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.
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.
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.
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.
Especially relevant for founders, agency owners, consultants, and established operators navigating what comes after the first phase of success.
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.
Especially relevant for professionals stepping into more intentional leadership, reinvention, or a more independent chapter.
You care about depth, originality, aesthetics, experience, and creating work that actually means something.
Especially relevant for designers, writers, photographers, strategists, marketers, creators, and people building brands rooted in meaning and experience.
Sometimes the biggest shifts happen after outward success.
Particularly meaningful for those navigating reinvention, refinement, independence, growth, and meaningful next chapters.
Sessions and workshops designed as a connected experience rather than standalone presentations.
Perspective, clarity, decisions, standards, and possibility.
Communication, leadership, relationships, experiences, and impact.
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.
Each speaker stays the full two days, on stage or in the room. You'll spend real time with each one.











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.
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.
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
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.
Buffet breakfast and lunch included both days. Camaraderie included throughout.
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.
Pay in full, or pay over time at checkout.
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