Chicago AI Mastermind Group

Join the Chicago AI Mastermind Group

A practical AI leadership community for business leaders who want to understand, adopt, and lead with AI strategically. The group meets virtually twice monthly, on the 2nd and 4th Fridays at 10:00 AM Central.

Compare membership options View the main Mastermind page

Membership options

Choose Essentials for peer learning. Choose Pro for added advisory support.

Mastermind Essentials Monthly

$35 / month
  • Two live virtual Mastermind sessions per month.
  • Peer learning, practical use cases, and AI strategy discussion.
  • Community resources, companion content, and member access.
Start Essentials Monthly

Mastermind Essentials Annual

$350 / year
  • Everything in monthly Essentials.
  • A lower annual rate for members who know they want the full year.
  • Ongoing access to the learning community and public companion work.
Start Essentials Annual
Pro advisory lane

Mastermind Pro

$100 / month
  • Everything in Essentials.
  • Recurring FCG advisory support for AI strategy, adoption, and execution questions.
  • Best for members turning Mastermind ideas into active decisions or projects.
Start Mastermind Pro

All paid membership options use Stripe checkout. Essentials is available monthly or annually; Pro adds an advisory lane for members turning AI learning into active decisions and projects.

Current schedule and October theme

The Chicago AI Mastermind meets virtually on the second and fourth Fridays at 10:00 a.m. Central. October sessions are scheduled for October 9 and October 23.

October: Delegation and Autonomy

October’s monthly theme is Delegation and Autonomy. Specific session topics are announced to members when the agenda is confirmed.

October 9 and October 23

Both October sessions are scheduled for 10:00–11:00 a.m. Central.

Ongoing schedule

The group meets on the second and fourth Fridays of each month. Upcoming topics are published only after they are confirmed.

Go deeper with companion videos

The AI Mastermind Companion Podcast extends group themes into public, shareable discussion.

Other ways to participate

Not every good participant enters through the same paid lane. The Scholar Program exists for limited, contribution-based access.

Scholar ProgramLimited, application/review-based seats for people who can contribute meaningful value. Community GuidelinesParticipation, privacy, and member-room expectations for the Mastermind.

Make AI leadership a recurring practice.

The Mastermind is a place to keep learning, compare notes with serious peers, and turn AI from novelty into operating capability.

Choose a membership