11 Informative Insights from Hosting High-Profile Epic Events with Cary Jack

The Happy Hustle Podcast

Ever thought about hosting your own mastermind or event but don’t know where to start?

If you're an entrepreneur looking to create a high-impact, high-ROI experience, listen up! After hosting epic events for over a decade—from backcountry masterminds in Montana to high-profile entrepreneur gatherings—I’ve cracked the code on how to make them not just profitable, but truly life-changing.

In this episode of The Happy Hustle Podcast, I break down 11 powerful insights to help you create a mastermind or event that delivers insane value, drives deep connections, and leaves people raving about their experience.

  1. Curate the Right People
    You’ve heard it before: Your network is your net worth. And when it comes to masterminds, this couldn’t be truer. Don’t just take anyone willing to pay—handpick attendees who align with your vision and energy. One bad apple can spoil the vibe, so be selective.

  2. Design Transformational Experiences
    A mastermind is NOT just an event. It’s an experience. Get people out of their comfort zones and into something immersive and unforgettable.

For example, in my Montana Mastermind, we go completely off the grid for five days—learning survival skills, practicing breathwork, and masterminding under the stars. This blend of adventure, learning, and deep connection creates breakthroughs like no other.
Incorporate adventure and nature.
Blend business strategy with personal growth.
Make it a full-body experience, not just a seminar.

  1. Facilitate Deep Conversations
    Networking? Overrated. Deep, authentic relationships? That’s where the magic happens.
    We use structured conversation techniques, like:
    🔹 Table Prompts: At every meal, one question is posed, and everyone at the table answers it.
    🔹 Hot Seat Sessions: One person shares their biggest challenge, and the group collaborates on solutions.

These strategies create vulnerability, connection, and breakthroughs in business and life.

  1. Optimize Energy, Not Just Business
    Entrepreneurs burn out. Your event should fuel them, not drain them.
    That’s why we integrate energy-boosting elements like:
    Morning breathwork & meditation
    Cold plunges & saunas
    Nutritious (but delicious) catered meals
    Minimal alcohol & no drugs (at least until the event wraps!)
    Your attendees will leave feeling energized and ready to execute.

  2. Create “Wow” Moments
    People don’t remember slideshows. They remember experiences. Surprise & delight your guests with moments that create emotional anchors.
    Some of our signature moments include:
    Long-range sniper shooting with ex-military trainers.
    Epic skiing & hot springs adventures.
    Game nights that turn grown men into giggling kids.
    Make it unforgettable, and they’ll keep coming back.

  3. Foster Real Accountability & Follow-Up
    The mastermind doesn’t end when the event does. The best masterminds have real follow-through.
    30-day follow-up calls
    Accountability pods
    Financial incentives for goal completion (yes, we put money on the line!)
    When attendees leave with a clear roadmap and accountability, they actually implement what they learn—leading to massive ROI.

  4. Monetize Without Losing Integrity
    Let’s be real—your event needs to be profitable. But it should also overdeliver on value.
    Charge a premium price, but make sure it’s worth it.
    Offer high-value upsells, like VIP days or 1-on-1 coaching.
    Build long-term programs that extend the relationship beyond the event.
    The goal: Attendees should walk away thinking, “I would’ve paid 3X for this.”

  5. Plan Like a Pro
    High-level events don’t happen overnight. Plan ahead.
    Secure venues, vendors, and logistics months in advance.
    Have a tight itinerary but allow room for flexibility.
    Create seamless onboarding so attendees feel taken care of from Day 1.
    A well-planned event = a stress-free event (for both you and your guests).

  6. Leverage Content & Marketing
    Your mastermind should fuel your content machine.
    Capture video testimonials & behind-the-scenes footage.
    Get high-quality event photos.
    Share insights from the event on social media & your podcast.
    Your event should market itself—let your attendees be your best promoters.

  7. Focus on Community Over Transactions
    Your mastermind should be more than just a one-time event—it should be a movement.
    Create a private online group to keep the momentum going.
    Offer yearly reunions or advanced-level masterminds.
    Build a tribe that people want to stay a part of.
    A thriving community leads to lifelong clients and raving fans.

  8. Have Fun, Damn It!
    This is YOUR event. Make sure you enjoy it too.
    If you’re stressed out and overwhelmed, your attendees will feel it. So have fun, be present, and let the magic unfold.

Life’s too short for boring events—let’s make something legendary!

Connect with Cary!
https://www.instagram.com/caryjack/
https://www.facebook.com/SirCaryJack
https://www.linkedin.com/in/cary-jack-kendzior/
https://twitter.com/thehappyhustle
https://www.youtube.com/channel/UCFDNsD59tLxv2JfEuSsNMOQ/featured

Get a free copy of his new book, The Happy Hustle, 10 Alignments to Avoid Burnout & Achieve Blissful Balance https://www.thehappyhustle.com/book
Sign up for The Journey: 10 Days To Become a Happy Hustler Online Coursehttps://thehappyhustle.com/thejourney/
Apply to the Montana Mastermind Epic Camping Adventurehttps://thehappyhustle.com/mastermind/

“It’s time to Happy Hustle, a blissfully balanced life you love, full of passion, purpose, and positive impact!”

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