The Compass at EO Chicago

Compass 01 · Cohort of 2027 · The inaugural cohort

Name It. Break It. Build It.

Every business that reaches its next stage breaks something that was working. Eight weeks for eight entrepreneurs to find theirs.

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What it is

A program for EO members.

Every operator hits forks in the road — a decision big enough to change the future direction of the business. They keep you up at night, with no clear map. The Compass is eight weeks of structured work to explore where you are, expose the fork, and set you towards a path. Not more theory or inspiration, but a bearing you can act on, taken alongside peers and seasoned entrepreneurs who’ve navigated the same kind of terrain.

Here’s what that looks like. A cohort of eight, selected by lottery, meets for eight consecutive Tuesdays at EO House. Instruction weeks bring seasoned entrepreneurs who have led through the cohort’s theme — sharing from lived experience and taking real questions. Cohort weeks are closed: the cohort applies that week’s topic to their own situations in EO Forum format, with a facilitator keeping the conversation in the five percent.

You bring your current state — an actual decision, not a hypothetical. If you’re in the middle of something hard and unfinished, this room was built for you. If you want the content without the commitment, come as Community.

Why this, why now

What got you here is what you’re protecting.

Every business that reaches its next stage has to break something that is currently working: the customer it was built on, the pricing model, the cost structure, the org chart, the founder’s own role. Most operators aren’t stuck for lack of ideas. They’re stuck because the thing in the way is a thing that works, and they built it.

Some of it is being decided for you. AI is breaking cost structures whether you choose it or not. Capital costs more. The customer you built the company on is changing. That is the fork in the road: hold what you have, or break it and build what comes next. Sometimes holding is the right call. Knowing which is the work.

That is hard to see alone, and harder to do alone. What works, in our experience, is doing it in a working room, with peers at the same fork and seasoned entrepreneurs who have broken something that worked and built what replaced it.

That is what this edition is for.

The arc

Three moves across eight weeks.

  1. Name it

    Dissatisfaction with the status quo. Say out loud what isn’t working, and what you’re protecting that keeps it that way: a role, a customer, a structure, a habit of control. Until it has a name, it runs the business.

  2. Break it

    Vision for the future. Describe the business at its next stage, and your relationship to it: what you do for it, and what it provides you. Held against that picture, it gets clear what has to go, and what you will not touch.

  3. Build it

    Plan to get there. Design what replaces what you broke, and take the first step while the room is still there to hold you to it.

The four Instruction weeks

Four things that break.

Working draft, to be refined with the Speaker lineup. Each Speaker answers the same questions from lived experience: what did you have to break, when did you know, what did you build in its place, and what did you refuse to break?

  1. The customer and the model

    The customer you built the company on, the pricing, the offer. What made the first stage work, and what caps the next one.

  2. The cost structure

    Capital, margin, and where the money goes. AI and the cost of capital are rewriting this one whether you choose it or not.

  3. The org chart

    The people and structure that got you here. Loyalty, roles that outgrew their owners, and the team the next stage needs.

  4. The founder’s role

    Your job, your habits, your control. A business grows to the limit of its operator’s willingness to let go.

What you’ll do in Cohort weeks

The closed week is where the work happens.

Each Cohort week, the cohort meets without the Community and without the Speaker. The session is run by an EO facilitator using EO Forum format. The work is the previous week’s topic, applied directly to your actual situation, with peers who’ve agreed to hold what gets said in the room.

You bring your actual situation. Not a case study. Not a hypothetical. The thing you’re protecting.

This is not a business school class on strategy. It is a confidential working room for entrepreneurs deciding what has to break for the business to go further.

The schedule

Eight Tuesday afternoons at EO House.

The Compass 01 cohort runs eight consecutive Tuesdays — March 30 through May 18, 2027 — from 4:00 to 7:00pm. Instruction weeks (March 30, April 13, April 27, May 11) are open to Community; Cohort weeks (April 6, April 20, May 4, May 18) are closed to the Class. Doors at 3:30, hard start at 4:00. Snacky food, no alcohol. An optional program kickoff is planned for March 16.

Attendance at all eight sessions is mandatory and a condition of holding a seat. The room only works if the full cohort is in it. If you can’t commit to all eight weeks, observing is the better fit this year.

Enter the Compass 01 lottery.

Eight seats, filled by lottery. Entries open September 1, 2026 and close December 1. Selection Day December 15.

Enter the lottery Join as Community