We recently connected with Emily Schmidt Riddle and have shared our conversation below.

Emily, thanks for joining us, excited to have you contributing your stories and insights. What was the most important lesson/experience you had in a job that has helped you as a business owner?

My first “real job” was as a sales associate at a local vintage store in college. At the time, it was my dream job, and I loved being so involved in the vintage and retail world- two things that I love. It taught me so much but the most important lesson was to fully immerse myself in every job and duty and to always put my stamp one everything I do, or try to.

I tried to take fully advantage of every little opportunity I was given there, and as a result was given more and more responsibility and able to work myself up to being an assistant manager and eventually had the owners even offer me the opportunity to buy the business. I got experience in buying, wholesale, going to market, going out to estate sales and homes to buy, reworking vintage clothing and homewares, designing and laying out for our seasonal store flips, coming up with and creating displays, making and selling my own items, social media, website building, making a blog, and so much more!

Everything I did, I put my full effort into, often going above and beyond to put extra time, outside of work, but also making sure I always delivered a product I was proud of. I also got a reputation for being extremely efficient because I would complete tasks quickly without getting distracted and while staying organized. I had a knack for being able to figure out the most efficient way to do things, which made me a valuable asset outside my creativity.

Overall this “little job” gave me the foundation to owning my own businesses, as it introduced me to all that goes into it behind the scenes and gave me a taste of ownership in my work and creativity.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I am an entrepreneur, designer, content creator, and community builder based in Versailles, Kentucky. I am the founder of Gathered Living and co-owner of several hospitality and lifestyle businesses, including The Amsden Coffee Shop, Gathered Play + Create, and The Aldenberg Hotel and Silk’s Steakhouse. I’m known for my love of storytelling, nostalgic design, and themed experiences, and specialize in transforming historic spaces into memorable destinations that bring people together. Through interior design, branding, social media, events, and placemaking, I try to create experiences that celebrate old-fashioned charm, family connection, and small-town community. Whether renovating a historic bank into a boutique hotel, designing imaginative children’s play spaces inspired by classic literature, or building viral social media campaigns, my work centers on creating places and experiences that feel both timeless and magical.

We’d love to hear a story of resilience from your journey.

As a senior in highschool I applied to the Interior Design program at UK and got denied. I never understood why: I had great grades and testing scores, and a strong and long list of extracurriculars and credentials. Thankfully though, I just moved on to my next major choice without giving it much thought at all. I graduated with an Art Education degree, but didn’t end up teaching a day in my life. I honestly thought I wanted to teach, even up to the end of student teaching, but soon started to realize it was not for me. I worked at Street Scene Vintage all through college (my first real job) and continued to after. I practically begged them to hire me and probably had the most embarrassing interview ever. I fell in love with retail and every aspect of the business. My bosses taught me so much and really let me take ownership in projects and try out my ideas. I started buying and selling vintage items on my own and Street Scene let me share space in their booth at Feather your Nest Antiques. I needed to come up with a quick name to put on my tags and decided on a whim to go with Miss Molly Vintage, named after our family dog Molly. After a few years of selling part-time, I took the leap to full-time and added my blog and online shop. A couple years later after continuing to share my home decor and renovations on my blog, I began receiving lots of requests for…..interior design. I decided to try out a few holiday decorating packages just to see how it went. I booked up immediately and the rest is history. I now have a waitlist year-round for decorating, I’ve helped hundreds of people decorate their homes, I’ve designed an entire boutique hotel, restaurant, coffee shop, and play cafe, and I don’t plan on stopping here. It may have taken longer than 4 years and a lot of hustle, but in the end, I ended up right where I needed to be. I have never needed a piece of paper to tell me what I can and can’t do, and you don’t either

Can you tell us about a time you’ve had to pivot?

Long before Gathered Play + Create existed, I spent several years hosting free children’s storytimes at The Amsden. Week after week, I watched families gather around books, crafts, and imaginative play, and I began to notice something bigger. Parents were actively seeking meaningful experiences they could share with their children, and there were very few spaces designed around creativity, connection, and old-fashioned play.

At the same time, I found myself increasingly dissatisfied with the retail side of The Amsden. While I have always loved retail and merchandising, I never felt I could dedicate the time, resources, or investment needed to truly create the kind of shopping experience I envisioned. The space was originally built around a local maker and vendor model, which was relatively unique when we started. Over time, that concept became increasingly common, and I found myself stuck in a cycle of constantly wanting more from the space but never feeling it fully reflected my vision. I’ve always been drawn to creating experiences that feel distinctive and ahead of the curve, and I knew I wanted to build something that couldn’t be found everywhere else.

Through years of storytimes and relationships with local families, I realized there was a much greater opportunity sitting right in front of me. Families weren’t coming for products as much as they were coming for connection, experiences, books, creativity, and community. In 2024, I made the decision to transform a large portion of our retail space into Gathered Play + Create, a storybook-inspired play café centered on imagination, children’s literature, art, and old-fashioned play.

What began as a simple renovation quickly became something much larger. Gathered Play + Create grew out of years of listening to families, observing unmet needs, and believing that childhood should be filled with wonder, creativity, and meaningful experiences. Today, it has become one of the most beloved parts of our business, serving thousands of children and parents each year through open play, storytimes, special events, and immersive literary-inspired experiences. Looking back, the play café wasn’t a pivot away from what we were doing—it was the natural evolution of everything we had been building all along.

Contact Info:

• Website: https://gatheredky.com
• Instagram: gathered living
• Facebook: https://facebook.com/gatheredky

Image Credits

hotel room photo and restaurant portrait- Seriously Sabrina Photography