I hate to say it… Chicago works, and not in the good way.

Before I moved to Chicago, I thought that the city’s reputation as The Windy City was more bark than bite.

That Is Until I Was Bitten

I had the initial idea for a Rideshare Advertising application in March of 2014. I had been driving for Uber since the fall of 2012 to earn a little extra dough. I was approached by the owner of my favorite restaurant to put a few menus in my rideshare vehicle to give to tourists.

I did it, and then I began talking to tourists that I would drive around the City of Chicago. Many of whom enjoyed my recommendations about what to do, where to go, and what to eat while visiting Chicago. Especially, the New Yorkers… They love Chicago’s food scene.

It hit me that, Rideshare Advertising had some real potential and I registered the domain for RideshareAdvertising.com, which we now use for Vugo’s blog.

What is Rideshare Advertising?

Rideshare advertising is displaying advertisements inside rideshare vehicles. Vugo is the first Rideshare Advertising platform. We display relevant, real-time ads inside rideshare vehicles that use apps like Uber, Lyft, Sidecar and Flywheel to connect passengers to drivers.

Ads are displayed after a proprietary determination of the passenger’s trip intent and demographics are analyzed. Vugo then displays the most relevant advertisement to influence the passenger into taking valuable action.

Vugo is an auction based platform that allows companies to compete in a transparent, real-time marketplace that benefits riders, advertisers and drivers. We pay drivers for their time, we help advertisers get the word out and riders discover great deals and new places. More importantly, we also pay taxes to the cities that allow free markets, and don’t prevent competition from innovative start-up businesses.

The Chicago Rideshare Ordinance

By this time, Rahm Emanuel had already drafted what would become the Chicago Transportation Network Provider Ordinance,which prohibits commercial exterior and interior vehicle advertisements.

Other cities that have enacted rideshare ordinances like Chicago’s have a similar rule, which applies ONLY to exterior advertising for safety reasons. Which isn’t ideal, as Taxi Cabs still have an monopoly on advertisements outside the vehicle, but at least it has some basis in reality.

This difference between Chicago’s Rideshare Ordinance and other cities, has nothing to do with safety… as over 2,850 taxi cabs currently operate with interior vehicle advertising in the City of Chicago. In addition to the numerous private dvd players, after market and factory screens that are used in private vehicles everyday throughout the City.

Was this a Taxi Cab Concession

Was preventing competition for cab companies a concession to big taxi in the City of Chicago, creating a defacto monopoly on vehicle advertising in the streets. As a startup in this space, and a resident of Chicago… I really care. But, why should I care if the City of Chicago hasn't been enforcing their ordinance anyway?

Since it’s adoption on September 2, 2014, drivers haven’t been notified of the compliance requirements, that is until last night, nearly 6 months later on February 24th of 2015, Uber, the largest transportation network provider in Chicago notified it’s drivers of the compliance issues presented by the Rideshare ordinance. It took a tech company valued at over 40 billion dollars nearly 6 months to message it’s partners about serious legal compliance issues. I find that hard to believe.

Why would Uber wait until the evening of the Mayoral election in Chicago to notify Uber drivers that they are currently in violation of Chicago’s rideshare ordinance?

Would Ari Emanuel’s (The Mayor’s brother) investment in Uber have anything to do with the lax enforcement of Chicago’s Rideshare Ordinance?

Is it because they were hoping headlines in Chicago would have been filled with news of a mayoral election?

Or was it just plain coincidence?

Why do you think the City of Chicago hasn’t been enforcing their own laws?

P.S. Vugo launched in Minneapolis, Minnesota which has a rideshare ordinance that doesn’t prohibit rideshare advertising inside TNC vehicles.