EP 261 The Truth About Confidence: Why Some Retreat Leaders Struggle to Fill Their Events with Nathan Jamail
Release Date: 03/12/2026
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 —...
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EP 258 What I Wish I Had Done Differently When I First Built My Retreat Business
The Retreat Leaders Podcast
When 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: What I personally wish I had done differently in the early days The most common mistakes I see retreat hosts still making today 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,...
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EP 257 Belonging Is the New Luxury: Why Retreats Matter More Than Ever with Dan Berger
The Retreat Leaders Podcast
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...
info_outlineConfidence 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:
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Imposter syndrome in the retreat industry
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Underpricing rooted in insecurity
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Overexplaining instead of leading
-
What confident messaging actually sounds like
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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
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Why confidence directly impacts conversions
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The hidden cost of underpricing
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How retreat leaders accidentally repel buyers
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The difference between loud marketing and confident leadership
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The discipline required to build real business confidence
Key Takeaways
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Imposter syndrome doesn’t disappear - it’s managed through action.
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Underpricing signals insecurity to your audience.
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Overexplaining weakens authority.
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Confident leaders make clear decisions and stand by them.
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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
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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.