Elite Live November 2026 | Elite Entrepreneurs

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Elite Live November 2026

Current Elite members: Register here

You Built a 7-Figure Company.

Now It’s Time to Lead at a Higher Level.

Elite Live is a curated, high-caliber room for growth-oriented founders who are ready to move beyond hustle and build alignment, clarity, and execution inside their company. This November, you’ll also get rare, direct access to Greg McKeown — bestselling author of Essentialism — sharing brand-new research live for the first time with our community.

Lock in $400 in savings — early bird pricing is available through September 18.

What Got You Here
Won’t Get You There

  • You’ve built a real business.

  • Revenue is strong. The team is growing.

  • But complexity is creeping in.

  • Decisions take longer.

  • Communication gets messy.

  • You feel like the bottleneck more often than you’d like to admit.

  • Hustle doesn’t fix this stage.

  • Leadership does.

  • Elite Live is designed specifically for founders who have outgrown their old way of operating and are ready to lead differently.

What You’ll Leave With:

A Planning Rhythm and Accountability System That Actually Sticks

Learn how to build a planning cadence your team follows long after the offsite ends — plus the OKR framework that turns big-picture priorities into outcomes people actually hit, department by department.

A Profit-First Growth Plan for 2027

Build your next financial plan starting with the profit you want, not just the revenue you’re chasing — and walk away with the systems and pricing confidence to protect your margins as you scale.

A Way to Finally Say What Needs to Be Said

Get brand-new, Cambridge-researched communication tools from bestselling author Greg McKeown — a simple four-step method for surfacing the real issue instead of dancing around it, in your leadership team and beyond.

This Is Not a Typical
Business Conference

This is not a pitch fest.
This is not a beginner room.
This is not surface-level networking.

Elite Live is a curated room of serious founders who:
  • Care deeply about their people

  • Value long-term growth over short-term wins

  • Are willing to be honest about what’s not working

  • Show up to contribute, not just consume

The conversations in this room are real.
The standards are high.
The caliber of leadership is different.

Join Us in November and Learn How To:

  • Scale yourself as a founder so your company can grow beyond your personal bandwidth.

  • Build leaders inside your organization instead of carrying the weight of every decision yourself.

  • Create a culture of ownership and accountability where high standards are upheld without micromanaging.

  • Recognize and prevent burnout before it quietly erodes performance and morale.

  • Lead through constant change while keeping your team aligned, resilient, and focused.

  • Talk about what actually matters - using new communication research from Greg McKeown's Cambridge Listening Lab to finally name the issues your team keeps talking around.

  • Use AI strategically at the executive level to improve decision-making and business insight.

  • Turn strategy into execution with practical communication and leadership frameworks.

Total Price $1,697

The earlier you commit, the more you save. $400 off ends September 18 — after that, it’s gone.

Current Elite members: Register here

FEATURED SPEAKER: Greg McKeown

Greg McKeown

Please Don't Misunderstand Me

After ten years working with hundreds of organizations, Greg McKeown has found the real bottleneck to becoming an Essentialist isn’t talent, strategy, or execution — it’s that most teams have never learned how to talk about what actually matters. Surface subjects are easy. The vulnerable, high-value conversations are the ones that unlock a team’s highest point of contribution, and most rooms never get there.

In this keynote, Greg shares brand-new research from his doctoral work at the University of Cambridge — a simple, powerful four-step loop he calls The Signalist Method. You’ll leave with a practical way to stop dancing around the real issue, stop hearing “let’s take this offline,” and start building the kind of understanding that changes how your team actually performs.

This is a rare opportunity to get this research live, in the room, before it reaches the broader market — and to bring it straight back into how you lead.

Friday, Nov. 6th 1:00 – 2:30PM

Author of New Your Times Bestseller
ESSENTIALISM

Meet the Speakers

Ben Kalkman

The Plan Was Never the Problem: 23 Cycles In, What I'd Tell Myself in Year One
Ben Kalkman has run 23 annual planning cycles at Rocket Media — and the early ones were mostly theater: a beautiful plan, a great offsite, a team quietly back to firefighting by February. The plan was never the problem. The rhythm was. In this Real Talk session, Ben shares what actually earned a permanent place on the calendar, what got cut, and how Rocket Media now runs its planning rhythm on an AI "second brain" that holds context and commitments between quarters — where most rhythms quietly die. Bring your own plan. You'll leave knowing exactly which part of it your team is going to ignore, and what to do about it.

Pam Jordan

Profit by Design: Build a 2027 Financial Plan That Starts with Profit, Not Revenue
Stop asking "how much do we want to sell?" Start asking "how profitable do we want to be?" Most owners set revenue goals but rarely plan for profit on purpose. Pam Jordan, a Fractional CFO with 20+ years of corporate finance experience, shares a proven framework for reverse-engineering revenue from your desired profit, protecting margins, pricing with confidence, and building a business that generates real, sustainable wealth — not just higher top-line numbers.

Jhana Li

Guarantee Your Growth: How to Build OKRs Your Team Actually Hits
Most businesses don't struggle because they lack goals — they struggle because there's a gap between strategy and execution. Jhana Li breaks down how to turn big-picture company priorities into clear, measurable outcomes across departments, teams, and individual contributors, so growth stops depending entirely on the founder.

Justin Colby

How To Win, During Uncertain Times
To get to the next level you will need to raise your glass ceiling to win in business when times are uncertain.

Brett Gilliland

It All Comes Together Here
This is the framework Elite has been teaching for years, and it's what sets Elite apart. At the center is HEART, a heart-driven approach to building a company that lasts, surrounded by four systems: Strategy, Performance, People, and Leadership. Brett walks you through the complete system for the first time, and what it means to build your company the Elite way.
Early Bird: Save $400 — Ends September 18

Elite Live — November 2026

Tuesday, November 4, 2026 — Optional Pre-Event

The Annual Planning Intensive

All day | Lunch included | Additional investment: $2,500 for up to 8 team members

This is where the real work happens before the room even opens. Bring your team and spend the day in facilitated annual planning led directly by Brett Gilliland — building your 2027 plan together, as a team, instead of trying to do it alone at your desk. Lunch is included, and this is consistently the part of the week attendees say had the biggest impact on their business.

This is a separate, optional add-on. It can be purchased on its own or added to your Elite Live seat.

That evening: Pre-Event Cornhole Gathering

Everyone attending Elite Live (whether or not you joined the planning intensive) is invited to kick off the event with a casual cornhole gathering. Low-key, high-connection, exactly how a week like this should start.

Thursday, November 5, 2026

A Full Day of Content

8:00 AM – 7:00 PM

The main event kicks off with a full day of speakers and sessions covering planning rhythms, profit-first financial strategy, OKRs that actually get hit, and more. Be sure to stick around for dinner!

Friday, November 6, 2026

Mastermind, Hot Seats, and Our Headliner

8:00 AM – 3:30 PM

The day opens with Mastermind groups and hot seat sessions — one of the most powerful parts of the entire week, where you work through real challenges directly with your peers.

After lunch, we get to spend 90-minutes with Greg McKeown, bestselling author of Essentialism, sharing brand-new research from his doctoral work at the University of Cambridge.

This Is For You If:

  • Founders, CEOs, and senior executives ready to scale beyond 7 figures

  • Leaders who want to build high-performing teams and sustainable culture

  • Entrepreneurs eager to integrate advanced leadership, AI, and strategic frameworks

  • Executives ready to invest in themselves and their growth, not just quick hacks

  • Founders, CEOs, and senior executives ready to scale beyond 7 figures

  • Leaders who want to build high-performing teams and sustainable culture

  • Entrepreneurs eager to integrate advanced leadership, AI, and strategic frameworks

  • Executives ready to invest in themselves and their growth, not just quick hacks

This Is Not For You If:

  • Those looking for surface-level business tips or one-off hacks

  • Founders unwilling to take ownership of leadership development

  • Leaders not open to new ways of thinking about culture, team development, or personal growth

  • Early-stage businesses not yet ready to invest in scaling infrastructure or leadership

  • Those looking for surface-level business tips or one-off hacks

  • Founders unwilling to take ownership of leadership development

  • Leaders not open to new ways of thinking about culture, team development, or personal growth

  • Early-stage businesses not yet ready to invest in scaling infrastructure or leadership

‘Saved Us 10 Years and Hundreds of Thousands of Dollars’

“Our investment in the Elite was hands-down the best money we have ever spent on our business. It literally saved us ten years and hundreds of thousands of dollars by exposing the on-ramp to the super-highway of business growth.

Since going through the program, our yearly revenue has expanded by 15 times! Even in the pandemic of 2020, we saw a $7 million increase in sales over the prior year thanks to the methods taught at Elite.

Thank you Brett and Team Elite for making your expertise and experience available to driven entrepreneurs who believe enough in their businesses to make the financial commitment to join. We are so blessed to have been a part of this program, and are so proud to be part of the Elite Family.”

Eric Sparrow CEO

Milkhouse Creamery, Inc.

Hear From Past Attendees

“We knew we were doing well and growing before the Elite content, but there were so many gaps in our knowledge when it came to figuring out exactly how to grow – how to get to the next level. We didn’t know how to use what we knew about our existing culture or team members to attract more like them. We lacked a clear vision of where exactly the company could go. Learning the Elite way solved this for us!”

Stephanie Holmes-Winton

CEO, The Money Finder

“I just attended the most amazing leadership session!

Dave and Brett Gilliland love people and business. This is the 1st day of their Elite Live event is amazing and has deep and meaningful learning.

They clearly live and walk the talk, they teach!

Thank you!”

Mike Toney

Conquest Training Systems

“I attended Elite for the first time in 2018. I loved the experience and after applying all the things I learned, my business grew over 40% in that year alone. The following year, I didn’t continue with the group because I thought I knew everything; I was wrong! My business did not grow the following year, so 2020 I decided to rejoin and we closed the year with 21% revenue growth.

We are back on track!

I highly recommend Elite. The group is amazing and the whole team challenges you to grow your business through fantastic speakers and amazing content.

Thank you Brett, Stephanie and the whole team!”

Gosia Baran

Helping Hands Commercial Cleaning

Current Elite members: Register here

Key Outcomes You Can Expect After 2 Days

  • Talking About What Actually Matters:
    A research-backed method for surfacing the real issue instead of managing around it.

  • Planning Rhythms That Survive Contact With Reality:
    How to build and run a planning cadence your team actually follows between meetings.

  • Profit-First Financial Planning:
    A framework for building your 2027 plan around profit, not just revenue.

  • OKRs That Actually Get Hit:
    Turning company priorities into measurable outcomes across every level of the team.

If you are still not registered for Elite Leadership Summit, then remember this…

You have 2 options:

Do what you have already been doing to grow your business (or avoid growing it).

Do what you have already been doing to grow your business (or avoid growing it).

Join us in Utah and get the small business strategy training you need to reach eight figures.

Join us in Utah and get the small business strategy training you need to reach eight figures.

Current Elite members: Register here

Frequently Asked Questions

We believe in clarity. Here’s everything you need to know before you secure your seat.

Who is Elite Live designed for?

Elite Leadership Summit is specifically designed for founders, CEOs and leaders who are leading 7-figure+ companies who are navigating the complexity that comes with growth.

This room is for leaders who care deeply about their people, culture, and long-term impact not just revenue.

If you are building a team, making higher-stakes decisions, and feeling the weight of leadership more than ever, this event is for you.

‘From Chaotic and Stuck to Aligned, Efficient and Profitable

“Elite Entrepreneurs has completely revamped our business. The tools and guidance we have received from Elite Entrepreneurs has helped our business tremendously. We are more aligned, more efficient and more profitable. There were other factors that have gone into our success (someone has to do the work) but Elite Entrepreneurs was the start we needed.

Personally, I have grown as a leader. Being able to grow and develop as a leader is the ONLY way our business and our team will be able to continue to grow. I’ve learned how to: 1. Prioritize what really matters in my life (i.e. get my personal life back); 2. Utilize and trust my team more than I have before; 3. Learn, Develop & Grow.”

Bill Harney

CEO, Keeping Current Matters

Current Elite members: Register here

Venue & Location

Avion Center | Chandler, Arizona

Elite Live is hosted at the Avion Center — a fantastic, purpose-built facility in Chandler designed for exactly the kind of focused, high-caliber gathering this event is built to be.

A note on lodging: The Avion Center does not have a hotel attached, so you'll want to book your own accommodations nearby. We will share some suggested locations once you are registered for the event.