What Every Startup Can Learn From a Chicago Street Hustler

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What Every Startup Can Learn From a Chicago Street Hustler

Lower Wacker Drive in Chicago is not for the faint-hearted. Whether you’re a Chicago native or a hopelessly lost tourist, the concrete wonder that is Lower Wacker Drive can be intimidating and, as proven by a July 2015 drag race, even deadly. Although drivers aren’t technically underground on LWD, not much daylight can be seen until you emerge onto Lakeshore Drive (always a sight for sore eyes) or any number of the Windy City’s side streets.

I’ve been driving in and around Chicago since I got my driver’s license at age 16. I can comfortably navigate the city and the surrounding suburbs. But my route will almost always avoid Lower Wacker, even if extra travel time is required. The vague lanes, dead ends that seemingly appear out of nowhere and the otherworldly atmosphere tip my anxiety scale toward flip out.

But on a December Saturday, Lower Wacker was exactly where I found myself. The too early or too late turn had me surrounded by concrete and sodium-vapor streetlights before I even was fully aware of what I had done.

As I was hurtling toward one of those pop-up dead ends that included parked cars and piles of construction debris I heard someone yell, “Whoa! Whoa! Whoa!” His booming voice startled me out of my confusion and made me more aware of my surroundings.

I maneuvered my car in the opposite direction of thousands of dollars of repairs as my savior ambled over. He wasn’t wearing any sort of official uniform, but he appeared confident, like he knew what I needed and that he could provide it.

“Where ya goin’, sweetheart?”

“South Bend,” I said.

“Here’s what you want to do,” he started. “Turn right at this street right here. That will get you on Lake Shore Drive. You’ll take Lakeshore for about 10 minutes to the 55 exit that will be on your right. Take 55 to 94 west and 94 to the Skyway. The Skyway will take you to the 80/90 Toll Road.”

During his machine gun delivery, I was reaching for a $5 bill in my wallet. Pretty salty for less than two minutes of service, but a cheap price to pay to make it to the toll road before sundown, believe me.

As I merged onto Interstate 55, I thought to myself, “Dang, he was good at his business! I wish he was my client.” My Chicago street hustler had everything on the list that I tell my clients they need to do:

Know your customer –non-Chicagoans who are desperate not to be on Lower Wacker Drive

Fill a need – I needed to get out of that pit!

Provide a quality product or service – detailed, simplified directions that I understood and that sent me toward daylight in less than 30 seconds

Choose a location that is good for the customer – the corner before certain doom

Don’t be shy about promoting your product or service – “Whoa! Whoa! Whoa!”

Starting a business isn’t easy, especially if your business involves standing on a semi-subterranean street corner during Chicago winters. But business basics are business basics, no matter what your product or service and sometimes learning the basics are as easy as getting a little help from a street hustler.

Tracie Davis

Before joining the North Central Indiana Small Business Development Center, Tracie Davis ran Dream Big Communications, her own strategic marketing communications consultancy. Her career includes leading marketing communications departments for Ivy Tech Community College, Southwestern Michigan College and University Park Mall. She also served as Community Affairs Supervisor for Martin’s Super Markets and Special Projects Coordinator for Michiana Community Hospital. She began her career in radio journalism. A lifelong resident of the Michiana area, she has a bachelor’s degree from Western Michigan University and a master’s degree from Indiana University.
Tracie Davis can be reached at tdavis@isbdc.org.
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