The Retreat Leaders Podcast

Shannon Jamail
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Welcome to The Retreat Leaders Podcast, a top 2% global podcast for retreat leaders, venue owners, and entrepreneurs building powerful retreat businesses. Hosted by Shannon Jamail of Retreat Ranch, this show shares real conversations, expert strategy, and behind-the-scenes insights from leaders in the retreat industry. From marketing and pricing to guest experience, operations, and avoiding expensive mistakes, you'll learn what it really takes to host retreats that are both transformational and profitable. Whether you're planning your first retreat or scaling an established retreat business, this podcast will help you lead with confidence and grow with intention. Learn more at https://theretreatleadersplaybook.com/

  1. EP 266 The Power of Proximity for Retreat Leaders and Entrepreneurs

    3D AGO

    EP 266 The Power of Proximity for Retreat Leaders and Entrepreneurs

    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 entrepreneurs. The result? Her business didn't just grow - it exploded. Because the rooms you choose to enter quietly shape: Your thinking Your standards Your opportunities Your results In this episode, Shannon breaks down the power of proximity and why retreat leaders who want to grow must intentionally place themselves in environments that challenge and expand them. If you've ever wondered whether investing in conferences, masterminds, or industry events is worth it, this conversation will change the way you think about it. What You'll Learn in This Episode • Why proximity is one of the most powerful growth accelerators in business • How the rooms you enter shape your thinking and expectations • The hidden opportunities that come from simply being present in the right environments • Why many entrepreneurs avoid high-level rooms • How retreat leaders can intentionally create proximity that fuels their growth Key Takeaways The Rooms You Choose Shape Your Results Who you spend time with influences: the conversations you hear the ideas you're exposed to the standards you adopt the opportunities you encounter Growth accelerates when you intentionally surround yourself with people who think bigger and operate differently. Proximity Changes Your Thinking Most people believe growth comes from: books courses information Those things matter. But often the biggest shifts happen through exposure. When you're in the right room, you start hearing conversations like: "How do we scale this?" "What systems are you using?" "What worked in your last launch?" "What's your revenue goal this year?" Your brain begins calibrating to a different level of thinking. Standards Are Contagious When you're around people operating at a high level, you start noticing things like: professionalism follow-through preparation attention to detail For retreat leaders, this might look like seeing how others: structure their retreats communicate with guests design experiences price their offerings market their events Suddenly you realize: "Oh… this can be done differently." The Hidden Opportunities Proximity Creates Some of the biggest opportunities in business don't come from marketing. They come from conversations. Many collaborations, referrals, and partnerships begin through simple interactions in the right rooms. Examples include: speaking opportunities partnerships referrals introductions collaborations These opportunities happen when people know and trust you. And trust is built through presence. Why Entrepreneurs Avoid These Rooms Many entrepreneurs hesitate to enter high-level environments because of: Fear "What if I'm not ready?" "What if I don't belong there?" "What if I'm the least experienced person in the room?" Money concerns investment in travel conference tickets mastermind memberships Sometimes it's also ego. But the truth is: Being the least experienced person in the room is often exactly where growth happens. If every room you're in feels comfortable, you're probably not stretching enough. Not Every Room Is the Right Room Discernment matters. The best environments include: Leaders who have actually built successful businesses People willing to share real strategies and lessons Collaborative energy rather than competition Participants who take action The right room should expand your thinking and challenge you to grow. Why Retreat Leaders Need Proximity The retreat industry can feel isolating. As a retreat leader you are often: holding space for others leading the experience making all the decisions Being around other retreat leaders helps you: share strategies troubleshoot challenges stay current with industry trends learn what's working right now You don't have to build your retreat business alone. How to Create Intentional Proximity You don't need to attend every event. But you should choose a few strategic rooms each year. Examples include: conferences industry forums mastermind groups retreats workshops Ask yourself: Where are the people who are doing what I want to be doing? Then make a plan to enter those spaces. Even if it feels uncomfortable. Final Takeaway Proximity changes what you believe is possible. When you see someone else building a thriving retreat business, scaling a company, or creating powerful experiences for their audiences, it moves from theoretical to real. Growth isn't just about what you know. It's about who you're around. Choose your rooms carefully. Because the right room can change everything. If you're serious about growing your retreat business, this is exactly why we created the Retreat Industry Forum. Rooms matter. Who you surround yourself with matters. And proximity to the right leaders can accelerate your business like nothing else. Learn more at: retreatindustryforum.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! Subscribe:  Apple Podcast | Google Podcast | Spotify _____ TIMESTAMPS The Power of Proximity in Business (00:01:04) Explains why being in the right room and around the right people is crucial for business success. Personal Experience with Masterminds (00:02:10) Shannon shares how joining masterminds and groups transformed her business trajectory. How Proximity Changes Your Thinking (00:03:11) Discusses how exposure to growth-minded groups shifts your mindset and expands your thinking. Raising Your Standards Through Community (00:04:31) Describes how being around high-achievers elevates your personal and professional standards. Hidden Opportunities in the Right Spaces (00:06:52) Explains how in-person networking leads to collaborations, partnerships, and unexpected business opportunities. The Importance of In-Person Presence (00:09:07) Stresses that real relationships and business growth happen through showing up in person, not just online. Retreat Industry Forum Announcement (00:10:43) Brief promo for the upcoming Retreat Industry Forum event in Denver, highlighting its unique value. Why People Avoid Proximity (00:11:41) Explores common fears and excuses that keep entrepreneurs from joining high-level groups and events. The Value of Paying to Be in the Room (00:14:05) Argues that investing money and time in quality events is essential for real business growth. Choosing the Right Room: Good vs. Bad (00:16:08) Shares tips on discerning which events and communities are truly valuable and aligned with your goals. Collaboration Over Competition (00:19:27) Highlights the importance of collaborative energy and networking over competition and ego. Why Retreat Leaders Need Community (00:20:28) Explains why retreat leaders especially need supportive spaces to share strategies and avoid isolation. Final Thoughts & Call to Action (00:22:13) Shannon summarizes her passion for in-person events and encourages listeners to get in the right rooms. Podcast Closing (00:23:19) Outro with reminders to subscribe, review, and access free resources.

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

    5D AGO

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

    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 not the first step. They're the amplifier. In this conversation, they cover: Why ads won't fix a broken offer or weak messaging What must be in place before you ever run ads How Facebook and Instagram ads have evolved over time The role of testing, patience, and strategy in ad success Real case studies - including a retreat where 76% of attendees came from ads Jenn also shares what she'll be teaching at the Retreat Industry Forum, where she'll go deeper into how retreat leaders can use ads the right way - without wasting time or money. If you've ever thought, "I'll just run ads to fill my retreat," this episode will shift your perspective fast.   What You'll Learn in This Episode • Why ads should NOT be your first step in marketing • What needs to be in place before running ads • How Facebook and Instagram ads have evolved • Why testing and strategy matter more than ever • How long it actually takes for ads to convert • Real results from successful retreat ad campaigns   Key Takeaways Ads Don't Fix Weak Foundations If your: offer messaging positioning sales process aren't working organically… Ads will only amplify the problem.   Ads Are an Amplifier - Not a Strategy Jenn emphasizes that ads should come after: product-market fit strong messaging proven organic traction   High-Ticket Retreats Require Nurturing Retreats are not impulse buys. They require: trust relationship building consistent touchpoints Ads are just one piece of a longer funnel.   The Algorithm Has Changed Facebook and Instagram now rely heavily on: dynamic creative AI-driven optimization automated testing Meaning… strategy matters more than ever.   Ads Take Time (And Patience) One example shared: 👉 76% of retreat attendees came from ads 👉 But the full conversion cycle took 9 months This is not instant gratification.   About the Retreat Industry Forum The Retreat Industry Forum brings together retreat leaders, venue owners, and industry professionals who are serious about building profitable and sustainable retreat businesses. Hosted by Shannon Jamail, Alison, and Erin, this is a room designed to elevate the entire industry. 📍 Denver, May 🎟️ https://luxuryinbusinessretreats.mykajabi.com/retreat-industry-forum  Or jump on the Paris list: https://luxuryinbusinessretreats.mykajabi.com/retreat-industry-forum-Paris2026    Info about Jenn: https://jennpossick.com/schedule ------ TIMESTAMPS Guest Introductions (00:01:13) Allison, Aaron, and Jen Pasek are introduced as guests and partners for the forum. Jen Pasek's Background and Services (00:01:48) Jen explains her expertise in Facebook/Instagram ads and describes her "done for you" and "done with you" services. Difference Between "Done For You" and "Done With You" Ads (00:02:25) Jen details the differences between her ad management approaches and how she works with clients. Personal Experiences with Ads and Learning Curve (00:03:51) Hosts and guests share their struggles and learning experiences with Facebook ads. Preview of Jen's Forum Presentation (00:04:48) Jen previews her upcoming forum talk, including case studies and strategies for filling retreats with ads. Ad Strategies for High-Ticket vs. Low-Ticket Retreats (00:06:06) Discussion on how ad strategies differ based on retreat price points and the importance of nurturing leads. Importance of Strategy, Messaging, and Brand Before Ads (00:07:06) Shannon and Jen discuss why foundational business elements must be in place before investing in ads. Sales and Funnel Readiness Before Running Ads (00:08:32) Aaron and Jen emphasize the need for sales skills and working funnels before spending on ads. When to Start Using Ads in Your Business (00:09:46) Aaron shares her timeline for incorporating ads after years of organic growth. Clarity on Offer and Results Before Advertising (00:10:14) The group discusses the necessity of knowing your offer and the results you deliver before running ads. Evolution of Facebook/Instagram Ads (00:11:38) Jen explains how ad platforms and strategies have changed since 2015, including new tools and algorithms. Adapting to Meta's New Tools and Features (00:14:23) Discussion on the importance of using new Meta features and how the algorithm may reward early adopters. Strategy and Testing in Ad Campaigns (00:17:00) The hosts discuss the importance of having a strategy, testing, and ongoing adjustments in ad campaigns. Continuous Testing and Ad Fatigue (00:19:06) Jen explains how ads can stop working over time and the need for ongoing creative and audience tweaks. Time and Money Investment in Ads (00:19:28) The group discusses the time and financial investment required for successful ad campaigns and managing expectations. Case Study: Retreat Sales Cycle and Ad Impact (00:21:12) Jen shares a case study about Aaron's retreat business, highlighting the long sales cycle and the impact of Facebook ads. Podcast Outro (00:22:42) Shannon and the outro voice wrap up the episode and invite listeners to subscribe and access free resources.

    23 min
  3. EP 265 The Communication Shift That Can Transform Your Retreats with Joel Weldon

    APR 9

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

    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 10,000 speakers through his Ultimate Speaking System. In this conversation, he shares practical, simple strategies retreat leaders can use to become more confident speakers and more powerful communicators. Because the truth is this: retreat leaders are not just hosts. They are guides, facilitators, teachers, and storytellers. And the more clearly you communicate your message - whether on stage, on social media, or in your marketing - the more your retreats will resonate with the right people. If you want to create deeper connection with your attendees, communicate your message more confidently, and elevate the experience you deliver inside your retreats, this episode is packed with insights you can immediately apply. You'll also hear Shannon and Joel discuss why communication is one of the highest-ROI skills any entrepreneur can develop. As Warren Buffett famously said: "You can improve your value by 50 percent just by learning communication skills and public speaking." For retreat leaders, that improvement can mean fuller retreats, stronger relationships with attendees, and experiences that people talk about long after the retreat ends. What You'll Learn in This Episode • Why speaking skills are one of the most important - and often overlooked - skills for retreat leaders • How confident communication helps fill retreats and build trust with your audience • Simple techniques to feel more comfortable when speaking during retreats • How to create stronger emotional connection with retreat attendees • Small speaking tweaks that dramatically improve social media videos and podcast interviews • Why storytelling and authenticity are key to powerful retreat facilitation • How strong communication builds loyalty, referrals, and repeat retreat guests About Joel Weldon Joel Weldon is a Hall of Fame professional speaker and speaking skills coach who has been paid to speak at more than 3,000 events around the world. He is the creator of the Ultimate Speaking System and has coached more than 10,000 speakers, helping entrepreneurs, executives, and thought leaders communicate with clarity, confidence, and impact. Joel specializes in helping professionals transform presentations into powerful experiences that inspire audiences and drive results. Learn more about Joel here: https://www.ultimatespeaker.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! Subscribe:  Apple Podcast | Google Podcast | Spotify _____ TIMESTAMPS The Power of Communication for Retreat Leaders (00:01:09) Shannon discusses the importance of communication skills for retreat leaders and introduces guest Joel Weldon. Welcoming Joel Weldon & Setting the Stage (00:02:25) Joel is welcomed, and the conversation is set up to use a real retreat as an example. Retreat Leader Mastermind Overview (00:03:24) Shannon describes her upcoming August retreat for retreat leaders and entrepreneurs. First Steps: Inviting People & Opening Tips (00:04:13) Joel explains how to invite people and the importance of not starting with personal pronouns. The "Know, Have, Feel" Opening System (00:06:09) Joel introduces the "know, have, feel" framework for opening presentations and invitations. The Value of Systems in Retreats (00:07:20) Joel emphasizes the need for systems in all aspects of retreat planning and communication. Retreat Industry Forum Announcement (00:08:07) Shannon briefly promotes the upcoming Retreat Industry Forum event in Denver. Emotions vs. Logic in Enrollment (00:09:05) Discussion on how feelings drive retreat enrollment, but logic also plays a role. Speaking is a Learned Skill (00:09:31) Joel shares his journey from being a poor speaker to a professional, emphasizing that speaking can be learned. Making Communication About the Audience (00:10:29) Joel illustrates how to shift communication from "I" to "you" for greater impact. Assignment: Audit Your Emails (00:12:51) Joel gives an assignment to review emails for pronoun usage and practice audience-focused writing. Segmenting Retreat Days & The Green Card Feedback Tool (00:13:54) Joel explains how to structure multi-day retreats and introduces the feedback card system. How to Use Feedback for Real-Time Improvement (00:17:19) Joel and Shannon discuss using feedback cards to adjust and improve the retreat experience as it unfolds. Mistakes, Growth, and Speaking Practice (00:22:29) They discuss learning from mistakes, the importance of practicing speaking, and how communication impacts every retreat aspect. Honesty and Authenticity as a Leader (00:25:18) Shannon and Joel talk about the value of being honest about your experience level with your audience. The 100 Units of Energy Concept (00:26:16) Joel introduces the idea of conserving energy for leaders and the importance of having a support team. The Importance of Team and Delegation (00:28:52) Shannon reinforces the need for a strong team so leaders can focus on presence and speaking. Call to Action & Session Closings (00:31:05) Joel explains how to end sessions with a call to action and why to congratulate, not thank, participants. Visualization and Final Encouragement (00:34:32) Joel guides listeners to visualize their success and encourages them to implement what they've learned. Closing Remarks and Resources (00:36:01) Shannon thanks Joel, promotes his resources, and wraps up the episode. Podcast Outro (00:36:40) Outro with reminders to subscribe, review, and access free resources.

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

    APR 8

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

    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 companies while raising a family to a life-altering 70-day hospital stay during COVID that led to a deeper calling to create something meaningful for the retreat industry. That calling became the International Retreat Association. Together, they dive into: Why the retreat industry has lacked structure and standards The need for a global association to support growth and professionalism How the Retreat Industry Forum, platforms like WeTravel, and associations are creating a full ecosystem Why collaboration - not competition - is the future of this industry What Holly is building with her membership model and long-term vision This episode also marks an exciting milestone as Holly and the International Retreat Association officially join the Retreat Industry Forum as a sponsor, further strengthening the movement to elevate the industry. This is not just a conversation about retreats. This is a conversation about where the entire industry is headed. What You'll Learn in This Episode • Why the retreat industry has lacked a central governing or support structure • The role of associations in building credibility and standards • How the Retreat Industry Forum fits into the larger ecosystem • Why collaboration is key to industry growth • What the International Retreat Association is building for retreat leaders Key Takeaways The Retreat Industry Has Been Fragmented Until now, there has been: no central hub no global standards no unified ecosystem This has created inconsistency across the industry. A New Ecosystem Is Emerging The combination of: events (Retreat Industry Forum) platforms (like WeTravel) associations (International Retreat Association) creates a more complete, connected industry.   This Is About Growth - Not Policing Holly makes it clear: This is not about controlling the industry. It's about: elevating standards supporting leaders creating connection building credibility   Community Will Define the Future The retreat industry is built on: connection transformation human experience And now it's building a foundation to support that at scale. Leadership Is Required As the industry grows, leaders who step up, collaborate, and operate at a higher level will shape its future.   About International Retreat Association The International Retreat Association is led by a 17x best-selling author, international speaker, host of the All Things Retreat Podcast, and founder of 12 startup companies with a track record of building purpose-driven businesses. After surviving a 70-day hospital stay with COVID that included time on a ventilator, her perspective on life, impact, and legacy shifted in a profound way. That experience became the catalyst for creating a global movement within the retreat industry. The Association was founded to bring together retreat leaders, venues, and aligned professionals into one collaborative ecosystem focused on growth, integrity, and shared standards. With a vision to elevate the entire industry, it provides connection, education, and strategic opportunities for those shaping the future of retreats worldwide. Learn more: https://internationalretreatassociation.org/    About the Retreat Industry Forum The Retreat Industry Forum brings together retreat leaders, venue owners, and industry professionals who are serious about building profitable and sustainable retreat businesses. Hosted by Shannon Jamail, Alison, and Erin, this is a room designed to elevate the entire industry. 📍 Denver, May 🎟️ https://luxuryinbusinessretreats.mykajabi.com/retreat-industry-forum  Or jump on the Paris list: https://luxuryinbusinessretreats.mykajabi.com/retreat-industry-forum-Paris2026    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! Subscribe:  Apple Podcast | Google Podcast | Spotify _____ TIMESTAMPS Introducing Co-Hosts and Special Guest (00:01:15) Shannon introduces Aaron and Allison, and Aaron announces Holly Porter as the special guest. Holly Porter's Background and Inspiration (00:02:03) Holly shares her entrepreneurial journey, family, and the near-death experience that inspired the International Retreat Association. Mission and Purpose of the Association (00:03:37) Holly explains the association's mission: collaboration, trust, global standards, and professionalism in the retreat industry. Need for a Governing Body and Industry Gathering (00:04:21) Aaron and Holly discuss the lack of a governing body and the importance of an annual industry event. Events, Platforms, and Associations Explained (00:05:30) Holly distinguishes between events, platforms, and associations in supporting the retreat industry. Value of Professional Associations (00:06:13) Allison shares the benefits of professional associations from her health and fitness background. Vision for a Collaborative, Evolving Association (00:07:01) Holly emphasizes community-building, flexibility, and co-creating the association's future. Membership Launch and Structure (00:07:43) Holly details the upcoming essential and founding memberships, pricing, and the leadership council. Membership Benefits and Toolbox (00:08:39) Holly describes member benefits: badges, a resource toolbox, opt-in opportunities, and master classes. Inclusivity and Growth Mindset (00:10:14) Holly discusses being open to change, learning from feedback, and growing the association together. Diversity of Retreat Types (00:10:59) Aaron highlights the wide range of retreat types and the need for an inclusive association. Retreats as Universal Business Tools (00:12:00) Allison notes retreats' relevance across industries and the growing demand for human connection. Alignment Between Forum and Association (00:12:32) Aaron asks Holly why she chose to sponsor the forum; Holly explains their aligned visions. Educating on Association Value (00:13:07) Holly discusses the need to educate industry professionals on the benefits of joining associations. Collaboration Over Competition (00:14:04) Holly advocates for industry unity, more events, and supporting each other rather than competing. Ethics and Standards in the Industry (00:15:02) Aaron and Holly discuss the importance of ethics, efficacy, and setting industry standards. Industry Growth and Need for Standards (00:16:03) Shannon addresses the industry's rapid growth, rise in fraud, and the need for basic standards. Closing and Thank Yous (00:17:07) Shannon thanks Holly, shares where to find more information, and wraps up the episode. Podcast Outro and Resources (00:17:39) Outro voice encourages subscribing, reviewing, and accessing free resources.

    18 min
  5. EP 264 Building Momentum: Staying the Course When Results Feel Slow

    APR 2

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

    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 soon. She also shares practical tools to help retreat leaders stay focused, track the right metrics, and build systems that create sustainable momentum. If you've ever questioned whether your retreat marketing is working, this episode will help you stay the course and keep building. What You'll Learn Why the "launch and crickets" phase is normal How retreat leaders sabotage their own momentum The difference between outcome metrics and activity metrics The 90-day focus rule for marketing Tools to maintain energy, discipline, and consistency Key Takeaways Most retreat leaders quit right before traction begins. Early signs of success are often small signals, not bookings. Consistency compounds over time. Systems reduce the emotional rollercoaster of entrepreneurship. Momentum comes from focused action sustained long enough to work. Episode Breakdown Why Retreat Leaders Stall Many retreat leaders experience the "launch and crickets" moment and assume their strategy isn't working. Often the real issue isn't the strategy — it's abandoning it too soon. Common traps include: Shiny object syndrome Constant pivoting Comparing your beginning to someone else's middle The truth is that many leaders quit right before momentum begins. Redefining What "Working" Looks Like Most leaders focus only on bookings. But bookings are the final step in a longer chain of signals. Early indicators that your marketing is working include: Direct messages Profile visits Email opens Questions from potential guests Conversations starting Instead of only tracking bookings, create a simple weekly effort scorecard and measure activity. The 90-Day Focus Rule One of the biggest mistakes retreat leaders make is constantly switching strategies. Instead, commit to one primary marketing channel for 90 days before evaluating results. Choose the platform where your ideal guest already spends time. Then give the strategy enough time to compound. A helpful tool is scheduling a weekly CEO Hour where you review progress without reacting emotionally to short-term results. Protecting Your Energy & Mindset Discouragement happens to every entrepreneur. The key is learning how to use it as information rather than letting it derail your progress. Create a momentum anchor — a list of past wins you can revisit when doubt creeps in. Another helpful tool is an evidence file. Save screenshots of: Kind messages Testimonials Bookings Positive feedback These reminders reinforce that progress is happening. Systems That Create Consistency Consistency becomes easier when systems are in place. Some simple examples include: Batch creating content so you're not starting from scratch every day Automating follow-up emails and reminders Creating simple marketing workflows Remember: a consistent B+ effort will outperform sporadic A+ bursts every time. Accountability Structures That Actually Work Entrepreneurship can feel isolating. Accountability structures help maintain momentum. One simple format is a weekly check-in with an accountability partner: What did I commit to? What did I actually do? What is my one focus next week? Tools like Notion, Trello, or even a simple notebook can support this system. The best tool is the one you will actually use. Final Takeaway Momentum is not created by doing more. It comes from doing the right things consistently - long enough to see them work. If you stay the course, traction will come.   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! Subscribe:  Apple Podcast | Google Podcast | Spotify _____ TIMESTAMPS Host's Studio Update & Listener Request (00:00:54) Shannon shares about her new studio setup and asks listeners to subscribe and review the show. Understanding Business Cycles & Common Challenges (00:02:10) Discussion of natural business cycles, shiny object syndrome, and comparison traps that retreat leaders face. Dangers of Shiny Object Syndrome & Comparison (00:03:09) Explains how distraction and comparing to others can derail progress; urges focus on personal strategies. Shutting Out the Noise & Social Media Boundaries (00:04:20) Advice on muting distractions, limiting social media, and focusing on your own business lane. Shifting Metrics: Activity vs. Outcome (00:05:19) Recommends focusing on activity metrics (conversations, content) instead of bookings to maintain motivation. Implementing a 90-Day Focused Marketing Plan (00:07:16) Suggests committing to one or two marketing channels for 90 days, targeting where your ideal clients are. Protecting Mindset and Energy (00:09:23) Stresses the importance of guarding your mindset and energy from negativity, news, and discouraging influences. Using Positive Evidence to Combat Discouragement (00:11:21) Encourages collecting positive feedback and reminders of past successes to counter self-doubt. Consistency, Systems, and Batching Content (00:12:15) Tips on batching content, automating follow-ups, and creating systems to maintain consistency. The Power of Accountability (00:13:15) Highlights the value of accountability, especially paid coaching or mentorship, to reduce loneliness and boost results. Closing Thoughts & Event Invitation (00:15:15) Shannon summarizes key points, guarantees results with consistency, and invites listeners to an upcoming event. Outro & Call to Action (00:16:03) Podcast outro with reminders to subscribe, review, and access free resources.

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

    MAR 26

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

    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 down - from marketing promises to post-retreat follow-up - and how retreat leaders can strengthen their businesses with clearer communication, better boundaries, and stronger operational standards. If you want your retreat guests to return, refer others, and rave about their experience, this episode will help you protect the most valuable asset in your business: trust. Key Takeaways The five most common places trust breaks down in retreat businesses How marketing promises can accidentally set retreat leaders up for failure Why unclear boundaries create confusion and resentment The operational gaps that quietly damage guest experiences The importance of post-retreat follow-up for long-term loyalty About Debbie: Debbie Simmons is a keynote speaker, author, leadership strategist, and CEO of Anchor Point, known as The Legacy Architect who guides high-capacity leaders from success into significance and lives of lasting impact. Her work is built on the Architecture of Trust, the principle that where you place your trust determines both your success and the legacy you build. Through her proprietary framework, The Obedience Engine, Debbie equips executives and entrepreneurs to align identity, leadership, and decision-making so clarity and momentum replace pressure and burnout. She is the author of The Heart of Legacy and the creator of the Vision Day experience, a private leadership environment where leaders reset their trajectory and architect their next chapter. Debbie's message is simple: you were not designed to merely pursue success, you were created to leave a legacy worth living and leaving. Learn more about Debbie here: https://thedebbiesimmons.com/  Grab her free book here: https://theheartoflegacy.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! Subscribe:  Apple Podcast | Google Podcast | Spotify _____ TIMESTAMPS Debbie's Background & "Legacy Architect" (00:01:25) Debbie shares her personal and professional background, explaining her role as the "Legacy Architect." The Architecture of Trust Explained (00:03:50) Debbie introduces the concept of "architecture of trust" and its importance in retreat businesses. Five Areas of Trust Leaks (00:04:20) Overview of the five critical areas where trust can break down: marketing, promises, boundaries, delivery/operations, and follow-up. Marketing Promises & Clarity (00:05:54) Discussion on the importance of clear, specific marketing promises and avoiding overpromising. Guest Fit & Scarcity Mindset (00:08:23) Why not every guest is a fit, the dangers of a scarcity mindset, and the value of specificity. Setting Boundaries & Screening Guests (00:15:23) The necessity of boundaries, guest screening, and clear behavior expectations to create a safe retreat environment. Communication & Assumptions (00:20:30) The pitfalls of assuming guests understand expectations and the importance of explicit communication. Follow-Up & Integration After Retreats (00:21:47) Strategies for post-retreat follow-up and integration to maintain trust and encourage repeat business. Learning from Experience & Continuous Improvement (00:27:15) Advice on incremental improvements, learning from mistakes, and building better systems over time. Debbie's Book & How to Connect (00:28:29) Debbie shares how listeners can work with her and offers a free book as a resource. Closing & Podcast Outro (00:29:16) Shannon thanks Debbie, wraps up the episode, and shares where to find more resources.

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

    MAR 19

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

    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 - and others don't If you want recurring revenue, repeat guests, and long-term brand equity, this episode will shift how you think about your retreat business. Recorded in our new studio space in Austin - and available on YouTube as well. What You'll Learn Why itinerary doesn't equal experience The role leadership energy plays in culture How to design belonging - not just activities How to turn one-time guests into long-term community The operational standards behind unforgettable retreats Key Takeaways Culture is what people feel, not what's printed on the schedule. Loyalty is built intentionally, not accidentally. Clear standards create consistency and trust. Raving fans are the result of alignment and leadership - not luck. Retreat businesses that scale focus on community, not just events. Watch on YouTube This episode was recorded in our new Austin studio space. You can now watch the full conversation on YouTube. Subscribe:  Learn more about Nathan: https://nathanjamail.com/ Join Nathan and Shannon at the Forum: https://luxuryinbusinessretreats.mykajabi.com/retreat-industry-forum 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! Subscribe:  Apple Podcast | Google Podcast | Spotify _____ TIMESTAMPS Defining Culture in Organizations (00:02:04) Nathan explains what culture means, using energy, attitudes, beliefs, and the thermostat analogy. Mandating Culture & Event Laws (00:03:00) Discussion on the importance of setting clear cultural expectations and event "laws" for retreats. Authenticity & Alignment in Retreats (00:04:43) Shannon and Nathan discuss the need for alignment between retreat leaders and attendees, especially for international retreats. The Dangers of Misalignment (00:05:47) Exploring how misaligned guests can negatively impact the retreat atmosphere and culture. Marketing to the Right People (00:07:13) Emphasizing the importance of targeted marketing and being clear about who the retreat is and isn't for. Gratitude and Team Culture (00:08:25) Lighthearted discussion about gratitude within their team, referencing team members Josh, Lily, and Sharon. The Cost of Keeping Misaligned People (00:09:12) Nathan explains why keeping misaligned people (for fear of loss) damages culture in both business and retreats. Quality Over Quantity: Pricing & Numbers (00:10:21) Debate on charging more for fewer, better-aligned attendees versus filling retreats with anyone. Hiring & Team Alignment (00:15:04) Common mistakes in hiring misaligned team members and the impact on guest experience. The Airport Test & Culture Fit (00:13:57) Nathan introduces the "airport test" as a way to assess cultural fit among team members and guests. Sacrificing Culture in Tough Decisions (00:14:33) How leaders often sacrifice culture first when making difficult choices, and the consequences. Setting the Tone: Messaging & Boundaries (00:18:09) Shannon shares practical ways to set cultural expectations from marketing to the retreat's opening night. The Ted Lasso Theory: Be Curious, Not Judgmental (00:20:03) Nathan references Ted Lasso to illustrate the value of curiosity and non-judgment in building culture. Energy as a Differentiator (00:21:37) Discussion on how the energy and culture you create is more memorable than content or location. Closing & Invitation to Future Events (00:22:18) Shannon and Nathan wrap up, reflect on past recordings, and invite listeners to join their upcoming event. Outro & Call to Action (00:23:54) Podcast outro with reminders to subscribe, review, and access free resources.

    25 min
  8. EP 261 The Truth About Confidence: Why Some Retreat Leaders Struggle to Fill Their Events with Nathan Jamail

    MAR 12

    EP 261 The Truth About Confidence: Why Some Retreat Leaders Struggle to Fill Their Events with Nathan Jamail

    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 messaging actually sounds like How to build real, earned business confidence They also share that this episode was recorded in their new studio space in Austin - and you can now watch the full conversation on YouTube. If you've ever doubted yourself while launching a retreat, this episode will challenge and strengthen you. What You'll Learn Why confidence directly impacts conversions The hidden cost of underpricing How retreat leaders accidentally repel buyers The difference between loud marketing and confident leadership The discipline required to build real business confidence Key Takeaways Imposter syndrome doesn't disappear - it's managed through action. Underpricing signals insecurity to your audience. Overexplaining weakens authority. Confident leaders make clear decisions and stand by them. Confidence is built through preparation, skill, and repetition - not affirmations alone. Watch on YouTube This episode was recorded in our new studio space in Austin - go watch the full conversation on YouTube. Learn more about Nathan Jamail: https://nathanjamail.com/ Join Nathan and Shannon at the Forum: https://luxuryinbusinessretreats.mykajabi.com/retreat-industry-forum  Subscribe here:  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! Subscribe:  Apple Podcast | Google Podcast | Spotify ------ TIMESTAMPS Podcast Introduction and Studio Setup (00:00:02) Shannon introduces the podcast, new studio setup, and her guest, Nathan, her husband. The Importance of Confidence for Retreat Leaders (00:02:09) Shannon highlights Nathan's confidence and introduces confidence as a key topic for retreat leaders. Confidence vs. Arrogance and Childhood Story (00:03:22) Nathan shares a story about their daughter and explains the difference between confidence and arrogance. Imposter Syndrome and Taking Action Afraid (00:05:33) Discussion about imposter syndrome, acting confident, and the importance of taking action despite fear. How Confidence Impacts Marketing and Messaging (00:06:31) Shannon explains how confidence (or lack thereof) affects marketing, pricing, and messaging for retreat leaders. Belief in Yourself and Authenticity (00:07:01) Nathan and Shannon discuss the need to believe in yourself first and the role of authenticity in confidence. Stage Fright and "Doing It Anyway" (00:09:18) Nathan admits to still feeling nervous before speaking, and Shannon encourages action despite nerves. Personal Example: London Workshop Doubts (00:10:14) Shannon shares her experience with self-doubt before hosting an international workshop and how she overcame it. Hospitality, Impact, and the Human Touch (00:11:55) Nathan discusses the difference between service and hospitality, and the unique impact of human connection. AI, Connection, and the Future of Retreats (00:12:52) They discuss how AI can't replace human connection, making retreats more valuable in the digital age. Example: AI Dating at Bars and the Need for Real Connection (00:16:07) Shannon and Nathan talk about people dating AI at bars, emphasizing the growing need for real-life connection. Projecting Confidence and Sales Conversations (00:17:13) They discuss how lack of confidence is projected in sales and the importance of confidently presenting value. Vulnerability, Mistakes, and Being Confidently Wrong (00:18:18) Nathan explains that vulnerability increases confidence and that it's okay to be wrong—just be confidently wrong. Learning from Mistakes and Seeking Knowledge (00:19:42) Shannon and Nathan discuss learning from mistakes, attending events, and the value of learning from others. The Power of Learning, Confidence, and Motivation (00:23:44) Nathan shares a formula: learning increases confidence, which boosts motivation, using events and yoga as examples. Closing and Call to Action (00:25:01) Shannon wraps up, encourages listeners to attend events, and thanks Nathan for joining the episode.

    26 min
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4.9
out of 5
85 Ratings

About

Welcome to The Retreat Leaders Podcast, a top 2% global podcast for retreat leaders, venue owners, and entrepreneurs building powerful retreat businesses. Hosted by Shannon Jamail of Retreat Ranch, this show shares real conversations, expert strategy, and behind-the-scenes insights from leaders in the retreat industry. From marketing and pricing to guest experience, operations, and avoiding expensive mistakes, you'll learn what it really takes to host retreats that are both transformational and profitable. Whether you're planning your first retreat or scaling an established retreat business, this podcast will help you lead with confidence and grow with intention. Learn more at https://theretreatleadersplaybook.com/

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