Southwest Michigan travelers are skipping airport parking thanks to this startup

Editor’s Note: This story is part of Momentum: The people and companies shaping what’s next, a weekly series that explores new ventures, founder support, and the resources powering entrepreneurship and small businesses across seven counties in Southwest Michigan. This project is sponsored by Southwest Michigan First. All photos are courtesy of Max Transportation.

Often, the worst part of an airplane trip is driving to the airport, figuring out where to park, and then determining how to get to the right terminal.  It can be especially grueling if you’re driving for about two and a half hours from, say, South Haven to Chicago’s O’Hare International Airport.

That was the plight of South Haven realtor Amy O’Sullivan-Wheeler, who goes to Mexico four to eight times annually to maintain a rental residence for vacationers.  Then she learned about a new business called Max Transportation & Car Service that gives her door-to-door service.  

“I was delighted to discover his business in town because it has made my travel so much easier. That trip into O’Hare is so stressful, and now I use Max, and it takes that stress out of it completely and just makes it a much more enjoyable experience.  And the cost is about the same as parking at O’Hare.”

Thirty-one-year-old Max Gleiss is an entrepreneur who is using the many services available for new businesses in Southwest Michigan, such as the South Haven Regional Business Hub, which provides support for new businesses from the first spark of an idea to regional expansion.

Last year, Gleiss joined the Hub’s Startup Series, attending

every session to build a foundation for his service-based enterprise. His dedication to fundamentals like licensing, insurance, and market positioning has paid off. Now, Gleiss has applied for the Hub’s

2026 Growth Series to further scale his vehicle fleet and operations.

“Over the past year, we’ve traveled more than 50,000 miles, joined the South Haven Chamber of Commerce, actively participated in South Haven Regional Business Hub events, and provided transportation for everything from the South Haven Icebreaker Festival to weddings, winery tours, airport transfers, and corporate events,” says Gleiss

Participation in the Hub’s 2026 Growth Series would focus on the systems needed to manage Max Transportation’s rapidly increasing mileage, need for drivers, and client base.  “I cannot say enough good things about the Hub,” Gleiss says. “I would not be where I am today without them.  They care and want to have the community grow, and that means so much to me to be part of that.”

The Hub awarded a $5,000 business grant to Max Transportation through a program of the Michigan Economic Development Corp.  Gleiss says the rest of his operation is self-financed.

Max Transportation’s workhorse vehicle is a 2024 Honda Odyssey minivan. A Ford Transit van holding up to 15 people is available for tours, and a 14-passenger bus might be added to the fleet if business is especially good during the summer. Gleiss has three part-time employees to help with the driving.

He has a bachelor’s degree in marketing from Northern Michigan University, and he formerly taught marketing and personal finance at a school in St. Joseph.  

The genesis of his business venture was hearing about somebody having difficulty arranging a ride to an airport. “A friend said, ‘I’ll pay you $200 if you take care of this,’” Gleiss says. “After that, I looked around and realized that there was a need for it in the area.”

Max Transportation now does much more than trips to airports.  Recently, Gleiss described a job he had coming up that involved a round-trip between Kalamazoo and Grand Rapids. “There’s a gentleman in Kalamazoo who loves to listen to live music, so we’re picking him up, and we’re taking him to his favorite band; they’re playing in a bar. And then after the event is over, we’ll be driving him home.”

From the beginning, Gleiss has benefited from the mentoring he received from South Haven businessman Steve Whittington, a member of the board of South Haven Regional Business Hub. “We meet on a monthly basis and talk about his business and talk about where he’s expanding,” Whittington says.

Whittington knows a lot about Max Transportation, having used the service for himself, his wife, her mother, and his parents.  “Max has transported our two-year-old Shih-poo (Shih Tzu-poodle mix) to and from my daughter in Chicago,” Whittington says.

“Max is a steady hand. He is very relaxed, very protective; he’s very thoughtful. He knows the importance of the passengers he’s moving around, human or otherwise.”