Spotlighting Jason's rise from deckhand to President, and what two decades on the water taught him about leading Shepler's.

Every portfolio company has a story worth telling—one built on innovation, resilience, and lasting impact. In our series 'From Vision to Value,' we typically spotlight the businesses within the Hoffmann portfolio, bringing their journeys, challenges, and successes to life in a way that captures their unique contributions.

This offshoot of the series flips the lens to the people building that value from the inside. At Hoffmann Family of Companies, we invest in talent from the ground up — and many of our leaders started at the beginning, forging their own path to the top through Hoffmann's investment in their growth.

First up: Jason Wiley, President of Shepler's, who's spent more than 20 years working the docks. He's proof of what's possible across our portfolio when hard work meets belief in the vision.

GEOFF:
Jason, I love your story, and I want others in the portfolio to be inspired by it. Take us back to the beginning. How did you end up at Shepler’s?

JASON:
I joined Shepler's in 2005, while I was still in high school. My plan was to get my captain's license, go to college for education, teach for nine months, and boat for three. I did that for about a year and a half. Then a position opened up at Shepler's for off-season projects, and what started as seasonal work gradually grew into something more — boat captain, organizational projects, reviewing systems, building structure. I stayed on that path through 2022.

GEOFF:
What was it like when Hoffmann Family of Companies came into the picture in 2022?

JASON:
Talk about a big moment in my career. What set this relationship apart from the start was that it wasn't a traditional private equity transaction—it was a family putting their own capital and their own name behind the investment. That mattered, because 2022 was a challenging season going in. Post-COVID, we had watched other businesses on Mackinac Island go through private equity transactions and seen leadership cleared out overnight...people we had worked with for years, just gone. So, there was natural hesitancy. But we quickly realized that wasn't going to be the case here.

We got to know your family, kept our jobs, and you instilled confidence in our team from the start. Four years later, not one outside hire has come into tell Shepler's who we need to be. The same people who have been here for 20 years are the ones running the company today.

GEOFF:
How has the investment changed Shepler’s day-to-day?

JASON:
HF Companies came in committed to letting Shepler's be Shepler's. Outside of continuous upgrades and quicker repair times on the boats, honestly, you don't notice much change, and that's intentional. What you do notice is the support behind the scenes: insurance expertise, IT resources, financial and governance guidance, and a corporate team that helps you solve problems you didn't even know you had.

They've simply given us better tools and a broader perspective — one that comes from being part of a portfolio of companies that have collectively seen just about everything. For example, we've developed mobile pay technology and rolled out a streamlined virtual ticketing system with QR code scanning that's cut boarding wait times. We've also made substantial investments in both security and infrastructure upgrades to improve guest experience across the board.

I think people get frustrated when we enforce rules that maybe were bent or overlooked in the past. But I wish they understood that everything we do is in the interest of providing safe, reliable transportation. Gas is expensive, and inflation has hit the whole island. What I can tell you is our staff loves their job and loves being on the water. We love this island, and we love still being able to serve our guests here.

GEOFF:
You were recently named President of Shepler’s. What does that mean to you?

JASON:
This past January, Chris Shepler stepped into the CEO role and I stepped into the presidency. But what makes that meaningful isn't the title; it's that everyone around me has grown within the company too. We're the same people who've spent years building this place together, and now we're leading it together.

GEOFF:
What do you want people to know about working at Shepler's, or working within HF Companies?

JASON:
When I started, the path forward was limited. What's changed is that being part of the Hoffmann portfolio opens up an entire network of industries, resources, and people that simply didn't exist for us before. We're not just hiring for a season or a position; we're building careers. The 2025 Family Equity Summit in St. Louis made that real for me. Getting into a room with leaders from across the entire portfolio, I finally understood the full scope of what HF Companies is. When you're connected to something this size, your options are endless.

GEOFF:
Thanks, Jason. I loved being on the water with you today!

JASON:
Thanks for coming out, Geoff.