I recently had the pleasure of sitting down with Jeannette Linfoot on the Brave Bold Brilliant Podcast to talk about something I’ve dedicated the last 17 years of my life to: helping family businesses thrive, survive, and create lasting legacies.
We covered a lot of ground, from my own journey out of the corporate world, to the real reasons family businesses fail, to what it actually takes to build something that outlives you.
Watch the full conversation below, or scroll on for the key highlights.
Getting Off the Ladder: My Own Story
I spent the first 25 years of my career climbing the corporate ladder.
After the Army, I joined a large conglomerate, worked through their management training program, and eventually helped grow a division from $30 million to nearly $500 million, taking it public and becoming CEO along the way.
And then I got to the top of the ladder. And I looked up. And there was more ladder.
I took a year off, intentionally. What I discovered during that time changed everything:
- I had been stuck in what I call the do-have loop: I have to do this to have that, without ever asking who I wanted to become.
- I needed to stop climbing and get grounded. Move from tactics to purpose.
- Once I let go of the doing and started serving others, things started happening naturally, and I didn’t even feel like I was working.
- My wife eventually asked when I was going to get a job. That’s when I officially became a business advisor. I hung up a shingle, and 17 years later, here we are.
The Family-First Business Turnaround
One of my most formative experiences was stepping in as CEO of a fifth-generation family business. There were 17 cousins involved and it was a hot mess. My job was to turn it around and sell it.
My second week on the job, I called all the cousins into my office, asked them to hand over their car keys and their Platinum American Express cards, and then let everyone go except the two who were actually producing value.
Why? Because this business had become a family first business, it was serving the needs and wants of the family above the needs of the business. That had to change. Key lessons from that experience:
- I negotiated my authority before I took the job. It took three months, not over salary, but over decision-making power. In a turnaround, you can’t lead by consensus.
- Employees and stakeholders were watching. The symbolic act of the family making sacrifices first gave the whole team permission to follow.
- We had to shift from family first to business first, and make it visible, decisive, and consistent.
- The business was eventually sold to a publicly traded Australian company. But not everyone was celebrating, some family members couldn’t let go of the legacy they’d imagined.
The #1 Strategic Decision Every Family Business Must Make
Are you a business first family? Or a family first business?
This is not a trick question. Both are legitimate choices. But you have to make it consciously, deliberately, and together, with all shareholders, majority and minority alike. Here’s why it matters so much:
- Most businesses start as family first, you’re just trying to get groceries on the table. That’s fine. But as the business grows, there needs to be a natural shift in philosophy.
- 60% or more of first-generation businesses don’t make it to the second generation. Only around 12-13% make it to the third. The inflection point that kills most of them? Failing to make this shift.
- The worst version isn’t choosing family first, it’s being indecisive. Saying you’re business first in the boardroom, then hiring cousin Harry because he needs a job. Your employees see it. Your customers see it.
- When a business declares it is business first, non-family employees understand there’s no ceiling, their name doesn’t have to be on the building to build a career here.
- Once the decision is made, every other strategic decision lines up against it. It becomes your compass.
The Most Overlooked Growth Lever: Governance
I know, when most people hear the word governance, they shrink. They think: don’t corporatize me. Don’t make me too formal.
But here’s my simple definition of governance: How do you make decisions, and how do you handle conflict? That’s it. And without a good architecture for those two things, you will hit a ceiling.
In most family businesses, the founder is the hub of every decision. That works, until it doesn’t. Here’s what gets businesses unstuck:
- Build decision-making structures so you’re not the bottleneck. Decentralize, but only once you have the right people in the right seats.
- Get the right management systems and cadence in place. Tighten all the lug nuts on the wheels of the race car before you hit the gas.
- Build the right culture and team around you. Jim Collins called it getting the right people on the bus. I’d add: they also need to be in the right seats.
- If you’re a startup, you don’t need a full board of directors with fiduciary responsibility yet, but get advisors. Get third-party perspective. Start early.
What I Learned When Selling Their Business Almost Broke a Founder
A few minutes before midnight, I got a call from a founder whose business was closing that night. He was in tears. It was the worst day of his life.
He was about to receive nearly twice the valuation he originally expected. Life-changing wealth. And he was devastated.
That phone call changed me. I had done an outstanding job preparing the business for the sale, and I had completely failed to prepare him. Now, when I work with any owner on an exit, I look at four things:
- Personal readiness: Are you emotionally prepared for what life looks like the day after the check clears?
- Financial readiness: Do you understand what this means for your long-term financial life?
- Business readiness: Is the company positioned to command maximum value?
- Quality of business: Are the systems, people, and governance in place to sustain performance without you?
If the owner isn’t personally ready, we slow down. The transaction can wait. The person cannot.
Stop Fighting to Be Right. Start Fighting for What’s Right.
Whether I’m in a boardroom or a family meeting, the pattern is always the same: people are fighting to be right rather than fighting for what’s right. And when you’re fighting to be right, you’re making someone else wrong, and that’s where conflict gets stuck.
Here’s what I’ve learned about resolving the real issue in any difficult conversation:
- Separate fact from opinion. People confuse the two constantly. Your feelings are yours, they’re real. Your perspective is just that, a perspective.
- Get to the other person’s experience. You may not have intended to make them feel a certain way. That doesn’t mean they didn’t feel it.
- Once both parties can see the real problem, distinct from emotion and reaction, you can usually move through it quickly.
- The same skills that make you better in business make you better in marriage, in parenting, in life. I’ve been married 45 years and my wife is probably better at calling for a clearing conversation than I am.
The 3 Decisions Every Founder Must Make to Build a Lasting Legacy
If you want your business to outlive you, these are the three decisions that matter most:
- Choose your philosophy: Are you a family first or a business first family? Make it consciously. Make it together. Live it consistently.
- Build governance that matches your stage: You don’t need a board of directors on day one, but you need someone advising you. Start building the decision-making architecture early.
- Manage your talent and your culture: Get the right people in the right seats, and invest in the culture that holds it all together. These two things are inseparable.
You Can Accomplish Anything if You Don’t Care Who Gets the Credit For It
Jeannette asked me what advice has stayed with me the longest. It’s something I heard early in my career, and I’ve tried to live by it ever since:
“You can accomplish anything if you don’t care who gets the credit for it.”
That’s the foundation of leading through influence. It’s how you grow with and through others, instead of at their expense.
If any of this resonates with where you are right now in your business, we’d love to hear from you. Book a complimentary and confidential call with one of our experienced advisors.