EP 259 Should You Have a Co-Host in Your Retreat Business?
Release Date: 02/26/2026
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_outlineKey Takeaways
- A co-host is shared leadership-not an assistant, not emotional support, and not a shortcut to sales.
- Partnerships multiply everything, including tension, misalignment, and risk.
- “Trust” alone is not a strategy-especially when your reputation is tied to someone else’s integrity.
- You need a real vetting process before partnering, not just good vibes on Zoom.
- If roles, money, ownership, and exit plans aren’t in writing, you’re building a future mess.
- Many retreat leaders need support systems (contractors/team), not a co-host.
- Build your retreat business solo first when possible-partner from strength, not dependence.
Shannon’s 3-Step Vetting System (Quick List for Skimmers)
- 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
First Partnership Mistake (00:01:24) Shannon shares her first negative partnership experience, including issues of trust and intellectual property theft.
Common Early Partnership Pitfalls (00:02:28) Discussion of new retreat leaders teaching prematurely and the risks of partnering with inexperienced people.
Red Flags & Consequences (00:03:24) Details on noticing odd behaviors, content theft, and fraudulent activity by a partner.
The Importance of Trust & Reputation (00:05:14) Emphasizes how a partner’s integrity affects your business and reputation.
Eroding Partnerships & Complexity (00:06:11) Describes partnerships that fade due to misalignment and how “fine” isn’t good enough in retreat businesses.
When Not to Co-Host (00:07:19) Advice on reasons not to seek a co-host, such as fear or seeking shortcuts.
Retreat Industry Forum Announcement (00:08:30) Brief promotion of the upcoming Retreat Industry Forum event.
Shared Leadership & Vetting System Introduction (00:09:32) Explains the need for structure in partnerships and introduces her three-step vetting system.
Step 1: Verify History & Credibility (00:10:32) Importance of knowing a potential partner’s full history and verifying their claims.
Step 2: Meet in Person (00:11:36) Stresses the necessity of in-person meetings to assess real compatibility and leadership under pressure.
Step 3: Clear Roles & Contracts (00:13:28) Outlines the need for crystal-clear roles, responsibilities, and written contracts in partnerships.
When Partnerships Make Sense (00:16:31) Describes scenarios where co-hosting is beneficial and when hiring contractors is preferable.
Solo First, Partner from Strength (00:17:34) Encourages building a solo retreat business before partnering, to ensure strength and independence.
Closing Thoughts & Invitation (00:18:56) Final advice on protecting your business and invitation to the Retreat Industry Forum.
Outro & Resources (00:19:17) Instructions to subscribe, leave a review, and access free resources.