What we learned giving 12 dozen donuts to Chicago rideshare drivers

What we learned giving 12 dozen donuts to Chicago rideshare drivers


We’re big fans of donuts here at Gridwise, and we heard that a few rideshare drivers in Chicago are as well. So we packed a few bags, grabbed a few donuts and about 60 cups of coffee and headed to Chicago’s O’hare and Midway airports to give away free donuts to rideshare drivers, and talk to them about being rideshare drivers in Chicago.

To our surprise, Chicago rideshare drivers LOVE to talk about their experiences.

We were able to learn more about the difficulties that rideshare drivers in the Midwest are having with the transportation network companies, passengers, and airports. While also learning about the strategies that rideshare drivers are leveraging to overcome those challenges.

So in today’s post, I want to share what we learned.

“Who are you guys?”

Every single driver that we talked to started the conversation with the same question… “Who are you guys?”.

Now, we didn’t build Gridwise to become world famous in the rideshare community, but we would love for you guys to know who we are so if you see us around town, you can come up, say hi, and talk to us about your experiences.

So this guy right here is our Co-Founder and CTO Brian Finamore.

And as for myself, Ryan Green, Co-Founder and CEO, I’m the hardworking gentlemen below talking to a local rideshare driver… You can also see Brian in this photo contemplating another donut.

Now that you know who we are, let’s talk about we we learned.

It’s Cold… and Chicago Rideshare Drivers are taking advantage of it

We arrived the night after a blizzard that produced 5 inches of snow, which Chicago drivers insist is a moderate snowfall, and assumed this would be a slow week for rideshare drivers because people would elect to stay in and stay warm instead of venturing out into the elements.

Rideshare drivers we talked to immediately let us know how wrong we were in that assumption.

Not only were drivers able to stay busy with rides, many drivers that we talked to had some of their best nights in months in the midst of the snow. A few cited making $300+ in one 8-hour night.

This is because people still HAVE to do certain things like make their flights, or head home from the office. They are in fact more likely to take a Uber or a Lyft because public transportation can be so hectic during these times. People also are not likely to cancel plans they had set in stone such as going to a show, a game, or a event just because of the snow.

So what’s the lesson here? Driving during inclement weather can be extremely profitable if you plan for it. So when you’re planning your week and deciding what events you want to focus on, take into consideration the weather during these events.

Use Gridwise to easily check for events and see the projected forecast during these events.


Drivers are SMART about destination filters

Rideshare drivers we talk to across the country are getting more and more savvy with one of the most powerful tools at their disposal, destination filters.

This feature that allows drivers to select what direction they want to travel towards with a rider, was intended to help drivers that are toward the end of their shift take passengers that are headed toward their homes, and drivers are certainly using the destination filters to do this. However, they are also using them to stay in areas that they know are lucrative.

For instance, one Gridwiser we spoke with noted that he loves to make runs to the airports and back, so he likes to stay near hotels to maximize his chances of getting a request from a passenger headed to O’hare or Midway. The problem is, that when the airport departures are not peaking, rides to the airport aren’t exactly plentiful.

So this driver uses his destination filters to drive between hotel areas during off peak hours. That way when the airport is peaking for departures, he’ll be in position to drive grab a rider headed to the airport.

Dozens of drivers we met are using Gridwise and destination filters in creative ways

Drivers are using Gridwise to predict when the departure peak hours are, and choosing when they should bounce back and forth between hotels, or stay near a hotel to get a ride to a airport.

Head towards hotels during peak departure hours to catch a ride to the airport…

Otherwise, you can bounce between hotels

Drivers can’t forget about the suburbs

Chicago has a sprawling suburban area with millions of households and residents. So even if drivers don’t plan to take a trip out to the suburbs, they are extremely likely to end up driving to one of Chicago’s many suburban cities, so it’s important to have a suburban strategy.

Many of the drivers that we talked to at O’hare actually focused on the suburbs because they are more likely to receive longer trips and less traffic, but they noted is harder to keep busy.

“It takes more work to get a ride out here in the suburbs, but if you know what events are going on in the downtown areas, you can get a ride.” says Jason, a Chicago driver we spoke with at O’Hare.

The downtown areas of Naperville, St. Charles, Aurora, and other suburbs can be just as profitable for rideshare drivers as downtown Chicago when their are events going on or during late night trips.

So before you decide to head back into the city from the suburbs, check and see if there are events going on around town or if there are any popular bar areas near you. If it’s slow, take advantage of one of your destination filters and head to O’hare, Midway, or a more popular area closer to downtown Chicago.

Talking suburban strategy with the Gridwise crew


Everyone likes donuts… Except for Midway Officers

Here’s a very important lesson we learned. Rideshare drivers know a good donut when they see one… But Brian’s officer friend at Midway was not…

Oh well, more donuts for the drivers!

Drivers like our stickers!

We also gave away Gridwise car window stickers at O’Hare and Midway, and rideshare drivers were happy to rep Gridwise!

We love to see drivers with Gridwise stickers, so we thought we’d show our appreciation with a little contest. We’ll be coming to Pittsburgh, D.C., and Chicago a few times over the next few weeks, and if you are the first driver that we spot with a Gridwise sticker that week, we’re going to give you a $100 on the spot.

Yep, simply have a Gridwise sticker on your car and you could win $100.

We have a lot to learn and are eager to do it

Above all else, we were reminded that the rideshare market is changing rapidly, and so are the pains of Gridwisers and drivers.

That’s why we’re going to be spending time in Pittsburgh, D.C., Chicago, and Philadelphia talking to even more drivers about your pains, your problems, and the solutions that we can provide.

So keep a look out for a couple guys with donuts at your airport!

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