What I’m Most Proud Of
Over the years, people have often asked me what business accomplishment I’m most proud of. Some assume it’s buying my first dealership in 1990. Others think it’s expanding into new markets, acquiring Harley-Davidson dealerships, or launching new ventures.
Those milestones certainly matter, but the truth is, none of them sit at the top of my list. The accomplishment I’m most proud of has nothing to do with buildings, inventory, or balance sheets. It’s watching people grow into leaders.
Looking back, I’ve realized that the greatest return on investment I’ve ever received wasn’t from a business deal. It came from investing in people and seeing them grow beyond what they thought was possible.
Leadership Isn’t About Being Needed
Early in my career, I believed leadership meant having all the answers. I thought if I worked harder than everyone else, stayed involved in every decision, and solved every problem, the business would succeed. And for a while, that approach worked.
But eventually, I learned a lesson that changed the way I lead. If every decision still has to go through you, you’ve built dependence, not leadership. The true measure of leadership isn’t how much you can accomplish on your own. It’s how many people you can develop to accomplish great things without you.
Organizations become stronger when leaders stop trying to be the hero and start building leaders around them.
Leadership Development Takes Time
One thing I’ve learned over the years is that leadership succession isn’t an event. It’s a process. People don’t become great leaders overnight. They grow through experience, accountability, challenges, and opportunities.
A great example is Sean Delaney.
Sean has spent more than 20 years growing within our organization. Over those years, he’s taken on different roles, learned difficult lessons, built relationships, and earned trust. His transition into the role of Chief Operating Officer wasn’t the result of one decision. It was the result of years of investment and development.
That’s how leadership should work. You don’t simply appoint leaders. You develop them.
Why Most Companies Get It Wrong
Many organizations focus heavily on sales, profitability, expansion, and strategy. Those things matter. But too often, leadership development becomes an afterthought. The healthiest organizations I’ve ever seen aren’t necessarily the ones with the best products or the biggest budgets.
They’re the ones where people are constantly growing. When employees feel invested in, challenged, and supported, they begin to take ownership. They become more engaged, more accountable, and more committed to the organization’s success.
Healthy businesses grow because their people grow.
What Developing Leaders Actually Looks Like
Leadership development isn’t complicated, but it does require intentionality.
It means:
- Giving people responsibility before they feel fully ready
- Allowing mistakes to become learning opportunities
- Coaching instead of controlling
- Creating accountability
- Investing in training and development
- Having difficult conversations when necessary
- Believing in people before they fully believe in themselves
Some of the best leaders I’ve worked with didn’t start out looking like future leaders. They simply had the willingness to learn, grow, and accept responsibility. Given the opportunity, they rose to the challenge.
Success Looks Different Today
At this stage of my life, success looks different from what it did 20 or 30 years ago.
I still enjoy building businesses. I still enjoy pursuing opportunities.
I still get excited about growth. But what excites me most today is watching other people succeed.
Watching someone step into leadership. Watching a manager become a mentor. Watching a leader help develop the next generation. Watching an organization grow stronger as people within it grow. That’s where the real reward comes from.
A Question Every Leader Should Ask
Whether you’re a business owner, entrepreneur, manager, coach, or community leader, I encourage you to ask yourself a simple question:
Who are you developing?
- Who is becoming better because of your leadership?
- Who is prepared to lead when you’re no longer in the room?
Because in the end, the best leaders aren’t measured by what they built. They’re measured by who they helped build.
Actionable Takeaway
This month, identify one person on your team with leadership potential.
- Invest time in them.
- Give them responsibility.
- Coach them.
- Challenge them.
- Encourage them.
The future of your organization may depend on it.