EP 280 The Fastest Way to Build a Profitable Retreat Business with Shari Leid
Release Date: 08/20/2026
The Retreat Leaders Podcast
What if the fastest way to grow your business wasn't working harder-but learning from someone who's already done it? In this episode of The Retreat Leaders Podcast, Shannon Jamail sits down with Shari Leid, internationally recognized keynote speaker, author, and entrepreneur, for a conversation about one of the most overlooked business skills: knowing when to ask for help. Shari has built an incredible career as a professional speaker, but like many entrepreneurs, she wanted to diversify her business by adding memberships and retreats as recurring revenue streams....
info_outlineThe Retreat Leaders Podcast
Why do some retreat leaders build thriving businesses while others give up after one launch? It's usually not because they're better marketers. It's not because they have a bigger audience. And it's rarely because they have the perfect retreat. It's because they keep showing up. In this solo episode, Shannon Jamail shares one of the biggest mindset shifts every retreat leader needs to hear: success doesn't come from avoiding failure-it comes from refusing to quit. Using Thomas Edison's famous light bulb story as a starting point, Shannon explains why...
info_outlineThe Retreat Leaders Podcast
Welcome to a brand-new season of The Retreat Leaders Podcast. This episode is a little different. Instead of diving into retreat marketing strategies or interviewing a guest, Shannon shares exciting updates about the future of the podcast, reflects on the incredible community that has helped grow the show into the top 2% of podcasts globally, and gives listeners a preview of what's ahead. The biggest change? The podcast is leveling up. Going forward, most interviews will be recorded in person from Shannon's new podcast studio in Austin, Texas. The goal is to create deeper...
info_outlineThe Retreat Leaders Podcast
Why isn't your retreat filling? It's one of the questions I get asked more than any other. And while marketing has changed dramatically since this episode first aired-with AI, SEO, and new ways people discover retreats-the core reasons retreats don't fill are surprisingly the same. That's why I'm bringing back this Throwback Thursday episode. In this conversation, I break down the most common reasons retreat leaders struggle to enroll guests and, more importantly, what you can do about it. We cover everything from mindset and messaging to marketing, pricing, and positioning because filling a...
info_outlineThe Retreat Leaders Podcast
Some retreat lessons never go out of style. In this Throwback Thursday episode of The Retreat Leaders Podcast, Shannon Jamail revisits one of her favorite conversations with Chelle Swierz, founder of Topia Boutique Retreat Center in Baja California Sur, Mexico. While marketing trends, AI, and visibility strategies continue to evolve, the core principles of creating exceptional retreat experiences remain the same. In this conversation, Chelle shares the common mistakes she sees retreat leaders make—and many of them are still happening today. From poor guest preparation and...
info_outlineThe Retreat Leaders Podcast
This week's Throwback Thursday episode tackles one of the biggest challenges facing retreat leaders today: Pricing. Because let's be honest... Most retreat leaders aren't struggling because they don't know how to host a great retreat. They're struggling because they're underpricing their expertise, their experiences, and the transformation they provide. In this popular episode, Shannon Jamail sits down with retreat pricing expert Erin Haag to discuss the difference between attracting price shoppers and attracting value-driven buyers. Together they explore why so many retreat leaders:...
info_outlineThe Retreat Leaders Podcast
This week's Throwback Thursday episode is one that will challenge your thinking. And that's exactly why I'm bringing it back. In this powerful conversation, Shannon Jamail sits down with Kyera Kacey, a bold entrepreneur, speaker, and retreat leader known for helping people break through limitations around money, confidence, and self-worth. Love her approach or disagree with parts of it, one thing is certain: Kyera challenges retreat leaders to think bigger. Much bigger. In this episode, Kyera shares how she launched and sold out her first retreat in Ireland, then went on to host luxury...
info_outlineThe Retreat Leaders Podcast
The Retreat Industry Forum is over... And I'm still getting messages. Every week, retreat leaders, venue owners, and wellness entrepreneurs are reaching out asking: "When is the next one?" "How do I get on the waitlist?" "I heard it was incredible. Are you doing it again?" But here's what's interesting: Most people aren't asking about the presentations. They're talking about the conversations. The connections. The collaborations. The feeling of being surrounded by people who understand this industry and are actively building something meaningful. In this episode of The Retreat Leaders...
info_outlineThe Retreat Leaders Podcast
What if your next retreat venue was a walkable, luxury beach community on the Texas Coast — fully furnished, photographer-ready, and designed to make your attendees feel like they're living in a neighborhood instead of checking into a hotel? In this episode, Shannon sits down with Lee Ann Peters, the powerhouse behind Cinnamon Shore — a New Urbanist luxury beach community on the Texas Coast that has become one of Southern Living's Top 10 Beach Towns in the United States. Lee Ann left a successful Atlanta real estate career in the middle of the Great Recession to build something most people...
info_outlineThe Retreat Leaders Podcast
If you’re building a retreat business, this episode is required listening. In this episode of The Retreat Leaders Podcast, Shannon Jamail sits down with Catherine Kontos, founder of RetreatBoss, RetreatMatch, and RetreatBoss Magazine, to talk about what it actually takes to build a sustainable and profitable retreat business. With over 14 years in the industry-and a background acquiring and selling over 100 businesses and properties-Catherine brings a level of real business strategy that most of this industry is missing. This conversation about the realities of running retreats as a...
info_outlineWhat if the fastest way to grow your business wasn't working harder-but learning from someone who's already done it?
- Why successful entrepreneurs ask for help sooner rather than later
- How to turn retreats into recurring revenue
- Why adding retreats can strengthen your existing business
- The value of learning from experienced retreat leaders
- How coaching and proximity accelerate business growth
- Why getting in the room matters more than consuming content online
- The mindset shift that separates successful entrepreneurs from struggling ones
- How to make money with retreats
- How to turn retreats into recurring revenue
- Why coaching accelerates business growth
- The power of mentorship and proximity
- Why entrepreneurs should invest in learning before launching retreats
- How to avoid common retreat mistakes
- Why asking for help is a business advantage-not a weakness
Key Takeaways
The Best Entrepreneurs Don't Go It Alone
- Join our Mastermind in Austin!
- 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
- Grab the Pitch to Profit Mini Course
- My two favorite social media tools: Metricool and ManyChat
---------------
TIMESTAMPS
Introducing Sherry Lead (00:00:52) Host Shannon Jamaal welcomes guest Sherry Lead, an attorney turned author, speaker, and now retreat leader, to the podcast.
Sherry's Journey into Retreats (00:02:04) Sherry explains why she sought mentorship to add retreats to her business, aiming for more stable revenue than speaking alone.
Adding New Revenue Streams (00:05:06) The discussion highlights the power of adding memberships and in-person experiences like retreats to grow a coaching or speaking business.
The Power of a Portfolio Career (00:06:32) Sherry explains how different business avenues like speaking, memberships, and retreats can all support and feed into each other.
Learning at The Forum (00:08:44) Sherry shares her experience attending a retreat leader forum, emphasizing the value of learning from experts with different business models.
Finding Your Unique Retreat Style (00:10:48) The importance of authenticity is discussed; your retreat should match your personality to attract the right people and feel genuine.
The Retreat Leader Mastermind (00:12:14) Shannon announces her upcoming mastermind event, designed to help retreat leaders with marketing, profitability, and building a supportive community.
Sherry's Retreats for Women (00:18:09) Sherry describes her women-only retreats, which focus on creating deeper connections to self, career, and community for up to ten women.
The "Flip" Framework (00:18:46) Sherry shares her personal story and the "Flip" framework she created to help people establish connection and a sense of belonging.
A Gift for the Audience (00:21:51) Sherry offers listeners a free "Flip" app on her website to help them practice and improve their connection skills.