Chicago, IL
Chicago Athletic Association
July 20–21, 2026

Your next chapter
isn't louder. It's more intentional.

Two days in Chicago for experienced business owners, leaders, and professionals ready for more clarity, better perspective, meaningful connection, and a more elevated approach to what comes next.

Reserve Your Seat Registration Open · $1,250
01The Invitation

You've built something. A business, a career, a reputation, a level of experience that changed how you think, work, and move through the world.

And yet, you sense there is another level available to you. Not necessarily through more hustle or more information, but through better perspective, more meaningful conversations, and greater clarity about how you want to work, live, and lead going forward.

That's what Inspire & Elevate Live is designed for.

Over two days, eleven speakers and four interactive workshops will bring together experienced business owners, creatives, leaders, and professionals for practical business strategies, leadership insight, personal growth, and meaningful conversations about what it truly means to elevate how you work, lead, and live.

And because this experience is designed to be deeply practical, you won't leave with vague inspiration or pages of disconnected notes. You'll leave with tangible ideas, meaningful relationships, and work that continues long after the event ends.

02Who Comes

A different kind of room.

Inspire & Elevate Live is not built around hustle culture, performative success, or surface-level networking.

The people drawn to this experience tend to be asking deeper questions about growth, alignment, relationships, wellbeing, and how they want success to feel moving forward.

Some are refining successful businesses. Others are stepping into a more independent chapter after years in established careers. Many are simply looking for a more intentional and elevated way of working, leading, and living.

What connects them is a shared desire for better conversations, clearer perspective, meaningful relationships, and environments that challenge them to think differently about what comes next.

The result is a room filled with thoughtful, experienced people who value meaningful conversation as much as practical strategy.

The lobby and reception of the Chicago Athletic Association
The lobby · Chicago Athletic Association
Business Owners & Entrepreneurs

You've already built something meaningful. The questions now are less about starting and more about refinement, sustainability, alignment, relationships, and what the next level actually looks like.

You may relate if
  • Growth is no longer the only metric that matters to you
  • You've outgrown surface-level business conversations
  • You want more intentionality in how you lead and operate
  • You're looking for people who understand the weight of responsibility and decision-making
  • You care as much about the quality of your life as the success of your business

Especially relevant for founders, agency owners, consultants, and established operators navigating what comes after the first phase of success.

Professionals & Executives

You may not call yourself an entrepreneur, but you think deeply about growth, leadership, relationships, and the kind of life you're building beyond your title.

You may relate if
  • You're stepping into a more independent or intentional chapter
  • You want conversations beyond productivity and performance
  • You've started redefining what success actually means to you
  • You value thoughtful environments and emotionally intelligent people
  • You're craving perspective outside your usual circles

Especially relevant for professionals stepping into more intentional leadership, reinvention, or a more independent chapter.

Creatives

You care about depth, originality, aesthetics, experience, and creating work that actually means something.

You may relate if
  • You're tired of loud, transactional networking environments
  • You want inspiration without performative "creative hustle"
  • You value beauty, atmosphere, and intentional experiences
  • You're seeking conversations that feel expansive rather than extractive
  • You want to be around thoughtful people who challenge how you think

Especially relevant for designers, writers, photographers, strategists, marketers, creators, and people building brands rooted in meaning and experience.

Leaders in Transition

Sometimes the biggest shifts happen after outward success.

You may relate if
  • You feel pulled toward something more aligned or elevated
  • You're entering a new chapter personally or professionally
  • You've outgrown environments that once fit
  • You're asking deeper questions about fulfillment, direction, and identity
  • You know something is evolving, even if you can't fully name it yet

Particularly meaningful for those navigating reinvention, refinement, independence, growth, and meaningful next chapters.

03The Program

Strategy and alignment,
side by side.

Sessions and workshops designed as a connected experience rather than standalone presentations.

Day One · July 20

How you think.

Perspective, clarity, decisions, standards, and possibility.

  • Nesha Pai · Don't Settle, Live Boldly
  • Katie Keller Wood · Align Your Life Mosaic
  • Tom Roberts · Flow Beyond Fear
  • Emily Paul · Bigger Than This
  • Tony Martignetti · Illuminating Hidden Brilliance
  • Annette Mason · What Now, What's Next?
Live Workshops
Led by Tom Roberts
From Fear to Flow
Learn how to break through old identities and limiting beliefs that keep you from stepping into your fullest potential.
Led by Katie Keller Wood
Design Your Life Mosaic
Hands-on work to create a more intentional life where success and fulfillment work together.
Day Two · July 21

How you show up.

Communication, leadership, relationships, experiences, and impact.

  • Kade Kimber · Premium Gifting Strategy
  • Julia Phelan · The Workshop Whisperer
  • Rob Hunter · Clear Communication
  • Shaneh Woods · Profit Is Protest™
  • Jeffrey Shaw · Luxury-Level Thinking
Live Workshops
Led by Kade Kimber
Premium gifting strategy in practice
Walk out with a defined organizational gifting strategy, built in the room using the Gift Intelligence™ workbook.
Led by Shaneh Woods
Profit Is Protest™
Challenge and reframe the beliefs that keep you from building a healthier relationship with money.
Panel Discussion
Moderated by Jeffrey Shaw
Success Without Self-Abandonment
A candid conversation about ambition, burnout, identity, and how to build meaningful success without losing yourself in the process.

Built in the room.

You won't leave with vague inspiration or pages of notes that never get used. You'll leave with clearer direction, stronger ideas, meaningful relationships, and tangible progress already underway.

  • iGreater clarity around a business, leadership, or life decision you've been overthinking
  • iiLanguage, positioning, or messaging that better reflects the value of what you truly offer
  • iiiPractical strategies you can immediately apply to your business, leadership, relationships, wellbeing, or next chapter
  • ivA sharper understanding of what needs your attention now and what no longer does
  • vRelationships with experienced, growth-minded people you'll continue learning from long after Chicago
  • viA renewed sense of energy, possibility, and confidence about what comes next
04The Speakers

Eleven voices.
Every one a business owner.

Each speaker stays the full two days, on stage or in the room. You'll spend real time with each one.

Day One · How you think July 20 · Six speakers · Two workshops
Nesha Pai
Nesha Pai
Don't Settle, Live Boldly
On recognizing where you're settling in life, and finding the courage to evolve into what's next for you.
Katie Keller Wood
Katie Keller Wood
Align Your Life Mosaic
On integrating your work, purpose, and personal life in a way that creates success without losing yourself in the process.
Tom Roberts
Tom Roberts
Flow Beyond Fear
On what high-speed racing reveals about fear, ego, flow, and performing at your fullest potential under pressure.
Emily Paul
Emily Paul
Bigger Than This
On understanding the feeling that something bigger is calling you, and turning it into a more meaningful life and impact.
Tony Martignetti
Tony Martignetti
Illuminating Hidden Brilliance
On breaking through internal limitations and accessing more of the person you already are at your best.
Annette Mason
Annette Mason
What Now, What's Next?
On creating clarity for what's next so you can navigate change with greater confidence, resilience, and direction.
Day Two · How you show up July 21 · Five speakers · Two workshops · One panel
Kade Kimber
Kade Kimber
Premium Gifting Strategy
On turning gifting into a thoughtful strategy that deepens loyalty, strengthens relationships, and keeps you top-of-mind.
Julia Phelan
Julia Phelan
The Workshop Whisperer
On turning your expertise into workshops and courses people don't just consume, but genuinely experience and remember.
Rob Hunter
Rob Hunter
Clear Communication
On capturing attention quickly, communicating clearly, and making your message land with authority and impact.
Shaneh Woods
Shaneh Woods
Profit Is Protest™
On seeing profit as more than money, but as ownership, agency, and the freedom to shape your future.
Jeffrey Shaw
Jeffrey Shaw
Luxury-Level Thinking
On raising your standards, refining your positioning, and becoming the luxury version of what you do.
The Chicago Athletic Association · est. 1890 · Michelin Key Hotel
05The Venue
Chicago, Illinois

A landmark club, reimagined.

Its History

Originally built in 1893 as a private social club for Chicago's elite, the Chicago Athletic Association has since been transformed into one of the city's most celebrated boutique hotels and a Michelin Key property known for thoughtful hospitality, layered design, and unforgettable atmosphere.

But what makes it the right setting for Inspire & Elevate Live goes beyond its history.

The Experience

There is an unmistakable sense of character the moment you walk in. Grand staircases and soaring ceilings balanced by intimate lounges, hidden corners, a game room tucked upstairs, and spaces that naturally invite meaningful conversation long after sessions end. It feels elevated without feeling performative.

Set directly across from Millennium Park with views stretching toward Lake Michigan, the entire property carries a feeling of momentum, renewal, and possibility. The kind of place that naturally pulls you out of routine and creates space to think differently about what comes next.

We chose it intentionally because environment matters. The setting should reflect the caliber of the work being done inside it.

Book Your Room

Stay where the event lives.

Stay at the Chicago Athletic Association and experience Inspire & Elevate Live the way it was designed to be experienced.

A limited room block has been reserved at a preferred rate for attendees. Reserve early to secure availability and make the most of the full event experience.

Credit card required to reserve. Payment due at hotel checkout.

Chicago Athletic Association Hotel
12 S Michigan Ave, Chicago, IL 60603, USA

Book Hotel
06Your Host

Presented by Jeffrey Shaw.

A leading voice on luxury sales and affluent buyer behavior. Forty years a business owner. Founder of National Self-Employed Day. Business coach behind the High Achievers Mastermind, from which every speaker on this stage proudly emerges.

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

Sell to the Rich The Self-Employed Life LINGO TEDx
07The Experience

Two days. Curated.

Buffet breakfast and lunch included both days. Camaraderie included throughout.

July 19
Arrival & private reception
Settle into Chicago. July runs long here, with Millennium Park across the street and Lake Michigan a few blocks east. Dinner is a walk from the door. DiamondEdge Status holders join an intimate, off-stage reception with the speakers. 6:00 to 8:00 PM CT.
July 20
Day One: how you think
Six speakers and two workshops on perspective, clarity, decisions, standards, and possibility. 9:00 AM to 4:30 PM CT. Buffet breakfast and lunch included.
July 21
Day Two: how you show up
Five speakers and two workshops on communication, leadership, relationships, experiences, and impact. 9:00 AM to 4:30 PM CT. Buffet breakfast and lunch included.
08DiamondEdge Status

Early access.
Real conversation.

The first 35 to register receive DiamondEdge Status at no additional cost. A private reception with every speaker the night before. No stage. No crowds. Just real conversation, before the room fills.

Open to the first 35 guests only.

  • iPrivate reception with all eleven speakers in the Game Room at the Chicago Athletic Association, July 19
  • iiPriority seating throughout the event
  • iiiPreferred room rates at the Chicago Athletic Association
Claim DiamondEdge Status
09The Invitation Stands

Two days that change
how you move forward.

Two-Day Pass $1,250 per attendee
Two days at the Chicago Athletic Association. July 20–21, 2026.
Reserve Your Seat

Pay in full, or pay over time at checkout.

Get in Touch

Have a question? Reach out.

Please allow 1–2 business days for a response.