Libsyn Directory

EP 257 Belonging Is the New Luxury: Why Retreats Matter More Than Ever with Dan Berger

Release Date: 02/05/2026

EP 269 Why Glamping and Retreats Are the Perfect Pair (And What Retreat Leaders Need to Know) with Sarah Riley

The Retreat Leaders Podcast

The retreat industry is evolving - and one of the biggest opportunities right now sits at the intersection of glamping and retreats. In this episode of The Retreat Leaders Podcast, Shannon Jamail sits down with Sarah Riley, a UK-based glamping industry expert and co-organizer of The Glamping Show America, to explore how glamping and retreats are becoming one of the most powerful combinations in experiential hospitality. Sarah has been working in the glamping and retreat space since 2010, helping entrepreneurs launch lifestyle businesses and navigate the realities of building glamping sites -...

EP 268 The Power of Retreats for Midlife Women: Building Community, Healing & Business with SOL Women

The Retreat Leaders Podcast

There is a powerful shift happening - and it’s centered around midlife women. Women who have spent years building careers, raising families, and showing up for everyone else are now asking a different question: What do I want? In this episode of The Retreat Leaders Podcast, Shannon Jamail sits down in person in Austin with the founders of SOL Women to talk about the rise of retreats designed specifically for midlife women - and why these experiences are more needed now than ever. SOL Women creates holistic, supportive retreat experiences that help women reconnect with themselves, prioritize...

Behind the Scenes of the Retreat Industry Forum: Why Logistics & Operations Make or Break Your Retreat

The Retreat Leaders Podcast

There’s what your guests see at a retreat… And then there’s everything happening behind the scenes. In this special edition of The Retreat Leaders Podcast, Shannon Jamail is joined by Alison and Erin (co-hosts of the Retreat Industry Forum) along with two of the Forum’s featured panel presenters - Matt Quinones and Daesha Donze - to talk about the operational side of running successful retreats. You can have an incredible concept, a beautiful location, and a powerful transformation… But if your logistics and operations aren’t dialed in, it will impact the entire experience. Matt...

EP 267 The Retreat Venue Gap: Why Retreat Leaders and Venues Struggle to Find Each Other with Emily Johnson

The Retreat Leaders Podcast

One of the biggest challenges in the retreat industry isn’t marketing, pricing, or programming. It’s the gap between retreat leaders and retreat venues. Retreat leaders struggle to find the right venues. Venue owners struggle to fill their calendars with the right retreats. And somewhere in the middle, opportunities are missed. In this episode of The Retreat Leaders Podcast, Shannon Jamail sits down with Emily Johnson, founder of Elevate Hospitality Collective, to talk about the disconnect between retreat leaders and venues - and how the industry can bridge that gap. Emily brings years of...

EP 266 The Power of Proximity for Retreat Leaders and Entrepreneurs

The Retreat Leaders Podcast

Success in business isn’t just about strategy. It’s also about proximity - who you’re around, the conversations you’re exposed to, and the standards of the rooms you choose to enter. In this solo episode of The Retreat Leaders Podcast, Shannon Jamail shares why being in the right rooms can dramatically accelerate your growth as a retreat leader and entrepreneur. For many years Shannon’s business was doing well. But about five years ago, something shifted. She started attending conferences, joining masterminds, and intentionally placing herself in rooms with other high-level...

Special Edition: Stop Wasting Money on Ads: What Retreat Leaders Need Before Running Facebook & Instagram Ads with Jenn Possick

The Retreat Leaders Podcast

Running ads to fill your retreat sounds like the obvious next step… But for most retreat leaders, it’s actually where they start losing money. In this episode of The Retreat Leaders Podcast, Shannon Jamail is joined by Alison, Erin, and Jenn Possick (The Ads Maven) to break down what retreat leaders really need to know before investing in Facebook and Instagram ads. Jenn specializes in helping coaches, wellness professionals, and retreat leaders run strategic, data-driven ad campaigns - offering both done-for-you and done-with-you services. And here’s what she makes very clear: Ads are...

EP 265 The Communication Shift That Can Transform Your Retreats with Joel Weldon

The Retreat Leaders Podcast

Retreat leaders spend months planning the location, the schedule, the experiences, and the transformations they want their guests to have. But there is one skill that quietly determines whether your retreat truly lands with your audience. Your ability to communicate. In this episode of The Retreat Leaders Podcast, Shannon sits down with Hall of Fame speaker Joel Weldon to talk about the powerful role communication plays in the success of retreats - from filling the room to creating deeper breakthroughs for attendees. Joel has been paid to speak at more than 3,000 events and has coached over...

The Future of the Retreat Industry: Why We Need Standards, Community & Leadership with Holly Porter

The Retreat Leaders Podcast

The retreat industry is growing so fast. Especially in the last 6 years. But here’s the problem: There has never been a central place for retreat leaders, venues, and professionals to connect, collaborate, and operate at a higher standard. Until now. In this episode of The Retreat Leaders Podcast, Shannon Jamail is joined by Alison, Erin, and Holly Porter, founder of the International Retreat Association, to talk about the future of the retreat industry - and why the timing for this shift couldn’t be more important. Holly shares her powerful personal story - from building 12...

EP 264 Building Momentum: Staying the Course When Results Feel Slow

The Retreat Leaders Podcast

One of the hardest moments in the retreat business is the quiet period after you launch something. You announce your retreat. You post about it. You send emails. And then… crickets. In this solo episode, Shannon Jamail talks about why slow results are not a sign that something is wrong. In fact, momentum in the retreat industry is rarely sudden — it’s usually the result of consistent, focused action over time. Shannon breaks down the common traps retreat leaders fall into when results don’t appear quickly, including shiny object syndrome, comparison traps, and abandoning strategies too...

EP 263 Trust Leaks in Retreat Businesses: The 5 Places Retreat Leaders Lose Credibility with Debbie Simmons

The Retreat Leaders Podcast

Trust is the currency of the retreat industry. Guests invest their time, money, and emotional energy into retreat experiences expecting transformation, connection, and professionalism. But often, trust doesn’t break in big dramatic moments - it slowly leaks through small gaps in leadership, communication, and delivery. In this episode, Shannon sits down with Debbie Simmons to discuss the five most common “trust leaks” in retreat businesses and how retreat leaders can repair them before they damage reviews, referrals, and long-term loyalty. They break down where trust most often breaks...

More Episodes

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
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:

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.

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