top of page
Chicago
July 20-21, 2026

THE EVENT

For The Person You Are Becoming

A two-day experience for business owners ready to step fully into their next version

Picture this: you arrive at an event where the energy is elevated yet grounded. Conversations flow with purpose, ideas spark like champagne bubbles, and you feel yourself thinking and operating at a higher level. Not because you're being pushed, but because the environment invites it. 

 

And you're ready for it.

 

This is Inspire and Elevate Live.

 

Thirteen speakers. Two immersive days. A carefully curated range of perspectives from business strategy to personal growth to future planning, brought together in a setting that naturally raises your standards.

Inspire and Elevate Live was created for business owners who know their next level isn’t just about more information, but about stepping into the next version of themselves with greater clarity, intention, and direction.

Hosted by Jeffrey Shaw, a 40+ year self-employed business owner, author of multiple books, internationally recognized speaker, business coach, and luxury expert who believes there's more available in every business owner. Not just in their businesses, but in how they operate, connect, and live.

After a year that asked many of us to transform — whether we wanted to or not — something new is emerging. A search for greater clarity. Reaching for higher standards. A desire for deeper relationships. To work with more intention and less noise. To get the results we want with greater ease. To become more efficient, more grounded, and more discerning with our time, energy, relationships, and direction.

 

In other words, a readiness to elevate. That's what Inspire and Elevate Live is designed for.

 

At its core is a simple promise:

No fluff. No performance. No empty showmanship. Each speaker is a member of Jeffrey's High Achievers Mastermind. They are exceptional, unique, and have a big message to share. They are business owners and subject matter experts themselves, who understand the real work and will share insights you can apply immediately, both professionally and personally. The cool thing is you get to hang out with them the entire two days. Pick their brains. Get to know them. They are not running on and off the stage.

Unlike conferences built around a single tactic or theme, Inspire and Elevate Live is intentionally holistic because real success doesn’t happen in silos. You’ll experience a broad range of perspectives, all honoring the full reality of what it means to build something meaningful and sustain it over time. Check out the Speakers Page to see the diverse and captivating topics that will be covered.

This is your opportunity to Step Out of the silos, Break Free of the “stay in your lane” mentality, and Immerse Yourself in an experience that sees the whole of you: the entrepreneur, the leader, the creative, the human being behind it all. 

At its heart, this is more than a conference. It’s a community. A carefully curated room. More like a large mastermind. Big enough to provide more than you can imagine, yet intimate enough to feel comfortable and memorable. Whether you thrive in a crowd or secretly prefer being home in your pajamas, you’ll feel welcome here. And if you're tired of typical conferences, this one is going to hit differently.

 

Because Inspire and Elevate Live isn’t just about learning.

It’s about becoming the next version of yourself.

THE VENUE

A History of Transformation

Chicago, voted the best big city in the U.S. nine years in a row, is the perfect backdrop for Inspire and Elevate Live. A city alive with energy, rich in history, and endlessly inspiring. From world-class architecture to its vibrant culture, Chicago is a place where creativity thrives and ideas take flight. It’s a city of possibility, making it the ideal setting for our gathering of visionary business owners ready to grow, connect, and elevate.

At the heart of it all is our venue, the iconic Chicago Athletic Association.

 

Originally opened in 1890 as a private men’s club for the city’s elite, it has transformed into something far greater—a space that welcomes everyone. After shuttering for years, it reemerged in 2015 as a hotel infused with purpose and story. Today, it holds the distinction of being a Michelin Key Hotel, known for its emphasis on inclusion and belonging.

 

Its grand lobby invites collaboration. Its intimate rooms encourage meaningful dialogue. Its game room invites play and conversation. Its hidden corners create space for conversations that don't happen on stages.

Once a symbol of exclusivity, it now embodies transformation. You’ll feel that spirit the moment you step inside. The energy of change, renewal, and elevation. It’s the perfect environment to get down to business with just a touch of luxury to remind you that you're allowed to want more. And you're ready for it.

Exterior_edited.jpg

Chicago Athletic Association

Dining Hall

Lobby and Shared Workspace

Madison_desks.png

Speaking Room

IMG_2212_edited.jpg

Millennium Park and Lake Michigan

as seen from dining hall

IMG_2208_edited.jpg

Game Room

DiamondEdge

Receive DiamondEdge benefits at no additional cost!

DiamondEdge is a limited early-registration experience for the first 35 attendees who understand the value of early access and meaningful connection
 

The defining benefit:

A Private Reception with the Speakers

The evening before Inspire and Elevate begins, DiamondEdge attendees are invited to an intimate, off-stage reception with the speakers. No performance. No crowds. Just real conversations. This early access changes the entire experience. 

Also includes:

  • Priority seating throughout Inspire and Elevate

  • Preferred room rates at the Chicago Athletic Association (limited availability)

Give yourself an edge— DiamondEdge.

YOUR HOST

JEFFREY SHAW

Inspire and Elevate Live is founded and hosted by Jeffrey Shaw, a force at the intersection of luxury, entrepreneurship, and business coaching.

 

Recognized as one of today’s leading voices on luxury sales and affluent buyer behavior, Jeffrey shows businesses of all kinds how to become the “luxury version” in their fields. With more than 40 years as a business owner, coach, and unwavering advocate for the self-employed—including founding National Self-Employed Day—he brings a depth of real-world experience and personal development rarely found.

 

He is the author of Sell to the Rich, The Self-Employed Life, and LINGO; a TEDx speaker; and the business coach behind the High Achievers Mastermind, from which every Inspire and Elevate speaker proudly emerges.

 

This is an event shaped by someone who has lived it, built it, and elevated others to do the same.

THE EXPERIENCE

At a Glance

Arrive July 19th (or sooner) in beautiful Chicago and settle into the energy of what’s ahead.

Private reception 6:00-8:00pm CT for DiamondEdge guests

July 20th & 21st are two full days of inspiration, camaraderie, and connection.
From 9:00am – 4:30pm CT, you’ll hear from 13 remarkable speakers, share ideas with fellow high-achievers, and build relationships that last long after the event.

We’ll take care of you along the way:

  • Buffet Breakfast (7:00am – 8:30am CT) both days — INCLUDED

  • Buffet Lunch (12:00pm – 1:30pm CT) both days — INCLUDED
     

Because Inspire and Elevate isn’t just about learning. It’s about fueling your growth, nourishing your connections, and creating space for real camaraderie.

Paolo-Verzani-13-CRPD1200x800.jpg

BOOK YOUR ROOM

Make the most of Inspire and Elevate Live by staying where the inspiration happens. At the stunning Chicago Athletic Association Hotel!

 

We’ve reserved a limited block of rooms at a special discounted rate, giving you the chance to immerse yourself in the event’s energy while enjoying one of Chicago’s most iconic hotels.

 

Secure your room early to guarantee the best rate and the full experience.
*Credit card needed to reserve but you don't pay until checkout.

The Event

Got questions? Happy to hear from you.

© 2025 Inspire and Elevate Live

bottom of page