EP 257 Belonging Is the New Luxury: Why Retreats Matter More Than Ever with Dan Berger
Release Date: 02/05/2026
EP 261 The Truth About Confidence: Why Some Retreat Leaders Struggle to Fill Their Events with Nathan Jamail
The Retreat Leaders Podcast
Confidence isn’t just mindset crap. It affects your pricing, your messaging, your sales conversations and your boundaries. And ultimately - whether your retreat fills or flops. In this episode, Shannon is joined by leadership expert, sales strategist, and bestselling author Nathan Jamail (she is biased, but he is pretty damn amazing) to unpack the real reason many retreat leaders struggle to sell out their events: lack of business confidence. They discuss: Imposter syndrome in the retreat industry Underpricing rooted in insecurity Overexplaining instead of leading What confident...
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A Special Edition: Announcing WeTravel as a Sponsor of the Retreat Industry Forum + Why Their Platform Is Built for Retreat Leaders
The Retreat Leaders Podcast
Running a retreat business requires more than just creating transformational experiences. Behind every successful retreat is a system that manages payments, bookings, logistics, guest communication, and operations. In this special episode of The Retreat Leaders Podcast, Shannon Jamail is joined by Erin and Alison, co-hosts of the Retreat Industry Forum, along with Mariana from WeTravel, to officially announce WeTravel as a sponsor of the upcoming forum. During the conversation, Mariana from WeTravel shares how their platform was specifically designed to support retreat...
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EP 260 Not All Events Are Equal: How to Discern Real Value in a Noisy Event Space with Dora Rankin
The Retreat Leaders Podcast
In today’s entrepreneurial world, there is no shortage of conferences, summits, masterminds, and learning forums. But here’s the real question: How do you know which ones are actually worth your time, energy, and money? In this episode, Shannon sits down with Dora Rankin to talk about discernment in business spaces - especially in a post-COVID world where the coaching and event industry has exploded with noise, hype, and inflated promises. They dive into: Why entrepreneurs are more discerning than ever The rise of “smoke and mirrors” marketing How to vet event hosts and speakers...
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EP 259 Should You Have a Co-Host in Your Retreat Business?
The Retreat Leaders Podcast
Partnerships can be powerful… and they can also quietly wreck your retreat business. In this episode, Shannon Jamail breaks down one of the most common questions retreat leaders ask: Should you have a co-host? After being asked this question during a keynote in LA, Shannon’s immediate answer-“Don’t.”-got a laugh… and opened the door to a real conversation retreat leaders need to hear. Shannon shares the good, the bad, and the expensive lessons she learned from early partnerships, including a situation involving copied content and the painful reality...
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A Special Edition: A Fireside Chat about The Retreat Industry Forum with Alison, Erin & Shannon
The Retreat Leaders Podcast
In this special fireside chat, Shannon Jamail, Alison, and Erin pull back the curtain on the evolving energy of the Retreat Industry Forum — and why this year’s attendee profile looks different than ever before. What started as a vision to elevate the retreat industry is quickly becoming a high-level gathering of experienced retreat leaders, business owners, venue operators, and industry professionals ready to scale smarter and connect strategically. The trio discusses: The shift toward seasoned retreat professionals attending Why the Forum is not a beginner workshop —...
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EP 258 What I Wish I Had Done Differently When I First Built My Retreat Business
The Retreat Leaders Podcast
When I first started building my retreat business, I made mistakes. Not small ones - real ones that cost time, money, energy, and unnecessary stress. In this episode, I’m pulling back the curtain and sharing: What I personally wish I had done differently in the early days The most common mistakes I see retreat hosts still making today And how to avoid burning out, underpricing, or building a retreat that looks good on paper but feels exhausting in real life If you’re hosting retreats (or thinking about it), this episode will help you build something that’s clear,...
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EP 257 Belonging Is the New Luxury: Why Retreats Matter More Than Ever with Dan Berger
The Retreat Leaders Podcast
In this episode of The Retreat Leaders Podcast, Shannon sits down with Dan Berger to talk about something the retreat industry doesn’t discuss nearly enough: belonging. Dan shares his personal journey—from selling his event-planning software company for $100M, to grappling with his own sense of belonging, to ultimately creating Assemble Boise, a retreat and gathering space intentionally designed for human connection. Together, Shannon and Dan dive into: Why men are facing a serious belonging and mental health crisis How retreats can act as temporary communities that create lasting impact...
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EP 256 Building Pilates Retreats in Europe: Creativity, Logistics, and Expansion with Bessie Refalo
The Retreat Leaders Podcast
In this episode of The Retreat Leaders Podcast, Shannon sits down with Bessie Refalo, a yoga and Pilates retreat leader who is carving out a unique lane in the wellness retreat industry - reformer Pilates retreats in Europe. Bessie shares the behind-the-scenes reality of creating retreats that require specialized equipment, including the challenges of finding venues with reformer Pilates machines and the creative solutions she’s used to make her retreats possible. From transporting reformers by lorry in Portugal to discovering bespoke studios in Italy, this conversation is a masterclass in...
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EP 255 Building a Soul-Led Retreat Business While Working Full-Time with Amy Jaggers
The Retreat Leaders Podcast
In this episode of The Retreat Leaders Podcast, Shannon sits down with Amy Jaggers, a coach and retreat leader who is building a soul-led retreat business while still working full-time. Amy shares how she helps professionals step off autopilot and reconnect with balance, clarity, and purpose through meditation, mindfulness practices, retreats, and wellbeing circles. She opens up about what it really looks like to grow a retreat business alongside a demanding career — including boundaries, time management, and integrating her “soul work” into her corporate role. Together, Shannon and Amy...
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EP 254 How to Make Your Retreat a Signature Brand Asset Instead of a One-Off Event
The Retreat Leaders Podcast
Many retreat leaders are stuck running one-off retreats - constantly reinventing the wheel, hustling for new sign-ups, and exhausting themselves with fresh marketing every time. But the smartest, most sustainable retreat businesses? They build signature retreats that become a recognizable, in-demand part of their brand. In this episode, Shannon breaks down how to turn your retreat into a powerful brand asset that builds loyalty, grows every year, and creates recurring revenue through alumni and long-term client pathways. You’ll learn how to create a retreat theme people return to annually,...
info_outlineIn this episode of The Retreat Leaders Podcast, Shannon sits down with Dan Berger to talk about something the retreat industry doesn’t discuss nearly enough: belonging.
Dan shares his personal journey—from selling his event-planning software company for $100M, to grappling with his own sense of belonging, to ultimately creating Assemble Boise, a retreat and gathering space intentionally designed for human connection.
Together, Shannon and Dan dive into:
- Why men are facing a serious belonging and mental health crisis
- How retreats can act as temporary communities that create lasting impact
- Why small, intimate spaces outperform big, flashy experiences
- How retreat leaders can design environments that feel safe, connective, and meaningful
- And why belonging—not content—is what people are actually paying for
This is a grounded, honest conversation about the responsibility retreat leaders hold and the opportunity they have to create spaces that genuinely change lives.
What You’ll Learn in This Episode
- Why people aren’t craving more content—they’re craving connection
- How Dan’s “belonging tank” framework applies directly to retreat design
- The four belonging personas every retreat leader should understand
- Why men’s retreats and men’s groups are more needed now than ever
- How intentional hospitality creates trust, safety, and transformation
- What post-COVID human connection really looks like (and why retreats are booming)
Notable Concepts Discussed
- The “Belonging Crisis,” especially among men
- Retreats as containers for community, not just experiences
- Small-group power vs. large-scale events
- Ethical considerations around AI and preserving human-made experiences
- Designing spaces that do the emotional work before the programming begins
Email Dan to get a free copy of his book, or to book his amazing retreat center and get a 3rd night free: dan@assemblehospitality.com
Buy Dan’s Book here: https://amzn.to/4qvuyts
About Dan Berger
Dan J. Berger is the author of The Quest: The Definitive Guide to Finding Belonging, and the CEO of Assemble Hospitality Group. He previously sold his SaaS company, Social Tables, for $100M. He lives in Boise, ID with his wife and daughter.
Connect with Dan here: https://assembleboise.com/
The Retreat Leaders Podcast Resources and Links:
- Learn to Host Retreats
- Join our private Facebook Group
- Top 5 Marketing Tools Free Guide
- Get your legal docs for retreats
- Join Shannon in Denver at the Retreat Industry Forum
- Join our LinkedIn Group
- Apply to be a guest on our show
Thanks for tuning into the Retreat Leaders Podcast. Remember to subscribe for more insightful episodes, and visit our website for additional resources. Let’s create a vibrant retreat community together!
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TIMESTAMPS
Dan’s Background and Journey (00:01:22) Dan shares his personal history, adoption, move from Israel, hospitality career, and founding a software company.
Writing the Book on Belonging (00:02:01) Dan discusses writing his book about belonging and its self-help/academic approach.
Importance of Belonging in Retreats (00:03:01) Shannon and Dan explore why belonging is central to retreats and how retreats foster community.
Men’s Groups and Community Building (00:04:10) Dan describes his men’s group, its structure, and how it builds ongoing relationships.
Men’s Belonging Crisis (00:05:53) Dan addresses the challenges men face with belonging, emotional expression, and the need for safe spaces.
Retreats as Solutions for Men (00:08:13) Discussion on how retreats can help men, and Dan’s hesitation about hosting men’s retreats.
Benefits of Extended Retreats (00:09:10) Shannon explains the deeper impact of multi-day retreats versus short meetings.
Belonging Frameworks for Retreats (00:09:48) Dan introduces two frameworks from his book: the “belonging tank” and four belonging personas.
Book Offer and Belonging Differences (00:12:09) Dan offers a free book to listeners and discusses gender differences in belonging.
Motivation for Opening a Retreat Center (00:13:59) Dan explains his shift from corporate retreats to opening a dedicated retreat facility.
Design and Features of The Symbol Boise (00:17:25) Dan details the layout, amenities, and unique aspects of his Boise retreat center.
Transparency and Marketing for Retreat Leaders (00:18:40) Shannon praises the clarity and marketing of Dan’s facility for retreat organizers.
Special Offer for Retreat Leaders (00:19:41) Dan shares a booking discount and explains the profitability and versatility of his space.
Closing and Resources (00:21:00) Shannon wraps up, shares links to Dan’s resources, and thanks him for joining.