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Preppy Podcast

Patricia Mae Olson
Preppy Podcast
Latest episode

300 episodes

  • Preppy Podcast

    Flaire Lighting

    2026/03/24 | 43 mins.
    Flaire Lighting is a luxury brand redefining the world of portable, battery operated lighting. The story began with our founders, husband and wife team Andrew and Claire, who saw an opportunity while searching for a battery-powered lamp for their charming 1920s home, which had limited outlets. Frustrated by the lack of unique, functional options, Claire immediately began sketching ideas for a new design. Her vision was simple: add a little FLAIR to every space, while creating the most durable and high quality lamp on the market at a price point one could justify for the quality. With experience as an interior designer in the hospitality industry, Claire has a deep understanding of the need for lighting that was both beautiful and practical. Having designed lighting for luxury hotels and restaurants, she knew that her lamp had to stand out by being stylish, functional, and exceptional. Moving away from the frustrating touchpad technology found in most battery lamps, she introduced the signature acrylic knob, combining on/off and dimming functionality in one elegant, intuitive design. After months of development and refinement, they  proudly launched their first style: THE ELIZA. Shop at https://flairelighting.com/
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  • Preppy Podcast

    Timeless Grace

    2026/03/17 | 45 mins.
    Timeless Grace Lifestyle Wear is a woman-owned small business based in St. Louis, Missouri, dedicated to helping women thrive in the many dimensions of modern life. We create luxurious yet functional garments that offer full coverage, comfort, and confidence—designed to support today’s woman in every role she embraces. Use code preppy20 for 20% off at https://timelessgracewear.com/
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  • Preppy Podcast

    Dana Small

    2026/03/10 | 39 mins.
    Dana Small is a South Florida based interior designer and the founder of Dana Small Designs, a full service firm specializing in residential projects of all sizes, from a single room refresh to full renovations and new builds.
    Known for her thoughtful approach to space and style, Dana creates interiors that blend timeless tradition in with coastal charm. Her work feels elevated yet approachable, layered with color, texture, and personality. She often incorporates antique rattan, wicker, and bold hues to infuse warmth and character into every room.
    With projects across the country and the Caribbean, Dana’s design perspective is shaped by travel, lifestyle, and a deep understanding of how people live in their homes. Her strong sense of space planning and keen eye for detail consistently result in inviting, livable interiors. Dana’s work has been featured in Coastal Living, Southern Living, Better Homes & Gardens, House Beautiful, HGTV, and more.
    Learn more at https://danasmalldesigns.com/  
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  • Preppy Podcast

    The Cookie Countess, Royal Mahjong Society and Crown & Coastal

    2026/03/03 | 1h
    For over 13 years, Hilary Ramos built a company called The Cookie Countess into one of the most trusted and beloved brands in baking and the cookie-decorating world. Yup — it’s a thing. 😉 It’s a world where creativity, community, and craftsmanship come together.
    After years of designing products that inspire joyful baking, she found herself falling in love with another kind of artistry: mahjong.
    And in the same way The Cookie Countess began — as a hobby (or, some might say, an obsession) — mahjong quickly became my new creative outlet. She was captivated by the history of the game, the sense of community it builds, and the way every tile set and tablescape tells a story about its owner.
    She searched for a set that felt like me — one that captured where I pictured playing the game: on our boat, surrounded by the ocean waters of Rhode Island. When sheI couldn’t find exactly what I was dreaming of, she started designing my own. First in her daydreams, and then in reality.
    The Newport Tile Set was where it all began. It celebrates everything she loves about summers on the East Coast — nautical stripes, lobsters, lighthouses, and hydrangeas, to name just a few icons of that world. From there while searching for the perfect mahjong bag she created Crown & Coastal, a handbag line. 
    The Royal Mahjong Society and Crown & Coastal were born from that same passion for design and detail that shaped The Cookie Countess — reimagining a classic game through modern themes, thoughtful storytelling, and beautiful craftsmanship.
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  • Preppy Podcast

    Up Down Sports

    2026/02/24 | 34 mins.
    Tennis is much more than a sport to this dedicated and engaged mother of four who lives in New York City. Her Friday tennis group, made up of close friends she’s known for over ten years, provided the spark and encouragement to create Up Down Sport. Week after week, they would show up with their tennis rackets in hand while juggling the day’s essentials. No one could find a bag they loved that could house their racket and all of the other things their active lives required. With an eye for design and detail, coupled with her ever-present desire to solve, Ashley set out to create something versatile— and beautiful— for her friends.  
    Like all things in Ashley’s life, Up Down Sport is anchored in her strong connection to family. The name itself, as well as the designs in her collection, are all inspired by the people she loves. When driving and listening to music with her daughter, singing a line from their favorite country song, Lily instantly lit up. Most tennis matches begin with a spin of the racket, choosing up or down to decide who will serve first. Up Down—that’s it! The name had meaning and the brand was born.
    Shop at https://updownsport.net/
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About Preppy Podcast

The Preppy Podcast features interviews every Tuesday with the brands, businesses and influencers who are keeping the modern preppy lifestyle alive.
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