Libsyn Directory

EP 244 Building Profitable Retreats Through Relationships with Lesley Jordan

Release Date: 10/16/2025

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...

EP 262 Culture Building: How to Create a Retreat Experience That People Come Back To with Nathan Jamail

The Retreat Leaders Podcast

Most retreat leaders focus on the itinerary. But what makes guests come back year after year isn’t the schedule - it’s the culture. In this episode, Shannon is joined by leadership expert and culture strategist Nathan Jamail (whom she is biased to say is amazing) to break down how retreat leaders can intentionally build culture instead of just planning programming. They discuss: How culture impacts everything How to create loyalty beyond a single event Alumni communities that actually stay engaged Setting customer experience standards Why some retreats create raving fans -...

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...

More Episodes

In this heart-filled and high-impact episode of The Retreat Leaders Podcast, Shannon Jamail sits down with luxury couples retreat host Lesley Jordan to explore the real keys to retreat success-and spoiler alert: it’s not just about the perfect venue or a pretty website.

From her beginnings as a travel agent to launching powerful, profitable retreats for couples of all backgrounds, Lesley shares how mentorship, strategic pricing, and relationship-first marketing changed the game for her. Together, Shannon and Lesley dig into:

How to actually pick the right business coach (hint: ask about profit)
Why building real connections beats flashy marketing
What it takes to design inclusive retreats that sell out and transform lives
The truth about vetting mentors in a saturated online space
Lesley’s upcoming LGBTQ+ and heterosexual couples retreats focused on love, intimacy, and reconnection

If you’re building a retreat brand that centers around depth, authenticity, and aligned growth—this one’s for you.

Learn more: www.lavishcouplesretreats.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:

Introducing Leslie Jordan (00:01:00)
Shannon introduces guest Leslie Jordan, highlighting her energy and inviting her to share her background.

Leslie’s Journey to Retreats (00:01:35)
Leslie shares her transition from travel agent to retreat curator, focusing on luxury retreats for couples and women.

The Power of Coaching in Retreat Business (00:02:25)
Discussion on meeting through a coach, the importance of having a coach, and the loneliness of entrepreneurship.

Finding the Right Coach (00:03:16)
Leslie describes her experience with different coaches, learning about business models, pricing, and defining her retreat offerings.

Building Relationships Over Pretty Marketing (00:04:00)
Leslie explains the importance of building genuine relationships with clients, not just relying on attractive websites.

Creating Lavish Couples Retreats (00:05:02)
Leslie talks about launching her own retreat business, focusing on reconnection and intimacy for various types of couples.

The Value of Multiple Coaches (00:05:24)
Shannon and Leslie discuss the benefits of having more than one coach with different expertise.

Marketing vs. Selling & Relationship Building (00:06:02)
Emphasis on turning marketing activities into real relationships and the changing landscape of the retreat industry.

Learning Strategy and Pricing (00:06:52)
Leslie shares how her coaches helped her with sales strategies, pricing, and repeat business.

Choosing Experienced Coaches (00:07:29)
Shannon stresses the importance of working with experienced coaches who understand the retreat business deeply.

Treating Retreats as a Business (00:09:00)
Discussion on treating retreats as a business model, not just an event, and integrating it with other offerings.

Overcoming Fear and Stagnation (00:09:18)
Leslie recounts how the wrong coaching held her back and how the right coaches helped her move forward.

Vetting Coaches and Profitability (00:10:36)
Advice on vetting coaches, asking about their experience, and ensuring they understand profitability in retreats.

Industry Trends and Red Flags (00:11:37)
Warning about inexperienced coaches and the importance of understanding all aspects of the retreat business.

Profitability is Essential (00:11:59)
Shannon and Leslie agree that breaking even is not a sustainable business model for retreats.

Attending Retreats as Research (00:12:31)
Leslie shares the value of attending retreats, especially those hosted by your coach, to learn logistics and marketing.

The Importance of Being an Attendee (00:13:11)
Shannon emphasizes that aspiring retreat leaders should attend retreats themselves to gain perspective.

Community and Networking Benefits (00:15:07)
Discussion on the community, networking, and collaborations that come from being part of a coaching group.

Ongoing Value of Retreat Attendance (00:16:24)
Leslie and Shannon discuss the ongoing benefits of attending retreats, including support, networking, and personal growth.

Leslie’s Upcoming Retreats (00:17:18)
Leslie shares details about her upcoming retreats for LGBTQ+ and heterosexual couples, and her inclusive approach.

How to Connect with Leslie (00:18:52)
Leslie provides her website and social media handles for listeners to learn more or join her retreats.

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