Is Madison Wearing Mom Jeans?

This issue is your go-to guide for all of Madison’s bests. If you’re like me, you’ll buy an extra copy and keep it in your guest room, so friends and family members visiting from out of town can discover for themselves how awesome our city is.

I beg you: Please tear out this page before placing the magazine in your guest room. What you’re about to read is impolite to say in front of company.

I’m worried that Madison—like that super-hot high school cheerleader who married the star quarterback, started a family and started wearing mom jeans—may have lost its hotness.

I know, all of the lists say we’re great. Kiplinger’s said we were a city where the jobs are. Money magazine has given both Middleton and Madison the shout-out as America’s best city. And in the past year Outside and Biking magazines named Madison a “best place” for their readers.

There’s only one problem.

Those lists are based on data that’s tucked—safe and sound—in the past. Sometimes years in the past. It’s like the people who use a ten-year-old photo for their LinkedIn profile; they don’t look like that anymore. Get a new picture!

What’s worse, being called a “best city” may be making Madison lazy. Charles Landry, author of The Art of City Making, addresses the curse of being a best city. He writes, “Beautiful people don’t have to try so hard.”

I’ve had a month of Friday furloughs to think this through, and I believe Madison has lost some of its moxie. Every year, we celebrate with the Raging Grannies for Peace at Fighting Bob Fest. Bob Fest is billed as the largest political gathering in the country. Whoopee. How does it make Madison a fertile mind field for our next generation of Bobs?

On this score—being a “best city” for the biggest brains and brightest minds who are creating transform-ative new industries and technologies—Madison falls short. A venture capitalist told me so.

Several of the people who care most about Madison’s ability to attract talent and capital recently told an audience of Madison business leaders, “It’s difficult to get young, talented executives to relocate to Madison to lead our startups.” Seems that Madison has become the place to end your career—either because you’re a Boomer who would like to retire here and enjoy our quality of life, or because you’ll have a hard time getting hired back in Silicon Valley after you’ve done your Madison tour.

Madison could be red-hot again, a melting pot for people, ideas and, yes, excellent microbrews. But we have to stop living in the past—on our past reputation and the things that other magazines say about us—and start getting creative about the future.
Here’s one idea to get Madison out of mom jeans and back in style.

What if we Madisonians started our own investment fund, based on Slow Money concepts, and invested only in entrepreneurs and startups that committed to keeping their businesses—and the jobs they create—in the region?

This could work brilliantly here, for two reasons. First, Madisonians already value “buying local.” Slow Money simply stretches it to
“investing locally.”

Second, we need to reward entrepreneurs who are committed to this region. Too often, we invest in great talent and ideas only to see their backsides as they head toward Boston or Silicon Valley, where they’re told they can “scale.” We need to keep their brains, their
philanthropy, and the jobs their companies create here.

Call it bribery. Call it creative financing. Just tell me that you agree that we need to invest in the future, as much as celebrate the past.

Rebecca Ryan lived in six cities before settling herself and her business in Madison in 2004. Catch her in her own words at

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