EP 258 What I Wish I Had Done Differently When I First Built My Retreat Business
Release Date: 02/12/2026
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...
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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...
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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...
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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...
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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 -...
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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...
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A Special Edition: Announcing WeTravel as a Sponsor of the Retreat Industry Forum + Why Their Platform Is Built for Retreat Leaders
The Retreat Leaders Podcast
Running a retreat business requires more than just creating transformational experiences. Behind every successful retreat is a system that manages payments, bookings, logistics, guest communication, and operations. In this special episode of The Retreat Leaders Podcast, Shannon Jamail is joined by Erin and Alison, co-hosts of the Retreat Industry Forum, along with Mariana from WeTravel, to officially announce WeTravel as a sponsor of the upcoming forum. During the conversation, Mariana from WeTravel shares how their platform was specifically designed to support retreat...
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EP 260 Not All Events Are Equal: How to Discern Real Value in a Noisy Event Space with Dora Rankin
The Retreat Leaders Podcast
In today’s entrepreneurial world, there is no shortage of conferences, summits, masterminds, and learning forums. But here’s the real question: How do you know which ones are actually worth your time, energy, and money? In this episode, Shannon sits down with Dora Rankin to talk about discernment in business spaces - especially in a post-COVID world where the coaching and event industry has exploded with noise, hype, and inflated promises. They dive into: Why entrepreneurs are more discerning than ever The rise of “smoke and mirrors” marketing How to vet event hosts and speakers...
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EP 259 Should You Have a Co-Host in Your Retreat Business?
The Retreat Leaders Podcast
Partnerships can be powerful… and they can also quietly wreck your retreat business. In this episode, Shannon Jamail breaks down one of the most common questions retreat leaders ask: Should you have a co-host? After being asked this question during a keynote in LA, Shannon’s immediate answer-“Don’t.”-got a laugh… and opened the door to a real conversation retreat leaders need to hear. Shannon shares the good, the bad, and the expensive lessons she learned from early partnerships, including a situation involving copied content and the painful reality...
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A Special Edition: A Fireside Chat about The Retreat Industry Forum with Alison, Erin & Shannon
The Retreat Leaders Podcast
In this special fireside chat, Shannon Jamail, Alison, and Erin pull back the curtain on the evolving energy of the Retreat Industry Forum — and why this year’s attendee profile looks different than ever before. What started as a vision to elevate the retreat industry is quickly becoming a high-level gathering of experienced retreat leaders, business owners, venue operators, and industry professionals ready to scale smarter and connect strategically. The trio discusses: The shift toward seasoned retreat professionals attending Why the Forum is not a beginner workshop —...
info_outlineWhen I first started building my retreat business, I made mistakes. Not small ones - real ones that cost time, money, energy, and unnecessary stress.
In this episode, I’m pulling back the curtain and sharing:
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What I personally wish I had done differently in the early days
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The most common mistakes I see retreat hosts still making today
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And how to avoid burning out, underpricing, or building a retreat that looks good on paper but feels exhausting in real life
If you’re hosting retreats (or thinking about it), this episode will help you build something that’s clear, sustainable, and aligned - not just pretty and stressful.
What You’ll Learn in This Episode
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Why unclear audience messaging makes retreats harder to sell
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How overbuilding your retreat actually weakens the experience
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Why marketing needs to start earlier than you think
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The real cost of underpricing and discounting
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Why doing everything alone hurts both you and your guests
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The mistakes I see retreat hosts repeat - and how to course-correct
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
Request for Reviews & Episode Overview (00:00:59) Shannon asks listeners to leave reviews and previews the episode’s focus on mistakes and lessons learned.
Learning from Mistakes in Business (00:02:24) Emphasizes the value of learning from mistakes and introduces the main theme: what she wishes she’d done differently.
Mistake #1: Lack of Clarity on Ideal Guest (00:03:27) Discusses the importance of defining your ideal retreat guest and the exhaustion from being too broad.
Mistake #2: Overbuilding the Retreat Experience (00:06:32) Warns against overpacking retreat agendas, stressing the need for downtime and integration.
Mistake #3: Marketing Too Late (00:10:43) Explains why marketing should start before all details are finalized, using her France retreat as an example.
Mistake #4: Ineffective Use of Ads (00:13:58) Advises testing content organically before spending on ads to avoid wasting money.
Mistake #5: Pricing for Comfort, Not Sustainability (00:14:54) Urges pricing retreats for sustainability, not just to fill spots, and explains the pitfalls of discounting.
Mistake #6: Not Asking for Support Early Enough (00:18:50) Shares the importance of hiring help for logistics, food, and guest relations to avoid burnout.
Common Mistake #1: Treating Retreats as One-Off Events (00:22:41) Highlights the value of making retreats part of a larger business ecosystem, not just single events.
Common Mistake #2: Discounting to Fill Spots (00:23:41) Reiterates the damage discounting does to brand and guest alignment.
Common Mistake #3: Weak Boundaries and Vague Policies (00:24:37) Stresses the need for clear boundaries, cancellation policies, and personal space for leaders.
Common Mistake #4: Copying Other Retreats (00:27:28) Encourages originality and authenticity instead of copying others’ retreat formats.
Common Mistake #5: Waiting for Confidence Before Acting (00:28:36) Explains that confidence is built through action, not as a result of success.
Final Reflections and Takeaways (00:30:43) Summarizes key lessons: aim for clarity, sustainability, and alignment, and learn from mistakes.
Closing and Call to Action (00:31:47) Thanks listeners, encourages sharing, and provides resources for further support.