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Along busy St. George Street in the heart of St. Augustine, Kyle Dellaire of Ben’s Pretzels, Mimi’s Crepes, Whips Waffle Company & Likit Ice Cream has created a collection of businesses shaped by creativity, opportunity, and constant evolution. Behind Ben’s Pretzels and Mimi’s Crepes, the Secret Garden has its own story. What was once an overgrown space with a few benches has gradually transformed into an inviting hidden getaway with tables, live music, a stage, the popular trinket box, and a place to slow down while exploring downtown. Locals love bringing visiting friends to discover the garden, and Kyle continues to find new ways to refine the space and create an experience people remember.

How does someone go from running one small ice cream shop with his brother and no employees to seeing possibilities for new businesses almost everywhere he looks? Kyle opens up about the mindset behind his growth, the ideas he keeps tucked away in his “vault,” and why some ideas are put into motion almost immediately while others develop quietly for years. He shares what he’s learned about building the right team, delegating as his responsibilities grow, remembering the names of people he meets, and creating genuine human connection in an increasingly digital world. There’s also a peek at what he’s dreaming up next—including Italian ice and the Roaming Cannoli—and why he believes sometimes you simply have to “take the leap of faith.”

Connect with Kyle Dellaire on Instagram: @Kyle_Dellaire

Check out Kyle's Businesses:

Likit Ice Cream: @Likit_SoftServe

Mimi's Famous Crepes: @Mimis_Famous_Crepes

Ben's Pretzels: @BensPretzelsStAugustine

Whips Waffle: @WhipsWaffleCo

Chapters

00:00 Introduction to Kyle Del Air and his entrepreneurial background
02:00 Growing up in an amusement park and early influences
03:09 Moving to Florida and starting in Saint Augustine
04:08 First business: Ice cream shop and early challenges
06:04 Evolving the business and discovering new opportunities
08:01 Sourcing products and innovating with Dole Whip
09:05 Expanding with multiple locations and testing new ideas
11:02 The creation of the secret garden and community space
13:08 Adding Mimi's Crepes and creating a complementary business
14:59 Building a strong team and leadership strategies
16:49 Mentors, books, and influences shaping Kyle’s mindset
19:03 Customer service philosophy and local relationships
21:10 Future plans, new ventures, and continuous growth
22:51 The importance of routines, travel, and personal development
24:57 Final thoughts on opportunity, community, and success

Connect with Host Leandra Sweet: @TheSoulLedSessions

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Just steps from the beach in St. Augustine, Tessa, Maggie & Mitchell of Sunrise Brew Coffee are proving that great coffee has the power to bring people together. As siblings building a business side by side, they've created far more than a neighborhood café—they've built a welcoming community where meaningful connection comes first. Originally from Utah, they quickly fell in love with St. Augustine and its incredible support for locally owned businesses, making it the perfect place to bring their vision to life. From cozy craft nights and seasonal themed events to plans for adding beer and wine, they're continually creating new ways for people to gather, connect, and enjoy a true "third space" beyond home and work.

This inspiring conversation explores entrepreneurship, family business, leadership, work-life balance, and the courage to start before you feel completely ready. Tessa, Maggie, and Mitchell share what it's like building a business as siblings, opening their café sooner than expected, and learning every step of entrepreneurship along the way. Drawing from previous jobs, managers, and life experiences, they've intentionally created a culture built on kindness, genuine hospitality, and mutual respect—striving to be the kind of leaders they always wanted to work for while empowering their team to make every guest feel like family. It's a heartfelt reminder that success isn't just about building a business—it's about creating a place where employees feel valued, customers feel welcomed, and community always comes first.

Check out Sunrise Brew Coffee on Instagram: @SunriseBrewCoffee

And on their website: https://sunrisebrewcoffee.com

00:00 Welcome to Sunrise Brew Coffee
00:35 The Story Behind Sunrise Brew Coffee
03:10 Dreaming of Opening a Coffee Shop
04:50 From Coffee Truck to Café
06:35 Taking the Leap into Entrepreneurship
10:20 Why St. Augustine Felt Like Home
12:00 Building a Business as Siblings
14:10 Why St. Augustine Supports Small Businesses
17:00 Creating Community Through Coffee
19:30 Working with Family & Spouses
22:00 Building a Culture of Kindness
24:00 Learning Entrepreneurship as You Go
29:15 Creating a True Community Gathering Place
31:30 Balancing Multiple Businesses
34:20 The Vision for Sunrise Brew's Future
39:00 Morning Routines & Entrepreneur Life
42:00 Advice to Their Younger Selves
46:30 Where to Find Sunrise Brew Coffee

Connect with Host Leandra Sweet: @TheSoulLedSessions

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Inspired by the vibrant spirit of St. Augustine, Sunny TV was born from an unexpected turning point. After losing his broadcasting job, Davey had just 30 days to figure out what came next. Instead of walking away from the career he loved, he took a leap of faith on an idea that had been living in his heart—a positive, community-driven variety show. Drawing on a lifetime of experiences in broadcasting, the art world, luxury retail, and even competitive athletics, he turned uncertainty into opportunity with the support of a tight-knit team that believed in the vision from day one and helped bring it to life.

Today, Sunny TV shines a light on the people who make the nation's oldest city so special. More than just a variety show, it's a platform where local businesses, community leaders, and nonprofits can share their stories, expand their reach, and receive professional content to continue promoting their organizations long after filming wraps. Built on friendship, collaboration, and a genuine love for the community, Sunny TV proves that when passionate people come together around a shared purpose, they can create something that truly makes a difference.

Check out SunnyTV on Instagram: @SunnyTV

Chapters

00:00 The Birth of Sunny TV
02:54 Creating a Positive Community
06:12 Empowering Nonprofits
09:14 The Art of Interviewing
12:00 Building a Supportive Team
15:00 The Power of Resilience
17:59 Connecting History and Culture
20:54 The Journey of a Dream
24:06 Lessons from Life Experiences
30:33 Navigating Grief and Growth
32:14 The Artistic Journey
34:49 Words as Art: The Power of Affirmations
36:28 Building Community Through Shared Experiences
38:25 Documentary Aspirations and Storytelling
41:32 The Importance of Connection and Compliments
46:02 Living the Dream in St. Augustine
51:02 Sustaining Joy Through Sponsorships and Community Support

Connect with Host Leandra Sweet: @TheSoulLedSessions