Not every breakthrough happens in a crowded conference hall. Instead of flying to massive events in destinations like Las Vegas and Chicago, entrepreneurs craving real connection are choosing smaller, more intentional gatherings. Because, for many founders, the future of networking isn’t in packed convention centers—it’s around a dinner table, during a morning walk or in a conversation that unfolds over a few unhurried days.
That shift reflects how the next generation of success-minded leaders approach community and networking in a more personal way. They’re seeking deeper relationships, real collaboration and the kind of environment where meaningful conversations can actually happen.
Taylor Smith, founder of The Power Table, a national leadership platform that supports women entrepreneurs, has leaned into that demand by turning her retreats on Florida’s Emerald Coast into a key part of her platform. Designed for a small group of entrepreneurs, the gatherings prioritize connection, reflection and strategic conversation.
“They’re looking to attend smaller retreats because those are more about them as an individual,” Smith says. “They can take time away and invest in themselves.”
After building a successful retreat model through The Power Table, Smith has learned what makes these intimate gatherings truly impactful. Here are her four top tips for hosting retreats that deliver.
1. Think Small, Connect Big
When it comes to retreats, size really does matter. That doesn’t mean business leaders are abandoning large conferences altogether; many entrepreneurs attend both. At the mega conferences, the goal is often scale—meeting as many people as possible, making new connections and finding clients or collaborators. Intimate retreats can’t compete with that reach, but they offer something just as valuable: depth and connection.
“It’s the opportunity for more in-depth connection with other people as well as the host,” Smith says. “We keep our retreats intentionally small for that deeper connection.”
That means resisting the temptation to keep adding seats just because there’s demand. The real value comes from quality, not quantity, and every extra seat can dilute the experience and make those meaningful conversations harder to come by.
In terms of a magic number, Smith says it depends on the kind of transformation you want your attendees to have. For highly immersive experiences, where participants can have one-on-one time with the host and each other, the sweet spot is typically 10 to 20 people. That’s the number Smith aims for at her twice-yearly retreats. With a group that size, everyone has a seat at the table, both literally and figuratively.
2. Know Your Audience
The key to a successful retreat isn’t just planning round-the-clock activities; it’s understanding exactly who you’re serving and what they need. For Smith, her audience is made up of seasoned, ambitious, serial entrepreneurs who are juggling multiple companies, projects and priorities. They’ve reached a certain level of success and are thinking about bigger-picture, legacy-driven decisions.
With that in mind, retreats can be designed to meet more than just professional goals, because going beyond business can be incredibly helpful. Smith’s retreats bring in breathwork facilitators to help attendees reset, and even include playful activities like a pasta-making class at their vacation rental. “They got to have this experience where they got to mess up, to be imperfect and laugh about it,” Smith says.
By intentionally blending business strategy with personal growth, these retreats give participants space to stretch in ways they normally wouldn’t, helping them return with insights that go far beyond the office.
3. Schedule Post-Retreat Accountability
Retreats are energizing by design. Participants leave inspired, buzzing from meaningful connections and the rare gift of uninterrupted time to focus on themselves and their ideas. But once reality sets back in—the 200 unread emails, mile-long to-do lists and everything else in the daily grind—how do you make sure that spark doesn’t fizzle? That’s where intentional post-retreat accountability comes in.
“I don’t like to think of these things as separate,” Smith says. “It’s very important to me that what we provide on the backend is integration and accountability. You want to set people up for success and teach them how to integrate what they learned at the retreat back into their business.”
At The Power Table, accountability is built into the retreat experience itself. One of the first follow-up calls is scheduled 30 days after the retreat to help participants maintain momentum. From there, additional calls and accountability pods keep goals top of mind and provide a structured space to check in, problem solve and celebrate progress.
By building follow-up into the retreat design, you ensure the insights, breakthroughs and inspiration generated during those few days don’t fade once attendees return to their busy lives—they turn into real action and measurable growth.
4. Focus on Location
Location can make or break a retreat. “It is hard to sell and fill tickets,” Smith says. “A big part of that is location.”
Unlike a large conference, where big-name speakers and a packed agenda are the draw, retreats rely on something more intangible—reset, reflection, communication and leadership. For The Power Table’s audience, attending a retreat means taking significant time away from work and family, rescheduling responsibilities and making a real investment of both time and money. The location has to be irresistible.
That’s why they choose locales like Destin, Florida, and Scottsdale, Arizona, spots with name recognition that people genuinely want to visit. But more than just a pretty backdrop, they offer the privacy and serenity that Smith says are essential.
“They want to be in a space where they have quiet and peacefulness to think and create and have conversations,” she says. “Bigger cities like Nashville and Las Vegas might be attractive for a conference-style perspective, but they are not conducive to focus because there’s a lot going on.”
By choosing locations that balance appeal with peace, retreat hosts set the stage for meaningful engagement, deep focus and the kind of transformation that participants will carry long after they leave.
Featured image provide courtesy of Steph Halas Photography and Ash Simmons Photography
