Entrepreneurial Masters Program (EMP)
2026-06-07 17:00 - 2026-06-11 09:00 (America/Chicago) | 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 | Five Iron Golf, 2131 North Elston Avenue, Chicago, IL, 60614
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

Virtual Event: Emma Grede - Powerhouse Speaker Series
2026-06-10 09:00 - 10:00 | Virtual
The EO Powerhouse Series is designed to give exclusive access to thought leaders and change-makers across various industries.
You will hear first-hand about their stories, challenges and the journeys that have brought them to where they are today through real-time virtual keynote and moderated interview sessions.
This series was created in partnership between EO Learning and the EO Board. It is FREE for all EO members.

BIO
Emma Grede is an entrepreneur and investor behind some of the most influential consumer brands of the last decade. As Co-Founder and CEO of Good American and Founding Partner of SKIMS, she has built businesses that combine scale, cultural relevance, and commercial performance.
Since launching Good American in 2016, Emma has helped redefine standards in fashion through a brand recognized for both innovation and inclusivity. She went on to co-found SKIMS, now valued at $4 billion and named one of TIME’s 100 Most Influential Companies, setting a new benchmark for product development and brand positioning.
On television, she is a recurring guest Shark on ABC’s hit series Shark Tank and has appeared as a Dragon on the BBC’s Dragon’s Den. She also co-hosts the Roku series Side Hustlers, which premiered as the number one on-demand title on The Roku Channel, where she, alongside Ashley Graham, helps female entrepreneurs turn their side hustles into full-time careers.
Emma serves on the board of the Obama Foundation and is Chairwoman of The Fifteen Percent Pledge, a non-profit organization that encourages retailers to dedicate at least 15 percent of their shelf-space to Black-owned businesses. Emma is also a board member of Baby2Baby, a nonprofit that provides children living in poverty across the country with diapers, clothing and necessities that every child deserves.
In this EO Powerhouse conversation, Emma joins us to explore what it takes to build brands that scale, resonate, and endure.

Please note that both AM and PM interviews will be different, as questions to Emma Grede will not be repeated, so you are welcome to register for both sessions.

Virtual Event: Emma Grede – Powerhouse Speaker Series
2026-06-10 20:00 - 21:00 | Virtual

2026 EO One Canada
2026-06-11 16:00 - 2026-06-14 10:00 | Waldorf Astoria Riviera Maya, Carr Federal Libre 307, Cancun-Tulum, Mexico, 77580
EO Canada has always led from the front. Their region is home to two of the earliest EO chapters. Canada House became a global sensation. Each milestone has shaped how EO entrepreneurs everywhere connect and grow.
In 2026, they lead again.
EO One Canada becomes the first AI-curated EO experience, making sure that every attendee is connected with a fellow member on the basis of a shared issue, shared focus, or shared need.
3 days at the Waldorf Astoria in Cancún will redefine what it means to learn, to lead, and to live beyond borders.

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 | IL
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.

Women of EO Happy Hour - Wolf & Company
2026-06-25 16:30 - 18:00 | Wolf & Company, 1752 North Western Avenue, Chicago, IL 60647, Chicago, IL, 60647, US
💜 Women of EO Happy Hour 💜
EO Women Summer Happy Hour!
We’ve been talking about getting together for a while, so let’s just make it happen.
Join us for a last-minute EO Women’s Happy Hour at Wolf & Company from 4:30–6:30 PM on Thursday, June 25. We’ll grab a drink, catch up, laugh a little, and enjoy some time with other amazing women entrepreneurs.
No agenda. No programming. Just a ladies’ night out with the EO women who always make life a little more fun.
Officially we’re there from 4:30–6:30, but after that… we’ll see where the night takes us.
Hope you can join us!

RSVP by: 6-23 Attendees: EO Chicago Members

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

Test Drive Forum
2026-06-29 13:00 - 16:00 | 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 | 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 | avec Restaurant, 615 West Randolph Street, Chicago, IL 60661, Chicago, IL, 60661, US
Q1 New Member Dinner

🍽️ 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)
