The Gentleman's Institution: Chicago Mastermind
Saturday, October 25th
One Day. Lifelong Brotherhoood
It's time to take everything we've built together offline - and into the real world.
On this unforgettable day in Chicago, you’ll join your elite circle of like-minded men for an in-person experience designed to sharpen your style, deepen your discipline, elevate your social — and forge connections that will last a lifetime.
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This is not just an event. It's a rite of passage.
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Hosted personally by James, this one-day mastermind is your opportunity to surround yourself with ambitious, refined men who are walking the same path. You will leave Chicago, more connected, more stylish, and more motivated than ever before.
Morning:
Breakfast mastermind
We begin with a laid-back breakfast where handshakes turn into conversations, and conversations into friendships. Then we'll launch our mastermind, where each man shares his biggest breakthroughs, his biggest challenges, and the next moves he is preparing to make. From this, you will gain fresh insights, renewed accountability, and the motivation to live out your purpose as a modern gent.
Afternoon
Shopping and styling tour
Step into the world of refined menswear as James personally guides you through Chicago’s best boutiques — from Ralph Lauren and SuitSupply to Peter Millar and Paul Stuart. You'll receive live feedback and personalized guidance on elevating your look. Optional appointments with top custom tailors like Enzo Custom and Proper Cloth are also available.
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Evening
Cigars and dinner
We’ll close the day with cigars and a private, chef-catered dinner at the exclusive Biggs Mansion - where membership would normally set you back $5,000. This is your chance to step into a world of gentlemanly refinement and seal the bonds you've formed throughout the day over beverages, stogies, and antipasti.
Spots are highly limited and exclusive to members of the Gentleman's Institution
Due to the intimate nature of this event, only 12 places are available - with several already claimed. Therefore, if you wish to join us in Chicago, do not hesitate to join the Gentleman's Institution for just $1 today and secure your place.
How much is the event?
The event is $750 per person. This includes breakfast, dinner, one cigar, and beverages.
How do I get my ticket?
You will be directed to purchase your ticket after joining the Gentleman's Institution. Purchasing your ticket is easy once you become a member.
What happens after the event?
You will be able to keep in touch with all your new friends inside the Gentleman's Institution online portal, which includes 2 weekly group calls, DMs, and an interactive map of all members worldwide.
If I have a question, who can I ask?
James will answer all questions directly via email - james@gent-z.com