153: Fathers, Sons, and the Legacy We Leave
Family, Business, and the Space In Between – Lessons on Reconciliation and What Truly Matters
Fathers, Sons, and the Legacy of Business
Most family businesses are about more than just profits and operations—they carry the weight of relationships, expectations, and sometimes, unresolved tensions. As a business owner, a father, and a son, I’ve seen firsthand how these dynamics play out, and I’ve experienced them in my own life.
This episode is different. It’s personal. A few weeks ago, I gave the eulogy at my father’s funeral. He was a small business owner, a CPA who built his career on integrity, service, and an almost unmatched work ethic. But more than the business he ran, it was the values he passed down that left the biggest mark on me.
The Unspoken Lessons of Family Business
My father and I had the privilege—and challenge—of working together. Like many fathers and sons, we had our differences. I was young, ambitious, and full of ideas. He was experienced, disciplined, and set in his ways. At the time, I didn’t fully appreciate what I was learning:
Resourcefulness – Business (and life) doesn’t always hand you the perfect tools or instructions. My dad taught me that sometimes, you just have to figure things out.
Work Ethic – The hours he put in were relentless, and as much as I resented them at times, I now see how they built the foundation for everything I’ve been able to achieve.
Integrity – He didn’t cut corners. He didn’t do “gray areas.” And that’s why people trusted him—for decades.
These weren’t just business principles; they were life principles. And they shaped not just the company he built but the man I became.
The Hard Parts—And the Healing
The reality is, not all father-son relationships are easy, especially in business. A few years after I left his firm our relationship took a nose dive. Family challenges, differing perspectives, unhealed wounds caused by hurtful words and life got in the way.
And yet, in the last few months of his life, we reconciled. I started spending Fridays with him, taking him to lunch, running errands, just being present. And I realized something powerful: reconciliation is not just about resolving the past; it’s about choosing to be in the present. Over the last several months of his life we were both able to heal, tending to the others wounds that we had inflicted.
In business, we talk a lot about legacy—how we build, what we leave behind. But legacy isn’t just about financial success or company size. It’s about the relationships we mend, the lessons we pass on, and the moments we choose to show up for.
For Business Owners, and For Everyone Else
If you’re running a family business, you know these dynamics well. Maybe you’re in the middle of a challenging father-son relationship yourself. Or maybe you’re struggling to communicate across generations. Here’s my encouragement:
Make the effort now – Don’t wait for “the right time” to have that hard conversation.
Separate business conflicts from personal relationships – They don’t have to be one and the same.
Remember what truly matters – The balance sheet is important. But the impact you have on the people around you is what will truly last.
My father’s life—and our relationship—taught me more than I realized at the time. His business didn’t make national headlines, but his character left an imprint on everyone he met. And that, in the end, is the best kind of legacy.
Now It’s Your Turn
Think about the family relationships in your life—whether in business or at home. Is there a conversation you’ve been avoiding? A relationship that needs mending? A moment you’ve been putting off?
Take the first step. Make the call. Have the conversation. Show up. Because at the end of the day, it won’t be the size of your business or the numbers in your bank account that matter most—it will be the people whose lives you touched and your family is at the top of that list.