The Compass A program for entrepreneurs · EO Chicago · Cohort begins March 30, 2027
Eight weeks. Ten entrepreneurs. The decision that’s keeping you up.
A working cohort for people running real businesses through real uncertainty with EO-style trust and candor, and seasoned entrepreneurs in the room while you make the call.
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 ten, 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.
The format
Eight weeks, alternating.
Each week is one of two kinds.
Instruction weeks are open to Community and led by a Speaker.
Cohort weeks are closed to the cohort, who use facilitated EO Forum format to work their application of the topic.
Week 1 · Mar 30
Instruction
Open to Community
Week 2 · Apr 6
Cohort
Cohort members only with an EO facilitator
Week 3 · Apr 13
Instruction
Open to Community
Week 4 · Apr 20
Cohort
Cohort members only with an EO facilitator
Week 5 · Apr 27
Instruction
Open to Community
Week 6 · May 4
Cohort
Cohort members only with an EO facilitator
Week 7 · May 11
Instruction
Open to Community
Week 8 · May 18
Cohort
Cohort members only with an EO facilitator
Compass 01 · Cohort of 2027
Growing Through Uncertainty.
Running a business when the path isn’t clear.
The inaugural cohort is built for operators needing change which is unclear — a market shift, a scaling decision, a capital question, a leadership inflection. The work happens in the room, on your situation, with peers who are doing the same.
Five working pillars, refined with the Speaker lineup:
- Reading the environment for signal
- Capital under ambiguity
- People decisions when the picture isn’t clear
- Strategic bets, sequencing, optionality
- The operator under pressure
The Speakers
Seasoned entrepreneurs in the room.
Each Speaker leads one Instruction week, open to the Class and Community. They bring lived experience and answer real questions from the room. The first Compass lineup is being recruited specifically against the uncertainty theme: operators with lived experience leading businesses through volatile periods.
Pricing & commitment
$1,000. All eight weeks. No exceptions.
The fee is the commitment to the program.
Attendance at all eight sessions is a condition of holding a seat. The room only works if the full cohort is there. If you can’t commit to all eight weeks, observing is the better fit this year. Cohort members who complete the program graduate as Compass 01 alumni, with standing in the alumni community and an invitation to mentor future cohorts.
- 10 seats — filled by lottery
- 8 Tuesdays, 4–7pm — attendance mandatory
- $1,000 program fee
- EO Chicago members