The Short Term Show

Join Brittany Magsig, a former social worker turned short-term rental investor and the creative mind behind Mountain Mama Cabins. Brittany shares her inspiring journey from the classroom to real estate, motivated by motherhood and the quest for freedom. She discusses her first cabin purchase in the Smoky Mountains, management hurdles, and her impressive TikTok strategy that drives over 70% of her bookings. The conversation also dives into adapting to market changes and the power of authenticity in growing a successful rental business.

Sandeep Nanda, a serial short-term rental investor and founder of AI MySTR, transitioned from corporate revenue management to building a rental empire. He discusses identifying early opportunities in short-term rentals and scaling his portfolio from one condo to over thirty. Sandeep shares insights on legal strategies for securing funding, leveraging data for market analysis, and applying AI to optimize rental operations. He emphasizes lessons on risk management, timing in investments, and the importance of adapting in an evolving real estate landscape.

Bethany LaFlam, a former attorney turned community architect and author of The Power of OPE, shares her insights on scaling businesses without burnout. She defines the importance of staying in your lane and leveraging other people's resources effectively. Bethany explains the ins and outs of syndications, emphasizing the necessity of becoming a true operator before raising capital. She also stresses transparent communication with investors during tough times and highlights common mistakes in syndication, ensuring listeners can grow their real estate ventures responsibly.

Frank Napolitano, a short-term rental owner in the Smoky Mountains, shares his journey into the rental market, highlighting how tax strategies like bonus depreciation influence his success. He discusses unique property features such as a pool and a tiki bar that enhance the guest experience. Frank emphasizes the importance of thoughtful amenities and holiday decorations in receiving 5-star reviews. He also outlines his future plans for expanding his property portfolio and offers advice on standing out in saturated markets.

Join Joe DelGrosso, a former TV producer turned short-term rental mogul and owner of Southern Sons Hospitality, as he shares his groundbreaking insights on property refreshes that can double revenue. He reveals how a modest Smokies cabin outperformed luxury options and discusses his unique boutique management approach. Joe emphasizes the importance of meticulous revenue management, the need for stunning design upgrades, and strategic growth. Plus, he offers invaluable advice for aspiring rental operators on staying focused and financially savvy.

In this engaging discussion, Thibault Masson, Head of Product Marketing at PriceLabs and former Booking.com product lead, shares his insights into the vacation rental industry. He unpacks the contrasting success of Booking.com in Europe versus the U.S. and introduces fantastic PriceLabs features like Dynamic Minimum Stay and the Listing Optimizer. Thibault also highlights the value of Market Dashboards for competitive analysis and a free revenue-management course for hosts. He wraps up with practical tips for new investors to thrive in the market.

On this week’s episode, Avery is joined by Toni Boer. Toni shares how she and her husband turned a $200k family getaway into a cash-flowing STR, eventually building an eight-property portfolio along Kentucky’s Bourbon Trail plus a new Florida beach house. She opens up about losing a riverfront property to a historic flood, the hard lessons she learned about insurance, and how she used those setbacks to strengthen her investing strategy. Toni also discusses deal-finding in emerging markets, using the “enemy method” to outshine competition, and why patience and persistence still uncover strong STR opportunities.     How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow Avery Carl on Instagram Follow Avery Carl on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode, Avery is joined by Tamara Brown. Tamara shares how she stumbled into real estate while caring for her grandparents, turning multiple family homes into rentals before purchasing her first STR in Destin, Florida. She explains how she analyzed her numbers, leaned on mentorship, and embraced the “enemy method” to size up competition. Tamara also talks through condo ownership fears, financing through a family sale, and why fear should never stop you from pursuing real estate opportunities.   How to connect with Tamara:  HELLOSUNSHINE.BIZ How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow Avery Carl on Instagram Follow Avery Carl on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode, Avery is joined by Amy Morehead. Amy shares how turning a family chalet in the Smokies into an STR during her mother’s Alzheimer’s caregiving season sparked a value-add strategy focused on “hot-mess” properties, smart renovations, and self-management. She explains why high-impact finishes beat flashy amenities for appraisal value and how she hunts deals with high days-on-market near the Smokies and along Kentucky’s Bourbon Trail. Amy also talks numbers, the refi-later mindset, and the education-plus-mentorship approach that helped her triple revenue after taking management in-house.   How to connect with Amy:  https://mapleleafpromise.com/https://strfixitpros.com/https://www.facebook.com/Strfixitpros/@STRFIXITPROS How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow Avery Carl on Instagram Follow Avery Carl on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

In this conversation, Annie Lee, co-founder of Hello Host and a seasoned short-term rental operator, explains how their AI platform automates guest communications seamlessly. She shares insights on how the AI learns from past interactions, makes judgment calls on guest issues, and emphasizes the importance of maintaining a human touch in hosting. Annie also discusses the future of AI in the industry, practical tips for evaluating AI vendors, and her journey in the tech startup world, providing valuable advice for hosts looking to enhance their guest experience.