational efficiency, but when the focus remains on keeping everyone happy, decisions like restructuring teams, reallocating resources, or letting go of underperformers become almost impossible. This leads to stagnation and limits growth.
I’ve seen this pattern repeatedly while consulting with CEOs. For many founders, their first company feels like a child—something they nurture with unwavering passion. But just like raising children, there comes a point where separation is healthy and necessary for growth. A company must stand on its own, separate from the founder’s identity, to thrive.
Transitional Partners
In the early days of a business, multiple founders often bring diverse skillsets and equal enthusiasm. Over time, however, one partner may emerge as more critical to the business’s success. Meanwhile, other owners or partners brought on along the way may no longer serve the company’s evolving needs.
This is where the concept of transitional partners comes into play. At some point, founders may look around and ask, “Do we really need all these owners?” Buying out remaining partners or bringing on new ones who align with the company’s next phase often becomes necessary.
This process is akin to a divorce—it’s tough, but sometimes people or partnerships grow apart. Ignoring the signs only leads to resentment, which can complicate the separation process. I’ve learned this firsthand—addressing these issues early, whether in business or marriage, is key to a smoother transition.
PE Funded Companies: A Shared Custody Analogy
There’s a stark difference between bootstrapped companies and private equity (PE)-funded ones. Having PE partners can feel like shared custody of your business—similar to an ex watching your kids for the day.
While you trust them to handle things, they’ll inevitably come back with feedback on what you didn’t do right—like not brushing the kids’ teeth or letting them stay up too late. Much like co-parenting, working with PE partners requires constant communication, alignment, and compromise. Having worked with PE-backed companies, I can tell you the similarities are striking.
First-Time CEO Mindset
First-time CEOs often approach hiring and decision-making with a tactical mindset, focusing on immediate needs like making employees billable or driving revenue. This approach stems from the belief that they must carry the entire weight of leadership, vision, and strategy while relying on employees to execute.
Many first-time CEOs are reluctant to trust others with responsibility. Their company feels deeply personal, and their ego may prevent them from seeking coaching or accepting help. This mindset creates bottlenecks, as the founder struggles to delegate and scale.
I fell into this trap myself when I ran my first consulting company. I was immature, both as a leader and in my personal life. I resisted coaching and felt threatened by seasoned professionals who could challenge my authority. Looking back, I realize how much this mindset stunted my growth and the company’s scalability.
It wasn’t until I remarried that my perspective shifted. My wife Susan Stasiak helped reshape my emotional maturity and taught me the importance of delegating and hiring for leadership. That shift allowed me to grow personally and professionally.
Today, I speak with founders every month who face these same challenges. Vulnerability and openness are key to progress. If this resonates with you, let’s connect—sometimes, a fresh perspective can make all the difference.
Your Second Marriage: Clarity and Connection
People often say the second marriage is where they find happiness. Why? Because they’ve learned from their first experience. The same is true for a second company:
Focused Vision: With clarity on strengths and opportunities, you build a business designed for success.
Efficient Operations: The culture becomes less about therapy and more about creating a high-performing team.
Strategic Relationships: Partners, investors, and advisors are chosen intentionally, aligning with long-term goals.
Your second company isn’t an emotional experiment—it’s a calculated pursuit of impact and success.
If you’re an employee looking to join a company, here’s a tip: Ask yourself whether the CEO is a first-time or seasoned leader. It makes a huge difference:
First-time CEO? Expect passion, idealism, and workplace therapy.
Second-time CEO? Look for structure, intentionality, and operational clarity.
Final Thoughts
I’ve often heard the saying: “The first company is where you learn, but the second company is where you make your money.” While there’s some truth to that, your first company must still succeed. It can’t simply be a stepping stone. The lessons, credibility, and foundation you build there are what make the second company possible.
Every month, I work with founders navigating these challenges. I specialize in helping leaders craft strategic insights, navigate complexities, and implement actionable frameworks for growth. If you’re facing leadership or scaling challenges, let’s connect.
Whether it’s your first or second company—or first or second marriage—the key is to learn, evolve, and build better.
