The answer lives in this podcast
Why did Shari Leid decide to add retreats to her speaking business?
Shari Leid added retreats to her speaking business because the speaking income alone was too unpredictable — lean months followed flush ones, with no reliable floor. As a solo entrepreneur, she wanted more steadiness, and identified retreats alongside a membership program as the two levers most likely to generate recurring, dependable revenue while deepening her connection with her audience.
The unpredictability of speaking — and the case for a steadier model
Speaking engagements are booked in bursts. For a solo entrepreneur like Leid, that means income can swing sharply from one quarter to the next — a reality she named directly in The Retreat Leaders Podcast. The problem isn't that speaking is unprofitable; it's that it's structurally lumpy, and running a business on lumpy income is stressful.
Retreats offered something speaking alone can't: a predictable, finite event with a known revenue ceiling per cohort. Leid runs women-only three-day retreats, capped at a maximum of 10 participants, and hosts two per year. That's a small-volume, high-intentionality model — designed to go deep with a tight group rather than scale wide.
Retreats as recurring revenue — not just a new product line
Leid's move into retreats wasn't an impulse. She approached it the way she approaches everything: by seeking out people who had already done it. That instinct — to ask "who can I learn from?" before launching — led her directly to Shannon Jamail and the community built around this podcast. Jamail described that posture as rare among high-achieving entrepreneurs, many of whom default to figuring things out alone.
Alongside retreats, Leid identified a membership program as the second pillar of her recurring revenue strategy. Together, the two formats address what speaking alone can't provide: a consistent base that doesn't reset to zero between gigs.
The decision also reflects how Leid thinks about connection — the core of her work. Her FLIP (Flip the Box) framework, built around the idea that genuine human connection can be established in under 60 seconds, maps naturally onto the retreat format. A small group, three days, capped at ten women: it's almost a structural expression of her methodology. You can hear that logic unpacked further in episode 280 of The Retreat Leaders Podcast.
"A lot of us have a good life, but if we don't feel connected, we're letting that good life stop us from a great life."
Shari Leid — Attorney, Author, Speaker, and Retreat Leader · Independent / Solo Entrepreneur
Leid trained as an attorney, then stepped away from practice to raise her children and begin writing. Her first book launched a portfolio career that now spans media contributions, speaking, and retreats. Her fifth book is due in February. The FLIP framework at the center of her work grew directly from a 2023 journey across all 50 U.S. states, where she shared a meal with a female stranger in each one. That project was not incidental — it was research, proof of concept, and personal mission rolled into one. Leid's backstory adds unusual weight to her focus on belonging: she was orphaned and found in a cardboard box, with no known birth date or identifying information. The question of connection, for her, is not abstract. It's the question her life started with — and the one she has built an entire body of work around. Her retreats, covered in depth on The Retreat Leaders Podcast, are a natural extension of that mission.
See also
What is Shannon Jamail's personal example of overcoming objections to attend a retreat?
Shannon Jamail shares that over a year ago, her friend Erin invited her to teach at a retreat in France, and despite significant objections — travel, cost, and timing — she ultimately went and the experience proved transformative.
What role does community and being in the right rooms play in sustaining belief for retreat leaders?
Shannon Jamail recommends that retreat leaders who are struggling with belief attend in-person events, masterminds, and conferences where they can be surrounded by others who are building profitable retreat businesses.
Why is visibility — not pricing — the most common technical reason a retreat does not sell?
Shannon Jamail notes that when retreat leaders contact her saying their retreat is not selling, a quick look often reveals the retreat cannot even be found — the core problem is visibility, not pricing.
Key takeaways
- The speaking business produces unpredictable, feast-or-famine income — retreats were Leid's answer to building a more stable revenue floor as a solo entrepreneur.
- Leid pairs retreats with a membership program: two formats that together create recurring income, rather than one-off fees.
- Her retreat model is deliberately small-scale — a maximum of 10 women, two events per year — prioritizing depth of connection over volume.
- She sought out expertise before launching, which led her to Shannon Jamail and the community explored throughout The Retreat Leaders Podcast.