EO Chicago

Launchpad Forum - May 2026
2026-05-27 13:00 - 16:00 (America/Chicago)
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: 5/22/26.
Attendees: New EO Members & Moderators of forums who are recruiting new members.

Women of EO: The Fire Within - TransFIREmation
2026-05-30 18:00 - 22:00 | The Sanctuary, 3070 Blackthorn Road, Riverwoods, IL 60015, Riverwoods, IL, 60015, US
Join us to kick off Spring with a transformative experience designed exclusively for the Women of EO — a chance to step away from the noise of daily life and come together as a community of bold, curious, growth-minded women.
Originally planned for the depths of winter, TransFIREmation has found its way to spring — and let’s be honest… we better not have snow in May.
This immersive experience is a journey into courage, clarity, and grounded confidence — blending ceremony, mindset work, and the primal power of fire.
Together, we’ll create space to reflect, challenge ourselves, and support one another as we explore the parts of ourselves we show the world… and the parts we’re ready to reclaim.
During this experience, you will:
• Recognize the 95% you operate from every day — the practiced, familiar, predictable version of yourself.
• Meet your hidden 5% — the untapped potential that fuels growth, intuition, and bold leadership.
• Access what’s within through intention, embodiment, and aligned action.

You’ll move through an arrow-breaking ceremony designed to release what no longer serves you, leading into the optional firewalk — a powerful, symbolic act of choice, liberation, and stepping forward with purpose.
Whether you walk the coals or simply witness the transformation, everyone leaves changed.
Spring is about renewal. Growth. New energy. Come together. Claim your fire.

Please wear comfortable clothing you can move freely in.
Layers are recommended for outdoor evening temperatures.
Slip on/off shoes will be removed immediately prior to the firewalk.
Food & Beverage: A light dinner and drinks will be provided.
Parking: Click here to view the parking map.
RSVP By: 5/21/26
Attendees: Women of EO and EOA

The evening will be guided by Executive Master Facilitator & Sakahan Firewalk Master Daphne Paras, who has facilitated transformational workshops and leadership experiences for executives and teams around the world.

EO Chicago 2026 Annual Town Hall
2026-06-02 15:00 - 18:00
EO Chicago 2026 Annual Town Hall: Simplify to Scale
It’s time to simplify what matters so we can scale what’s possible.
Join us at EO House as we pass the baton from outgoing President Kurt Schnakenberg and his board to incoming President Mark Bealin and his team.
Next year’s chapter focus—Simplify to Scale—is about cutting through the noise, creating clarity, and building momentum where it counts. You’ll hear the vision for the year ahead and how we’ll align as a chapter to make growth feel more focused, effective, and impactful.
Why you won’t want to miss this:

Celebrate the leadership transition and meet the new board
Get a clear, focused view of the year ahead
Connect with members in a high-energy, engaging environment

Simplify how you engage. Scale the impact of your membership.
RSVP By: 5/27/26

Attendees: EO Members, EOA (Accelerators) & SAPs

Test Drive Forum
2026-06-03 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!

Attendees: EO Members, Membership Committee & Prospects

From Dropout to $930M Exit: The Steps in Between w/Bob Casey
2026-06-04 15:00 - 17:00
Over the last decade, Bob Casey has launched, invested in, scaled, and exited companies across SaaS, ag-tech, logistics, and real estate. Most notably, Tegus, which grew to $100M+ in ARR before selling for $930M.
In this fireside chat moderated by Yan Pesotskiy, Bob will walk through what most founder stories skip: concentration & focus, building the team & culture, go-to-market strategy, scaling, and knowing when to sell.
Whether you’re scaling, launching something new, or figuring out what comes next, this event is worth the evening.
If you’re an overachiever and aspire to have the best Q&A questions, be sure to read A Hot Knife Through Butter about Bob’s journey at Tegus.
RSVP By: 6/28/26
Attendees: EO, EOA & SAP

Entrepreneurial Masters Program (EMP)
2026-06-07 17:00 - 2026-06-11 09:00 | MIT Endicott House, 80 Haven Street, Dedham, MA, 02026
Welcome to the Entrepreneurial Masters Program (EMP), an exclusive opportunity that guides a carefully selected and diverse cohort of 68 EO members through a transformative three-year journey. Embark on a path of personal and professional growth as you engage with thought leaders, industry experts, and like-minded peers, all centered around our five core pillars:

People
Strategy
Finance
Leadership
Execution

Over the course of these three years, you will be equipped with the tools, perspectives, and thought leadership to:

Uncover your distinct leadership style, equipping you to strategically build exceptional teams, foster a thriving company culture, and adeptly lead your staff.
Master the art of cash flow management, optimizing value and ensuring your financial strategies align with your business objectives.
Define your fundamental values and articulate a clear vision, providing the foundation for a robust, personalized action plan that harmonizes your professional aspirations with a fulfilling life journey.

Are you ready to begin your journey? Take your business, life, community, and family to the next level by applying for EMP.
This application-based program is scheduled for 7-11 June 2026 in Dedham, Massachusetts, USA.
Learn more about the application process here.

EO Women Summit 2026
2026-06-08 13:00 - 2026-06-11 11:00 | Pestana Palace Lisboa, R. Jau 54, 1300-314 Lisboa, Lisbon, Portugal
This is your invitation to step away from the day-to-day and into a space created just for you. A space where women entrepreneurs, leaders, and visionaries come together not to compete—but to connect. To be seen, heard, challenged, and supported by a global community of women who understand what it means to build, lead, and grow in today’s world.
Lisbon is an extraordinary city — bright, coastal, and full of movement. Its sunlit streets and creative energy offer a natural setting for reflection and connection, shaping the tone for this year’s summit. Here in Portugal, the EO Women Summit brings women together to learn, reflect, and build connection through shared experience.
The EO Women Summit has become one of EO’s defining global gatherings. It is the most inclusive event in EO, welcoming EO Members, Spouses/Life Partners, Key Executives, and Accelerators into a space designed for open conversation and shared growth. It brings together women who understand the realities, responsibilities, and rewards of entrepreneurial life.

EO Chicago End-of-Year Volunteer Social: Lunch & Golf at Five Iron
2026-06-09 12:00 - 14:00
Let’s celebrate the people who made this year happen.

Join us at Five Iron Golf for an end-of-year board social bringing together everyone who has served and supported EO Chicago this year. This is our moment to step away from the day-to-day, connect, and have some fun together.

Lunch will be served, with plenty of time to connect and rotate through the bays at your own pace. Whether you’re there to golf or just hang out, it’s a chance to spend time together and wrap up the year on a high note.

Hope you can make it—we’d love to see you to say thanks!

Attendees: Executive Board, Extended Board, EOA AG Coaches, Past Presidents

RSVP By: 6/2/26

Cocktail Crafting Experience at The Aviary: Inside The Office
2026-06-11 18:30 - 20:00 | The Aviary, 955 West Fulton Market, Chicago, IL 60607, Chicago, IL, 60607, US
Step into the hidden world of The Aviary’s exclusive speakeasy, The Office—an intimate, high-design space filled with rare spirits, vintage decor, and a little bit of mystery.
This is a hands-on, high-energy cocktail experience where you’ll shake, stir, and sip your way through some of The Aviary’s most iconic creations—featuring either seasonal favorites or their greatest hits.
Led by expert mixologists, you’ll learn the craft behind each cocktail while enjoying light bar snacks (dinner will not be served) and connecting with fellow EO Chicago members in a truly unforgettable setting.
Expect great drinks, great people, and a night that is all about EO!

Let’s get behind the bar. 🍸

RSVP By: 06/03/26
Attendees: EO Members

Virtual Execution Day Session 1
2026-06-17 09:00 - 14:00 | Webinar/Virtual Learning
EO members will lead you through an engaging day to explore how to use business execution to drive overall growth!
As an entrepreneur, it can be daunting to try and grow your business on your own. In this session you’ll explore tools to help you better understand and grow your business the way you choose to. Led by EO members who are also running businesses over $1M in revenue, you’ll have the chance to learn from the best and practice in real time!

EO Chicago Fitness Club – Spartan Whitewater Trail Run
2026-06-20 07:00 - 12:00 | Rice Lake Nature Trail, 7950 State Park Drive, Whitewater, WI, 53190
Join us for a scenic trail running experience at Spartan Whitewater. This is all about getting outside, moving your body, and enjoying the challenge of varied terrain—at your own pace.
Race Options:

10K (6.4 miles)
Half Marathon
50K

What to Expect:
Trail running is very different from road running—expect hills, uneven terrain, and a naturally slower, more steady pace. It’s less about speed and more about endurance and enjoying the journey.
Best Practices:

Walk the hills early and often—this is completely normal on trails
Expect your pace to be slower than road running
Focus on time on your feet, not pace or speed
Trail shoes are helpful but not required
Fuel and hydrate consistently, especially for longer distances

Whether it’s your first trail run or your fiftieth, this is about getting out there, challenging yourself, and having a great time on the course.

RSVP: This event is produced by Spartan. You must complete your official registration on their website in order to participate:
https://www.spartan.com/en/race/detail/9920/overview?index=2
Once you’ve registered through Spartan, please return here to RSVP on Eventbrite so we know you’re attending. We’ll also add you to the WhatsApp group for updates and coordination.
Discount code: ORM26 (20% OFF)
Attendees: EO, EOA, SAP, SLP, Prospects, & Friends

Launchpad Forum - June 2026
2026-06-25 13:00 - 16:00
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: 6/18/26
Attendees: New EO Members & Moderators of forums who are recruiting new members.

Sanctuary Dinner: A Backyard Summer Evening at the Pagel's
2026-06-27 18:00 - 21:00
Summer Nights at the Pagel Home

Join us for an intimate summer evening at the Pagel home—good food, great people, and real conversation under the Chicago summer sky.
Sanctuary Dinners are designed to slow things down and create space for deeper connection in a relaxed, beautiful backyard setting. Enjoy a thoughtfully chef prepared outdoor dinner, meaningful conversation, and a small group that allows you to truly engage.
Come as you are. Leave more connected.
The Details

Location in Logan Square (shared before the event)
Dinner is provided – please note any dietary restrictions when registering
Bring one bottle of wine or beverage of choice per person (two per couple)

Space is limited!
Registration places you into a lottery for the opportunity to be selected to attend. To keep the experience intimate and impactful, only a small group will be selected for this gathering. Confirmations will be sent by June 19, 2026.
️Please note: To respect the experience and your fellow members, no-shows or cancellations within 48 hours will incur a $200 fee.
Attendees: EO Members + SLP’s
RSVP By: 6/16/26

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

Launchpad Forum – July 2026
2026-07-23 13:00 - 16:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647
Coming soon!

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

Launchpad Forum - August 2026
2026-08-19 13:00 - 16:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647

Sanctuary Dinner: Humans Leading Humans in the AI World
2026-09-03 18:30 - 21:30 | TBD

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

Launchpad Forum - September 2026
2026-09-23 13:00 - 16:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647

EO Chicago Fitness Club – Spartan Midwest Challenge
2026-09-26 06:00 - 11:00 | Badlands Off Road Park, 3968 North Xavier Road, Attica, IN, 47918
Get ready to conquer the Badlands Off-Road Spartans—a 1,200-acre Midwest adventure built to test your endurance in nature at its toughest.
This is a mix of trail running and obstacle challenges designed to test strength, endurance, and grit. You’ll move through sand dunes, rocky terrain, forests, and creek beds while taking on obstacles like carrying, climbing, and crawling. From mud-filled burpees to steep climbs, every section brings a new challenge.
This is a scalable experience—go at your own pace, take breaks when needed, and focus on completing each section step by step. Ultimately, it’s about embracing the elements and pushing yourself in a rugged outdoor environment.
Distance Options:

Sprint (~5K + obstacles)
Super (~10K + obstacles)
Beast (~13 miles + obstacles)

Best Practices:

Use a jog/walk approach between obstacles to recover and maintain energy
Train grip strength ahead of time (you’ll use it more than you think)
Be prepared for obstacle penalties if an attempt isn’t completed (burpees)
Kids race available — a great family-friendly option

This event is about resilience, effort, and pushing yourself in a supportive environment—not perfection or speed.

RSVP: This event is produced by Spartan. You must complete your official registration on their website in order to participate:
https://www.spartan.com/en/races/midwest?index=1
Once you’ve registered through Spartan, please return here to RSVP on Eventbrite so we know you’re attending. We’ll also add you to the WhatsApp group for updates and coordination.
Attendees: EO, EOA, SAP, SLP, Prospects, & Friends

EO’s Global Speakers Academy (GSA) - The Power of Your Story
2026-09-28 09:00 - 2026-10-02 18:00 | TBD
Join EO’s Global Speakers Academy (GSA) for a transformative experience on mastering your presentation skills and crafting your story for impact.
During this immersive, five-day program, EO members receive unparalleled training to develop, refine, and deliver a compelling Signature Talk with personalized coaching from communication experts.
Your story is one of your most powerful leadership tools. When your message is clear, your impact multiplies.
What you’ll gain as a GSA participant:

An immersive experience designed to elevate your storytelling and public speaking skills
Strategic, repeatable frameworks to enhance leadership, communication, persuasion, and stage presence
Five focused days of expert-led workshops and personalized one-on-one coaching
Structured practice with real-time feedback from coaches and peers to build confidence and polish delivery
Lasting, meaningful connections with EO members from around the world on a shared journey of growth

Opportunity to earn GSA certification and unlock new speaking engagements! Subject to evaluation and confirmation by the GSA Certification Review Team.
Attendees: EO Members

EO Chicago Fitness Club – HYROX Simulation
2026-10-17 11:30 - 14:30 | WATTAGE, 1044 West Kinzie Street, Chicago, IL 60642, Chicago, IL, 60642, US
This is a full-body endurance workout that blends running with functional fitness stations for a fast-paced, high-energy challenge. You’ll move through 1K runs followed by workouts like sled pushes, burpees, lunges, and more—repeated for 8 rounds.
It’s simple in structure, but sneaky in difficulty. The goal is steady movement, smart pacing, and finding your rhythm as fatigue builds.
Whether you’re going solo or teaming up, this workout is designed to be scalable, supportive, and surprisingly fun—just don’t be surprised if your legs and lungs have a conversation halfway through.
Workout Format:
8 rounds of:

1K run
Functional workout station (sled push, burpees, lunges, and more)

Best Practices:

Don’t go out too fast—effort compounds quickly
Keep your run pace controlled, not aggressive
Break stations into small, manageable sets early
Expect grip and leg fatigue first—pace your effort accordingly
Can be done in teams (a great, accessible option for all levels)

To help cover the gym rental, we kindly ask for a $30 contribution via Zelle to Joe at (630)776-7697.

RSVP By: 10/17/26
Attendees: EO, EOA, SAP, SLP, Prospects, & Friends!

EO XCentric Cleveland
2026-10-25 14:00 - 2026-10-27 22:00 | Hilton Cleveland Downtown, 100 Lakeside Ave E, Cleveland, OH, 44114
EO XCentric Cleveland is built for entrepreneurs who crave what’s next. It’s a few days to step out of the noise, challenge your thinking, and reconnect with the energy that started it all.
You’ll trade ideas, stories, and lessons with people who understand the grind and the thrill of building something real. Every moment is designed to move you forward and remind you what it means to create, lead, and evolve.
Cleveland is a city that understands reinvention, where creativity and resilience are part of the culture. It’s the ideal place for intentional growth, change, and rejuvenation. Join us, and be part of the evolution.

EO's 2027 Global Leadership Conference (GLC) - Kyoto, Japan
2027-04-11 08:00 - 2027-04-13 17:00 | TBD
Save the date!

Xcentric 2027 - Austin
2027-09-15 08:00 - 2027-09-17 17:00 | TBD
