2026 EO Global Leadership Conference
2026-04-15 09:30 - 2026-04-17 22:00 (America/Chicago) | The Convention Centre Dublin (CCD), Spencer Dock, North Wall Quay, Dublin, Ireland, 1 D01 T1W6
This April, EO invites you to gather in one of Europe’s most storied capitals–Dublin, Ireland–for the 29th Global Leadership Conference.
Set against the River Liffey and housed within the world-class Convention Center Dublin, this event calls upon every EO leader to embrace the extraordinary and build a legacy that lasts.

As entrepreneurs, we are called to build boldly and challenge what’s expected. But no one creates meaningful impact alone.
The leaders we remember and the stories worth retelling are not defined by titles or achievements, but rather the courage they showed, the collaboration they embraced, and the lasting impact they made.
Leadership becomes legend not when it is simply remembered–but when it’s retold.
Their legacy lasts not because they stood apart, but because they stood together in service of something greater.

This is your invitation:
To act with bravery. To grow with others. To lead with purpose.

The question isn’t whether you’ll succeed–it’s whether your leadership will become a story worth telling.
Will you make it legendary?

People Day Deep Dive Session 1
2026-04-21 09:00 - 11:00 | Webinar/Virtual Learning
This training will be led by EO trainer & member, Michael Caito

Join Michael Caito, Senior Trainer for the EOA Community, as he guides you through the five key strategies to optimize people and performance.
The Deep Dive is a 120 min event including Q&A.

EO SLP Dinner: Connection & 5% Conversations
2026-04-21 18:00 - 20:00 | Ada Street, 1664 North Ada Street, Chicago, IL, 60642, United States
Join fellow EO SLPs for a private dinner. This evening is a chance to connect with other spouses in a relaxed setting over great food and drinks. Cari and Kristy will also share a short introduction to Forum and guide a brief “5% conversation” so you can experience the kind of deeper connection many SLPs value in Forum. Spouses and Life Partners not in a forum are encouraged to come— you do not have to be in a forum to attend.
RSVP By: 4/15/26
Attendees: SLPs currently not in a forum

"The Pitch" - Turn 30 Seconds Into Your Next Opportunity
2026-04-22 09:00 - 11:00 | IL
In just 30 seconds, you can either confuse your network—or create opportunity.
This interactive session is designed exclusively for EO Accelerator participants to sharpen their 30-second elevator pitch so others clearly understand what you do and how to refer business to you.
EO members are encouraged to attend, listen, and offer feedback—while gaining a deeper understanding of Accelerator businesses they can support through referrals.
Each Accelerator participant will:

Deliver their 30-second pitch
Receive 1–2 minutes of questions from the audience
Hear what others understood about their business
Get quick feedback to improve clarity and memorability

The goal is simple:
Be Clear. Be Remembered. Get Referrals.
Come prepared with your 30-second pitch. Your network is one of your greatest sources of opportunity—but only if they know how to talk about you when you’re not in the room.
EOA presenters: reserve your spot. EO members: come support, give feedback, and discover businesses you can refer.
RSVP By: 4/16/26
Attendees: EOA.
*EO members are welcome to join and give feedback to accelerators

EO Membership Interview Day
2026-04-22 13:00 - 16:00 | IL
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, EOA & Prospects

Launchpad Forum - April 2026
2026-04-23 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: 4/16/26
Attendees: New EO Members & Moderators of forums who are recruiting new members.

YPO Gold Chicago Poker Event
2026-04-23 18:00 - 23:30 | Wurkwel Ventures, 303 W Erie St., Suite 500, Chicago, IL 60611, Chicago, IL, 60611, US
Get ready to shuffle up and deal!
Join YPO Gold on April 23rd for an exciting YPO Poker Tournament filled with high-stakes action, great company, and plenty of thrills. Whether you’re a seasoned card shark or just looking for a fun night out, this tournament promises competitive play and an unforgettable atmosphere.
Players will battle it out for top prizes, bragging rights, and the ultimate title at the final table. Expect great energy, strategic showdowns, and plenty of suspense as the chips stack up and the pressure builds.
Spots are limited, so be sure to register early to secure your seat at the table. Bring your best poker face—we’ll see you on April 23rd! ♠️
Note: Family and friends are welcome to attend. Initial buy-in is $200 and due upon registration. No refunds.

AGENDA:

6:00 p.m. Arrivals & Socializing (Open Bar)
7:00 p.m. Poker Games Start at this time (SHARP)
11:30 p.m. Conclusion of Poker Tournament

DAY CHAIR: Ken Hachikian
PARKING INSTRUCTIONS: Please park in the open lot next to the building at no charge. Limited to 27 cars.
ATTIRE: YPO Casual
INVITED: YPO Members, YPO Spouses/Partners, EO Members, EO Spouses/Partners & YNGers, Family Members and Friends are invited!
For questions and to register, email Maggie Divarco, Chapter Manager for YPO Gold Chicago.
REGISTER HERE

The Great EO Chicago Family Scavenger Hunt
2026-04-25 12:45 - 15:00 | IL
Get ready for a fast-paced, clue-solving adventure through downtown Chicago! In The Great EO Chicago Family Scavenger Hunt, adults and kids team up to crack clues, complete missions, snap photos, and explore iconic spots in our fabulous city.
Teams race to earn points, collect items, and work together—because the highest-scoring team wins. It’s fun, active, and perfect for families, friends, and anyone who’s up for an unforgettable Chicago challenge.
Your mission starts now… if you choose to accept it.

Space is limited, so be sure to reserve your place early.
Starting location to be revealed just prior to the event.

Attendees: EO Chicago Members, SLPs & their Children
RSVP By: 4/7/26

The EO/London Business School Growth Forum (EO/LBS)
2026-04-26 16:00 - 2026-04-30 14:30 | Landmark London, 222 Marylebone Road, London, United Kingdom, NW1 6JQ
This four-day executive education program at London Business School gives entrepreneurs practical tools to refine strategy, strengthen leadership, and build environments where creativity and performance thrive.

EO/LBS stands out among EO’s Executive Education programs for its use of the case method, featuring real, EO-like companies that faculty often know intimately — bringing each lesson closer to the realities entrepreneurs face every day.

✔️ 4 days of faculty-led sessions and study group work culminating in a concise, one-page growth plan tailored to each EOer’s business.
✔️A deep-dive assessment of your growth opportunity, alongside world-class faculty at a top business school
✔️ Connections, peer learning, and inspiration with over 70 growth-minded EOers from around the world

Attendees: EO Members

Lead to Close: Sales & Marketing Webinar for EO Accelerator
2026-04-27 09:00 - 13:00 | Webinar

Rediscover WOW - EO Chicago Takes on Texas - Meow Wolf 2026
2026-04-29 12:00 - 2026-04-30 09:00 | Meow Wolf Grapevine’s The Real Unreal, 3000 Grapevine Mills Parkway #Suite 253, Grapevine, TX, 76051
Rediscover WOW | April 29–30 | Grapevine, TX
What can 24 hours of WOW do for your business?
Join EO Chicago in Dallas for 24 hours of high-impact learning and connection with EO Dallas and fellow Texas chapters. By day, experience authentic Texas networking and collaboration; by night, a private takeover of Meow Wolf Grapevine will challenge how you think about creativity, leadership, and growth.
This is our Clear the Calendar Inspirational Learning Event of the Year — designed to spark bold ideas, deepen connections, and deliver business-changing WOW in just one day.

Highlights:
✈️ Fly out April 29 – Return April 30.
🎨 Private Meow Wolf experience + dinner
🤝 Daytime Kickoff with EO Dallas
💰 $400 travel stipend reimbursed after the event for those who attend (**Agenda and recommended flights + hotel provided upon registration)

Open to EO Members only.
Register Soon – Limited Spots – First Come First Serve
Pack your bag, clear your schedule, come play with us and Rediscover WOW.

Give Back with EO Chicago + The Grace Network - Family Event
2026-05-03 17:00 - 19:00 | IL
A Family-Friendly Impact Night
Impact matters. Helping our city matters. And doing it together matters even more.
Join EO Chicago for a casual, feel-good evening supporting The Grace Network—a local organization doing powerful work to help Chicagoland students fight hygiene insecurity.
This event is open to members and their kids and is designed to be meaningful, hands-on, and easy to say yes to.
What to expect:

Hear directly from The Grace Network about the impact they’re making in our city
Stuff hygiene care packs that will go directly to those in need
Enjoy a laid-back pizza party with fellow EO families

No pressure. No programming overload. Just good people, good hearts, and real impact.
This is our third year in a row supporting The Grace Network, and it’s become one of those EO Chicago traditions that reminds us why community matters so much.
If you’d like to learn more about the organization or how to deepen your involvement, feel free to reach out to our Event Day Chair, Ross Rocklin.
Bring your kids. Bring your heart. Come make an impact with us.

About The Grace Network:
The Grace Network is a Chicago-based nonprofit ensuring no child faces the indignity of hygiene insecurity. By partnering with schools to provide essentials like deodorant, shampoo, clean clothing, and even in-school laundry facilities, they help kids show up at school clean, confident, and ready to learn.
Together, we can make a tangible difference in the lives of students who need it most.
🛒 Want to do even more?
Check out The Grace Network’s EO Wish List and help stock their care closets:
👉 https://wishlist.gracenetworkchi.org/EO
🎥 Watch this short video to learn more:
👉 https://youtu.be/4zNPLpJYB50
Let’s pack with purpose. Let’s show up with heart. Let’s be the reason a kid walks into school with their head held high.
RSVP Now – We can’t wait to see you there!

RSVP By: 5/24/26
Attendees: EO, EOA, SAP, SLP, Children, Elumni & Prospects

Q4 EOA Coach & Trainer Dinner
2026-05-06 18:00 - 21:00 | IL
Join us for our quarterly EOA Dinner at EO House Chicago, held before our EOA Learning Day – Execution.
We’re keeping things in-house with a private chef and a relaxed vibe — the perfect setting to unwind, connect, and come together before the big day.
Please RSVP so we can plan accordingly for dinner and seating.
Looking forward to an evening of great food and even better company!

RSVP By: 4/29/26
Attendees: EOA Committee, AG Coaches, Facilitator

Execution Learning Day
2026-05-07 08:30 - 17:00 | IL
Build a stronger team: Learn how to align, lead, and grow your people. Develop a Strategic Advantage Over Your Competitors.
One common challenge that quietly sneaks up on successful scaling companies is the subtle transition from excellent, precise execution to passivity, complacency, and eventually poor execution disciplines. Tightening up your execution habits can dramatically improve your gross margins and profitability while reducing the time it takes to get work done.
🗓️ Tentative Agenda:

8:30 AM – Soft Start, Breakfast
9:00 AM – Hard Start: Morning Session
12:00 PM – 1:00 PM – Lunch
1:00 PM – Afternoon Session
5:00 PM – Conclusion

Printable Materials to Bring:

EOA Execution Day 2026 Participant workbook
Vision Summary
EOA Execution FORM RSVP By: 4/30/26 Attendees: EOA, EO & SAPs

Q4 Forum Training
2026-05-12 08:00 - 17:00 | IL
In-Person Forum Training with Patty Campagna

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: 5/1/26.
Attendees: New Members & SLPs (Members & their SLP must train separately.)

ZOOM Call: Demystifying Forum for SLPs
2026-05-12 20:00 - 22:00 | Zoom Session
EO Global is excited to invite your Spouses and Life Partners (SLPs) to join the last Demystifying Forum for SLPs workshop of this fiscal year — a dynamic introduction to Forum designed to inspire curiosity and connection.

📅 Date: May 12, 2026 — Tuesday
🕙 Time: 8:00 pm – 10:00 pm Central time
📍 Where: Online via Zoom

This interactive two-hour session is the perfect introduction for SLPs who are new to Forum. They’ll discover:

What Forum is and how it works
Why it’s such a powerful tool for growth and connection
How it can enrich their personal journey and relationships

To save your spot: Register Here
This is your chance to step into Forum for the first time, connect with others, and experience the impact it can have.

We look forward to welcoming you!

Attendees: SLPs

Q4 Moderator Outing: Chinatown Nights & Karaoke Lights
2026-05-14 18:00 - 21:30 | New Furama Restaurant, 2828 South Wentworth Avenue, Chicago, IL, 60616
Join us for our Q4 Moderator Outing —a chance to step out of the Forum room and into something a little more flavorful.
We’ll kick off the evening in Chinatown at New Furama Restaurant with dim sum, great conversation, and a chance to share Forum insights—followed by karaoke to keep the energy going.
Our goal is to have every Forum represented. If you’re unable to attend, please send your Moderator-Elect or another Forum member in your place.

Attendees: Moderators, Moderator-Elect, & Forum Committee
RSVP by: 5/6/26

Hackathon: EO Chicago AI
2026-05-18 09:00 - 16:00 | IL
Don’t know what a Hackathon is? You should be here.

Full-day, hands-on hackathon built for EO Chicago members who want to stop watching AI from the sidelines and start putting it to work in their business. Forget the lectures and theory — every minute is spent in live demos, guided workshops, and heads-down building alongside technical talent. You’ll learn practical AI skills and frameworks you can apply well beyond the event, while simultaneously building a real deliverable — a working tool, automated workflow, or functional prototype that solves an actual problem in your business. We’ll share what we’re building and learn from each other. No technical background required. Just bring a business challenge worth solving.
Breakfast & Lunch will be served + happy hour to follow from 4pm – 6 pm!

RSVP By: 4/30/26
Attendees: EO Members + Key Executive/Guest

2026 Moderator Training
2026-05-19 08:30 - 16:00 | IL
The Moderator Training Program teaches Forum Moderators how to lead their Forum in terms of vision, mission and goal-setting and how to manage their Forum processes and members. They receive step-by-step instruction on critical Forum meeting functions, and have the opportunity to practice Forum facilitation skills and processes.
In a full day training, gain tools to enhance your skills to be a leader among leaders. Understand how to balance the three roles of a moderator as a leader, manager, and participant. Learn from others how to apply meeting best practices to take your Forum to the next level.
Take the next step in your Forum Journey!
You’ll learn:
*Moderator responsibilities, tools available to Moderators, and how the Moderator role collaborates with other peer collaborators.
*The benefits of being Moderator, both personally and professionally, and how to leverage this experience.
*Important logistics and best practices to successfully moderate.
*Management of group dynamics and tips for maximizing meetings

8:30am – Soft Start & Light Breakfast
9:00am – Hard Start.
12:00pm – Lunch.
4:00pm – End

Attendees: Members & SLPs.
RSVP by: 5/8/26

YPO-EO Mentor of the Year Luncheon
2026-05-20 12:00 - 14:00 | Sushi-San – Lincoln Park, 1950 North Halsted Street, Chicago, IL, 60614
YPO Gold Chicago and EO Chicago Mentorship Luncheon
We are excited to host the inaugural luncheon presented by the YPO Gold Chicago and EO Chicago Mentorship Committees. During the luncheon, we will present the Mentor of the Year Award, a new recognition honoring a YPO mentor who has made a meaningful and lasting impact within our Mentorship Program.
This award celebrates a mentor who has significantly supported their mentee—whether by helping drive business growth, guiding personal development, navigating a critical challenge, or consistently showing up with wisdom, integrity, and commitment.
More than a recognition, the Mentor of the Year Luncheon creates a rare and emotionally meaningful moment centered on impact and gratitude. As stories of growth, challenge, and transformation are shared, the event highlights the powerful role mentorship plays in shaping leaders and strengthening our entrepreneurial community.
In addition to honoring this mentor, the luncheon will strengthen the connection between the YPO Gold and EO Chicago chapters while elevating the Mentorship Program through its first in-person gathering.

RSVP By: 5/11/26
Attendees: Current Mentor & Mentee Pairs, Prospective YPO Mentors & EO Mentees and YPO & EO Chapter Leadership

EOA North Asia Summit 2026
2026-05-21 08:00 - 2026-05-23 17:00 | IL
We are excited to invite you to the very first North Asia EOA Summit, bringing together EOA members from across the region and beyond for 2.5 days of learning, connection, and growth.
The Summit will feature international keynote speakers, a specially curated EO event, a tailored workshop on EOA Execution tools, and unique opportunities to connect with EOA peers, EO members, and industry experts from across North Asia.
We will also gather for a North Asia EOA Gala – a warm, celebratory evening designed to deepen relationships and strengthen our regional community.

Sales and Marketing Mastermind
2026-05-26 08:30 - 17:00 | IL
This is a bonus learning day for EOA and members.

Led by Josh Sweeney, FounderScale
You’ve spent money on sales and marketing tactics that didn’t deliver. Now, it’s time to learn what actually works to generate leads, close deals, and scale revenue. Join us for a full-day, hands-on workshop designed for entrepreneurs who are ready to take control of their sales strategy and build a repeatable growth system.
This isn’t just another theory-based seminar. Expect real, actionable insights from industry experts and fellow entrepreneurs who have done the work and seen the results. Whether you’re fine-tuning your sales process or looking for a complete overhaul, this workshop will provide you with proven strategies to increase revenue and build a sustainable pipeline.
Agenda:
8:30 – 9:00 – Breakfast
9:00 – 9:15 AM | Housekeeping – Connect with peers and set the stage for an impactful day.
9:15 AM – 12:00 PM | Workshop – Financing Revenue Growth – Learn the fundamental components that dictate whether you will hit or miss your revenue goal.
12:00 – 12:45 PM | Lunch – Network and recharge.
12:45 – 4:00 PM | Workshop – Building the Execution Plan – Learn what works for B2B and B2C companies while building your custom sales and marketing plan.
4:00 – 5:00 PM | Happy Hour & Speed Networking – Build valuable connections with like-minded entrepreneurs.
Reserve your spot now and learn how to build a sales engine that drives real results.
RSVP By: 5/20/26
Attendees: EOA, EO & SAPs

Launchpad Forum - May 2026
2026-05-26 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: 5/22/26
Attendees: New EO Members & Moderators of forums who are recruiting new members.

EO Minnesota's Entrepreneurs’ Rally XIV: Focus Forward Scaling with Intention
2026-05-27 07:45 - 14:30 | Union Depot, 214 4th Street East #Unit 120, Saint Paul, MN, 55101
EO Minnesota’s signature event — keynote, mentor tables, founder stories, connection, breakfast + lunch.

Entrepreneurs don’t struggle from lack of opportunity — they struggle from lack of focus.
Entrepreneurs’ Rally XIV is a one-day working experience designed to help founders step out of the noise, pressure-test real business decisions, and leave with clarity on what to focus on next.
This isn’t a conference built around passive listening or surface-level networking. Rally brings entrepreneurs into structured conversations, shared experiences, and practical frameworks that translate immediately into action.
The day begins with expert-led collaboration tables, where founders tackle real challenges alongside peers and subject-matter experts. Over lunch, EO founders share honest stories about what actually worked — and what didn’t. The experience culminates with Dr. Benjamin Hardy’s Science of Scaling workshop, helping attendees connect insights from the day into intentional next steps for growth.
Attendees: EO & EOA

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, EOA, SAP & SLPs
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.

Take Me Out to the Ball Game: SLP Family Event
2026-05-31 13:30 - 16:30 | Impact Field – The Outlook (Club Level), 9850 Balmoral Avenue, Rosemont, IL, 60018
We’re heading to the Chicago Dogs game on May 31st at 3 PM at Impact Field—and you’re invited to bring the whole crew!
Your game day experience:

⚾️ 1:30 PM gates open for on-field catch + player autographs (until 2:15 PM)

BYO gloves, balls, and markers!

🌭 2:30 PM: Ballpark buffet opens (2 hours of food + fun)
🎉 3:00 PM: Game time!

This is one of those easy, memorable family days—kids running the bases, parents relaxing, and everyone enjoying time together.
Parking: $3 per car

Space is limited, so grab your spot early—first come, first serve!

RSVP By: 5/10/26
Attendees: EO Members, SLP, & Children

EO Chicago's 2026 Annual Town Hall
2026-06-02 15:00 - 18:00 | IL
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

Mock Forum
2026-06-03 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

From Dropout to $930M Exit: The Steps in Between w/Bob Casey
2026-06-04 15:00 - 17:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647
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.
