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EP 275 Retreat Leaders vs Venue Owners: The Disconnect Costing You Money

Release Date: 06/18/2026

EP 275 Retreat Leaders vs Venue Owners: The Disconnect Costing You Money

The Retreat Leaders Podcast

If you’re building a retreat business, this episode is required listening. In this episode of The Retreat Leaders Podcast, Shannon Jamail sits down with Catherine Kontos, founder of RetreatBoss, RetreatMatch, and RetreatBoss Magazine, to talk about what it actually takes to build a sustainable and profitable retreat business. With over 14 years in the industry-and a background acquiring and selling over 100 businesses and properties-Catherine brings a level of real business strategy that most of this industry is missing. This conversation about the realities of running retreats as a...

EP 274 Why Your Retreat Isn’t Filling (Even Though You’re Posting Every Day)

The Retreat Leaders Podcast

If you’re posting every day and your retreat still isn’t filling…You’re not alone. But you are likely focusing on the wrong thing. In this episode of The Retreat Leaders Podcast, Shannon Jamail breaks down the real reasons your retreat isn’t filling-even when you feel like you’re “doing all the things” on social media. Posting is not a strategy Visibility takes time to build And most retreat leaders don’t give it enough time Shannon walks through the biggest mistakes retreat leaders make when it comes to marketing and visibility-and what to do instead if you actually...

EP 273 How Venue Networks & Influencers Are Changing the Industry with Anna VanAgtmael

The Retreat Leaders Podcast

If you’ve ever felt like hosting a retreat is way more complicated than it should be… You’re not wrong. In this episode of The Retreat Leaders Podcast, Shannon Jamail sits down with returning guest Anna VanAgtmael to talk about what’s broken in the retreat industry-and what she’s building to fix it. Because right now: 👉 Retreat leaders have the audience but not the logistics 👉 Venues have the space but can’t fill it consistently 👉 And everyone is trying to figure it out on their own Anna shares her new venture-a curated retreat center directory and collaboration with Tiny...

EP 272 Reinvention Isn’t Optional: The Inner Work Behind Building the Life (and Retreat Business) You Actually Want with Dr. Kim Dang

The Retreat Leaders Podcast

If you’ve ever felt like: your dreams are “too big” you’re “too much” or you know you’re capable of more… but you’re not living it yet This episode is for you. In this in-studio episode of The Retreat Leaders Podcast, Shannon Jamail sits down with Dr. Kim Dang, a mathematician, reinvention strategist, and founder who has rebuilt her life and career multiple times-from Yale professor to entrepreneur in the retreat and knowledge space. Dr. Kim flew in from New York to record this conversation live in Austin-and it goes deep. This isn’t just about retreats. This is about the...

EP 271 From Zero to 70 Leads in 24 Hours: Unlocking Meta Ads for Retreat Leaders with Jaymie Tarshis

The Retreat Leaders Podcast

What if one focused day could completely change how you market your retreat business? In this episode, Shannon sits down with Jaymie Tarshis - aka The Ad Expert - a digital marketing strategist with over a decade of experience helping businesses scale using Facebook and Meta ads. Jaymie flew from San Diego to Retreat Ranch for a VIP day with Shannon's team, and the results were jaw-dropping: over 70 new leads in less than 24 hours. Shannon and Jaymie pull back the curtain on exactly what happened during that VIP day - from building a custom ad strategy from scratch, to crafting compelling...

Special Release | From Dream to Dirt - How We Built Retreat Ranch From Scratch

The Retreat Leaders Podcast

What does it actually take to build a retreat center from scratch? The land, the structures, the permits, the parking, the storage, the vision - and the marriage that has to survive all of it? In this episode, Shannon sits down with her husband Nathan Jamail - world-renowned leadership and sales keynote speaker, and co-owner of Retreat Ranch - to pull back the curtain on the real journey of building one of Texas Hill Country's most unique retreat destinations. This is not a highlight reel. This is the honest, practical, sometimes hard-won story of what it takes to go from a dream to a...

EP 270 Retreat Insurance: What Every Retreat Leader Must Know with Event Helper

The Retreat Leaders Podcast

Let’s talk about something most retreat leaders avoid… until they absolutely can’t. Insurance. In this episode of The Retreat Leaders Podcast, Shannon Jamail sits down with Myles Anderson from Event Helper, an insurance provider specializing in events and retreats, to break down why insurance is not optional in the retreat industry - it’s essential. Because here’s the reality: You are responsible for people’s safety, experiences, and well-being during your retreat. And without the right coverage in place, one incident can put your entire business - and personal assets - at risk. In...

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...

More Episodes

If you’re building a retreat business, this episode is required listening.

In this episode of The Retreat Leaders Podcast, Shannon Jamail sits down with Catherine Kontos, founder of RetreatBoss, RetreatMatch, and RetreatBoss Magazine, to talk about what it actually takes to build a sustainable and profitable retreat business.

With over 14 years in the industry-and a background acquiring and selling over 100 businesses and properties-Catherine brings a level of real business strategy that most of this industry is missing.

This conversation about the realities of running retreats as a business.

They dive into:

The biggest mistakes retreat leaders make
Why Airbnb and VRBO are NOT designed for retreat businesses
The legal and insurance risks most people ignore
What makes a venue truly “retreat ready”
Why venue owners carry more risk than most people realize
The importance of contracts, vetting, and site visits
Why both retreat leaders and venue owners need training and strategy

If you’ve ever felt like the retreat industry lacks structure, standards, or clarity-this episode will explain why.

And more importantly, what to do about it.

What You’ll Learn in This Episode

• How to build a sustainable retreat business
• Why Airbnb and VRBO are risky for retreats
• What “retreat ready” actually means for venues
• The importance of contracts and legal protection
• How to properly vet retreat venues
• The biggest disconnect between retreat leaders and venue owners

Key Takeaways

Retreats Are a Business-Not an Event

And they need structure, strategy, and protection.

Airbnb Is Not Built for Retreats

Using it for business events can create:

legal issues
cancellations
insurance gaps

Venue Vetting Is Critical

Not all venues are equipped to host retreats-even if they look good online.

Contracts Matter More Than You Think

Most people:

don’t read them properly
don’t negotiate
don’t understand the risks

Venue Owners Carry Massive Responsibility

From liability to operations, hosting retreats is not simple-and requires planning.

Training Is Not Optional

Both retreat leaders AND venue owners need:

coaching
strategy
professional development

About Catherine

Catherine Kontos is a strategist, business builder, and ecosystem founder shaping the future of the retreat and human experience industry. As the founder of RetreatBoss, RetreatMatch, and RetreatBoss Magazine, she brings more than 14 years of experience to the space. With a track record that includes acquiring and selling over 100 businesses and properties, including retreat venues, Catherine brings a rare blend of transformational experience design and serious commercial acumen. Through certification, consulting, media, and international collaborative partnerships, she helps retreat leaders, venues, and experience-based brands build offerings that are not only meaningful, but strategically positioned for visibility, profitability, and lasting legacy.

Learn more at: https://retreatboss.com/

The Retreat Leaders Podcast Resources and Links:

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TIMESTAMPS

Introducing Catherine Kontos (00:01:26) Guest Catherine Kontos introduces herself and her company, Retreat Boss, which matches venues with professionals and includes a magazine.

Pivoting During the Pandemic (00:02:28) Shannon and Catherine discuss the challenges of running a retreat business during COVID-19 and the importance of entrepreneurial pivoting.

Common Mistakes: Venue Sourcing (00:04:41) The discussion shifts to common mistakes retreat leaders make, specifically focusing on the risks of booking venues like Airbnb.

The Dangers of Booking on Airbnb (00:05:06) Shannon and Catherine detail the legal, insurance, and cancellation risks of using vacation rental platforms for business retreats.

The Importance of Contracts (00:08:11) Catherine emphasizes the necessity of reading contracts thoroughly, understanding what's included, and negotiating terms with venues.

Why Direct Booking is Better (00:12:08) Booking directly with a venue is often cheaper and more secure than using third-party platforms like Airbnb.

About the Retreat Boss Platform (00:12:55) Catherine explains her platform, which only lists vetted, "retreat-ready" venues to ensure a high-quality experience for leaders.

What "Retreat Ready" Means for Venues (00:15:36) Catherine outlines the criteria for a venue to be considered "retreat ready," including equipment, setup, niche focus, and staff training.

Coaching for Venue Owners (00:18:32) Catherine describes her training programs that help new and existing venue owners prepare their properties and staff for hosting retreats.

Mistakes Venue Owners Make (00:20:19) The conversation covers the significant work and liability involved in owning a venue and the need for a solid business plan.

Advice for Retreat Leaders (00:21:57) Catherine advises retreat leaders to get proper training and treat their work as a serious business, not a hobby.

Episode Wrap-Up (00:23:08) Shannon thanks Catherine for her insights, promotes her magazine and website, and concludes the episode with a call to action.

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