City Life

Best of Madison Business: Six leaders who are building up this city

Meet these talented, forward-thinking individuals.

We are watching Madison mature as a city right in front of our eyes. In our case, it’s taken a while—a hundred years or so. What can we say? We’re late bloomers. But we can see it happening. It is, in part, growth. Madison is unlikely to ever be a big city; you see, there’s that whole isthmus thing we’ve got going. But density is no longer a dirty word, and we’re filling out at the edges. And a quarter of a million in population is no small potatoes. But maturity also encompasses our ability to embrace change, take risks and write our own story. In 2017, Madison’s business community and its leaders are doing just that.

What we’re seeing is not just the old transforming into the new, but rather, the two being fused together. And thus, this year’s Best of Madison Business honorees are emblematic of that transformation. Development and construction, retail and recreation, brewing and food-related businesses are all part of Madison’s bedrock. And to our great fortune, players in those fields have deep roots in our region—but are also contributing to its future. It’s not a stretch to suggest that a walk of a mile or so down East Washington Avenue would unveil at least a hint of the influence of the six people we are recognizing this year.

Otto Gebhardt III’s influence is more than a hint. It’s a gigantic skyscape-defining, ever-growing footprint that is, among other things, home for so many of the millennial entrepreneurs, makers, chefs and artists who are creating the Madison of the 21st century. Gebhardt is part of a legacy; his father ran Gebhardt Realty. In 1991 Otto started his own company, Gebhardt Development. So, real estate and development is in his blood. His holdings are spread throughout the city and county, but it’s his work along East Washington Avenue that signifies Madison is a city that’s come of age. He might not have been the first to see the potential in the newly conceived Capitol East District, but when the concept needed someone to step up and invest, Gebhardt was all in. Gebhardt’s investment was crucial and the necessary catalyst to kick-start the East Washington Avenue renaissance. His Constellation and Galaxie developments are the pillars on which the Capitol East District is being built, as well as the Cosmos project, a mixed-use development that will include an entertainment venue and will house the entrepreneurial hub StartingBlock when it’s completed (slated for later this year).

But a thriving, once-in-a-lifetime new neighborhood needs more pillars in it than mixed-use buildings. It needs entertainment. And Steve Schmitt, Vern Stenman and Conor Caloia are in the entertainment business. Schmitt is the owner of the Madison Mallards Northwoods League baseball club, Stenman is club president and Caloia is the COO. The three are partners in the ownership of three other Northwoods teams in Wisconsin—under the name of Big Top Baseball—and have discussed the possibility of bringing professional minor-league soccer to Madison. Schmitt is also the owner of The Shoe Box, a shoe store in Black Earth (which is considered an entertainment venue in its own right). Schmitt, Stenman and Caloia are also partners in the operation of the newly-renovated Breese Stevens Field, bringing the Capitol East District some of the amenities required to make this revitalized neighborhood a home, a great place to work and a destination. The Bodega, a free outdoor market with local foods and crafts; Catch & Reel, a Friday night fish fry and movie series; high school sports; and outdoor ticketed concerts (like the Steve Miller Band and Wilco)—plus regular appearances by Salvatore’s Double Decker Pizza Bus—are all events at Breese Stevens that are bringing folks back to one of Madison’s local landmarks. And that’s good for business.

You are also, of course, likely to find a Spotted Cow Ale at Breese Stevens, or at other establishments along East Washington Avenue. While Madison has become a haven for talented, artisan brewers and terrific, handcrafted brews, Spotted Cow is the beloved standard. And that makes Deborah Carey of New Glarus Brewing Co. the godmother of local brewing. While headquartered in New Glarus, the brewery Carey founded (her husband Daniel is the brewmaster), has won numerous awards, a trip to the White House to meet President Barack Obama and a special place in the hearts of beer lovers everywhere, especially in Wisconsin. Carey’s entrepreneurial resume includes starting her first business at age 16, so business is clearly in her blood. We’ll consider New Glarus a Madison suburb for the sake of this year’s Best of Madison Business awards. If you’re a visitor to Madison, enjoying all this wonderful place has to offer, the beer you should be drinking first is a Spotted Cow.

And if you live here, and the six-pack of Spotted Cow is in the refrigerator in your kitchen awaiting the dinner with which it will be served, that dinner might be arriving courtesy of EatStreet. In less than seven years, the online and mobile food ordering service co-founded in Madison by Matt Howard has grown to the largest such site in the country. EatStreet has signed on some 15,000 restaurants in more than 250 cities, attracting more than $27 million in investment in the process. This past year, the business, which currently employs 135 people, moved into a bigger space in the AT&T Building on West Washington Avenue. With seemingly limitless growth potential, EatStreet is one of the bigger success stories that will someday be viewed as the beginning of Madison’s position in the new global economy. And Howard’s commitment to keeping the business here is widely viewed in the entrepreneurial startup world as a key indicator of Madison’s ability to retain home-grown talent.

Otto Gebhardt III, Steve Schmitt, Vern Stenman, Conor Caloia, Deborah Carey and Matt Howard: Six business leaders at the forefront of the greater Madison region’s economic future with businesses rooted in the city’s history. It’s a blend that helps define our city’s brand as a place that knows where it’s been, where it’s going and has the business leaders to get us there.


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