EP 257 Belonging Is the New Luxury: Why Retreats Matter More Than Ever with Dan Berger
Release Date: 02/05/2026
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,...
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EP 253 Everything You Do Either Attracts or Repels and That’s a Good Thing
The Retreat Leaders Podcast
Everything you put into the world is doing something. Your website. Your social posts. Your emails. Your videos. Your interviews. In this episode, Shannon Jamail breaks down a truth most retreat leaders avoid: if you’re not repelling anyone, you’re probably being too generic. Attraction is only half the conversation. Sustainable retreat businesses are built on clarity - and clarity naturally attracts the right people while filtering out the wrong ones. Shannon explains why repelling misaligned guests isn’t a flaw, it’s a leadership skill, and how trying to please everyone leads to...
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EP 252 Ethical Marketing, Outsourcing, and Building Trust in Business with Dawni Baxter
The Retreat Leaders Podcast
In this episode, Shannon sits down with Dawni Baxter — founder of a boutique marketing agency and a multi-passionate entrepreneur leading the movement in ethical, human-first marketing. Dawni brings a refreshing perspective to an industry filled with noise, inflated promises, and confusing pricing structures. Together, Shannon and Dawni dive into: ✨ How to navigate marketing relationships with confidence ✨ Why transparency and trust are the backbone of ethical marketing ✨ What to look for (and avoid) when hiring a marketing agency or contractor ✨ The power of outsourcing — even...
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EP 251 Stop Discounting Your Retreats: The Damage It Causes & What to Do Instead
The Retreat Leaders Podcast
In this episode, Shannon gets fired up about one of the biggest mistakes retreat leaders make: discounting their retreats. While a discount might feel like an easy way to fill a few spots, the long-term damage is real - it devalues your experience, trains your audience to wait for price drops, signals desperation, and hurts the entire retreat industry. Shannon breaks down exactly why discounting is harmful, what it communicates to potential guests, and better alternatives like early-bird bonuses, pay-in-full perks, and smart payment options. She also unpacks the real reason...
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EP 250 Both Sides of the Retreat: Hosting, Supporting, and Finding Balance with Kim DeMoss
The Retreat Leaders Podcast
In this episode of The Retreat Leaders Podcast, Shannon sits down with Kim DeMoss - Retreat Ranch’s Executive Assistant, Yoga Teacher Training host, and long-time retreat collaborator - to talk about what it’s really like to experience retreats from both sides: hosting and supporting. From her early days hosting retreats with Shannon to now managing the logistics behind the scenes, Kim shares candid insights on burnout, boundaries, work-life balance, and how she found her groove in the retreat industry. They also dive into the digital...
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EP 249 If You’re Not Failing, You’re Not Trying Hard Enough
The Retreat Leaders Podcast
In this solo episode, Shannon Jamail gets real about something every retreat leader needs to hear: failure isn’t the enemy - it’s proof that you’re in the game. If you’re not failing, you’re not trying hard enough. Shannon dives into why “falling short” - whether it’s your finances, your workshop, your attendance, or your execution - isn’t something to avoid, it’s something to learn from. You can hire the best coach, join the smartest program, and learn from the pros… and you’ll still make mistakes. The difference? You’ll...
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EP 248 Why Retreat Leaders Who Don’t Evolve in AI + SEO Will Be Left Behind
The Retreat Leaders Podcast
If you’re still marketing your retreats like it’s 2022, you’re already behind. In this solo episode, Shannon Jamail drops the truth about how the digital marketing landscape has shifted - and why AI integration isn’t optional anymore. From Google rewriting your meta descriptions to the rise of algorithmic visibility, the retreat industry is evolving fast. Shannon breaks down how retreat leaders can start using AI tools strategically - not just for blogs and social media, but to analyze data, personalize messaging, and scale visibility. She also gives a sneak peek at...
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.