Podcast
STR Investing, The Podcast
Hosted by Mark Lumpkin & Taylor Jones · EN
Unlock financial freedom through short-term rental investing with hosts Mark Lumpkin and Taylor Jones. Each week, they sit down with the biggest names in the STR industry to uncover what’s working right now — from acquisitions and design to operations, marketing, and scaling portfolios.
Taylor has helped acquire and manage over 500+ STRs, while Mark brings years of hands-on experience transforming properties into high-performing investments.
Together, they break down real strategies, real numbers, and real stories that help investors grow smarter and faster.
Whether you’re buying your first Airbnb or expanding a multi-market portfolio, this show is your roadmap to building wealth and freedom through short-term rentals.
Subscribe and start turning your STR goals into results.
22episodes
Episodes
Newest firstAll episodes
Monday Market Data: Breakdown of West Palm, FL Amenities Market
1w ago00:10:24Tap to summarizeIn 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 competitionKey takeaways:4-bedroom properties average over $100K annually6-bedroom properties average more than $200K annuallyTop performers can exceed $300K+ per yearPool + Hot Tub + Waterfront is the highest-performing amenity combinationOnly 4% of properties have pickleball courtsLess than 1% have movie theatersIf 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.
Transcribe →28 Years in the Hospitality Industry
1w ago00:35:51Tap to summarizeWhat 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 onWhether 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 SearchSTR 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
Transcribe →Monday Market Data: Breakdown of Sevierville, TN Amenities Market
2w ago00:07:52Tap to summarizeIn 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.
Transcribe →STR Tax Loophole with Ryan Carriere
2w ago00:50:50Tap to summarizeTax 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 taxesIf you're buying short-term rentals for cash flow, appreciation, and tax savings, this episode is essential listening.Connect with Ryan Carrier:Website: CarrierTaxConsulting.comLinkedIn: Ryan Carrier, CPAYouTube: Ryan Carrier, CPA__Episode Sponsored By:STR SearchSTR 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
Transcribe →Monday Market Data: Breakdown of Seattle, WA Market
3w ago00:07:54Tap to summarizeIn 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 seasonalityThe impact of corporate and mid-term rental travelersCurrent STR regulations and licensing requirementsWhy occupancy and revenue vary so dramatically across the marketThe amenities that can instantly separate your property from the competitionThe 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.
Transcribe →Dream Cleaning with the Dream Team
3w ago00:37:41Tap to summarizeA dirty property can ruin a guest experience before the vacation even begins.In this episode, Mark sits down with Logan, founder of Dream Clean Team, one of the largest vacation rental cleaning companies on Florida's Emerald Coast. Starting as a side hustle with his wife cleaning properties during summer break, Logan has grown the business into a full-service operation serving hundreds of short-term rentals across Northwest Florida.The conversation dives into one of the most overlooked parts of STR success: cleaning systems, guest readiness, and operational consistency.You'll learn:• The difference between a clean property and a guest-ready property • Why laundry is often the biggest bottleneck in vacation rentals • How professional operators scale cleaning across hundreds of properties • The systems and SOPs that transformed a small side hustle into a major operation • How cleaning impacts reviews, rankings, and repeat bookings • Real stories of the wildest guest damage and turnover situations they've encountered • How AI is helping streamline operations without replacing peopleIf you're an STR owner, host, property manager, or investor, this episode will change the way you think about cleaning, guest experience, and operational excellence.__Episode Sponsored By:STR SearchSTR 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
Transcribe →Monday Market Data: Breakdown of Yosemite, CA Amenities Market
4w ago00:09:26Tap to summarizeYosemite is one of the most visited national parks in America, attracting more than 4 million visitors every year. But when it comes to short-term rentals, the opportunity may be even bigger than most investors realize. In this week’s Monday Market Data Report, Mark Lumpkin breaks down the Yosemite STR market, including travel demand, regulations, seasonality, and the amenities that separate average properties from true standouts.Here's what the data shows: Fire Pits → 64% of listings Hot Tubs → 61% Pools → 13% Home Gyms → 13% Game Rooms → 10% Saunas → 8% Playgrounds → 6% Waterfront → 4% Pickleball Courts → 1% The takeaway?Most Yosemite rentals stop at a fire pit and hot tub. The investors who add game rooms, pools, saunas, or pickleball courts create true unicorn properties with very little competition.If you're looking for a mountain market where differentiation still matters, Yosemite deserves a closer look.
Transcribe →AI-Generated Direct Bookings
May 2900:29:13Tap to summarizeAI 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 workUsing automation to increase direct bookingsWhy hospitality still matters more than AIThe future of Airbnb algorithms and booking platformsAI tools that save operators hours every weekHow hosts can leverage guest data more effectivelyThe importance of owning your customer relationshipsReal examples of AI-generated revenue growthMark 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 SearchSTR 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
Transcribe →Monday Market Data: Breakdown of Galveston, TX Market
May 2500:07:53Tap to summarizeMark Lumpkin breaks down the short-term rental market in Galveston — one of the fastest-growing and most competitive beach markets on the Gulf Coast.With over 6,000 active listings and supply up more than 50% in just two years, Galveston has become a major target for STR investors. But despite the competition, there’s still a clear path to winning.In this episode, Mark covers: The travel demand driving Galveston tourism Why cruise traffic creates consistent STR bookings The amenities that are now mandatory to compete And the rare amenities that can still create a true “unicorn” property Here’s what the market looks like today: Pools → 35% of listings Fire pits → 29% Waterfront → 27% Hot tubs → 20% Those are expected.The real opportunity comes from the amenities almost nobody has: Pickleball courts → 2.2% Mini golf → 1.5% Movie theaters → <1% Saunas → almost nonexistent The takeaway? If you want to stand out in Galveston, you need more than just a pool and a beach house.
Transcribe →STR Lessons From Surviving a Million Dollar COVID Loss
May 2200:34:06Tap to summarizeWhat happens when a short-term rental operator loses over $1,000,000 during COVID?In this episode of the STR Investing Podcast, Mark Lumpkin sits down with Jason Baxter to talk about the highs, lows, and future of the short-term rental industry.Jason shares how he accidentally got started in Airbnb over 10 years ago, scaled to a portfolio of 50 lofts in Montreal, and then watched everything collapse during the COVID shutdowns in Canada.Facing bankruptcy, Jason rebuilt from the ground up by leaning into technology, automation, hospitality, and smarter booking strategies.In this episode, they dive into:The early days of Airbnb automationSurviving a million-dollar loss during COVIDThe biggest mistakes STR hosts make with techWhy hospitality still matters more than AIHow Airbnb algorithms really workPricing strategy and booking optimizationThe future of direct bookings and alternative platformsWhy “short-term rentals are a long-term game”Jason also explains how the right positioning and strategy helped one property grow from $65,000/year to over $210,000/year in bookings.If you’re an STR investor, property manager, or host trying to scale smarter, this is an episode you don’t want to miss.__Episode Sponsored By:STR SearchSTR 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
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