The Hardest Lesson My Family Taught Me About Wealth and Business

By Brad Connors

We often think of wealth in terms of numbers: the value of a business, the size of a bank account, or the worth of a family home. But sometimes, the most profound financial lessons aren’t about dollars and cents. Instead, they’re about the ties that bind us, and what happens when those ties are tested.

A Family Legacy Begins

My family’s story with wealth began in 1949, when my grandfather, a determined and resourceful man, launched Connors Plumbing. In those postwar years, he built his business brick by brick, pipe by pipe, with his own two hands. For decades, Connors Plumbing wasn’t just a company; it was the heartbeat of our family. It provided for us, brought us together, and gave us a sense of shared purpose and pride.

Every holiday, we’d gather in the old family home, stories of the business echoing through the halls. The business was more than an income—it was a legacy, a tradition, and a source of unity.

The Turning Point: When Planning Fails

But as the years rolled on and my grandfather grew older, something crucial was overlooked: succession planning. No one wanted to talk about what would happen when he was gone. Maybe it felt too soon, or maybe we were afraid to face the future. Regardless, the conversation never happened.

When the time came to pass the torch, there was no clear plan. Who would take over? How would ownership be divided? What would happen to the employees who had become like family themselves? In the absence of answers, uncertainty crept in.

The Cost of Poor Succession Planning

What followed was heartbreaking. Family members disagreed about the direction of the business. Some wanted to sell, others wanted to expand, and a few simply wanted out. Arguments flared, relationships fractured, and the business—once a symbol of unity—became a source of division.

The holidays, once filled with laughter and warmth, became tense and awkward. The traditions we cherished faded, replaced by silence and distance. The hardest lesson wasn’t losing money or business opportunities—it was losing what really mattered: each other.

This experience taught me that wealth is about more than assets. It’s about relationships, trust, and the legacy you leave behind. When those are lost, no amount of money can fill the void.

Why Family Business Succession Planning Matters

Our story isn’t unique. In fact, nearly 40% of family-owned businesses in the United States transition into second-generation enterprises, but many struggle with the same challenges my family faced. Succession planning is about more than just choosing who takes over; it’s about ensuring the business continues to thrive, relationships remain intact, and the family legacy endures.

Without a clear plan, even the strongest family businesses can face unnecessary conflicts, interruptions in business continuity, and the erosion of both wealth and relationships. Succession planning provides a roadmap for the future, helping families avoid the pain my own family experienced.

Real Wealth: Lessons Learned

Looking back, I realize the most valuable lesson my family taught me about wealth is this: Money comes and goes, but relationships and legacy are irreplaceable. The business was a vessel for our family’s values, work ethic, and dreams. When we lost sight of that, we lost more than money—we lost each other.

How to Start Protecting Your Legacy

If you’re a business owner, you might be wondering: “If something happened to me tomorrow, would my business and family be okay?” If you’re not sure, you’re not alone. Here’s where to start:

• Create a Buy-Sell Agreement: This is a legal contract that outlines what happens if an owner dies, becomes disabled, or wants to leave the business. It sets clear terms for how ownership will be transferred and at what value, helping to prevent disputes down the road.
• Update Your Estate Plan: Make sure your wills, trusts, and beneficiary designations reflect your current wishes. Consider how your business assets will be distributed and who will be responsible for key decisions.
• Host a Family Meeting: Don’t leave your family in the dark. Bring everyone together to discuss your plans, answer questions, and address concerns. Open communication is essential for preventing misunderstandings and aligning everyone’s expectations.
• Identify and Prepare Successors: Whether you’re grooming a single successor, sharing leadership among siblings, or bringing in external management, start early. Provide training, mentorship, and gradually transition responsibilities to ensure a smooth handoff.
• Seek Professional Guidance: Succession planning can be complex, involving legal, financial, and emotional considerations. Don’t hesitate to consult with advisors who specialize in family business transitions.

Common Succession Planning Approaches

Every family business is unique, and there’s no one-size-fits-all solution. Here are some common succession planning models:

• Single Succession Leadership is where one family member is groomed to take over as CEO or owner. This is best when there are businesses with a clear, capable heir.
• Multiple Family Ownership is ownership is split between several family members, each managing different areas. This is for families with multiple interested members.
• Joint Leadership is leadership responsibilities are shared among siblings or relatives. This leverages diverse skills within family.
• External Management is where an outside professional is brought in to run the business, possibly preparing for a sale or IPO. This is the best course for families where no family member ready/interested.
• Gradual Transition is where the current leader steps back slowly, mentoring the successor over time. This helps to ensure continuity and mentorship.
• Sale and Merger is when the business is sold or merged if no succession is possible within the family. This is used when there is no suitable family successor.

Each approach has its pros and cons, and the right choice depends on your family’s goals, values, and circumstances.

The Role of Communication and Transparency

One of the most overlooked aspects of succession planning is communication. Too often, families avoid difficult conversations, hoping issues will resolve themselves. In reality, silence breeds confusion and resentment.

Talking openly about money, business, and the future isn’t about control—it’s about preserving relationships and protecting what you’ve built. Include your family in financial discussions, share your vision, and invite questions. Transparency builds trust and helps everyone feel invested in the outcome.

Teaching the Next Generation

Financial education starts at home. Children learn by watching how their parents handle money, business decisions, and even mistakes. Involve the next generation in the business early on—let them see the challenges and rewards firsthand. Allow them to make small decisions and learn from the results, so they’re prepared for bigger responsibilities later.

Storytelling as a Tool for Connection

Stories are powerful teachers. Sharing your family’s business journey—its triumphs and struggles—can help younger generations understand the true meaning of wealth. It’s not just about what you have, but about what you stand for and the relationships you nurture along the way.

My Final Word: Walking the Path Together

If you’re facing the daunting task of succession planning, know this: you’re not alone. I’ve walked this path, and I’ve felt the pain of getting it wrong. But I’ve also learned that it’s never too late to start the conversation, to put a plan in place, and to protect what matters most.

Wealth isn’t just about money—it’s about legacy, relationships, and the values you pass on. If you’d like help starting that process, I’d be honored to walk it with you. Because the hardest lesson my family taught me about wealth is also the most important: Protect the things that truly matter, before it’s too late.