CF
Colin Fraley
Founder β€’ Advisor β€’ Podcast Host
πŸŽ™οΈ Season Two of β€œSTARTUP or SHUTUP!” Podcast Starts Tuesday May 28th 2026!
ChicagoMonthlyIRL + Hybrid

Side Hustle β†’ Solopreneur

A monthly meetup in Chicago for makers, side-hustlers, and indie founders who want real connections and real momentum. Come for the people. Leave with energy.

I started this group because building alone is hard. The internet is great, but nothing replaces sitting across from someone who's going through the same thing. This meetup is the community I wish I had when I was starting out.

When
Monthly β€” dates announced on social media and via email list
Where
Chicago (rotating venues) + virtual hybrid option
Who
Creators, side-hustlers, solopreneurs, indie founders, and anyone building something
Vibe
Casual, supportive, action-oriented. Zero pretension.
What to expect

Not your typical networking event.

This is a community, not a mixer. Here's what makes it different.

Casual, not corporate

No name tags, no awkward icebreakers. Just real people having real conversations about what they're building. Think coffee shop vibes, not conference room energy.

Connections that stick

The people you meet here become collaborators, accountability partners, and friends. This isn't networking β€” it's community building.

Practical takeaways

Every meetup includes a focused topic or workshop. You'll leave with something actionable β€” not just a stack of business cards.

Hot seats and feedback

Bring your biggest challenge and get real-time feedback from people who get it. No judgment, just honest perspectives from fellow builders.

Momentum and accountability

Set a goal at one meetup, report back at the next. The group keeps you honest and moving forward.

Hybrid option available

Can't make it to Chicago? Join virtually. The hybrid format means you can participate from anywhere.

Who it's for

If you're building something, you belong here.

It doesn't matter if you're pre-revenue or profitable. If you're putting in the work to build something meaningful, this group is for you.

Side-hustlers building something after hours
Solopreneurs who are already full-time on their thing
Aspiring entrepreneurs still figuring out their idea
Freelancers and creators looking for community
Anyone who's tired of building alone

Stop building alone.

The next meetup is coming up. Drop your email and I'll send you the details β€” or just reach out and say hi.