Today we’d like to introduce you to Ashley Skaer-Tilley.
Hi Ashley, thanks for joining us today. We’d love for you to start by introducing yourself.
I moved to Florida nearly seven years ago from a very small country town in southern Illinois, but my journey into event planning and supporting small businesses started long before that—right in my local church. Our church didn’t believe in taking out loans, so whenever something needed to be repaired or updated, we found ways to fund it ourselves. When the church needed new pew covers, I organized a vendor show to help raise the money, and that experience sparked my love for small businesses and community-driven events.
From there, things naturally grew. I started hosting vendor events in the church hall, then expanded to a local venue called The Grange. Eventually, just before moving to Florida, I was renting out our town’s elementary school gym and hallways for large vendor shows with food trucks. Around that same time, I went back to college and earned my degree as a certified international and event wedding planner, with a secondary focus in fundraising.
While still in Illinois, I was also involved in an organization called The Modern Woodmen Of America—an organization my grandparents were part of, that I later joined, and now my daughter is involved in as well. Each year, we hosted fundraisers for local nonprofits. Through that work, I helped organize events for causes close to my heart, including raising funds for a local woman battling breast cancer and, most notably, organizing a fundraiser for our all-volunteer fire department to help them purchase new oxygen tanks.
When I moved to Florida, I wasn’t planning to continue in events at all. I actually came down as a vendor myself, running a small business with Chalk Couture. The turning point came at my very first local event—a quarter auction at the local Social Club. The woman running the event was overwhelmed and unsure how to manage everything. I offered to help, drawing on my past experience, and before I knew it, she left the building entirely. Suddenly, I found myself—new to Florida, knowing no one—running the event on the spot for 17 vendors and a room full of attendees.
It was a little bumpy, but it worked. Two months later, I organized and ran my own quarter auction from start to finish, and it was a success. Through those events, I connected with an incredible group of vendors, and from there my first Florida vendor show was born—at the local VFW hall. It sold out quickly. I did it again, expanded outdoors, and realized very quickly there was a huge and thriving small business community here that needed more space and opportunities.
Since then, I’ve continued to grow, now hosting large vendor shows across Flagler, Putnam, Clay, and St. John’s counties, renting fairgrounds and larger venues. I’ve been doing these events consistently since late 2019.
As I grew closer to vendors, I kept hearing the same challenge over and over—the exhaustion of setting up for hours, vending all day, and breaking everything down. Vendors wanted a place where they could display their products, walk away, and focus on creating and growing their businesses. That idea stuck with me. I combined that need with inspiration from a marketplace back home in Illinois, and that’s how Serendipity Marketplace was born.
Serendipity has now been open for nearly three years, and the growth has been incredible. We’ve expanded our vendor community, added popular classes and workshops, hosted special events, and created recurring favorites like monthly bingo and Funko meetups. Everything we do is centered around bringing people together—supporting small businesses, creating joy, and giving the community a welcoming place to gather, shop, and connect. What started as a simple fundraiser years ago has truly turned into something bigger than I ever imagined.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
No, it definitely hasn’t been a smooth road—and I don’t think any meaningful business journey ever is. There are always bumps along the way, and Serendipity Marketplace has been no exception.
One of the biggest challenges came before I ever opened the doors. At the time, the city of Palm Coast wasn’t familiar with the type of marketplace I was creating, and because the concept was new to them, I wasn’t initially granted approval to open. I had to spend months clearly outlining my vision—explaining how the business would operate day-to-day, sharing photos, and walking through what the store would look like six months to a year into the future. It took persistence, patience, and a strong belief in the concept before I was finally able to move forward.
Another ongoing challenge comes with the nature of running a vendor-based business. With over 60 local vendors under one roof, change is inevitable. Some vendors grow and move on, some step away from their businesses entirely, and others may feel discouraged if sales don’t meet expectations right away. While those moments can be difficult, they’re also part of supporting small businesses through different seasons.
This has never been a business built on constant glamour. There will always be challenges—whether personal, internal, or influenced by the world around us—but each one has reinforced the importance of adaptability, resilience, and staying true to the original vision.
Appreciate you sharing that. What should we know about Serendipity Marketplace, Inc.?
Serendipity Marketplace is a curated vendor marketplace designed to support and elevate local small businesses while creating a welcoming space for the community. We are home to over 60 local vendors offering handmade, boutique, vintage, and specialty items, all under one roof. What sets us apart is our business model—we give vendors the opportunity to display their products in a permanent retail space without the constant stress of setting up and breaking down at shows, allowing them to focus on what they do best: creating and growing their businesses.
Beyond shopping, Serendipity Marketplace is known for its sense of community. We host classes, workshops, and special events that bring people together, from creative experiences to monthly gatherings that encourage connection and fun. We pride ourselves on being more than just a store—we are a place where small businesses are supported, friendships are formed, and the community feels at home.
What I’m most proud of is the environment we’ve built: a space where vendors feel supported, customers feel welcome, and creativity is celebrated. At the heart of our brand is the belief that shopping small is powerful, and when local businesses are given the right opportunities, the entire community benefits.
Can you talk to us about how you think about risk?
Opening any business is a risk, and I’ve taken that leap more than once. I currently own two businesses—Charming Sisters Events and Serendipity Marketplace—and while both involve risk, they are very different in how that responsibility shows up.
Charming Sisters Events is run solely by me. The risks there are personal—my time, my income, and my reputation. Serendipity Marketplace, however, carries a much deeper level of responsibility. It involves the livelihoods of over 60 local vendors, the trust of customers who walk through our doors, and the day-to-day reality of managing a physical space, inventory care, and ongoing expenses. That kind of risk isn’t just financial—it’s relational and emotional as well.
I don’t necessarily see myself as a reckless risk-taker, but I do believe in thoughtful, intentional risk. I take the time to plan, research, and listen, but at some point you have to trust your experience and take the step forward. For me, risk has always been tied to purpose. Every major risk I’ve taken has been rooted in supporting small businesses, creating opportunities, and building something that serves more than just myself.
The biggest risk I’ve taken was opening Serendipity Marketplace, knowing that success wouldn’t just affect me—it would impact dozens of families and small businesses. That responsibility pushes me to be careful, adaptable, and fully invested. To me, risk isn’t about fearlessness; it’s about believing in the vision enough to move forward, even when there are no guarantees.
Contact Info:
- Website: https://www.theserendipitymarketplace.com/
- Instagram: https://www.instagram.com/serendipitymarket2023/
- Facebook: https://www.facebook.com/theserendipitymarketplace
