STR Investing, The Podcast

AI-Generated Direct Bookings

29 min · 29 de may de 2026
Portada del episodio AI-Generated Direct Bookings

Descripción

AI is moving faster than most short-term rental hosts realize. In this episode of the STR Investing Podcast, Mark Lumpkin welcomes back Boostly founder Mark Simpson for a deep dive into how AI agents, automation, and direct booking technology are changing the future of hospitality. Mark Simpson shares how he went all-in on AI at the beginning of 2026, replacing repetitive manual tasks with AI agents that now help run parts of his business 24/7. What started as simple experiments quickly turned into real revenue, operational efficiencies, and entirely new systems for managing guests, marketing, and direct bookings. Throughout the conversation, they discuss the difference between basic AI chat tools and true AI agents, how operators can use AI without losing the hospitality element, and why most hosts are still thinking too small when it comes to automation. They also break down: * AI agents and how they actually work * Using automation to increase direct bookings * Why hospitality still matters more than AI * The future of Airbnb algorithms and booking platforms * AI tools that save operators hours every week * How hosts can leverage guest data more effectively * The importance of owning your customer relationships * Real examples of AI-generated revenue growth Mark also shares details about Boostly Connect, the new platform designed to help hosts better manage guest data, automate outreach, and improve direct booking performance. If you’re trying to stay ahead in the short-term rental industry, this is an episode you don’t want to miss. __ Episode Sponsored By: STR Search STR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com [http://strsearch.com/]

Comentarios

0

Sé la primera persona en comentar

¡Regístrate ahora y únete a la comunidad de STR Investing, The Podcast!

Empezar

2 meses por 1 €

Después 4,99 € / mes · Cancela cuando quieras.

  • Podcasts exclusivos
  • 20 horas de audiolibros / mes
  • Podcast gratuitos

Todos los episodios

127 episodios

Portada del episodio Monday Market Data: Breakdown of West Palm, FL Amenities Market

Monday Market Data: Breakdown of West Palm, FL Amenities Market

In this week's Monday Market Data Report, Mark Lumpkin breaks down the short-term rental market in West Palm Beach, Florida, combining bedroom-count revenue data with amenity-stack analysis to show investors exactly where the biggest opportunities exist. West Palm continues to see strong tourism growth, with more than 10 million annual visitors and growing demand fueled by major corporate relocations from cities like New York, Philadelphia, and Washington D.C. In this episode, Mark covers: • Revenue potential by bedroom count • Why 4, 5, and 6-bedroom homes dramatically outperform smaller properties • The amenity combinations driving $200,000+ annual revenue • What amenities are becoming mandatory in the market • How investors can still stand out from the competition Key takeaways: * 4-bedroom properties average over $100K annually * 6-bedroom properties average more than $200K annually * Top performers can exceed $300K+ per year * Pool + Hot Tub + Waterfront is the highest-performing amenity combination * Only 4% of properties have pickleball courts * Less than 1% have movie theaters If you're investing in South Florida, this episode provides a roadmap for building a high-performing STR that stands out in a growing market. Subscribe for new Market Data Reports every Monday and expert guest interviews every Friday.

22 de jun de 202610 min
Portada del episodio 28 Years in the Hospitality Industry

28 Years in the Hospitality Industry

What does it take to stay relevant in the short-term rental industry for nearly three decades? In this episode, Mark Lumpkin sits down with Michael St. Pierre, a hospitality veteran with 28 years of experience spanning vacation rentals, luxury resorts, revenue management, owner acquisition, and some of the industry's most recognized brands. Michael shares how he got started in the business, the lessons he learned from working in Hawaii and with Hyatt-affiliated properties, and why hospitality is still the foundation of long-term success in a rapidly changing industry. They also discuss: • What investors can learn from luxury hotel brands • Why relationships are one of the most valuable assets in business • The evolution of revenue management and dynamic pricing • How AI is changing the vacation rental landscape • The importance of building systems, standards, and memorable guest experiences • What the next generation of STR operators needs to focus on Whether you manage one property or hundreds, this conversation is packed with practical insights on hospitality, growth, and building a sustainable business in the vacation rental industry. Connect with Michael St. Pierre on LinkedIn to learn more about revenue management, owner acquisition, and the future of short-term rentals. 🎧 Listen now and be sure to subscribe for more STR Investing Podcast episodes. __ Episode Sponsored By: STR Search STR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com [http://strsearch.com/]

19 de jun de 202635 min
Portada del episodio Monday Market Data: Breakdown of Sevierville, TN Amenities Market

Monday Market Data: Breakdown of Sevierville, TN Amenities Market

In this week's Monday Market Data Report, Mark Lumpkin breaks down one of the most competitive short-term rental markets in America: Sevierville. With more than 15 million annual visitors to the Great Smoky Mountains and over 13,000 active short-term rentals in the surrounding market, Sevierville has become the perfect example of the "Amenities Arms Race" that has transformed the STR industry. The data is eye-opening: • Hot Tubs → 94.8% of listings • Game Rooms → 77.8% • Fire Pits → 52% • Pools → 45% • Pool Tables → 50% These aren't luxury amenities anymore. They're the baseline. In this episode, Mark breaks down what amenities you need just to compete and which upgrades can still help you stand out from thousands of competing cabins. If you're investing in the Smokies, this episode is a masterclass in understanding what it takes to win in a mature STR market. Tune in for new Market Data Reports every Monday and expert guest interviews every Friday.

15 de jun de 20267 min
Portada del episodio STR Tax Loophole with Ryan Carriere

STR Tax Loophole with Ryan Carriere

Tax season just got a lot more interesting. In this episode, Mark Lumpkin sits down with CPA and real estate tax strategist Ryan Carriere to break down one of the most powerful tax strategies available to short-term rental investors today. Ryan explains how the return of 100% bonus depreciation under the One Big Beautiful Bill impacts investors, why the Short-Term Rental Tax Loophole remains a game changer for high-income earners, and the specific rules you must follow to qualify. They cover: • The return of 100% bonus depreciation and what it means for investors • How the Short-Term Rental Tax Loophole actually works • The 7-day average stay rule explained • Material participation requirements and common mistakes • How to track hours correctly for audit protection • Personal use rules that can destroy your tax benefits • Why most investors need a tax strategist, not just a tax preparer • Real-world examples of how investors can potentially save six figures in taxes If you're buying short-term rentals for cash flow, appreciation, and tax savings, this episode is essential listening. Connect with Ryan Carrier: Website: CarrierTaxConsulting.com [https://carrieretaxconsulting.com/] LinkedIn: Ryan Carrier, CPA [https://www.linkedin.com/in/ryancarriere/] YouTube: Ryan Carrier, CPA [https://www.youtube.com/@ryancarrierecpa] __ Episode Sponsored By: STR Search STR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com [http://strsearch.com/]

12 de jun de 202650 min
Portada del episodio Monday Market Data: Breakdown of Seattle, WA Market

Monday Market Data: Breakdown of Seattle, WA Market

In this week’s Monday Market Data Report, Mark Lumpkin heads to the Pacific Northwest to break down the short-term rental market in Seattle, Washington. With more than 5,000 active listings, nearly 40 million annual visitors, and inventory growth exceeding 50% over the past few years, Seattle has become an increasingly competitive market for STR investors. But despite the growing competition, the data reveals something surprising: Seattle may be one of the least amenitized STR markets we've analyzed. In this episode, Mark covers: * Seattle's tourism demand and seasonality * The impact of corporate and mid-term rental travelers * Current STR regulations and licensing requirements * Why occupancy and revenue vary so dramatically across the market * The amenities that can instantly separate your property from the competition The takeaway? Unlike many markets where amenities have become standard, Seattle still offers tremendous opportunity for investors willing to create something unique. A simple hot tub and gym combination immediately puts you ahead of most of the competition, while a true "super property" would have virtually no competition at all. If you're considering investing in Seattle, this episode provides a roadmap for how to stand out in one of the country's fastest-growing STR markets. Subscribe for new Market Data Reports every Monday and expert guest interviews every Friday.

8 de jun de 20267 min