The Compass at EO Chicago

Compass 01 · Cohort of 2027 · The inaugural cohort

Growing Through Uncertainty.

Running a business when the path isn’t clear — for ten entrepreneurs in the middle of it.

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Why this, why now

The room is for people in the middle of something hard and unfinished.

The 2020s have rewarded operators who can think well under ambiguity. Markets move sideways. Capital costs more. AI is reshaping cost structures in real time. Talent decisions feel reversible and irreversible at once. Few of the playbooks we built between 2012 and 2022 read cleanly now.

What works, in our experience, is doing the thinking with peers who are in the same weather. Not in a workshop. Not in a webinar. In a working room, with seasoned entrepreneurs who’ve been through volatility — multiple cycles, multiple sides — and who are willing to sit with you in the not-knowing.

That is what this edition is for.

The five pillars

What the eight weeks cover.

Working draft. Pillars will be refined with the Speaker lineup before lottery entries open.

  1. Reading the environment

    Separating signal from noise — in markets, customers, competition, and macro. What changes are real, what changes are vibes, and how to tell the difference in your own data.

  2. Capital under ambiguity

    Runway, financing, cash discipline, and reinvestment decisions when the picture isn’t clear. When to hold, when to deploy, when to raise, and when to wait.

  3. People decisions

    Hiring, restructuring, holding, and letting go without certainty about what’s next. How to make org calls that hold up across more than one possible future.

  4. Strategic bets

    Committing versus hedging. Sequencing. Optionality. Knowing what not to do and being able to defend that to a board, a team, or yourself.

  5. The operator under pressure

    Decision discipline. Communicating uncertainty to teams without losing the room. Personal resilience when you are the one carrying the weight.

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 decision. Not a case study. Not a hypothetical. The one that is keeping you up.

This is not a business school class on strategy. It is a confidential working room for entrepreneurs navigating real uncertainty in their businesses right now.

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.

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

Enter the lottery Join as Community