Being a small business in Milwaukee, or any American city for that matter, your biggest challenge is discovery. Many places come and go before anyone knows they've existed in the first place. Yelp has done a lot to make local business on equal footing with big chains with their web and mobile apps, but they're about to be integrated with the iPhone's digital assistant Siri.
An article on Cult of Mac points out that this is going to be the way that Apple can help smaller businesses. Though he extrapolates a host of features in the upcoming revision to iOS that can help business, Yelp and Open Table in Siri are going to be a huge benefit for Milwaukee's downtown dining scene. Groupon and Living Social have both had pretty decent acceptance in Milwaukee and have shown that embracing tech can help your business. The Passbook feature of iOS could allow local business to put their loyalty card on people's phones right next to their national competitors.
Mobile has the best chance of driving the Internet to lead users to discover their own towns. This isn't a panacea, but it's another vector for business to interact and build their community of customers. Something small business can do that their national chain competitors cannot.