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EP 280 The Fastest Way to Build a Profitable Retreat Business with Shari Leid

The Retreat Leaders Podcast

Release Date: 08/20/2026

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More Episodes

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.
 
Instead of trying to figure it out alone, she invested in learning from someone already doing it.
She reached out to Shannon for coaching, attended the Retreat Industry Forum in Denver, and ultimately booked Retreat Ranch for her upcoming retreats.
 
This episode isn't just about retreats.
 
It's about humility.
 
It's about investing in yourself.
 
It's about surrounding yourself with people who have already solved the problems you're trying to solve.
 
If you're an entrepreneur who wants to host retreats profitably, this conversation will encourage you to stop reinventing the wheel and start accelerating your growth.
 
In This Episode You'll Learn:
  • 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
Whether you're a coach, speaker, consultant, author, or entrepreneur exploring retreats as a new revenue stream, this episode offers practical wisdom that can save you years of trial and error.
 
What You'll Learn
  • 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

Successful business owners know they don't need to be the expert in everything.
 
They find people who already are.
 
Retreats Can Become a Powerful Revenue Stream
 
When done strategically, retreats don't just create unforgettable experiences-they can become a profitable extension of your existing business.
 
Learn From Someone Else's Mistakes
 
Experience is valuable. Borrowing someone else's experience is even more valuable.
 
Proximity Accelerates Growth
 
Books, podcasts, and courses are helpful.
 
But getting in the room with experienced entrepreneurs changes everything.
 
Retreats Should Support Your Business-Not Distract From It
 
The best retreat leaders don't create retreats because they're trendy.
 
They create them because they align with their expertise, audience, and long-term business strategy.
 
About Shari Leid
 
Shari Leid is an internationally recognized keynote speaker, author, entrepreneur, and founder dedicated to helping people create meaningful lives and businesses through connection, courage, and intentional growth.
 
As she expands her business to include memberships and transformational retreats, Shari demonstrates exactly what lifelong learning looks like: investing in mentorship, surrounding yourself with experts, and taking action.
 
Learn more at:
 
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

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.