The Skyway Solution?


SkywayMyWay“Google maps GPS doesn’t work well — if at all — when you’re in the Minneapolis skyways,” entrepreneur Mike Bleakmore reminds me when talking about his software startup. “And when it does, the clutter is terrible.”

A self-described ‘skyway sherpa’, Bleakmore has teamed up with Daine Billmark to create SkywayMyWay, a web-based application designed to improve everyday skywalkers’ experience.  For 18 months, the duo has been moonlighting their technology with the goal of solving a niche pain point and turning a profit in the process.

Bleakmore’s data suggest that there are 2.6m weekly skywalkers who use downtown’s 78 skyways that stretch over 8 miles of tubes. From the business perspective, he counts 1,000 different vendors (roughly 25% of which are restaurants), 25 banks, 4,000 hotel rooms and 2,000 apartments/ condos.

Without advertising, the site is seeing 5,000 visits/month, presumably from those who are either in the skyway at the moment or will be soon — making the site a key digital medium to target a captive audience.

“Many of the people who live, work, or frequent downtown have such a beaten path which they’re accustomed to that stems from of a fear of the unknown.  Who wants to get lost…or even look lost? We help expose the world around you. Maybe there’s a better parking spot or an better alternative to that regular Starbucks visit?  And that’s not considering the larger group of people who are completely unfamiliar with the Skyway. We all know how it can be a very intimidating and time consuming adventure…as a state, we should want to make it easier for visitors to embrace our unique system.”

But SkywayMyWay isn’t the only product available in this space. Skyway App was actually first to market, although Bleakmore sees their iPhone only approach as very limiting. While SkywayMyWa has both an iOS and Android apps in the works, their bet is that a mobile-friendly website accessible from any smartphone will ultimately prevail.



The software features:

  • Building by building directions which are consistent with the actual signage,  providing intuitive navigation later on top of the map.
  • ‘Meet me here’ allows users send a quick link with step by step directions for colleagues to illustrate where they will be meeting for lunch or a meeting.
  • Vendors can claim/add/edit listings and supply rich content
  • Open Table API integration for seamless restaurant reservations
  • Markings for public transportation info and parking lot details.
  • Daily deals powered by local startup DealStork

SkyWayMyWay has yet to peg the ideal way to monetize their efforts; targeted contextual advertising is the most obvious here, but their research indicates that selling to individual vendors is a tediously challenging approach with low margins.

“We’ve looked more towards selling to large commercial property owners who want to offer technology tools like ours to create additional awareness and revenues for their tenants. From the few parking companies that control most of the blacktop to the hotel that wants to unload a few rooms for the eventing — there is a real opportunity to connect these people who need each other.”

What’s next?

“We’re focused pinning down the appropriate sales/revenue models while we look at other potential skyway markets like Toronto, Des Moines or Seattle…and Allie’s Deli in the Rand Tower is hands down the best kept secret for scones,” he reveals in true guru style.


  • Ry4an

    Do they covers skyway hours?  Not knowing which routes are and aren't open after, say, 6pm keeps me on the ground in the evenings.