EO Chicago

People Learning Day
2026-02-25 08:30 - 16:00 (America/Chicago) | 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.

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, Chicago, IL, 60647, US
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.

Learning Workshop w/Tanner Holmes - From Operator to Empire: Scaling Yourself Across Multiple Businesses
2026-04-07 13:00 - 15:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL 60647, Chicago, IL, 60647, US
From Operator to Empire: Scaling Yourself Across Multiple Businesses
Most entrepreneurs build their first company through grit, hustle, and personal effort—only to eventually hit an invisible ceiling. This two-part EO Member-Led Workshop is designed for founders asking the next question: why and how do I expand beyond a single business?
Together, we’ll break down the real strategic reasons entrepreneurs choose to move past one company—wealth creation, risk diversification, leverage, personal freedom, and values alignment—then explore the practical paths founders actually take. From holding companies and franchising to partnerships and the shift from operator to investor, we’ll unpack what works, what doesn’t, and the common pitfalls that derail even the most capable serial entrepreneurs.
The objective is simple: help you identify the path that best aligns with you and your long-term strategy.
This session is led by Tanner Holmes, a Chicago-based multi-unit entrepreneur, investor, and EO board member. Tanner has owned and scaled multiple brands across health, wellness, and beauty; exited three businesses; and currently operates and invests in a growing portfolio of multi-location franchised companies. He’s lived the transition from hands-on operator to portfolio builder—and made plenty of expensive mistakes along the way.
Expect real numbers, real stories, and clear frameworks. If you’re feeling the pull toward “what’s next,” this workshop will help you think bigger, move smarter, and build with intention.
RSVP By: 3/31/26
Attendees: EO Members, EOA (Accelerators) & SAPs

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.

Member Roundtable: Living by Design, Not Default: The Intentional Family Workshop w/Alex & Kristy Zatvor
2026-04-24 17:00 - 18:30 | EO House Chicago, 1714 N. Damen Avenue Ste. 3rd Floor, Chicago, IL 60647, Chicago, IL, 60647, US
“We have four young kids—and our connection, budget, goals, and sex life are honestly the best they’ve ever been.”
In this adults-only workshop, Alex & Kristy share the “Family Operating System” that turned daily chaos into clarity, momentum, and a lot more fun, so your family stops running on default.
RSVP By: 4/17/24
Attendees: EO Members, EOA, SAPs, SLPs & Prospects

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.

Hackathon: EO Chicago AI
2026-05-18 09:00 - 16:00 | EO House Chicago, 1714 North Damen Avenue 3rd Floor, Chicago, IL, 60647
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: 5/11/26
Attendees: EO Members + Key Executive/Guest

YPO-EO Mentor of the Year Luncheon
2026-05-20 12:00 - 14:00 | TBD
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

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

People
Strategy
Finance
Leadership
Execution

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

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

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

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

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!

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
