What happens when a bakery pivot turns into a full-blown Airbnb empire? In this episode, we sit down with Andrew Llewellyn, an entrepreneur who went from scooping ice cream and selling blueberry muffins to running high-end short-term rentals in Louisville, Kentucky at the heart of bourbon country. Andrew shares how one property purchase changed everything, the systems he uses to run his Airbnb portfolio like a boutique hotel, and why creating memorable experiences for guests (from bachelor parties to corporate retreats) is the real key to success in hospitality. You’ll learn how to spot opportunities others overlook, why experiences drive premium pricing, and what it takes to scale a short-term rental business beyond just “Airbnb side hustle” into a serious, sustainable venture. Whether you’re curious about boutique hotels, real estate investing, or building a hospitality brand that stands out, Andrew’s story is packed with takeaways you can apply right now.

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Previous Guests Include:

Brandon Turner, Tarek El Moussa, Henry Washington, Rich Somers, Mikey Taylor, Tom Wheelright, David Greene, Tony J. Robinson, Robert Croak, Chad “Coach” Carson, Brett Hundley, Devon Kennard and Marques Colston.

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Disclaimer: The information provided on this podcast is for educational and informational purposes only. It should not be considered as financial advice or a recommendation to buy or sell any financial instrument or engage in any financial activity. The content presented here is based on the speaker's personal opinions and research, which may not always be accurate or up to date. Financial markets and investments carry inherent risks. Individuals should conduct their own research and seek certified professional advice before making any financial decisions. The links in the episode descriptions may include referral or affiliate commissions, and we may receive compensation from partner websites.