Kentucky’s Wandering Realtor

Stephon Lewis
  • 5.0 (4)
  • Places & Travel

Kentucky's Wandering Realtor is your guide to the neighborhoods that make the Bluegrass State feel like home. Hosted by a Louisville native with a passion for real estate and storytelling, this podcast explores the people, businesses, and history that give Kentucky communities their unique charm. From bustling local hotspots to hidden gems, each episode dives into the stories of neighbors, entrepreneurs, and traditions that make every corner special. Whether you're a local, newcomer, or just curious, join us as we wander through the places and faces that make Kentucky unforgettable.

  1. 2d ago

    1,000 Bottles, One Garage with Jay Jacobs

    Woodford Bourbon Guy Jay Jacobs opens up his private bourbon collection of nearly 1,000 bottles, and the story behind it is bigger than whiskey. Jay Jacobs, known online as Woodford Bourbon Guy, turned an ordinary garage into one of Kentucky's most talked-about private bourbon bars, starting with a bar he found on Marketplace and bolted straight to the floor. But the real story isn't the shelves, it's how a passion that began as something he did for his mom turned into a trusted voice in the bourbon community. In this episode of Kentucky's Wandering Realtor, Jay shares why he originally forced himself to learn to like whiskey, how Woodford Bourbon Guy grew from a social media handle into a name bourbon fans trust before they spend their money, and what that responsibility actually feels like. We talk Penelope Bourbon, American Light Whiskey, and Stagg Jr., a few Kentucky bourbon opinions that might get him in trouble, the bottles that deserve way more attention, and whether owning nearly 1,000 bottles ever gets in the way of just enjoying the pour. Because the name Woodford Bourbon Guy carries more weight than most people realize, we also dig into the culture, food, and character of Versailles and Woodford County, and what Jay thinks visitors miss when they only see the tourist version. Plenty of bourbon. Plenty of laughs. But at its core, this is a conversation about everything that gets built around the bottle, family, community, and connection. 1,000 Bottles, One Garage with Jay Jacobs, on Kentucky's Wandering Realtor. #WoodfordBourbonGuy #KentuckyBourbon #BourbonCollector #VersaillesKY #WoodfordCounty #KentuckysWanderingRealtor #BourbonCommunity #WhiskeyPodcast

    1,000 Bottles, One Garage with Jay Jacobs

  2. Aug 10

    Who is he without the applause? with Richard Sullivan

    Louisville artist and former Atlanta Braves minor league player Richard Sullivan joins Kentucky's Wandering Realtor for a raw conversation about identity, healing, and who you are when the applause stops. For Episode 50, Richard Sullivan, the 2024 Kentucky Derby Festival poster artist whose work has been featured by the National Baseball Hall of Fame, Louisville Slugger Museum & Factory, and Kentucky Derby Museum, opens up about the space between being admired and being truly known. We talk about: - How baseball became a childhood safe haven, and what happened to his identity when the uniform came off - The fear of creating without seeking approval - A spiritual awakening that led to deep healing and self-discovery - Reconnecting with his inner child through his newer artwork - His return to Louisville's historic Portland neighborhood - Building BNK St. Gallery + Studio, a creative space in Louisville's West End This isn't just a baseball story or an art story. It's the story of a man who spent his life mastering performance — and is now learning how to live without it. If this conversation resonates, like the episode, subscribe for more Kentucky stories, drop a comment, and share it with someone who needs to hear it. IN THIS EPISODE: Richard Sullivan's journey from Louisville to the Atlanta Braves Life after professional baseball Becoming a full-time artist The psychology of achievement and identity Spiritual awakening and the healing journey Creating art without seeking approval The 2024 Kentucky Derby Festival poster Portland Louisville and BNK St. Gallery + Studio Learning who you are beyond success Guest: Richard Sullivan Podcast: Kentucky's Wandering Realtor Episode: 50 Location: Louisville, Kentucky #KentuckysWanderingRealtor #RichardSullivan #LouisvilleArtist #AtlantaBraves #KentuckyDerbyFestival #BNKStGallery #PortlandLouisville #LouisvillePodcast #CreativeJourney

    Who is he without the applause? with Richard Sullivan

  3. Aug 3

    The Mission After Service with Luis Martinez JR

    THE MISSION AFTER SERVICE | Luis Martinez Jr. of Whiskey Valor Foundation What happens when the uniform comes off, but the need for purpose, brotherhood, and service remains? In this episode of Kentucky's Wandering Realtor, Stephon Lewis sits down with Luis Martinez Jr., Marine Corps veteran and founder of the Whiskey Valor Foundation, for a deeply personal conversation about identity after military service, veteran mental wellness, family, and the mission that continued long after his time in uniform. Luis shares how his journey took him from the Marine Corps into military intelligence, higher education, and the Pat Tillman Foundation community. He also reflects on how a wellness retreat in Louisville helped shift his understanding of what veterans need after service, and planted the seed for what would eventually become Whiskey Valor. Whiskey Valor Foundation uses community events, partnerships, wellness retreats, and its RideShare Initiative to support veterans and their families, promote responsible drinking, and help reduce DUIs within the military community. Rather than judging veterans for where they are, Luis and his team are committed to meeting them there with accountability, connection, and meaningful resources. We also had the honor of joining Whiskey Valor for a special barrel pick through its partnership with the Blue Skies Foundation, together, we selected a whiskey expression that will help raise money for an incredible cause. In this conversation, Luis opens up about: The person he was before joining the MarinesWhat military service gave him and what it demandedThe identity shift that followed leaving the uniform behindThe 2022 Pat Tillman Foundation Wellness Retreat in LouisvilleThe unconventional idea that became Whiskey ValorUsing whiskey as an invitation to connection, not the hero of the storyThe mission behind Whiskey Valor's RideShare InitiativeWhy some veterans may be searching for more than a safe ride homeCreating Whiskey Valor's own wellness retreatMarriage, fatherhood, and serving the people closest to himWhat he hopes his children will one day understand about his missionThis episode is about much more than whiskey. It's about brotherhood, vulnerability, responsibility, and finding a new way to serve when one chapter of service ends. A special thank-you to Onyx & Amber Tasting Room and Tartan House for once again opening their doors and giving us the space to share another meaningful story. Listen and subscribe to Kentucky's Wandering Realtor on YouTube, Spotify, and Apple Podcasts for more conversations with the people, founders, veterans, chefs, creators, and community leaders whose stories deserve to be heard. #WhiskeyValorFoundation #VeteranMentalHealth #MarineVeteran #PurposeAfterService #KentuckysWanderingRealtor #LouisvilleKY #BourbonCommunity #VeteranStories #MilitaryCommunity

    The Mission After Service with Luis Martinez JR

  4. Jul 27

    More Than the First with Brittany Penny

    Brittany Penny, founder of The Nine Bourbon, made history as one of the few Black women to launch her own bourbon brand, but this Kentucky's Wandering Realtor conversation reveals why her story means far more than being first. Watch More Than the First with Brittany Penny, follow Kentucky's Wandering Realtor on Instagram, and check out The Nine Bourbon at 2centsinc.com. Brittany opens up about the journey behind The Nine Bourbon, from the sleepless nights of new motherhood that helped spark the idea to building a company alongside her husband, James. She shares how her love of bourbon began, what it took to develop her first blend, and the pressure that comes with entering an industry where few people look like her. We also talk about the difference between being welcomed into a room and truly being given access, how rejection has shaped her ambition, the responsibility she feels as a trailblazer, and what she hopes her daughter will one day understand about the legacy she is building. The conversation also includes Louisville culture, bourbon industry truths, a founder's offer from Darth Vader, and a major announcement from Brittany about what's coming next. This is more than a conversation about bourbon. It's a story about motherhood, marriage, representation, ownership, perseverance, and the woman behind The Nine. Follow Kentucky's Wandering Realtor on Instagram:https://www.instagram.com/kentuckys_wandering_realtor The Nine Bourbon: 2centsinc.com #BrittanyPenny #TheNineBourbon #KentuckyBourbon #WomenInBourbon #BlackOwnedBourbon #LouisvilleKY #BourbonCulture #Entrepreneurship #FounderStory #KentuckysWanderingRealtor

    More Than the First with Brittany Penny

  5. Jul 20

    Two Palates, One Legacy with Jason Brauner & Jereme McFarland

    Bourbons Bistro has shaped Louisville's bourbon and food scene for over two decades. In this episode of Kentucky's Wandering Realtor, Jason Brauner and Executive Chef Jereme McFarland share how rare bottle collecting, kitchen leadership, and two very different journeys built one of Louisville's most important bourbon destinations. Jason talks about helping open Bourbons Bistro in 2005, what he saw in Kentucky bourbon before the tourism boom, and how collecting rare bottles led him into blending his own expressions. Jereme walks through his path from cooking for hundreds of Marines to becoming executive chef, the fear of stepping into that role, and what it takes to protect a menu that loyal guests already love. We get into the real relationship between bourbon and food, the pressure of carrying forward something people already care about, and the mistakes customers never saw happen. Bourbons Bistro is located in Louisville, Kentucky and has been a cornerstone of the city's bourbon tourism scene since 2005. Subscribe to Kentucky's Wandering Realtor for more conversations with the people shaping Louisville's food, bourbon, business, and culture: https://youtube.com/@kentuckyswanderingrealtor?si=1y-cI5Rr7bzLTDbw Visit Bourbons Bistro: https://bourbonsbistro.com #Louisville #BourbonsBistro #KentuckyBourbon #LouisvilleFood #BourbonCulture #ExecutiveChef #LouisvilleRestaurants

    Two Palates, One Legacy with Jason Brauner & Jereme McFarland

  6. Jul 13

    From Barber Chair to Pursuit with Tim Van Riper

    From a SoCal barber chair to Kentucky bourbon: Tim Van Riper's unlikely path into the whiskey industry with Pursuit Spirits in Louisville. In this episode of Kentucky's Wandering Realtor, I sit down with Tim Van Riper, Operations Manager at Pursuit Spirits in Louisville, Kentucky, for a conversation about whiskey, reinvention, storytelling, and the unexpected journey from a barber chair in Southern California to building a life in Kentucky bourbon. Tim's story starts in SoCal, where he worked as a barber in a shop that served beer and whiskey with its services. When he moved to Louisville after following love to Kentucky, the original dream was to bring that same barbering, hospitality, and whiskey culture with him. But life did not unfold exactly the way he expected. Instead, that unexpected pivot opened the door to the spirits industry. In this conversation, Tim shares what it was like moving from Southern California to Louisville, how barbering taught him to connect with people, what happened when his original plan did not pan out, and how whiskey became the next chapter in his life. We also talk about his journey with Pursuit Spirits, creating memorable whiskey experiences, managing operations, blending, Louisville culture, and what it means to finally be part of building a brand. From Barber Chair to Pursuit is more than a whiskey conversation. It is a story about following love, finding purpose, adjusting when life changes the plan, and staying open enough to discover a dream you did not see coming. If you love bourbon, whiskey, Louisville stories, Pursuit Spirits, entrepreneurship, hospitality, or conversations about people finding their path, this episode is for you. In this episode, we talk about: Tim Van Riper's journey from Southern California to LouisvilleHow barbering shaped the way he connects with peopleFollowing love to Kentucky and staying for whiskeyThe original dream that did not work out as plannedBreaking into the bourbon and spirits industryWorking with Pursuit Spirits in LouisvilleCreating whiskey experiences that people rememberThe difference between pouring whiskey and telling a storyOperations, blending, and behind-the-scenes work in the spirits industryLouisville culture, bourbon culture, and what Tim is still pursuingWatch the full episode and let us know in the comments: What dream in your life changed form but still led you somewhere meaningful?

    From Barber Chair to Pursuit with Tim Van Riper

  7. Jul 6

    Pit Daddy, Plug-In Chef, MeeshMeesh & Mill Iron 4 with Noam Bilitzer & Dustin Olsen

    Louisville restaurants, barbecue, and Mediterranean food collide in this episode of Kentucky's Wandering Realtor, where I sit down with two of the city's most talked-about restaurant owners: Dustin Olsen, butcher, pit master, and owner of Mill Iron 4, and Chef Noam Bilitzer, chef/owner of MeeshMeesh Mediterranean and executive chef/owner of Mill Iron 4. This conversation brings together food, friendship, legacy, culture, humor, and the deeper stories behind two of Louisville's most talked-about restaurants. Dustin shares the story behind Mill Iron 4, a name rooted in his family's Western ranching history. His grandfather Marty registered the Mill Iron 4 cattle brand in Wyoming back in 1947, and Dustin is now carrying that legacy into Louisville through whole-animal butchery, dry-aged beef, barbecue, rancher relationships, and a neighborhood steakhouse built with intention. Chef Noam Bilitzer opens up about the heart behind MeeshMeesh, his Levant-inspired restaurant that celebrates the flavors, culture, and shared-table experience of the Eastern Mediterranean. We also talk about the recognition MeeshMeesh has received, including James Beard attention, and why Noam continues to point that recognition back to his team. Together, Dustin and Noam share the story of their friendship, the building of Mill Iron 4, what they've learned from each other, and what it means to create restaurants that go beyond the plate. We talk about MeeshMeesh, Mill Iron 4, Louisville food culture, whole-animal butchery, barbecue, ranch culture, restaurant life, leadership, legacy, and why the best meals often come with a story behind them. If you love Louisville restaurants, chef stories, barbecue, steak, Mediterranean food, local business, bourbon culture, or conversations that go deeper than the surface, this episode is for you. Featured in this episode:Dustin Olsen — Butcher, pit master, and owner of Mill Iron 4Chef Noam Bilitzer — Chef/owner of MeeshMeesh Mediterranean and executive chef/owner of Mill Iron 4Restaurants: MeeshMeesh Mediterranean and Mill Iron 4Location: Louisville, Kentucky Links:MeeshMeesh Mediterranean: https://meeshmeesh.com/Mill Iron 4: https://www.milliron4.com/Kentucky's Wandering Realtor: https://www.instagram.com/kentuckys_wandering_realtor/ Subscribe for more conversations with the people, restaurants, creators, and local businesses shaping Kentucky's culture. #LouisvilleFood #LouisvilleRestaurants #MeeshMeesh #MillIron4 #KentuckyFood #LouisvilleKY #RestaurantLife #ChefInterview #Barbecue #Steakhouse #MediterraneanFood #KentuckysWanderingRealtor #LocalStories #SupportLocal

    Pit Daddy, Plug-In Chef, MeeshMeesh & Mill Iron 4 with Noam Bilitzer & Dustin Olsen

  8. Jun 22

    Bar Toast: Built Through Connection with Dave Astorga

    In this episode of Kentucky’s Wandering Realtor, I sit down with Dave Astorga, owner of Bar Toast, for a conversation about whiskey, entrepreneurship, relationships and the power of connection. What started as a small garage barrel project grew into Bar Toast, a brand built around great pours, shared stories and unforgettable moments with good people. Dave opens up about his journey with whiskey, the lessons he learned while building the business, and why authentic relationships are at the heart of everything Bar Toast represents. We also talk about the difference between networking and real connection, the people behind the pour, and what it means to build something that brings people together. If you enjoy whiskey stories, bourbon culture, entrepreneur journeys and conversations rooted in community, this episode is for you. Watch now and connect with the story behind Bar Toast: Built Through Connection.

    Bar Toast: Built Through Connection with Dave Astorga
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Ratings & Reviews

5
out of 5
4 Ratings

About

Kentucky's Wandering Realtor is your guide to the neighborhoods that make the Bluegrass State feel like home. Hosted by a Louisville native with a passion for real estate and storytelling, this podcast explores the people, businesses, and history that give Kentucky communities their unique charm. From bustling local hotspots to hidden gems, each episode dives into the stories of neighbors, entrepreneurs, and traditions that make every corner special. Whether you're a local, newcomer, or just curious, join us as we wander through the places and faces that make Kentucky unforgettable.

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