Chicago, IL
July 19–21, 2026

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

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.

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 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.

02Who Comes

A different kind of room.

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.

The Inspire & Elevate Live stage set at Convene in Chicago
The room · Chicago
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.

July 19 · Evening

Welcome Cocktail Party.

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.

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 · The Paradox of Pause
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.
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 Chicago 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 Chicago.

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.

  • iA clearer sense of what is possible for your next chapter in business, leadership, life, or work
  • iiLanguage, positioning, or messaging that better reflects the value of what you truly offer
  • iiiPractical strategies you can immediately apply to your business, relationships, wellbeing, or personal growth
  • ivA sharper understanding of what needs your attention now and what no longer deserves your energy
  • vNew perspective from people who challenge how you think, not just what you do
  • viRelationships with experienced, growth-minded people who understand the questions you are asking
  • viiA renewed sense of confidence and momentum to move toward what comes next
04The Speakers

Eleven voices.
Every one a business owner.

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.

July 20 · 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
The Paradox of Pause
On pausing with purpose, before circumstances choose for you, so you can design change instead of waiting for burnout or crisis to force it.
July 21 · 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.
Chicago · named the best big city in America nine years running
05The Setting
Chicago, Illinois

Built in Chicago.

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.

Convene event space set for Inspire & Elevate Live in Chicago
Convene Meetings & Breakfast 311 West Monroe Street
The dining room at Beatrix in Chicago
Beatrix Lunch 155 N Wacker Drive
An interior at The Royal Sonesta Chicago Downtown
The Royal Sonesta Chicago Downtown Partner Hotel 71 E Wacker Drive
City Winery on the Chicago Riverwalk
City Winery Cocktail Party 11 W Riverwalk
Partner Hotel

The Royal Sonesta Chicago Downtown.

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

Book Hotel
06The Night Before

A cocktail party.
Real conversation.

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.

  • iAll eleven speakers, off-stage and unhurried
  • iiCity Winery on the Chicago Riverwalk · 11 W Riverwalk
  • iiiThe evening of July 19 · 6:00 to 8:00 PM CT
Reserve Your Seat
07Your 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
08The Experience

A curated gathering.

Buffet breakfast and lunch included each day. Camaraderie included throughout.

July 19
Arrival & cocktail party
Settle into Chicago. July runs long here, with Millennium Park, the Riverwalk, and Lake Michigan all close at hand. All attendees are invited to a cocktail party at City Winery with all eleven speakers. 6:00 to 8:00 PM CT.
July 20
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
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.
09The Invitation Stands

A clearer way
to move forward.

Full Event Access $1,250 per attendee
A gathering built in Chicago. July 19–21, 2026.
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Get in Touch

Have a question? Reach out.

Please allow 1–2 business days for a response.