The Retreat Leaders Podcast – Details, episodes & analysis

What if one focused day could completely change how you market your retreat business? In this episode, Shannon sits down with Jaymie Tarshis - aka The Ad Expert - a digital marketing strategist with over a decade of experience helping businesses scale using Facebook and Meta ads. Jaymie flew from San Diego to Retreat Ranch for a VIP day with Shannon's team, and the results were jaw-dropping: over 70 new leads in less than 24 hours.

Shannon and Jaymie pull back the curtain on exactly what happened during that VIP day - from building a custom ad strategy from scratch, to crafting compelling media and copy, to setting up the tech and tracking to make it all work. Whether you're a retreat leader who has never run an ad or someone who's tried and felt frustrated, this episode will shift your perspective.

They cover the real deal on ad budgets (it doesn't have to break the bank), the biggest misconceptions retreat leaders have about paid ads, and why strategy has to come before you ever spend a dollar. If you're ready to grow your retreat business and fill your programs with more ease, this is your episode.

Key Takeaways:

• What a Meta ads VIP day actually looks like from strategy to launch
• The truth about how much budget you really need to start
• Common misconceptions about ads that are keeping retreat leaders stuck
• How to generate leads fast - without guessing
• Why tracking and tech setup is the secret weapon most people skip

About Jaymie

Jaymie Tarshis is a highly-sought after Facebook Ads Strategist + Consultant that's been featured in Yahoo! News, Medium, Thrive Global, and Yahoo! Finance as one of the 10 Ad Experts To Watch.  Her passion is helping impact-driven coaches, course creators, and service providers leverage the power of ads to attract leads & sales on autopilot so they don't have to post every day, create more content, or show up online 24/7 in order to grow and scale their businesses. Since 2018, Jaymie has taught thousands of business owners through her programs and services and has helped clients generate over $10 million in revenue to date.

 

Learn more: https://www.instagram.com/theadexpert/ 

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
• Grab the AI + SEO Mini Course

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

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TIMESTAMPS

Introducing Jamie (00:01:13) Jamie introduces herself as a marketing and Facebook ads strategist who helps businesses generate leads and sales on autopilot.

What is a VIP Day? (00:02:06) Jamie explains her VIP day offering, where she helps clients build and launch their entire ad strategy in one day.

The Power of In-House Ad Management (00:03:24) Shannon and Jamie discuss the benefits of learning to manage your own ads versus outsourcing, highlighting control and empowerment.

When to Start Using Ads (00:06:23) The importance of having a proven, organically successful offer before investing money into advertising is discussed.

The Importance of Strategy (00:07:56) Shannon praises Jamie's strategy-first approach, which customizes the plan to the business before touching any technical ad setup.

Immediate Results and Ongoing Support (00:09:35) Shannon shares she received 20 leads within 24 hours and discusses the support Jamie provides after the VIP day.

Why Ads Fail (01:10:49) Jamie explains that when ads don't work, it's rarely the ad itself but rather the underlying strategy and customer journey.

Marketing as an Experiment (01:12:54) Treating marketing and ad tweaking as a fun experiment can lead to better long-term results and business growth.

The Fun of Ad Management (01:14:40) Shannon describes how Jamie's process made ad management feel creative and fun, rather than intimidating and technical.

The Evolution of Facebook Ads (01:16:48) Shannon reflects on how Facebook ads have become more complex over time, reinforcing the need for expert guidance.

Empowerment in Action (01:18:37) Shannon shares how she and her team successfully launched a new ad campaign on their own after the VIP day.

Jamie's Other Offerings (01:20:56) Jamie outlines her other services, including digital products for DIYers, one-off consulting, and limited monthly management for larger accounts.

Who Should Use Which Service (01:23:11) Shannon breaks down which of Jamie's offerings is best for entrepreneurs at different stages and budget levels.

The ROI of a VIP Day (01:24:55) Jamie notes that most VIP day clients see a return on their investment within the first 30 to 60 days.

The Limits of Organic Reach (01:26:08) The conversation covers how ads overcome the limitations of organic social media, where posts reach less than 1% of followers.

How Much to Spend on Ads (01:29:01) Jamie explains that ad spend should be based on specific business goals, not a generic number, and introduces her budget calculator.

Using Ads for Your Existing Audience (01:32:49) Jamie highlights the powerful and cost-effective strategy of running ads to your warm audience who already know and trust you.

The Most Common Ad Mistake (01:34:30) The biggest mistake is skipping strategy and focusing only on the ad creative. Messaging is now more important than targeting.

How to Connect with Jamie (01:36:40) Jamie shares her Instagram handle, @theadexpert, as the best place for listeners to connect with her.

What does it actually take to build a retreat center from scratch? The land, the structures, the permits, the parking, the storage, the vision - and the marriage that has to survive all of it?

In this episode, Shannon sits down with her husband Nathan Jamail - world-renowned leadership and sales keynote speaker, and co-owner of Retreat Ranch - to pull back the curtain on the real journey of building one of Texas Hill Country's most unique retreat destinations. This is not a highlight reel. This is the honest, practical, sometimes hard-won story of what it takes to go from a dream to a fully operating retreat center. 

And this episode is especially meaningful because it's releasing on the five-year anniversary of opening Retreat Ranch's doors for the very first retreat - hosted by Kim DeMoss with Project Mindful Movement. Five years later, what started as a vision has grown into a thriving retreat destination that has welcomed countless guests, retreat leaders, and transformational experiences.

Retreat Ranch is a 46-acre, nature-forward glamping retreat and event space in the Texas Hill Country, sleeping up to 32 guests, featuring horses, goats, hens, a sauna, dipping pools, aerial yoga, and a heart-centered team that lives and breathes hospitality. But it didn't start that way - and this episode is all about the road to get here.

In this episode:

• Why you must start with the long-term vision before you break ground on anything
• The "not sexy" things that will make or break your retreat center - storage, parking, infrastructure
• Why building too small for your vision is one of the most expensive mistakes you can make
• How to take a big vision and execute it in strategic, bite-sized phases
• What it's really like to build a business with your spouse - the wins, the hard conversations, and the non-negotiables
• The business decisions behind Retreat Ranch that every aspiring retreat center owner needs to hear
• What Nathan - a global leadership expert - learned about building a team and a culture at the ranch

If you've ever dreamed of owning a retreat center, or if you're already in the process of building one, this episode will save you time, money, and a lot of headaches.

 

Learn about Retreat Ranch: https://theretreatranch.com/

Learn about Nathan: https://nathanjamail.com/

Learn about Project Mindful Movement: https://projectmindfulmovement.com

 

The Retreat Leaders Podcast Resources and Links:

• Learn to Host Retreats
• Join our private Facebook Group
• Get your legal docs for retreats
• Join our LinkedIn Group
• Apply to be a guest on our show
• Grab the AI + SEO Mini Course

 

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

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TIMESTAMPS

Building a Retreat Venue (00:01:54) Shannon and Nathan introduce the episode's topic: the journey, successes, and mistakes of building their retreat venue, Retreat Ranch.

Choosing Texas Over California (00:03:12) They discuss the initial plan to build in California and the logistical and business reasons that led them to Texas instead.

Finding and Developing Raw Land (00:04:37) The story of finding the 46-acre property, which was undeveloped with no roads, water, or power, and their intentional clearing process.

The Importance of Infrastructure (00:10:02) Discussion on the necessity of planning for infrastructure like plumbing and electricity, and the "Shannon pipe" for future expansion.

Mistake: Not Planning Big Enough (00:11:25) They share their biggest mistake: not planning for their maximum capacity from the start, leading to spaces like the dining hall being too small.

Elevating the Guest Experience (00:13:45) The importance of details, like high-quality robes and linens, to create an elevated, "bougie" experience for guests.

Knowing Your Niche (00:17:08) They emphasize building the venue for a specific audience (retreats) rather than trying to cater to everyone, which ensures high standards.

Starting Small and Evolving (00:19:07) How the ranch started with minimal accommodations and has grown over five years, adding more features and bathrooms along the way.

Marketing to a Specific Audience (00:23:04) The strategy of marketing exclusively to retreats, which has led to being booked a year or more in advance.

Planning for Future Growth (00:27:16) Discussing their annual business planning, including adding an office, podcast studio, and expanding the horse barn to keep the venue fresh.

The Vision for a Multi-Use Space (00:30:01) Plans for a future indoor/outdoor multi-use space to serve as a backup for bad weather and for corporate meetings.

Vision vs. Execution (00:31:43) Shannon's role as the visionary and Nathan's role in execution, using the evolution of the pool area as an example.

Key Advice for Venue Builders (00:35:15) Advice for aspiring venue owners: plan for non-sexy things like storage and parking, and understand what a retreat group needs.

What Makes Retreat Ranch Unique (00:38:39) They discuss their key differentiators, including free-ranging horses, exceptional attention to detail, and a high-serving team.

The Power of a Great Team (00:42:56) A special shout-out to their on-site manager, Josh, and the entire team for creating a loving and supportive environment.

Final Thoughts and Encouragement (00:45:01) Reflecting on their seven-year journey and encouraging others interested in the booming retreat industry to pursue their vision.

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

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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.

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:

1. What did I commit to?

2. What did I actually do?

3. 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.

 

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.

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.

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

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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.

 

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 leaders, tour operators, and experience-based businesses by simplifying the operational side of running retreats.

From building professional booking pages and collecting payments to managing logistics and participant information, WeTravel helps retreat leaders streamline their systems so they can focus on what they do best - delivering incredible experiences.

Shannon, Erin, and Alison also discuss why operational tools like WeTravel are essential for retreat leaders who want to move beyond spreadsheets and manual systems and build retreats that are both transformational and professionally run.

If you host retreats or are planning to start, this episode will give you a behind-the-scenes look at one of the most widely used platforms in the retreat industry.

What You'll Learn in This Episode

• Why WeTravel has become a leading platform for retreat leaders and tour operators
• How retreat leaders can simplify payments, logistics, and guest management
• The benefits of using professional booking and payment systems
• Why operational systems are critical for scaling a retreat business
• How WeTravel supports retreat leaders globally

Key Takeaways

Running retreats is both an experience business and an operations business.

Successful retreat leaders need systems that support:

• payment collection

• booking management

• guest communication

• logistics and documentation

Platforms like WeTravel help retreat leaders streamline these processes, create professional booking pages, and manage their retreats with greater efficiency and clarity.

About the Retreat Industry Forum

The Retreat Industry Forum is a gathering for retreat leaders, venue owners, and retreat industry professionals focused on elevating the business side of retreats.

Hosted by Shannon, Erin, and Alison along with other industry experts, the forum brings together experienced retreat leaders who want to grow profitable and sustainable retreat businesses.

Learn more about the upcoming forum at:

https://luxuryinbusinessretreats.mykajabi.com/retreat-industry-forum

About WeTravel

WeTravel is a booking and payment platform designed for multi-day and group travel businesses, including retreats, tours, and experiential programs.

The platform allows retreat leaders to:

• create professional booking pages

• collect payments and deposits

• offer payment plans

• manage participant information

• track retreat logistics

WeTravel helps retreat leaders streamline operations so they can focus on delivering exceptional retreat experiences.

Learn more at:

https://www.wetravel.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

Panel Introduction & Special Announcement (00:01:09) Shannon introduces Allison, Aaron, and Mariana; Erin announces WeTravel as a main sponsor for the Retreat Industry Forum.

WeTravel Origins & Mission (00:02:29) Mariana shares WeTravel's founding story, its purpose, and how it was created to solve retreat admin challenges.

Why WeTravel Benefits Retreat Leaders (00:04:00) Discussion on how WeTravel is uniquely designed for retreat leaders, covering all aspects from sales to logistics.

Comprehensive Features of WeTravel (00:05:10) Panelists highlight WeTravel's all-in-one capabilities, including bookings, payments, waivers, and logistics.

Challenges of Piecemeal Retreat Management (00:06:23) Shannon discusses common issues with using multiple tools and the legal risks of not having an integrated system.

Peace of Mind for Retreat Leaders (00:07:32) Panelists discuss how WeTravel provides security and organization for retreat leaders, ensuring nothing falls through the cracks.

Why Partner with the Retreat Industry Forum? (00:08:11) Mariana explains why WeTravel chose to sponsor the forum and their commitment to supporting the retreat industry.

Alignment of Missions: Elevating the Industry (00:09:40) Discussion on the shared mission to professionalize and elevate standards in the retreat industry.

WeTravel Beyond Wellness (00:10:43) Clarification that WeTravel serves all types of retreats, not just wellness-focused ones.

Defining WeTravel as an Operating System (00:11:43) Mariana and Shannon agree on calling WeTravel an "operating system" for retreat management.

Retreats Across All Industries (00:12:06) Panelists discuss how retreats can be valuable in any industry, not just wellness.

Sales Strategy & Authentic Outreach (00:13:15) Aaron and Allison share their positive experiences with WeTravel's genuine outbound sales approach.

Professionalism & Trust in Retreats (00:14:57) Mariana discusses how using a professional system like WeTravel builds trust and credibility for retreat businesses.

WeTravel's Broad Clientele (00:16:41) Mariana emphasizes WeTravel's wide range of clients and retreat types, not limited to wellness.

Forum Attendance & Final Thoughts (00:18:48) Mariana confirms she'll attend the forum; panelists express excitement and encourage listeners to join.

Podcast Outro (00:20:00) Closing voiceover thanks listeners, encourages subscriptions, and promotes free resources.

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 properly
• What to look for beyond viral posts and flashy branding
• Why collaboration over competition is the future
• How to choose rooms that stretch you without compromising your values
• The importance of structured sales systems alongside marketing

If you've ever invested in a room that felt fluffy, performative, or misaligned — this episode will help you make smarter decisions moving forward.

Key Takeaways

• Not all entrepreneurial events are built on substance — discernment matters.
• Post-COVID attendees expect measurable ROI, not hype.
• Viral marketing does not equal proven expertise.
• Testimonials, references, and tangible results matter more than aesthetics.
• Alignment with leadership style and values is critical.
• Growth rooms should challenge you — not manipulate you.
• Collaboration expands credibility and industry standards.
• Structured sales systems are as important as marketing strategies.

About Dora:

Dora Rankin is a powerhouse business coach, sales strategist, and author of USA Today bestselling book, The Heart Sell, dedicated to empowering women entrepreneurs to scale their businesses and unlock their highest earning potential. Host of The Heart Sell Signature Summit, Camp Heart Sell Club & Retreats as well as mentor for entrepreneurial organizations like NASDAQ and Tory Burch, Dora is intentional about rolling up her sleeves to build roadmaps to revenue through relationship building strategies. Whether you're a startup or scaling past a million, her Heart Sell methodology produces purpose driven successful businesses for women. 

 

Join Dora at the Heart Sell Summit: https://dorarankin.com/thsss2026 

 

Learn more about Dora here: dorarankin.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

Setting the Scene & Topic Introduction (00:01:07) Hosts discuss their locations, previous meeting, and introduce the main topic: discernment in entrepreneurial events.

Explosion of Coaching & Retreat Industry (00:02:24) Dora shares her perspective on the noisy, crowded event space and the need for discernment.

Proving Value & ROI in Events (00:03:29) Discussion on the necessity for event leaders to show real credentials and tangible results.

Industry Growth Post-COVID (00:04:20) Shannon explains how COVID-19 led to a surge in new entrepreneurs and coaches, increasing competition and skepticism.

Smoke and Mirrors in the Industry (00:05:37) Concerns about inexperienced leaders making big promises without real experience or results.

Attendee Disillusionment & Need for Proof (00:05:55) Dora shares that many clients come after spending heavily on ineffective programs, seeking real, proven guidance.

Facade of Success & Authenticity (00:07:21) Hosts discuss the disconnect between online personas and actual business success among some industry leaders.

Discernment Tips: Testimonials & References (00:08:26) Advice for attendees to ask for proof, testimonials, and references before trusting event leaders.

Collaboration Over Competition (00:09:26) Shannon and Dora emphasize the importance of collaboration in the industry, not competition.

Risks of Inexperienced Leaders (00:10:39) Discussion on the dangers of unqualified leaders hosting events, leading to negative attendee experiences.

Impact of Lived Experience (00:12:25) Dora highlights the importance of real, lived experience in providing valuable learning environments.

Discernment Checklist for Attendees (00:14:02) Shannon outlines what attendees should look for: experience, testimonials, references, and alignment.

Personality & Teaching Style Alignment (00:15:32) Advice to ensure the leader's style and values align with the attendee's needs, while being open to healthy challenge.

Accessibility vs. Vanity Metrics (00:16:54) Dora warns against choosing events based on fame; stresses the importance of leader accessibility.

Entertainment vs. Actionable Value (00:17:43) Distinguishing between motivational/entertainment events and those offering actionable business strategies.

Integrity in Event Fit & Leader Recommendations (00:19:10) Shannon and Dora discuss the importance of leaders being honest about event fit and referring attendees elsewhere if needed.

Sales Cycle & Long-Term Relationships (00:21:42) Dora explains the value of long-term relationships over single ticket sales in the retreat industry.

Dora's Heart Sell Summit Overview (00:22:37) Dora introduces her upcoming Cleveland summit, focused on practical sales training for women entrepreneurs.

Shannon's Testimonial for Dora's Methods (00:24:23) Shannon shares her personal success using Dora's sales techniques, endorsing the summit.

Sales vs. Marketing: Key Differences (00:25:55) Dora explains the difference between sales and marketing, and the need for both in business growth.

Wrap-Up & Final Thoughts (00:28:05) Closing remarks, gratitude, and encouragement to connect further with resources and future events.

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 that trust is not a strategy. She explains why many retreat leaders pursue co-hosts for the wrong reasons, how "fine" partnerships still create unnecessary complexity, and the exact 3-step vetting system she now uses before partnering with anyone.   If you've ever considered a co-host because you're nervous, overwhelmed, or hoping it will make marketing easier-this episode will save you time, money, and headaches. Key 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) Step 1: Know their full history Proof, testimonials, real work, integrity, originality. Step 2: Meet in person Stress reveals everything. Watch how they handle pressure. Step 3: Get crystal clear in writing Roles, money, decision-making, list ownership, IP, exit plan. 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:

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.