A Chicago gathering 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 the course of the gathering, 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.
This is a boutique gathering for thoughtful, experienced people who want something deeper than another crowded conference or transactional business event.
The people drawn to this experience are often asking bigger questions about growth, alignment, relationships, wellbeing, and how they want success to feel moving forward.
Some are refining already successful businesses. Others are stepping into a more independent chapter after years in established careers. Many are looking for a more intentional, elevated way of working, leading, and living.
What connects them is not a shared title, industry, or stage of business. It is a shared desire for better conversations, clearer perspective, meaningful relationships, and an environment designed to help them think differently about what comes next.
Because the gathering is intentionally intimate, the experience feels more personal, more immersive, and more connected. The result is a room filled with thoughtful 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.
An informal evening with all eleven speakers at City Winery on the Chicago Riverwalk — open to every attendee. 6:00 to 8:00 PM CT.
Perspective, clarity, decisions, standards, and possibility.
Communication, leadership, relationships, experiences, and impact.
You will not leave with vague inspiration or pages of notes that never get used. You will leave with clearer perspective, stronger ideas, meaningful relationships, and tangible progress already underway.
This is not a conference where speakers fly in, give a talk, and disappear.
Each speaker stays for the full event, on stage and in the room. You will hear from them during sessions, then have the chance to continue the conversation over meals, during breaks, and in the intimate seating areas throughout the space.
Eleven speakers. Two full days. Shared meals, continued conversations, and the kind of access most conferences do not offer.











This year, Chicago is the centerpiece. Named the best big city in America nine years in a row, it's a place of real beauty and unmistakable character — bold architecture, a glittering riverfront, and a skyline that set the standard every city after it would follow.
And it's wonderfully, distinctly Chicago. A city that burned down and rebuilt itself, resilient. That reversed the flow of its own river, practical. That raised the world's first skyscraper, innovative. That gave us the brownie, Cracker Jack, and the Ferris wheel, fun. And that's home to the tallest building in the world designed by a woman architect, diverse.
Chicago has always been the city of building hopes, dreams, and lives. With breakfast and meetings, lunch, your hotel, and our cocktail party each in its own iconic location, you won't simply attend Inspire & Elevate Live — you'll experience the city it was built in.
We've secured a discounted group rate at our partner hotel, The Royal Sonesta Chicago Downtown — an ideal location on the river, steps from where the experience comes to life.
A limited block of rooms has been reserved at this preferred attendee rate. Reserve early to secure availability and make the most of the full Chicago experience.
Credit card required to reserve. Payment due at hotel checkout.
The Royal Sonesta Chicago Downtown
71 E Wacker Drive, Chicago, IL 60601, USA
Every attendee is invited to a welcome cocktail party at City Winery on the Chicago Riverwalk the evening of July 19. All eleven speakers, no stage, no crowds. Just real conversation before the event begins.
Included with every ticket.
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 each day. Camaraderie included throughout.
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