You do not need money to find customers. You need effort, and you need to be where they are.
The clinic meets in Hyde Park, and that is a good place to start — but your customers are all over the South Side: Kenwood, Woodlawn, South Shore, Bronzeville, Washington Park, Grand Crossing, Chatham, Englewood, Bridgeport, the South Loop. Decide how far you will drive for a job, and work everything inside that circle.
Your first customers are people who already trust you: your building, your ward, your kids' school, your family's friends. Your plan asked you to name three of them. Call them this week. Do not wait until you feel ready.
People across the South Side use the Nextdoor app constantly, and it works by neighborhood.
Join the local groups and watch for people asking for help. Post your services on the days the group allows it.
For cleaners, handymen, and dog walkers: the high-rises on Lake Shore Drive, 53rd Street, in the South Loop, and along the lakefront hold hundreds of customers behind one door.
Dress clean. Ask the doorman or concierge politely if you can leave a small stack of flyers for residents. Be friendly to the staff — they decide whether you get in.
After every finished job, leave three business cards or flyers with the happy customer. Say: "If you give these to neighbors and they hire me, I'll take $10 off your next service." The customer who just watched you work is your best salesperson.
The University of Chicago runs on quarters. Students move in and out in September, January, March, and June. If you clean, move, or assemble furniture, those are your busiest months. Plan for them.
Once you have done a few jobs, the fastest way to grow is other people saying you are good.
Where do your customers actually live or work? Which neighborhoods? Bungalows or high-rises? Students or families? Your mentor can help you pick the two or three places on this list that fit your business — not all of them.