People keep asking me, “Scott, why are you still going so hard after all these years?”
The answer’s simple: I’m not done. I’m still passionate. I still love the game. And I still see opportunities that excite me, not just for growth, but for impact.
Recently, I made two big moves. I acquired Harley-Davidson dealerships in Milwaukee and West Bend, and I partnered on something totally new for me, a waterfront food truck park in Cape Coral called Slipaway.
These decisions weren’t about staying busy. They were about purpose, people, and potential.
What Pulled Me to Milwaukee and West Bend?
Honestly, it didn’t start with a desire to expand in that region. It started with an opportunity. The market looked strong, and as we dug deeper, it became clear, this was more than just a good business move. This was a chance to bring leadership to a market that needed it.
And let’s be real: it’s Milwaukee. The birthplace of Harley-Davidson. One of the stores is literally called Milwaukee Harley-Davidson. That name carries weight. That comes with legacy, and I don’t take that lightly. I saw a chance to do what we do best: build culture, lead from the front, and elevate both the brand and the customer experience.
Why Now—After 40+ Years?
If you look at the motorcycle industry, the product evolves, but the customer base stays relatively steady. People talk about the rider demographic aging out, sure, but others are aging in. It’s a cycle.
What’s changed is how I lead. I’ve got a solid team around me now. I’m not in the trenches every day like I used to be, and that gives me the freedom to look up, zoom out, and ask, “Where do we go next?”
These new dealerships gave me that answer. They opened a door for my team to step up, lead, and be part of something bigger. I’m proud to help them grow into owners and decision-makers, not just managers.
So, What Excites Me Most About the New Stores?
It’s the people, both the team and the customers. I believe these dealerships have been underserved. The culture just hasn’t been where it needs to be, and we can change that.
Customers want to believe in their dealership. They want to be proud to wear the brand. That only happens when leadership is intentional and shows up consistently, for both the people who buy the bikes and the people who sell them.
Our job now is to restore that pride. We’re here to lead with purpose and rebuild the culture from the inside out.
Why a Food Truck Park?
Now this is the curveball. It’s way outside the motorsport lane, but that’s what makes it fun.
One Sunday morning, I got a call from my buddy Jeff Miloff. He said, “Scott, I’ve got something I want you to hear.” When Jeff calls, I know it’s worth listening.
What caught my attention wasn’t just the food truck concept; it was the location. Right on the water in Cape Coral. With a marina. As a boater, that had me hooked instantly.
Slipaway isn’t just about food trucks and cold beer. It’s about creating a community hub, a space where locals and boaters can gather, relax, and enjoy something different. After the hurricanes, we lost a lot of those gathering places. This fills that gap in a way that feels authentic and fun.
And honestly? It’s exciting to do something new. I’ve never been involved in a project like this. The team Jeff brought together is strong, and we’re all aligned on the vision. For me, this investment isn’t about legacy; it’s about being part of something that brings joy and connection to our hometown.
How Community Shapes My Decisions
Whether it’s Milwaukee or Cape Coral, community is always at the heart of what I do.
In Milwaukee, we’re stepping in to reestablish pride in the Harley brand and the experience. That starts with building trust, setting the tone, and empowering a team that customers believe in.
In Cape Coral, this one hit close to home. Our community was hit hard by hurricanes, and recovery has taken time. But there’s a need, a real hunger for connection again. Slipaway isn’t just a business venture. It’s a way to contribute to the rebuilding process. A place where families can laugh, friends can catch up, and boaters can pull in for a quick bite or sunset drink.
That’s what fires me up. That’s what gets me to say yes.
Is This Legacy? Reinvention? Or Something Else?
People ask me all the time, “Scott, I thought you retired?” And yeah, I get it. On paper, it looks like I should be winding down.
But the truth is, I’ve never felt more aligned. I’ve built businesses, and now I’m focused on building leaders. I want my team to run the day-to-day. I want to coach, guide, and give them the tools to take ownership.
That’s what this chapter is about. Not chasing legacy, not reinventing myself, just continuing the work. Continuing to lead, serve, and enjoy the ride.
If legacy happens along the way, great. If not, I’m still doing what I love, surrounded by great people, building things that matter.
For Anyone Feeling “Comfortable” But Craving More
If you’ve got that itch to do something bold, do it! But don’t do it alone. That’s the key.
Build your team first. Have structure. Surround yourself with people who can execute and keep you grounded. I’ve seen too many people take one big swing late in life and lose everything because they didn’t have the right support.
I’m not doing this alone. John Greene, my longtime teammate and now co-owner of the Milwaukee and West Bend Harley-Davidson dealerships, has been shoulder to shoulder with me through this whole process. His operational insight and leadership on the ground are a big part of why I felt good about saying yes to this deal. And Kimberly Haskins, our CFO at Scott Fischer Enterprises and Co-Owner of the Milwaukee and West Bend Harley-Davidson dealerships, is the steady hand behind the numbers and the structure. She ensured that this move made sense not just emotionally, but also financially. I trust both of them fully, and I’m excited to see how they lead this next chapter.
Big moves need big stability. And that’s what I’ve got now. A team I trust, a clear vision, and a mindset that says, we’re not finished yet!