Questions, answered.

Is this for me?

If you're an established business owner who's been operating for several years, paying yourself well, and asking what comes next — yes. Three audiences cluster here: the established operator (20+ years in, restless), the aspiring premium brand (moving upmarket), and the encore entrepreneur (post-corporate, building something fully their own). If two of those describe you, this is your room.

If you're early-stage, looking for tactical playbooks, or hoping for a how-to-get-started event, this is not it. The room assumes you've already built something.

How is this different from other business conferences?

Three structural differences. First, the room is intentionally small — small enough that people can actually hear each other. Second, all eleven speakers stay both days. No drive-by keynotes, no walk-on appearances. The lineup was chosen because the speakers belonged together, and because each of them benefits from being in the room as much as you do. Third, the program is built around four workshops, not just sessions. You leave with built work, not a notebook of ideas.

Will I leave with anything tangible?

Yes. The four workshops are designed around concrete outputs you can apply to your business, leadership, or next chapter. Plus the broader takeaways — clarity on a decision you've been overthinking, sharper positioning and messaging, a clearer sense of what needs your attention now, and peer relationships at your level you'll keep long after Chicago.

Will there be networking?

Not in the conference-style "exchange business cards in the lobby" sense. The structure of the event creates the conversations — same room, same group, two full days, workshops that put founders at the same table. The relationships that form here form because you've actually worked alongside each other.

Where exactly is it?

The Chicago Athletic Association — 12 South Michigan Avenue, Chicago. The venue is a historic 1893 building reborn as a Michelin Key hotel. We'll be in their event spaces, with both days held at the property.

What are the dates and times?

July 19 — Optional arrival day. DiamondEdge Status holders join a private reception with all eleven speakers, 6:00–8:00 PM CT.

July 20 (Day One) — How you think. 9:00 AM to 4:30 PM CT.

July 21 (Day Two) — How you show up. 9:00 AM to 4:30 PM CT.

Is hotel included?

Lodging is not included in the ticket price. A limited room block has been reserved at the Chicago Athletic Association at a preferred rate for attendees. Reserve directly via the booking link on the home page. Credit card required to reserve; payment due at hotel checkout.

What's included in the ticket?

Both full days of the program. Buffet breakfast and lunch on both days. All program materials, including workshop workbooks. Seating in the workshops. Access to the speaker reception (DiamondEdge Status holders only). Coffee, tea, and refreshments throughout.

Not included: travel to and from Chicago, lodging, dinners (the city is yours after 4:30 PM each day), and incidentals.

Dress code?

Smart casual. The room itself is unpretentious — no required suits, no required heels. Most attendees will land somewhere between elevated weekend wear and creative-professional. Comfortable enough to spend two full days in.

Dietary restrictions?

Yes — the venue accommodates all major dietary needs (vegetarian, vegan, gluten-free, kosher, halal, allergies). Indicate your needs at checkout or email the team after registration. The Chicago Athletic Association's catering is exceptional and works with us on this in advance.

Will sessions be recorded?

No. The event is intentionally an in-room experience. Recording would change the conversations — speakers would speak differently, attendees would ask different questions. The work happens because it's not being captured for an audience that isn't there.

How do I register?

Through the Reserve Your Seat button on any page. Registration is handled through a secure checkout that captures your details and payment. Confirmation arrives within minutes, with a follow-up email containing logistics and pre-event materials in the weeks leading up to the event.

What is DiamondEdge Status?

A complimentary tier for the first 35 attendees to register. DiamondEdge Status holders receive: access to the private speaker reception on July 19, priority seating throughout the event, and preferred room rates at the Chicago Athletic Association. Once 35 holders are confirmed, DiamondEdge Status closes for the year.

Refund policy?

Through January 31, 2026 — full refund, minus a $50 administrative fee.

February 1 to April 30, 2026 — 50% refund, minus a $50 administrative fee.

After May 1, 2026 — refunds are no longer offered. Transfers to another attendee remain available up to seven days before the event (see below).

If the event is canceled or postponed for reasons within our control, all attendees receive a full refund or the option to transfer to the next event.

Can I send someone in my place?

Yes — at no charge, up to seven days before the event. The room is curated, so any transfer needs the replacement attendee to fit the audience profile. Email clare@jeffreyshaw.com with the new attendee's full name and email and we'll confirm within one business day.

Group rates for teams?

No formal group rate. The room is built for individual decision-makers and the conversations between them. If you're considering bringing a team member or business partner, email the team — we'll talk through whether it's the right fit.