TOM COTTINGHAM ’82 IS AN IDEA GUY—an alpha entrepreneur, he’ll tell you—but he’s also a personality, and he’s not afraid to show it.
It surfaces in different forms…mostly in orange. From the neon sign that says “Hi” as it peeks out over Market Street to the color that dominates the interior of the offices of Insider Louisville to the color of his 1999 Porsche. In a city of reds, blacks, and chestnut browns, his orange commands your attention.
Cottingham does, too. It’s not surprising that moments after hello, we’re in his office listening to him noodle on a carbon fiber guitar. He can play. He’s the same guy who took a year off from Wabash to go on tour with his band. He’s still a member of the Nashville Songwriters Association, but sums up the business side of the music industry by asking, “You want to make money writing the next hit song for whomever? Good luck.”
The great thing about Cottingham is that he has a story and an opinion on practically everything. Life on the road. Check. Silicon Valley, Bill Gates, and venture capitalism. Check. Bert Stern—he has great stories about Bert—and the Wabash English professors of his generation. Check. Fantasy football and the NCAA. Check.
So when Wabash Magazine sat down with the entrepreneur and publishing executive who has called Louisville home since 1984, Cottingham suggested we talk on the outdoor patio on the third floor of the historic Stock Yards Trust Company building downtown.
It was a great idea on a beautiful late-October day. The force of Cottingham’s personality and the depth of his experience need more room than the standard corporate office. And during a generous two-hour conversation he touched on a multitude of topics, many of them centered around Louisville and the climate that makes it a city on the rise.
FOR THE FORMER ENGLISH MAJOR and 2000 Ernst & Young Entrepreneur of the Year, Louisville has the size, infrastructure, and sense of community to make things happen.
“It’s a city that is big enough to have most of the things you need, both from a business and personal standpoint. There are a lot of midsized cities like this—1.5 to 3 million—that are really interesting and very livable. Almost everything you need is here.”
Cottingham points out that the cost of living in Louisville is cheaper than coastal locations like New York, Miami, San Francisco, or Los Angeles. To make his point, he relates things to the essentials.
“I don’t want to spend the bulk of my income on housing and most of my time in a car or in public transportation. Here I work downtown and live on the edge of town, not in the suburbs. I’m 15 minutes from work and get mad if it takes longer.”
Cottingham has long had his finger on the entrepreneurial pulse of the city. He has built and sold numerous businesses and has been involved in venture capital efforts within Louisville at the ground level through efforts like Open Coffee and CommonWealth Crowdfunding.
His current venture, Insider Louisville, is a Web-based news source that focuses on business development, government accountability, lifestyle, entertainment, and Internet buzz about Louisville. It builds on the city’s strong sense of community.
Through the work of Insider Louisville and the help of social media, communities of interest naturally form. The key is connecting those like-minded people.
“We embrace the fact that there is a group of people in this town who make an impact on a daily basis. Those people think of themselves as a community who are engaged in the city and want things to happen.”
Making the connections among the various communities is even more important. It’s all about relationships between organizations and people in Louisville.
“Personally, I like that you are two or three degrees of separation away from anybody in this town.”
Now that he has spent 30 years in the city, the strength of those connections pays off for Cottingham in a personal way.
“I’ve worked with the same core group for almost 30 years. That’s not by accident. We were just talking about how proud we are of the fact that people who worked with us are currently either working for companies we sold, started new companies of their own, or are working for us now. That’s kind of cool; I get a lot of pleasure out of that.”
Cottingham has designs on expanding his Insider Louisville concept to cities like Indianapolis, Cincinnati, Columbus, and Nashville. He says to hit him up if you want to join the team.
For Cottingham, ideas are easy. They come to him all the time (ask him about 3D-printed guitars). The ability of Cottingham and his team to follow through comes down to passion and one other factor.
“Getting [ideas] done is really, really hard,” he says. “The only thing that carries you through is having a ton of passion. It’s way harder than anybody thinks. You’ve got to treat people right. Karma is very important.”