What’s Your Setup?
A room of Chicago founders, freelancers, solopreneurs, builders, and agency owners comparing how we actually run our days.
Because you're not slow. You're doing the same work twice.
Same proposal from a blank page. Same explanation to a new client. Same twenty minutes every morning working out where to start, navigating tools, finding information, blocking calendars, documenting work.
None of it billable. All of it important. And chances are, someone else in the room has figured out a better way to do at least some of it.
Last time, we heard about second brains, AI-powered job searches, automated research, content workflows, project management systems, and tools people had built into their everyday work.
This time, we're going deeper.
Hosted by Anindya Singh Obi, building HuTouch.
What you'll see on the 1st
Two people are bringing setups they actually use.
Annie connected her task list to her notes with AI in between, so the context comes back with the task instead of getting rebuilt from scratch every time she switches. For a freelancer, that's the hour that goes to pitching instead.
Ximena works in AI and data strategy. Hers finds job openings, verifies they're real, and hands back a list that's already been checked. For anyone searching, that's the evening that goes to tailoring one good application instead of sorting through listings that closed in March.
Both of them automated the part nobody pays for. Neither automated the part that needed judgment.
How it works
Take away the setup from the presenters and come ready with two things:
1. One pain you need solved.
Something repetitive, annoying, time-consuming, or something you've tried to fix and still haven't figured out.
2. One idea you can share.
A tool, workflow, automation, prompt, AI setup, system, or weird little hack that's made your work easier.
Everyone gets to share.
Then we open it up to the room. We're not looking for polished presentations. Show us the messy version that actually works.
How the afternoon runs
2:00 - Doors, snacks, settle in
2:15 - Why we're here + quick introductions
2:30 to 4:00 - One conversation at a time. Share your pain. Share your setup. Get ideas. Trade notes. Trade LinkedIns. Trade skills.md files.
At the end, everyone writes down whose idea they're actually going to try that week. Most mentions takes home the goody bag.
We'll ask a few questions when you register about what you do, where your time goes, and the tools and systems you already use.
That helps us curate a mix of people bringing different problems, experiences, and ideas to the table.
What you take home
One thing you can set up this week.
One problem you hopefully don't have to solve alone anymore.
A few people you can message when you're stuck.
And the specific relief of finding out it isn't just you.
Who should come
Builders. Freelancers. Solopreneurs. Consultants. Small agency and studio owners. People running two or three things at once.