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Chicago
July 20-21, 2026

THE EVENT

For The Business Owner Ready to Operate at a Higher Level

A two-day, immersive experience, designed to help you gain clarity, figure out your next steps, and elevate how you run your business and life.

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.

 

You’ve built something.
You’re experienced.
You may have come from a successful career before this or have been in business for a few years if not decades.

And yet, you know there’s more. Something is asking for refinement. The times we are living in demand it. And 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.

Not necessarily more.

But better.

 

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

 

What You Will Walk Away With

By the end of these two days, you won’t just feel inspired. You will have made meaningful progress in areas that directly impact how your business and life move forward.

You can expect to leave with:

  • Clearer positioning — a sharper understanding of how to present your work and message so it resonates more naturally to attract the right opportunities and ideal clients
     

  • More confident decision-making — clarity on at least one important decision you’ve been considering or overthinking
     

  • A more refined way of operating — improving how you manage your time, energy, clients, and priorities so things feel less effortful and more intentional
     

  • Perspective on what’s next — whether that’s growth, simplification, a shift in direction, or who you are becoming
     

  • Meaningful connections — conversations with other business owners who are thinking at a similar level and navigating similar questions
     

This isn’t about leaving with more to do.

It’s about leaving with a clearer, more effective way forward.

Delivered by a carefully curated group of speakers who are business owners themselves, delivering no-fluff, practical, real-life actionable information, covering the whole of your life, not the typical siloed approach.

(Visit the Speakers Page to see the wide range of topics covered)

What Makes This Experience Different

This is not a sit-and-listen event.

You will be actively engaged in your business, your decisions, and your direction throughout the two days.

The experience is intentionally designed to combine:

  • Strategic insight (how your business runs and grows)
     

  • Personal growth (how you think, decide, and lead)
     

Because real progress doesn’t happen in isolation.

 

How you operate becomes the difference.

A Carefully Designed, Highly Intentional Room

Inspire and Elevate Live brings together a curated group of business owners who are ready for more—not just in results, but in how they operate.

Led by author, business coach, and speaker Jeffrey Shaw, with a select group of experienced business owners contributing their expertise, every element of this experience is designed with intention.

The speakers are not the focus.

The experience you have and the progress you make are.

And because the speakers are present for the full two days, you’ll have real access. Real conversations. Real connection. No separation between speaker and attendee.

Why This Matters Now

Many business owners reach a point where the question is no longer only:

“How do I grow?”

But also:

“How do I make this work better?”
“How do I navigate this changing world?”
“What do I want next and how do I move toward it with clarity?”

A desire to:

  • Work with more intention and less noise
     

  • Make better decisions, faster
     

  • Simplify without losing momentum
     

  • Build something that reflects who you are now and who you are becoming
     

That’s the moment this experience is designed for.

More Than a Conference

This is a working session for your next level as a business and as a person.

A space to step out of the day-to-day, gain perspective, and move forward with greater clarity and confidence.

A room that challenges you, supports you, and raises your standards without pressure or pretense. 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.

 

This Is For You If…

You’re a business owner who:

  • Has experience, but knows there’s a better way to operate
     

  • Feels ready for your next chapter, even if it’s not fully defined yet
     

  • Wants clarity and direction without more overwhelm
     

Values both smart strategy and meaningful perspective

 

Inspire and Elevate Live isn’t about doing more.

It’s about how you move forward from here.
With the support and peers you need.

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.

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Chicago Athletic Association

Dining Hall

Lobby and Shared Workspace

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Speaking Room

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Millennium Park and Lake Michigan

as seen from dining hall

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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.

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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

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