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EP 270 Retreat Insurance: What Every Retreat Leader Must Know with Event Helper

Release Date: 05/14/2026

EP 270 Retreat Insurance: What Every Retreat Leader Must Know with Event Helper

The Retreat Leaders Podcast

Let’s talk about something most retreat leaders avoid… until they absolutely can’t. Insurance. In this episode of The Retreat Leaders Podcast, Shannon Jamail sits down with Myles Anderson from Event Helper, an insurance provider specializing in events and retreats, to break down why insurance is not optional in the retreat industry - it’s essential. Because here’s the reality: You are responsible for people’s safety, experiences, and well-being during your retreat. And without the right coverage in place, one incident can put your entire business - and personal assets - at risk. In...

EP 269 Why Glamping and Retreats Are the Perfect Pair (And What Retreat Leaders Need to Know) with Sarah Riley

The Retreat Leaders Podcast

The retreat industry is evolving - and one of the biggest opportunities right now sits at the intersection of glamping and retreats. In this episode of The Retreat Leaders Podcast, Shannon Jamail sits down with Sarah Riley, a UK-based glamping industry expert and co-organizer of The Glamping Show America, to explore how glamping and retreats are becoming one of the most powerful combinations in experiential hospitality. Sarah has been working in the glamping and retreat space since 2010, helping entrepreneurs launch lifestyle businesses and navigate the realities of building glamping sites -...

EP 268 The Power of Retreats for Midlife Women: Building Community, Healing & Business with SOL Women

The Retreat Leaders Podcast

There is a powerful shift happening - and it’s centered around midlife women. Women who have spent years building careers, raising families, and showing up for everyone else are now asking a different question: What do I want? In this episode of The Retreat Leaders Podcast, Shannon Jamail sits down in person in Austin with the founders of SOL Women to talk about the rise of retreats designed specifically for midlife women - and why these experiences are more needed now than ever. SOL Women creates holistic, supportive retreat experiences that help women reconnect with themselves, prioritize...

Behind the Scenes of the Retreat Industry Forum: Why Logistics & Operations Make or Break Your Retreat

The Retreat Leaders Podcast

There’s what your guests see at a retreat… And then there’s everything happening behind the scenes. In this special edition of The Retreat Leaders Podcast, Shannon Jamail is joined by Alison and Erin (co-hosts of the Retreat Industry Forum) along with two of the Forum’s featured panel presenters - Matt Quinones and Daesha Donze - to talk about the operational side of running successful retreats. You can have an incredible concept, a beautiful location, and a powerful transformation… But if your logistics and operations aren’t dialed in, it will impact the entire experience. Matt...

EP 267 The Retreat Venue Gap: Why Retreat Leaders and Venues Struggle to Find Each Other with Emily Johnson

The Retreat Leaders Podcast

One of the biggest challenges in the retreat industry isn’t marketing, pricing, or programming. It’s the gap between retreat leaders and retreat venues. Retreat leaders struggle to find the right venues. Venue owners struggle to fill their calendars with the right retreats. And somewhere in the middle, opportunities are missed. In this episode of The Retreat Leaders Podcast, Shannon Jamail sits down with Emily Johnson, founder of Elevate Hospitality Collective, to talk about the disconnect between retreat leaders and venues - and how the industry can bridge that gap. Emily brings years of...

EP 266 The Power of Proximity for Retreat Leaders and Entrepreneurs

The Retreat Leaders Podcast

Success in business isn’t just about strategy. It’s also about proximity - who you’re around, the conversations you’re exposed to, and the standards of the rooms you choose to enter. In this solo episode of The Retreat Leaders Podcast, Shannon Jamail shares why being in the right rooms can dramatically accelerate your growth as a retreat leader and entrepreneur. For many years Shannon’s business was doing well. But about five years ago, something shifted. She started attending conferences, joining masterminds, and intentionally placing herself in rooms with other high-level...

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

The Retreat Leaders Podcast

Running ads to fill your retreat sounds like the obvious next step… But for most retreat leaders, it’s actually where they start losing money. In this episode of The Retreat Leaders Podcast, Shannon Jamail is joined by Alison, Erin, and Jenn Possick (The Ads Maven) to break down what retreat leaders really need to know before investing in Facebook and Instagram ads. Jenn specializes in helping coaches, wellness professionals, and retreat leaders run strategic, data-driven ad campaigns - offering both done-for-you and done-with-you services. And here’s what she makes very clear: Ads are...

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...

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...

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...

More Episodes

Let’s talk about something most retreat leaders avoid… until they absolutely can’t.

Insurance.

In this episode of The Retreat Leaders Podcast, Shannon Jamail sits down with Myles Anderson from Event Helper, an insurance provider specializing in events and retreats, to break down why insurance is not optional in the retreat industry - it’s essential.

Because here’s the reality:

You are responsible for people’s safety, experiences, and well-being during your retreat.

And without the right coverage in place, one incident can put your entire business - and personal assets - at risk.

In this conversation, Shannon and Myles discuss:

Why retreat leaders need event insurance
Why venues should require it
What can actually go wrong at a retreat
The real consequences of not having proper coverage
How retreat leaders can protect themselves, their guests, and their business

This episode is not fear-based - it’s reality-based.

If you host retreats, events, or group experiences, this is one of the most important conversations you can listen to.

What You’ll Learn in This Episode

• Why insurance is essential for retreat leaders
• What types of risks exist at retreats and events
• Why venues require insurance (and why you should expect it)
• What can happen financially and legally without coverage
• How insurance protects both the host and the guest experience

Key Takeaways

You Are Responsible as the Host

When you host a retreat, you are taking on responsibility for:

participant safety
activities
environment
logistics

Even with the best planning, things can happen.

Insurance Protects More Than You Think

Insurance isn’t just about worst-case scenarios.

It protects:

your business
your personal assets
your reputation
your ability to continue hosting retreats

Venues Require It for a Reason

Professional venues often require retreat leaders to carry insurance.

This protects:

the venue
the retreat host
the guests

If a venue doesn’t require it, that’s something to pay attention to.

Without Insurance, the Risk Is Real

Without proper coverage, retreat leaders could face:

liability claims
legal costs
unexpected financial loss

And in some cases, it could shut down a retreat business completely.

This Is About Being a Professional

Running a retreat is not just about creating a great experience.

It’s about operating a real business.

And real businesses protect themselves.

About Event Helper

Event Helper provides event and retreat insurance designed to protect hosts, organizers, and venues.

They specialize in offering coverage for a wide range of events, helping business owners operate with confidence and reduce risk.

Learn more at:
https://www.theeventhelper.com/#retreatleaders

The Retreat Leaders Podcast Resources and Links:

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

Myles’ Background and Role (00:01:07) Myles explains his role at Event Helper and their focus on event liability insurance.

Venue vs. Event Host Insurance (00:02:16) Discussion on the difference between a venue’s insurance and an event host’s insurance policy.

Why Event Hosts Need Insurance (00:03:15) Myles details why event hosts need their own liability insurance and what it covers.

Cost and Value of Event Insurance (00:05:08) Shannon and Myles discuss the typical costs and the importance of investing in event insurance.

Real-Life Claims and Examples (00:06:08) Myles shares examples of claims, including property damage and injury incidents at events.

Legal Defense and Coverage Scope (00:07:51) Explanation of how insurance policies provide legal defense, not just payouts for damages.

Participant Injuries and Waivers (00:08:39) Discussion about participant injuries, waivers, and when hosts may or may not be liable.

Personal Liability Risks (00:10:34) Shannon warns about personal liability and the financial risks of not having insurance.

Coverage Limits and Host Liquor Liability (00:11:42) Myles explains coverage limits, options up to $5 million, and inclusion of host liquor liability.

Honesty in Policy Applications (00:12:35) Importance of accurately disclosing retreat activities when applying for insurance.

Exclusions and High-Risk Activities (00:12:49) Myles discusses exclusions, higher-risk activities, and how Event Helper handles special cases.

Participant Coverage Options (00:14:29) Explanation of liability vs. participant coverage for athletic or sporting retreat components.

Event Helper as Preferred Partner (00:15:10) Shannon shares why her venue prefers Event Helper and the ease of working with them.

International Event Insurance (00:16:11) Discussion on Event Helper’s efforts to help with international event insurance coverage.

Challenges of International Coverage (00:17:28) Myles explains the difficulty of finding coverage for events outside the US.

How to Apply for Event Helper Insurance (00:18:05) Overview of Event Helper’s simple online application process and customer support.

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