Test Drive Forum
2026-06-29 13:00 - 16:00 (America/Chicago) | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL, 60647
Your Path to EO Chicago Membership – This is your formal interview for potential acceptance into EO Chicago.
Meet with current members and other prospects in a forum like setting. We will show you what it looks like to be part of EO, with existing members. This is an opportunity for us both to assess membership, core values and cultural fit.
We’re excited to connect and explore the possibility of welcoming you into the chapter.

We look forward to seeing you there!

Attendees: EO Members, Membership Committee & Prospects

Jumpstart July — Virtual Learning Series
2026-07-13 08:00 - 2026-08-02 17:00 | Virtual
Join EO’s three-week virtual experience designed to help you strengthen execution while staying fully engaged in your business. Gain practical insights, test ideas in real time, and translate them into action immediately.

Virtual Execution Day Deep Dive Session 1
2026-07-21 09:00 - 11:00 | Webinar/Virtual Learning
This session will be facilitated by Michael Caito

This is a 120 min session including Q&A.
Open to all current Accelerators; select seats available for Members & Chapter Staff

EO Chicago Kick Off Party: Yacht Rock Revival - 2026/2027
2026-07-21 18:00 - 22:00 | Columbia Yacht Club, 111 North Jean Baptiste Pointe du Sable Lake Shore Drive, Chicago, IL, 60601
The new EO Chicago year officially sets sail on July 1… and we’re kicking it off with a Yacht Rock party aboard the legendary Columbia Yacht Club.

Think summer nights, skyline views, smooth music, heavy apps, cocktails flowing, and an EO Chicago crowd ready to let loose and reconnect before the year ahead.

We will be having a yacht rock band that will be bringing all the classics. Break out your best captain’s hat, linen, loafers, gold chains, aviators, and full-on “channeling Kenny Loggins” energy. Bonus points if someone shows up looking like they walked straight out of a 1978 marina party.

Whether you’re brand new to EO or have been around for years, this is one of those nights that reminds you why this community is so special — fun, relaxed, wildly connected, and full of people you actually want to spend time with.
Come sail away with us.

RSVP By: 6/14/26 Attendees: EO & EOA (Renewed Members), SAP, SLP

Launchpad Forum - July 2026
2026-07-23 13:00 - 16:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647
A Space for New Members Not in a Formal Forum to go 5%.

Launchpad Forum is a space designed exclusively for new EO members and Forum moderators actively recruiting new members. This curated experience allows participants to explore the power of Forum, practice going 5%, and build meaningful connections—all within EO’s enhanced Forum Framework tailored to support every stage of the entrepreneurial journey.
RSVP By: 7/20/26
Attendees: New EO Members & Moderators of forums who are recruiting new members.

EO Chicago Monthly Happy Hour
2026-07-23 16:00 - 17:00, 2026-08-19 16:00 - 17:00, 2026-09-23 16:00 - 17:00 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL 60647, Chicago, IL, 60647, US
EO Chicago Monthly Happy Hour
Join us for our monthly EO Chicago Happy Hour. Grab a drink, catch up with fellow members, meet someone new, and strengthen the relationships that make our chapter great.
Who should attend?
EO, EOA, Prospects, SAP

What’s included? Beer, wine, non-alcoholic beverages, and light bites.

EO Chicago Fitness Club – Great Lake Plunge
2026-07-26 07:00 - 09:30 | Dempster St. Beach Launch Facility, 1251 Lake Shore Boulevard, Evanston, IL 60202, Evanston, IL, 60202, US
An open water swim in Lake Michigan designed to challenge your endurance in a natural environment. Expect open water conditions that are very different from pool swimming—more dynamic, more exciting, and at your own steady pace.
Distance Options:

1K
2K
4K

Best Practices:

Be comfortable swimming continuously for extended periods
Practice sighting (lifting your eyes to navigate while swimming)
A wetsuit is highly recommended for warmth and buoyancy
If possible, train in open water—not just a pool
Go at your own pace and stay aware of conditions at all times

This is a true open-water experience focused on endurance, comfort, and confidence in the lake.

RSVP: Official registration for the Great Lake Plunge must be completed through the race organizer’s website: https://runsignup.com/Race/IL/Evanston/GreatLakePlunge
Once registered, please RSVP here on Eventbrite so we know you’re attending and can add you to the WhatsApp group.
Deadline to register: 7/24
Attendees: EO, EOA, SAP, SLP, Prospects, & Friends

Test Drive Forum
2026-07-27 13:00 - 16:00 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL 60647, Chicago, IL, 60647, US
Test Drive Forum

Your Path to EO Chicago Membership

This is your formal interview for potential acceptance into EO Chicago.
Meet with current members and other prospects in a forum like setting. We will show you what it looks like to be part of EO, with existing members. This is an opportunity for us both to assess membership, core values and cultural fit.

We’re excited to connect and explore the possibility of welcoming you into the chapter.
We look forward to seeing you there!

RSVP by: 7/25
Attendees: EO Members, Membership Committee & Prospects

Q1 Forum Training
2026-07-28 08:00 - 17:00 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL, 60647
This will be a full day, in-person forum training for all new Members and SLPs.
Forums are at the heart of EO. These safe, confidential groups foster EO members’ peer-to-peer discussion and reflection in a supportive, noncompetitive and nonjudgmental atmosphere. An SLP Forum works the same way, but allows members’ SLPs to meet regularly with others who may share a similar mindset and who may be going through—or have gone through—similar experiences as the SLP of a leading entrepreneur.
In preparation for Forum Training, we would like to help set your expectations to ensure you get the maximum value.
You might be wondering how this training could possibly consume a full day. We understand that you are busy and getting away for a day is challenging! So please allow us to explain…
The training will provide you with the knowledge and techniques necessary to get the maximum benefit out of your Forum – for both your business and personal growth. You will learn the mechanics of how Forum works, best practices to help you get added value, and you will actually practice the tools the techniques with your new Forum. You will learn and share with your Forum mates, and start discussing what you want out of this Forum experience.
Please view this day as an investment in your own development, where you will gain tools that you can utilize in both your personal and professional life – not just in Forum!
Please plan to work without technology. There will be small breaks for you to check your phone.

Agenda: 8:00am ~ Soft Start and Light Breakfast available,
8:30am ~ Hard Start,
12:00pm ~ Lunch,
5:00pm ~ End

RSVP by: 6/21/26
Attendees: New Members & SLPs (Members & their SLP must train separately.)

The AI Revenue Engine w/ Darren Goonawardana
2026-07-29 10:00 - 11:30 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL, 60647
You’re probably already drowning in AI tools, marketing platforms, and agency invoices — and still not seeing the results you need. Leads. Deals. Dollars. Sound familiar?
Darren Goonawardana — EO Chicago / Europe, CEO and co-founder of Collectiv — got tired of paying outside agencies and juggling disconnected tools. So he built something different: an AI-powered marketing and lead generation engine, implemented inside his own company.
The result? Attributable results for the first time ever. Form fills doubled. Marketing costs cut by 10x. No agency. No bloated tech stack.
In 90 minutes you’ll get

Why AI marketing is no longer optional — and what your competitors are doing while you wait
How to cut agency dependencies and take back control of your marketing — while reducing costs
A practical blueprint you can adapt and implement AI for marketing and sales in your own business

For entrepreneurs who want to Lead with AI.
RSVP By: 7/27 Attendees: EO, Accelerators, Kep Executives, Prospects, SAP

EO Chicago Summertime Breakfast @ Beatrix Fulton Market
2026-08-11 08:00 - 09:30 | Beatrix, 834 West Fulton Market, Chicago, IL 60607, Chicago, IL, 60607, US
Join fellow EO Chicago members for a relaxed summer morning of coffee, breakfast, and connection at Beatrix Fulton Market.
Whether you’re looking to reconnect with familiar faces or meet members you haven’t crossed paths with yet, this casual gathering is a great way to start your day and strengthen your EO network.
Capacity is intentionally limited to encourage meaningful conversation.
RSVP By: 8/5 Attendees: EO Members, Prospects, & SAP

Let's Celebrate Anthony Ramirez
2026-08-17 16:30 - 18:00 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL 60647, Chicago, IL, 60647, US
One of our own is about to help lead EO around the world.
Join EO Chicago as we celebrate Anthony Ramirez’s appointment as EO Global Chair-Elect—the first member from our chapter to serve in this role. After leading at the chapter, regional, and now global level, Anthony’s journey reflects the leadership, generosity, and commitment that define our community.
To mark this historic milestone, we’re honored to welcome EO Founder Verne Harnish to EO House for the very first time as he joins our chapter in celebrating Anthony’s incredible achievement. It’s a special evening that recognizes both a historic moment for EO Chicago and an exciting new chapter for our community.
Reconnect with fellow members, meet new faces, and be part of a celebration you’ll remember for years to come.
Raise a glass as we toast Anthony, welcome Verne to EO House, and celebrate EO Chicago’s place on the global stage.

Attendees: EO Members, Accelerators, SAP, Elumni, & Prospects

RSVP by: August 12

Launchpad Forum - August 2026
2026-08-19 13:00 - 16:00 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL, 60647
A Space for New Members Not in a Formal Forum to go 5%.
Launchpad Forum is a space designed exclusively for new EO members and Forum moderators actively recruiting new members. This curated experience allows participants to explore the power of Forum, practice going 5%, and build meaningful connections—all within EO’s enhanced Forum Framework tailored to support every stage of the entrepreneurial journey.
RSVP By: 8/12/26
Attendees: New EO Members & Moderators of forums who are recruiting new members.

Q1 EOA Coaches Dinner
2026-08-19 17:30 - 19:30 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL 60647, Chicago, IL, 60647, US
Join your fellow EO Accelerator Coaches and Committee members for dinner the evening before Cash Day.
This gathering is an opportunity for our coaching team to connect, align, and prepare for the Learning Day ahead. We’ll spend the evening with Greg Crabtree, our Cash Day facilitator, discussing the EO Accelerator experience, sharing coaching perspectives, and providing Greg with valuable context to help make Cash Day as impactful as possible for our participants.
We look forward to seeing you there.

RSVP by: August 13

Attendees: EO Accelerator Coaches & Committee Members

CASH Learning Day
2026-08-20 08:30 - 17:00 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL, 60647
🚀 Fueling Growth Through Financial Mastery
Do you have consistent sources of cash to fuel your growth
In this high-impact session, you’ll dive into five essential financial levers that can make or break your ability to scale. Whether you’re tightening your cash cycle, shifting to recurring revenue, or exploring smarter compensation strategies, this workshop will give you practical tools to build a more profitable, fundable business.
You’ll explore fresh insights and revisit foundational concepts from Scaling Up, creating a clear, actionable roadmap to strengthen your financial engine. You’ll leave with a personal action plan—and peer accountability to keep you moving forward throughout the quarter.

🗓️ Tentative Agenda:

8:30 AM – Check-In, Breakfast & Connection
9:00 AM – Hard Start: Morning Session
12:00 PM – 1:00 PM – Lunch (Provided)
1:00 PM – 2:45 PM – Afternoon Session
3:00 PM – 4:00 PM – Panel Discussion
5:00 PM – Conclusion

Materials to Bring: Coming soon.

Attendees: EOA, EO, SAP

Test Drive Forum
2026-08-24 13:00 - 16:00 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL 60647, Chicago, IL, 60647, US
Your Path to EO Chicago Membership

This is your formal interview for potential acceptance into EO Chicago.
Meet with current members and other prospects in a forum like setting. We will show you what it looks like to be part of EO, with existing members. This is an opportunity for us both to assess membership, core values and cultural fit.
We’re excited to connect and explore the possibility of welcoming you into the chapter.
We look forward to seeing you there!
RSVP by: 9-20
Attendees: Prospects, EO Members, Membership Committee

Q1 New Member Dinner
2026-08-25 18:00 - 21:00 | TBD, 444 West Lake Street #900, Chicago, IL 60606, Chicago, IL, 60606, US
🍽️ Join us for an evening of connection, conversation, and community at our Q1 New Member Dinner.
This special gathering brings together EO Chicago’s newest members, EOA graduates, and SLP’s for a relaxed dinner designed to help you build relationships and deepen your connection to the chapter. Whether you’re new to EO or transitioning into your next stage of involvement, this is an opportunity to meet fellow entrepreneurs, share experiences, and expand your network in an intimate setting.
With a small group and private dining experience, you’ll have the chance to engage in meaningful conversations and start building the relationships that make EO so valuable.
We look forward to welcoming you to the community.

RSVP By: 8/19/26 Attendees: Executive Board, New Members, and Significant Life Partners (SLP’s)

Montrose Beach Bash: Q1 Moderator Outing
2026-08-27 17:00 - 19:00 | The Dock at Montrose Beach, 200 West Montrose Harbor Drive, Chicago, IL 60640, Chicago, IL, 60640, US
Montrose Beach Bash: Q1 Moderator Outing

Join your fellow EO Chicago Moderators for a relaxed evening of beach games, great conversation, and dinner on the lakefront.
Schedule

5:00 PM – Beach games at Montrose Beach (volleyball and more!)
6:00 PM – Dinner and Forum discussion at The Dock
7:00 PM onward – Stick around for live music

Whether you’re diving into a volleyball game, cheering from the sidelines, or simply joining us for dinner and conversation, this is a great opportunity to reconnect with fellow moderators and kick off Q1 together.
Attendees: Forum Moderators

*If you cannot attend please ensure one person from your forum can! We would love all forums to be represented.
RSVP by: August 20

EO Under the Stars: Ray LaMontagne at Ravinia
2026-08-29 17:00 - 21:00 | Ravinia Festival, 200 Ravinia Park Road, Highland Park, IL 60035, Highland Park, IL, 60035, US
EO Under the Stars: Ray LaMontagne at Ravinia

Trade the boardroom for a blanket on the lawn and join your EO community for an unforgettable summer evening at Ravinia.
EO Chicago is covering your concert ticket—you bring the picnic! Pack your favorite snacks, drinks, lawn chair, and blanket, then settle in for a relaxed evening of connection and incredible live music as Ray LaMontagne takes the stage.
What to Bring

Your favorite food and beverages
Lawn chair and/or blanket
Small picnic table (optional)

Event Details

Doors Open: 5:00 PM
Concert Begins: 7:00 PM
Rain or Shine
EO Chicago provides your lawn ticket

🎟️ Tickets are limited! We’ll begin with 25 tickets and open additional spots if demand is high, so don’t wait to RSVP.
Come unwind, enjoy an incredible performance, and experience one of Chicago’s favorite summer traditions with fellow EO members and SLPs.

Attendees: EO Members & SLP’s
RSVP by: August 15

SLP Cupcake Decorating Social
2026-09-03 18:00 - 20:30 | Give Me Some Sugar, 2205 West Belmont Avenue, Chicago, IL 60618, Chicago, IL, 60618, US
Join us for a fun, no-mess cupcake decorating session at Give Me Some Sugar! Swing by starting at 6:00 — snacks and drinks provided — for a little mingling before we get hands-on with icing, sprinkles, and decorations to create our own beautiful (and delicious) cupcakes. No experience needed. All equipment and supplies are provided, plus a box to take your creations home.
Attendees: SLP’s

RSVP by: August 26th

EO @ Oxford: Unlocking Strategic Innovation
2026-09-06 15:00 - 2026-09-11 12:30 | Blavatnik School of Government, University of Oxford Radcliffe Observatory Quarter Woodstock Road, Oxford, England, OX2 6GG
A New Perspective on Your Company’s Future
Imagine standing in the heart of historic Oxford University, where some of the world’s greatest minds shaped the future. Now picture yourself there—not as a visitor, but as a participant—immersed in a program that will transform how you shape the future of your business. EO@Oxford: Unlocking Strategic Innovation is an opportunity to redefine what innovation means for you, your business, and its future.
Working alongside successful entrepreneurs from around the globe, and guided by Saïd Business School’s pre-eminent strategic innovation faculty, you will discover answers to key questions about your company’s long-term success:

How do I adapt and lead in the face of uncertainty and disruption?
How do I future-proof my business using the right data to make the right decisions?
How do I establish a company-wide culture of creative problem-solving?
What can I learn from top companies that use innovation as a competitive differentiator?

EO@Oxford delivers proven techniques and actionable plans to keep you and your teams nimble and adaptable over the long term—and the connections you’ll form with fellow entrepreneurs who share your ambition to face any challenge. What can you achieve with the tools to think boldly, innovate fearlessly, and lead with purpose? Find out at EO@Oxford 2026.
Attendees: EO Members

Past Presidents Council - Fall 2026/2027
2026-09-09 09:00 - 14:00 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL, 60647
🎯 Join EO Chicago’s Past Presidents Council for a strategic discussion focused on the year ahead.
This annual gathering brings together EO Chicago’s past presidents and current chapter leadership to share insights, discuss priorities, and help shape the future direction of the chapter as we plan for the 2026–2027 year.
Schedule:
• 8:30 AM – Coffee & Light Breakfast
• 9:00 AM – 12:00 PM – Past Presidents Council Meeting
• 12:00 PM – 2:00 PM – Group Lunch (walkable restaurant)
RSVP By: 9/2/26 Attendees: EO Chicago past presidents, current president, and Executive Director

Sanctuary Dinner - Fall in Fulton Market
2026-09-18 18:30 - 22:00
Sanctuary Dinner – Fall in Fulton Market

Please note: Registering enters you into a lottery—it does not reserve your seat. Only 8 EO members will be selected and notified after registration closes.
As the seasons change, join us for an intimate evening of exceptional food, meaningful conversation, and authentic connection.
Our Fall Sanctuary Dinner brings together a small group of EO members for a chef-hosted dinner in a beautifully appointed Chicago penthouse with breathtaking city views and an inviting outdoor terrace.
Come as you are. Leave more connected.

Eligibility: EO Members Only
Capacity: 8 EO Members (Selected by Lottery)
Lottery Entry Deadline: September 4
Location: Shared with selected attendees only

EOA 2026 Graduation Celebration
2026-09-22 17:30 - 20:30 | TBD, 444 West Lake Street #900, Chicago, IL 60606, Chicago, IL, 60606, US
Congratulations! It’s time to celebrate!
We’re incredibly proud of our EO Chicago Accelerator graduates—Alison Cummins, Prateek Mathur, and Ian Beacraft—for completing the program and achieving this important milestone in their entrepreneurial journeys.
Join us for a special evening of laughter, connection, and inspiration as we honor their accomplishments alongside the coaches, teammates, life partners, and chapter leaders who have supported them along the way.
This isn’t just a dinner—it’s a milestone celebration. Let’s raise a glass, share some stories, and send Allison, Prateek, and Ian into the next chapter of their journey with the recognition they deserve.
Come celebrate. Come connect. Come be inspired.

RSVP By: September 9 Attendees: Graduates, Executive Board, EOA AG Coaches

Launchpad Forum - September 2026
2026-09-23 13:00 - 16:00 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL, 60647
A Space for New Members Not in a Formal Forum to go 5%
Launchpad Forum is a space designed exclusively for new EO members and Forum moderators actively recruiting new members. This curated experience allows participants to explore the power of Forum, practice going 5%, and build meaningful connections—all within EO’s enhanced Forum Framework tailored to support every stage of the entrepreneurial journey.
RSVP By: 9/16/26
Attendees: New EO Members & Moderators of forums who are recruiting new members.

Q2 2026/2027 Board Strategy Session
2026-09-24 09:00 - 14:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647
Save the date!

Q2 2026/2027 Board Strategy Session
2026-09-24 09:00 - 14:00 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL 60647, Chicago, IL, 60647, US
Join us for the EO Chicago Board Strategy Summit, a focused day of planning, collaboration, and leadership alignment as we shape the year ahead.
This year features a new summit format, bringing together the Executive Board and Extended Board for dedicated strategy sessions designed to maximize impact.
Facilitated by Dan Heuretz, this interactive workshop will spark fresh ideas, strengthen collaboration, and help us build a clear plan for an exceptional year.

Schedule:

Executive Board☕ 8:30 AM – Breakfast

🗓️ 9:00 AM–12:00 PM – Strategy Session

All Board Members🥗 12:00–12:30 PM – Lunch

Extended Board📋 12:30–2:00 PM – Committee Strategy Session

🍻 Optional Happy Hour at EO House immediately following the summit.

Attendees: Executive Board (9-2) Extended Board (12-2)

RSVP by: 9-16

Test Drive Forum
2026-09-25 10:00 - 13:00 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL 60647, Chicago, IL, 60647, US
Your Path to EO Chicago Membership
This is your formal interview for potential acceptance into EO Chicago.
Meet with current members and other prospects in a forum like setting. We will show you what it looks like to be part of EO, with existing members. This is an opportunity for us both to assess membership, core values and cultural fit.
We’re excited to connect and explore the possibility of welcoming you into the chapter.
We look forward to seeing you there!
RSVP by: 9-18
Attendees: Prospects, EO Members, Membership Committee
