EO Chicago

Virtual Strategy Day Make-Up Session
2025-12-09 10:00 - 15:00 (America/Chicago) | Webinar/Virtual Learning
Virtual Strategy Day Make-Up Session

If you missed Strategy Day, now’s your chance to dive in with this online make-up session from Global, but you must register in advance. There are limited spots available.
EO members will lead you through an engaging day to explore and build a strategy for your business!
If 2025-26 is the year you want more cash, clearer strategy, stronger people, and bullet-proof execution, the EO Accelerator curriculum is your roadmap. We’ve packaged the essentials into four seasonal sprints—each one laser-focused on a key constraint holding founders back.

Sign Up Here!
https://www.eventbrite.com/e/virtual-strategy-day-session-1-suitable-for-usa-canada-europe-mepa-lac-tickets-1557721469849?aff=oddtdtcreator

Attendees: EO & EOA

EO Women's Circle Gathering in Lakeview
2025-12-14 17:00 - 20:00 | Anna Loibner-Davidson’s Home, IL
Since our women’s Transfiremation event was postponed this Sunday due to all the snow, Anna Loibner-Davidson has generously opened her home to still bring everyone together. 💛
Join us for a cozy Women’s Circle Gathering in Lakeview — an evening of good food, wine, cheese, meaningful conversation, and plenty of laughter.
This will be a relaxed, come-as-you-are night. No agenda, no pressure — just a chance to connect, exhale, and be surrounded by other incredible women.

Details:

Date: Sunday, December 14
Time: 5:00pm–8:00pm
Location: 421 W Melrose, Apt. 15D, Chicago, IL

Please RSVP here on Eventbrite so Anna knows how much food and wine to have ready.
If you need anything day-of, you can text or call her at 630-842-1135.

RSVP By: 12/12/25
Attendees: EO Women – Members, Accelerators, SAPs and SLPs

Member Roundtable w/Crews and Co: Why Your Marketing Isn’t Working Anymore—And How to Fix It in 2026
2025-12-16 11:00 - 12:30 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647
Member Roundtable w/Crews and Co – Why Your Marketing Isn’t Working Anymore—And How to Fix It in 2026
As 2026 approaches, many businesses are feeling the pressure. Customer acquisition costs are rising, audience behaviors are shifting, and tried-and-true tactics are falling flat.
Join this in-person roundtable to reflect, reframe, and recharge your marketing strategy for the year ahead. The session will be led by one of our EO Chicago SAP’s, Steve Gradman, a growth strategist who has helped scale startups and multi-million dollar companies by leading high-impact marketing transformations.

What You’ll Learn:

Why your marketing may be underperforming, and what to do about it
Smarter ways to plan and allocate your marketing efforts in 2026
How your peers at EO Chicago are navigating shifting marketing landscapes

Come for the discussion. Stay for lunch!

RSVP By: 12/12/25.
Attendees: EO, EOA & Key Execs

Member Roundtable: Building a Modern Personal Brand on LinkedIn: Practitioner Insights, Real-World Experiments & Audience-Driven Learning
2026-01-08 15:30 - 17:00 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL, 60647
Member Roundtable: Building a Modern Personal Brand on LinkedIn: Practitioner Insights, Real-World Experiments & Audience-Driven Learning

Ready to kick off 2026 by showing up powerfully on LinkedIn?
If you’ve been posting without traction—or not posting at all—this is your chance to reset. Join us for a high-impact, interactive session on building a standout personal brand on LinkedIn in 2026 and beyond.
Led by our very own EOA member Jared Gibson, a LinkedIn content practitioner, and supported by EO member Asif Rehmani, this session blends expert insights, real-world perspective, and live attendee interaction for maximum value.
What you’ll get:

What’s actually working on LinkedIn right now
Why your personal brand matters more than your company page
The real impact of LinkedIn’s new 360Brew update
Simple fixes for common posting mistakes
Frameworks to post consistently without overwhelm

Bonus: Stay for a relaxed happy hour with fellow entrepreneurs afterward. Start the year strong—on social and in community.
Reserve your spot now and step into 2026 with confidence.
RSVP By: 1/2/26
Attendees: EO, EOA & SAPs

Table for Growth: An evening at Maxwells Trading
2026-01-09 18:30 - 21:30 | Maxwells Trading, 1516 West Carroll Avenue, Chicago, IL, 60607
Private dinner with EO Chicago

🍷 EO Private Dinner at Maxwells Trading
Join us for an intimate evening at Maxwells Trading, the vision of Josh Tilden and James Beard Award–winning chef Erling Wu-Bower.
Maxwells was created as a place to unwind, eat, drink, and share ideas with friends—a perfect setting for EO connection. Their mission is simple but powerful: soul-satisfying food, crisp cocktails, engaging wines, and great music, all served with a spirit of community and sustainability.
We’ll gather in the Kinzie Industrial Corridor, where Maxwells is part of a vibrant collective of food, design, and sustainability-focused ventures. Expect Chicago-inspired cuisine that reflects the chef team’s heritage and creativity, in a setting built for conversation and connection.
Space is limited—reserve your spot for this unforgettable night of food, conversation, and community.
RSVP By: 1/2/26
Attendees: EO Members & SLPs

2026 US Central, West, and Canada Moderator Summit - Las Vegas
2026-01-14 17:00 - 2026-01-16 11:00 | Bellagio Hotel & Casino, 3600 S Las Vegas Blvd, Las Vegas, NV, 89109
We are excited to invite you to the US Central, West, and Canada Joint Forum Moderator Summit, being held 14-16 January 2026 in Las Vegas, Nevada.
Moderator Summits are EO’s premiere event for YOU, the Forum moderator. Designed to acknowledge and support moderators as the most pivotal leaders within our organization, Moderator Summits offer face to face connection and deep exploration of the most impactful moderator concepts. This event is open to all US Central, West, and Canada Moderator trained members, Moderator-elects, SLP and Key Executives, Forum Chairs, and Forum Experts.
During the summit, our expert Forum facilitators will guide you through topics such as open coaching, effective 5% Reflections, creating meaningful parking lots, building Deep Dives and managing critical conversations. You will return to your chapter energized, inspired and with a new understanding of how to elevate your Forum experience and leadership journey from fellow moderators across. Sign up now to dive deep with your fellow moderators, Forum chairs, and Forum experts to be inspired, challenged, supported, and heard.
Moderator training is a requirement. If you are not yet Moderator trained, please contact your Chapter Staff to get signed up for Moderator Training prior to this event.
Register HERE!
EO has negotiated a group rate at the Bellagio, BOOK HERE!
Attendees: Moderators, Moderator-Elects, Forum Chairs, Moderators of SLP Forums and Moderators of Key Executive Forums

Launchpad Forum - January 2026
2026-01-20 13:00 - 16:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647
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: 1/12/26.
Attendees: New EO Members & Moderators of forums who are recruiting new members.

EO Talks 2026: Third Annual Storytelling Experience
2026-01-21 16:00 - 19:30 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647
✨ Rated the best EO Chicago learning event for two years running—EO Talks is back for its third year!
This year, we’re raising the bar: amplifying the promise, hitting the 5%, and engaging YOU, the audience, even more.
Four of our inspiring members—Julie Hoffman, Erin Huizenga, Nolan Lee, and Hernan Silva—will step into the spotlight to share their stories of resilience, growth, and transformation. Guided by the incomparable Sally Lou Loveman (former Oprah audience producer), they’ve been crafting talks that reflect not only their personal journeys but also the true spirit of EO.
But EO Talks isn’t just about listening—it’s about connection. These aren’t polished highlight reels. They’re raw, real, and honest 5% moments that reveal who we are beyond business. As an attendee, you’ll be invited to lean in, get curious, and reflect on your own story alongside your peers.
This is more than an evening of storytelling—it’s a chance to celebrate courage, spark curiosity, and connect more deeply with each other through the stories that shape us.
What’s New This Year

Intimate + Member-Only Space – To deepen connection, this year’s EO Talks is exclusive to EO Chicago members. (Each speaker may bring one special guest.)
Audience Engagement – Expect more ways to interact with the stories, the speakers, and each other.
Amplify the Promise – The theme of the year comes alive: showing up fully, vulnerably, and authentically as yourself.

Agenda:
4:00 – 6:30pm Talks & Presentations.
6:30 – 7:30pm Social & Connection.
About Our Host: Sally Lou Loveman knows that the #1 fear people have is public speaking. It just happens to be the one fear she never had. After years as the audience producer for The Oprah Winfrey Show, Sally Lou now coaches people to love their story, connect with their audience, and speak without fear. Her book SPEAK: Love Your Story, Your Audience is Waiting shows how storytelling can become your superpower.
RSVP By: 1/12/26.
Attendees: EO Members, EOA & SAPs

EO Membership Interview Day
2026-01-22 13:00 - 16:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647
Your Path to EO Chicago Membership
This is your formal interview for potential acceptance into EO Chicago.
You’ll meet one-on-one with two existing EO members for a conversational interview centered on our core values, culture fit, and your entrepreneurial journey. This is an opportunity for us to get to know you—and for you to experience what makes EO such a powerful and supportive community.
We’re excited to connect and explore the possibility of welcoming you into the chapter.
Following the interviews, we’d love for you to stay and join us for happy hour.
Attendees: EO Members, EOA Members, & Prospective Members

2026 US + Canada Presidents Meeting
2026-01-26 18:00 - 2026-01-28 17:00 | Hard Rock Hotel & Casino Punta Cana, Km 28, #74, Blvd., Turístico del Este, Punta Cana 23000, Dominican Republic
The 2026 US + Canada Presidents’ Meeting invites all US + Canada Regional Councils, Presidents, President-elects, President elect-elects, and Chapter Staff to collaborate, share best practices, and plan for the upcoming year. The official Presidents Meeting dates are 26-29 January 2026.
Schedule of Events:

Saturday, January 24th: Canada Regional Council Arrivals
Sunday, January 25th: US Regional Council Arrivals, US East President Elect Arrivals, Canada Regional Council Meeting
Monday, January 26th: Regional Council Meetings, President/ Elect/ Chapter Staff Arrivals, and Presidents Meeting Welcome Reception
Tuesday, January 27th: Presidents Meeting Day 1
Wednesday, January 28th: Presidents Meeting Day 2
Thursday, January 29th: Departures + Canada RC Debrief Meeting

Register HERE
For hotel booking link for Presidents and President-Elects, click HERE.

Learning Workshop: Leading Growth in 2026: How Great Leaders Develop Their People w/Patty Campagna (Leading Teams)
2026-01-27 10:00 - 12:00 | EO House Chicago, 1714 North Damen Ave. 3rd. Fl, Chicago, IL, 60647
To grow your business, you need to grow your people. Employee development doesn’t happen in annual reviews—it happens in everyday conversations.

This highly interactive 2-hour workshop is designed for members + one key executive to attend together. We will examine The GROWTH Conversation, a simple leadership framework designed to help you use 1:1 meetings more effectively – driving connection, personal development, and alignment. Participants will learn how to balance performance, strengths, and growth in a way that supports both the individual and the business.

Because great development starts with self-awareness, participants will also reflect on your own growth goals for 2026, clarifying how you want to show up for your teams in the year ahead.

You will practice the GROWTH framework in real time with one of your key executives and leave with a personalized development plan.

NOTE: We encourage you to take your Key Exec out for lunch following the workshop to continue the conversation 1:1 and build on what you learn.

Key takeaways:

A repeatable framework for effective 1:1 development conversations
Increased confidence in supporting, coaching and challenging your people
A concrete development plan for one direct report
Clarity on your own leadership growth focus for 2026
Practical tools that align individual growth with business priorities

RSVP By: 1/21/26
Attendees: EO Members + one Key Exec

Accelerator Connection Dinner: A Facilitated Conversation for Growth
2026-01-30 19:00 - 21:00 | Yardbird, 530 N. Wabash Avenue, Chicago, IL, 60654
Join us for an intimate Accelerator Connection Dinner—a small-group, high-impact evening designed to deepen connection, spark insight, and fuel your personal and professional growth. We’ll gather over dinner at a Chicago restaurant (location shared closer to the date – city location)
Each pod may send up to 2 participants.
Space is extremely limited, with only 8 seats available total.

Important Details

Open to all EO Accelerators
Dinner + facilitated discussion
8 total spots, max 2 per pod
Registration does not guarantee your seat
Your spot is only confirmed once you receive an email from Michelle
If two members from your pod register before you, you will be waitlisted

This is a unique opportunity to step away from the routine, share a great meal, and engage in meaningful conversation with fellow Accelerators.
Reserve your spot—then watch for your confirmation! Parking: Valet parking and self-parking available.
RSVP By: 1/19/26.
Attendees: Accelerators (max 2 per pod)

Closeness - Deepen the Connection with Those Who Matter Most
2026-02-04 17:00 - 21:00 | Room 1520, 1520 West Fulton Street, Chicago, IL, 60607
Closeness: A Workshop for Brave Connection

Come solo or with your partner—both are equally welcome.
In EO we talk about going beneath the surface—fast. That takes courage. This 3-hour, hands-on workshop gives entrepreneurs a safe, energizing place to practice it. You’ll build the skills that create real closeness—trust, self-awareness, clean communication, and shared enjoyment—so you can deepen the relationships that matter most at home, in business, and in life.
This is not a couples therapy session and not a dance class. It’s a high-engagement experience rooted in movement and the relational language of Tango (no experience needed). Activities are accessible whether you arrive solo or with a partner; we’ll rotate and pair thoughtfully so everyone participates comfortably.
Why come?

Turn friction into fuel: transform conflict into clarity and stronger bonds
Practice brave conversations: ask for what you need without armoring up
Build daily micro-habits of connection: small moves, big impact
Leave with a simple “Connection Playbook” you can use the same day

Who it’s for: Entrepreneurs and their partners who want deeper, more honest, more resilient relationships. Bring your spouse/partner(highly encouraged), invite the relationship that you value most, or come on your own — your call.
What to expect: 3 hours, movement-based exercises (think posture, attention, and timing—not choreography), guided reflections, and practical tools you can take back to your family, your team, and your forum. Sustenance and libations will be offered.
Bottom line: The quality of your life is determined by the quality of your relationships. Closeness is a skill. Let’s practice it—bravely.
Call to action:
Take the brave step. Reserve your spot—solo or with your partner.
Facilitator: Anna Lecat.
RSVP By: 1/23 25
Attendees: EO Members, EOA, SAP & SLPs

EO Chicago Q3 Forum Training
2026-02-05 08:00 - 17:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, 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: 1/29/26
Attendees: New Members & SLPs (Members & their SLP must train separately.)

From Stress to Strength: Finding Balance Through Mindfulness
2026-02-11 16:00 - 18:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647
From Stress to Strength: Finding Balance Through Mindfulness

The complex nature of managing businesses requires us to juggle multiple responsibilities and navigate unprecedented uncertainties with a high level of intensity and focus. These demands if not managed mindfully, can take a toll on our body and mind as stress and create further imbalances.
While avoiding stress may not be possible, you can learn to function from a deep state of restfulness, so you can deal with every curveball that life throws at you.
This 2-hour workshop with Rajesh Ramani focuses on insights, tools and techniques to help you slow down and step into a mindful space and harness the power to break away from repetitive stress cycles.
This workshop will help you to:
 Reconnect with yourselves
 Become resilient to stress and anxiety
 Recharge and rebuild your innate abilities.
Key takeaways:
 3 tools to resolve stress and retain balance
 3 wisdom insights to build right attitude and focus
 Tips to build your personal mindfulness routine

RSVP By: 2/4/26
Attendees: EO Members, Accelerators & SAPs

About:
Rajesh Ramani is an internationally sought-after mentor, teacher and retreat facilitator. Over the past two decades, he’s led retreats on emotional and spiritual transformation, facilitated a variety of mind-body wellness programs and run leadership seminars across the world.
Rajesh’s approach is influenced by his background as a banker-turned-monk. He has nearly three decades of meditation and Eastern philosophical training, including 13 years embracing a monastic life as a spiritual teacher at the Oneness University, India. He’s also an International Coach Federation (ICF) registered ontological coach.
Among his many international residencies, Rajesh was previously based at Kamalaya Wellness Sanctuary in Thailand, where he worked as a teacher, mentor and life coach for 10 years. In this role, he consulted with clients from around the world, focusing on personal growth, relationship enhancement and emotional balance. He has also worked with Young Presidents’ Organization (YPO) and Chief Executive Organizations (CEO) and Entrepreneurs Organization (EO) chapters across Asia and Europe
In 2018, Rajesh and his life partner, Smitha Jayakumar, co-founded ‘New Insight Retreats’ – a platform for mental, emotional and spiritual wellbeing. They run retreats in Europe and Asia, sharing spiritual principles, mind-body practices and transformative tools that can be used in daily life.
In 2019, Rajesh established the ‘Responsible Leadership Institute’ alongside a consortium of business economists, natural and social scientists, engineers, governance and spiritual scholars. Offering a range of holistic training programs and retreats that mindfully integrate work and life, this vanguard initiative seeks to build a holistic bridge between science and spirituality in the leadership sphere.
https://mindfulnessandbeyond.org/

Q3 New Member Dinner
2026-02-17 18:30 - 21:00 | RPM Seafood, 317 N. Clark St., Chicago, IL, 60654
What’s great about EO is that we have resources to help you grow in all aspects of your life. Whether it’s direct peer-to-peer learning and networking, connections to experts or once-in-a-lifetime experiences, EO can help you reach your goals. This dinner is designed to discuss your EO Membership and how you can best utilize EO’s resources to help you grow. We will review various committees, the forum placement process, events, tools and offer insight into how EO is structured so you get the most out of the next 30, 60, 90 days and beyond.
This is also a night to introduce your spouse (or significant other) to the organization. We welcome all members that joined within the last two years.
We look forward to connecting with you!
RSVP by: 2/9/26
Attendees: New Members, Executive Board, Membership Committee, SLP

Launchpad Forum - February 2026
2026-02-18 13:00 - 18:00 | The Chicago Club, 81 East Van Buren Street, Chicago, IL, 60605, United States
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.
**Launchpad followed by dinner will be held at The Chicago Club.
Parking: We recommend using the parking lots located on the corner of Van Buren Street and Wabash Avenue or the Grant South Parking Garage at their daily rate.
Dress Code: Please read.
There is no jeans policy at the club, and a sport coat is preferred.
RSVP By: 2/13/26
Attendees: New EO Members & Moderators of forums who are recruiting new members.

Bowling Strike Night
2026-02-18 19:00 - 22:00 | Pinstripes – Oakbrook, 7 Oakbrook Center Mall, Oak Brook, IL 60523, Oak Brook, IL, 60523, US
Friendly competition. Great food. EO energy. Let’s bowl.
How strong is your competitive streak? Find out at Pinstripes with an evening of bowling, food, drinks, and friendly rivalry. Open to EO Members, SAPs, and their SLPs—come for the strikes, stay for the connections.
Bring your 5% to the lanes. This night is less about perfect form and more about showing up, leaning into your competitive edge, and strengthening connections outside the boardroom. Expect laughs, light rivalry, and the kind of camaraderie that only happens when you put your guard down and roll the ball.
RSVP By: 2/11/26.
Attendees: EO Members, SAPs & SLPs

Q3 Moderator Dinner - 2025/2026
2026-02-19 18:30 - 21:30 | Ocean Prime, 87 E Wacker Dr., Chicago, IL, 60601
Please join us for our quarterly Moderator dinner.
This is a fantastic opportunity to share insights, ask questions, and pass along forum best practices. If you can not attend, please send your Moderator-Elect in your place. We look forward to a valuable discussion and providing some useful tools you can take back to your forum.
Attendees: Moderators, Moderator-Elect, & Forum Committee
RSVP by: 2/12/26

Q3 EOA Coach & Trainer Dinner
2026-02-24 18:00 - 21:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647
Join us for our quarterly EOA Dinner at EO House Chicago, held before our EOA Learning Day – People.
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: 2/16/26 please!
Attendees: EOA Committee, AG Coaches, Facilitator

Past Presidents Meeting
2026-02-25 08:30 - 11:15 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647
Let’s continue shaping the future of EO Chicago.
Join us for the next session in our 10-Year Goals conversation as we build on the foundation we set in our first meeting. We’ll dig deeper into key initiatives, address emerging challenges, and align on next steps to bring our long-term vision to life.
Your insights and energy are vital as we keep the momentum going and turn ideas into action.
Breakfast will be served.
RSVP By: 2/16/26.
Attendees: Current, Incoming & Past EO Chicago Presidents

People Learning Day
2026-02-25 08:30 - 16:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647
EOA People Learning Day – Build a Stronger Team
Scaling a business isn’t just about strategy and numbers—it’s about people. Growth companies rise or fall based on one thing: getting the right people in the right seats. Is your team truly aligned, accountable, and driving results?
Step back from working in your business to work on your business. Together, we’ll cut through the noise and focus on what really builds high-performing teams.
In this session, you’ll learn how to:

Hire smart and keep your best people
Align roles so the right people are in the right seats
Create a culture of accountability and trust
Lead with clarity and confidence through strong communication
Build and grow talent with effective compensation, development, and performance practices

Whether you’re hiring your first employees or leading a growing team, this workshop gives you the tools and insights to attract A-players, lead with confidence, and build a culture that fuels long-term growth.
Lead People. Grow Teams. Get Results.
🗓️ Tentative Agenda:

8:30 AM – Soft Start, Breakfast
9:00 AM – Hard Start
10:30 AM – Break
12:00 PM – Lunch
1:00 PM – Speaker Panel then quick break to reset
2:15 PM – Resume Content
2:30 PM – End of content – Review, Summary
4:00 PM – End day

Printable Materials to Bring:

People Learning Day Workbook
People Learning Day Worksheets

Pre Read:

Scaling Up by Verne Harnish People Chapter (pages 35-84)

RSVP By: 2/18/26
Attendees: EOA, EO & SAPs

EO Global's Virtual AI Summit #4: Transforming to an AI-First Company
2026-02-26 09:00 - 15:00 | Webinar/Virtual Learning
AI is no longer just a competitive edge—it’s becoming the foundation of how modern businesses operate. As technologies like GPT-4o, Gemini, Claude, and AI agents mature, the question is no longer if but how fast companies can evolve into AI-first organizations.
The 4th EO Global AI Summit brings together leading minds and forward-thinking entrepreneurs to explore what it truly means to embed AI at the core of your business. From rethinking company strategy and redesigning workflows to implementing AI responsibly and at scale—this summit is your practical guide to transformation.
Whether you’re experimenting with your first AI use case or scaling a fully automated company, this event offers real-world insights, proven tools, and a clear roadmap for making AI a sustainable driver of growth.
For EO members ready to lead—not follow—in the AI revolution.

EO Exploration: Sri Lanka 2026
2026-02-28 14:00 - 2026-03-06 09:00 | Jetwing Lighthouse Hotel, 433 A, Dadella, Galle, 80000, Sri Lanka
Journey to the jewel of the Indian Ocean, where golden shores meet emerald highlands, and timeless traditions flow seamlessly into modern life. From 28 February –6 March 2026, you and fellow EOers from around the world will begin in the coastal charm of Galle before traveling inland to the tranquil lakeside sanctuary of Kandalama, with a seaplane passage to Kandy—the cultural capital of Sri Lanka—woven into the experience. This exploration reveals the very soul of the island: vibrant, spiritual, and endlessly welcoming.
Each day offers a balance of curated adventures and moments of spontaneous discovery. From riding waves on sunlit beaches and venturing into rainforests that end in hidden pools, to encountering whales on the horizon or dining beneath the historic lighthouse, your time in Galle is filled with energy, history, and wonder.
From the southern coast, the journey shifts inland to Kandalama, where the jungle embraces ancient cities and elephants wander freely. Here, you will climb Sigiriya Rock at dawn, visit UNESCO World Heritage temples that hold centuries of devotion, and walk the paths of the ancient village of Puranagama. In this timeless setting, you’ll share conversations with local people and artisans who keep traditional crafts and stories alive. A highlight awaits with a seaplane journey to Kandy, where sacred rituals at the Temple of the Tooth, music, and dance connect you to the living spirit of the island.
Evenings bring moments of connection—farm-to-table dinners, starlit skies mirrored on the lake, and conversations that linger long into the night. Each sunrise, each shared meal, each blessing in a sacred place deepens the sense that this is more than a trip.
This is an exploration of spirit, culture, and community. By journey’s end, Sri Lanka will leave its mark on your heart, with memories and friendships that endure far beyond its shores.

Escape the Ordinary: The EO 5% Experience
2026-03-11 18:15 - 21:15 | Fox In A Box Escape Room Chicago, 47 W Polk Street, Suite Lower 5, Chicago, IL 60605, Chicago, IL, 60605, US
An Elite Escape Room Challenge for EO Teams Ready to Think Faster—Together

EO Escape Room + Pizza 🍕🔐
Ready to test your problem-solving skills outside the boardroom?
Join us for a fun, fast-paced escape room experience, where we’ll break into teams and tackle one of these missions:

Rob the Bank 💰
Escape the Bunker 💣
Outsmart the Zodiac Killer 🔍
Break Out of Prison 🚔

Expect clever puzzles, teamwork, laughs, and a little friendly competition along the way.
After the escape, we’ll head to Lou Malnati’s for deep-dish pizza, drinks, and great EO conversation. 🍕
No prep, no pressure—just a chance to connect, think differently, and enjoy a great night with fellow EO members.
Escape first. Pizza second.
The perfect EO equation.

Location:
Fox in a Box Escape Room Chicago is located in the lower level of Dearborn Galleria. To find them, look for the Roots Pizza across from Dearborn Station. They are in the big red Dearborn Station building with a clock tower — go in under the clock tower and walk to the sign with their logo near the stairs and follow instructions.
Parking:
Metered street parking is available at a cost of $4/hour for up to 3 hours. All day “stack” parking is available behind the building (pricing varies by the demand/whim of the attendant). ParkWhiz.com has numerous nearby options showing a map with price for the duration you require. (Following the link to ParkWhiz should give a $5 discount for first time users.)
RSVP By: 3/6/26.
Attendees: EO Members, EOA, SAPs & SLPs

EO Membership Interview Day
2026-03-12 13:00 - 16:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL 60647, Chicago, IL, 60647, US

Learning Workshop w/Bobby Achettu - Behind the Deal: A Founder & His Investment Banker Deep Dive
2026-03-17 10:00 - 14:00 | EO House, 1714 N. Damen Avenue 3rd Floor, Chicago, IL, 60647
Tuesday March 17 (St. Patrick’s Day!)
10am-1pm with lunch & happy hour afterwards from 1-2pm
Behind the Deal: A Founder & His Investment Banker Deep Dive
Tools, insights, and real‑world lessons to prepare you for a future exit
Selling a company is one of the most consequential decisions a founder will ever make: emotionally, financially, and operationally. Even the strongest leaders discover that the process reveals complexities you simply can’t see until you’re inside it.
In this interactive workshop, you’ll hear the same transaction told from two sides: the founder who built the company and the investment banker who guided the deal. This isn’t a lecture. You’ll explore the transaction from both perspectives and work through structured, hands‑on worksheets that equip you with practical tools to bring back to your organization.
Your Guides:
Bobby Achettu: Founder, Operator, Seller

A 12‑year EO member and former Chicago Chapter President, Bobby founded his company in 2009 and scaled it to 120 employees, earning five consecutive Inc. 500 rankings. In 2022, he sold to a strategic after a rigorous 10‑month process involving dozens of intro calls/in-person meetings, multiple expressions of interst, one signed LOI, and a diligence sprint that tested every part of the business.
Seth Deutch: Investment Banker, Operator, Deal Architect
Seth has had a diverse career as an M&A leader, including having been the president of a major business unit inside a Fortune 500 company, overseeing more than 10,000 employees and driving both organic and inorganic growth. Today, he is the CEO of Sampson Partners, leveraging his experience leading 100+ transactions. Seth has “written the book” on M&A, both literally and figuratively.
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Over the course of three hours, we’ll walk through the four stages of a transaction:
1. Decisioning: Should you sell, and when?

How founders know it’s time
Industry consolidation signals
Personal vs. business readiness
The hidden costs of waiting too long

2. Deal Sourcing: Finding the right banker and the right buyer

What a banker really does
What buyers look for early
How Bobby and Seth aligned on strategy and valuation

3. Diligence: The most intense 90 days of your career

What diligence really feels like
Avoiding deal‑killing landmines
What buyers obsess over

4. Post‑Transaction: Life after the wire hits

Integration realities vs. expectations
Cultural challenges
What founders wish they’d done differently

Together, Bobby and Seth will walk you through the wins, mistakes, surprises, and lessons that only come from living a deal end‑to‑end.
And by the way, there are worse ways to spend St. Patrick’s Day than leveling up your exit strategy.
RSVP By: 3/12/26
Attendees: EO, EOA, SAP & Prospects

Virtual People Day Session 1
2026-03-18 09:00 - 14:00 | Webinar/Virtual Learning
EO members will lead you through an engaging day to explore and build a strategy for your business focused on people!

If 2025/26 is the year you want more cash, clearer strategy, stronger people, and bullet-proof execution, the EO Accelerator curriculum is your roadmap. We’ve packaged the essentials into four seasonal sprints—each one laser-focused on a key constraint holding founders back.

Q4 Executive Board Strategy Summit
2026-03-18 09:30 - 14:30 | EO House Chicago, 1714 North Damen Ave. 3rd Floor, Chicago, IL 60647, Chicago, IL, 60647, US
As we move into Q4, we are excited to invite you to our Executive Board Strategy Summit—an essential opportunity to align, innovate, and elevate our collective impact.
What’s on the Agenda:

Q3 Review & Key Takeaways: Reflect on our wins and challenges from Q3, ensuring we carry forward the lessons that will sharpen our execution.
Strategic Alignment: Revisit and refine our priorities to confirm we’re aligned with our vision and positioned to hit our rocks with clarity and confidence.
Future Focus: Explore new opportunities, anticipate potential challenges, and set bold goals that will propel us into the next stage of growth.

This summit is designed to strengthen our momentum, deepen collaboration, and ensure every board member is empowered to drive meaningful results. Your presence and insights are vital as we chart the course for an impactful Q4 and beyond.

RSVP By: 3/11/26.
Attendees: EO Executive Board, #2s & Facilitator

Launchpad Forum - March 2026
2026-03-18 13:00 - 16:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647
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: 3/13/26.
Attendees: New EO Members & Moderators of forums who are recruiting new members.
