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PODCAST

STR Investing, The Podcast

Taylor Jones & Mark Lumpkin

Welcome to STR Investing, The Podcast, where hosts Taylor Jones & Mark Lumpkin reveal the keys to financial freedom through short-term rental investing. Whether you"re taking your first step into this lucrative market or looking to expand your portfolio, this podcast is your ultimate resource for success.Taylor, who has successfully acquired over 200+ properties, brings not only his personal experiences but also sits down with industry experts to share insights and stories from every corner of

business investing

All Episodes

37:25

Investing in STRs with Amish with Landon Schlabach

STR Investing, The Podcast ·

2025/04/18

From Handwritten Checks to Managing 115+ STRs Across 14 States w/ Landon Schlabach In this episode, Landon Schlabach shares his remarkable journey from flipping houses to building a thriving short-term rental property management company. Starting with just a few homeowners and handwritten checks, Landon scaled his operations to managing over 115 homes across 14 states—with deep roots in the Amish and Mennonite communities. We dive into: Why he pivoted away from rental arbitrage early onHow th...

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34:53

Mastering the Guest Experience with Derek Gisriel

STR Investing, The Podcast ·

2025/04/04

What if your short-term rental could save you hundreds of thousands in taxes and generate serious cash flow? That’s exactly what happened to Derek Gisreal. In this episode of STR Investing, Derek shares how a single investment—originally just a tax strategy—became a full-fledged short-term rental business. We cover: The tax loophole that saved him nearly $200KHow he tripled the revenue of an existing STRUsing a cash-out refi to scale fasterThe power of personalized guest experiences—han...

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41:52

Drive 60% Direct Bookings with Mark Simpson

STR Investing, The Podcast ·

2025/03/21

Are you tired of high OTA fees eating into your short-term rental profits? In this episode, Mark Lumpkin sits down with direct booking expert Mark Simpson, founder of Boostly, to uncover the secrets to maximizing direct bookings while keeping a balanced approach to Airbnb, Booking.com, and other platforms. Mark shares valuable insights on: The real percentage breakdown of direct vs. OTA bookings and why 65% direct is the sweet spot.Why going 100% direct booking can be just as risky as relying...

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37:26

Secrets To Paying Less Taxes With Airbnbs Featuring...

STR Investing, The Podcast ·

2025/03/11

Host Taylor sits down with tax strategist Nathan Sosa to break down the biggest tax advantages available to short-term rental investors. They dive deep into key strategies, including material participation, real estate professional status, cost segregation, bonus depreciation, and the game-changing 1031 exchange. Whether you’re a first-time investor or managing a growing portfolio, this episode is packed with expert insights to help you maximize deductions, optimize cash flow, and legally min...

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44:14

Insider Information on Airbnb From a Former Employee...

STR Investing, The Podcast ·

2025/02/14

In this episode, new host Mark Lumpkin sits down with industry veteran Paul Kromidas, who transformed his career at Airbnb into launching a highly successful short-term rental business. Paul explains how he overcame “imaginary barriers”—a common mindset among parents and aspiring investors—and embraced bold, calculated risks to build an asset-heavy, cash-flow–rich model. He offers actionable insights on raising capital, balancing host and guest experiences, and leveraging innovative str...

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36:34

North Georgia Isn’t Dead: Finding Cashflow in the...

STR Investing, The Podcast ·

2025/02/07

Taylor Jones sits down with Connor Cushman, a sharp short-term rental agent and investor, to explore his innovative "slow burster" strategy—a refined twist on the traditional buy, rehab, rent, refi, repeat model. Connor explains how blending the steady fundamentals of long-term rentals with the high revenue and cash flow of short-term rentals lets you hold a property for a full year of proven performance, thereby transforming equity and opening doors to premium refinancing or sale opportuniti...

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38:26

Super Mom: Growing a STR Portfolio While Working...

STR Investing, The Podcast ·

2025/01/29

Join us for Mark Lumpkin’s very first episode as the newest host of the STR Investing Podcast! In this debut, Mark interviews Rachel—a hands-on short-term rental owner and the founder of Up Close Marketing—to discuss how she bootstrapped her way into buying her first cabin, then expanded into properties in Big Bear and Maui. Rachel shares her secrets on delivering exceptional guest experiences through small, thoughtful touches that lead to stellar reviews and repeat bookings. She also reveals...

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28:29

Investing in STRs, Boutique Hotels, & Management...

STR Investing, The Podcast ·

2024/12/20

In this episode of the STR Investing Podcast, host Taylor interviews seasoned short-term rental entrepreneur Josh Hatter, who has scaled from a single one-bedroom condo to managing over 100 listings and operating boutique hotels. Josh shares how early challenges pushed him to build a business centered on solid fundamentals, rather than relying on a “quick win” mentality. He unpacks the importance of accurate underwriting, avoiding emotional decisions, and knowing when to invest in the right t...

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52:20

Direct Bookings Made Easy with Gil Chan (CEO of...

STR Investing, The Podcast ·

2024/11/01

In this episode, we’re diving into the world of short-term rentals with Gil from Crafted Stays. Gil shares his journey, from launching his first Airbnb to becoming fully immersed in the business, discussing how a single night of high bookings ignited his passion for STRs. We explore the mindset shift that led him to expand quickly, leveraging skills from his tech background and previous roles in hospitality to optimize the guest experience. Gil and Taylor discuss the importance of understandi...

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28:09

Scaling Airbnbs in the "Bourbon Capital" of the US...

STR Investing, The Podcast ·

2024/10/11

In this episode of the STR Investing Podcast, host Taylor welcomes Jay Bowman, a seasoned real estate investor with over 20 years of experience, to discuss his journey into short-term rentals. Jay shares how a conversation with a friend about the impressive earnings potential of Airbnb sparked his transition from long-term and college rentals to short-term rentals. He delves into his approach of purchasing distressed properties, navigating Louisville's evolving regulations, and converting dup...

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31:19

Buying Raw Land in Oklahoma & Building Luxury Airbnbs...

STR Investing, The Podcast ·

2024/09/23

In this episode, host Taylor welcomes Max Gagliardi, an oil and gas entrepreneur who cracked the code on luxury short-term rentals. Max reveals how he transformed his real estate side hustle into a thriving business, building high-end properties that attract premium guests and skyrocket revenue. From nailing down cost basis strategies to developing jaw-dropping, waterfront properties, Max shares the exact tactics he’s used to scale fast in a cutthroat market. Tune in to learn how design, mark...

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33:02

Inspiring Moments In The Wild with Eric Moeller (CEO...

STR Investing, The Podcast ·

2024/09/06

In this episode of the STR Investing Podcast, host Taylor dives into a comprehensive discussion with Eric Moeller from Freewyld. Eric shares his extensive journey in the short-term rental industry, starting with his early days in rental arbitrage, through his evolution into property management, and now leading Freewyld.With a focus on creating exceptional guest experiences, Eric highlights the shift from mere rental transactions to prioritizing hospitality, especially post-COVID. He also touc...

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25:26

Building a Portfolio of Short Term Rentals Before...

STR Investing, The Podcast ·

2024/08/09

In this episode of the STR Investing Podcast, Taylor chats with Brett, a young short-term rental entrepreneur who started his journey before even reaching the legal drinking age. Brett shares how he transitioned from aspiring realtor to successful short-term rental investor, highlighting his first major deal—a set of cabins in Hocking Hills, Ohio, which he transformed into a thriving venture by leveraging data and marketing. He also discusses his strategic shift to unique, high-demand pr...

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29:38

How to Drive $100,000 in Bookings From Instagram with...

STR Investing, The Podcast ·

2024/07/12

In this episode of the STR Investing, The Podcast, host Taylor Jones welcomes Ben Wolff, the man behind "unique stays" and a pioneer in the short-term rental market. Ben shares his journey from humble beginnings in New York City to creating extraordinary treehouse hotels and innovative outdoor hospitality experiences. He delves into the game-changing power of influencer collaborations, recounting a remarkable story where a single influencer helped generate $25,000 in direct bookings with...

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28:35

How I Turned a $55,000 Drug House Into a $1.5M Airbnb...

STR Investing, The Podcast ·

2024/06/27

In this episode of the STR Investing Podcast, host Taylor Jones welcomes Tyann Marcink, dubbed the "Queen of Guest Experience," to discuss her journey in turning overlooked properties into successful short-term rentals. Tyann's transformation of the drug house into a lucrative Airbnb involved extensive renovations and strategic upgrades, turning the dilapidated property into a desirable vacation rental. This impressive feat highlights her ability to see potential where others might...

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30:36

Transforming Airbnb Expenses Into Revenue Streams...

STR Investing, The Podcast ·

2024/06/19

Welcome to another episode of STR Investing, The Podcast, hosted by Taylor Jones. In this episode, we are thrilled to have Allen Meringolo join us to dive deep into the strategies and insights on how to transform your Airbnb expenses into lucrative revenue streams. Allen, an experienced short-term rental expert, shares his proven methods for maximizing profits, cutting unnecessary costs, and leveraging innovative approaches to turn every dollar spent into a profitable investment. Whether you'...

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22:20

How to Turn 1 Airbnb into 3 with One Transaction:...

STR Investing, The Podcast ·

2024/06/10

Join us for an insightful episode featuring Rob Leventhal, a seasoned short-term rental investor with a remarkable journey and effective real estate tactics. In this episode, Rob shares his experience in building a successful short-term rental portfolio, including his strategic decisions, challenges, and triumphs. Learn about the importance of return on equity, the power of 1031 exchanges, and how Rob managed to turn a single property into multiple high-performing assets. Whether you're new t...

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37:16

Unlocking the Future of Direct Bookings with Eric...

STR Investing, The Podcast ·

2024/05/30

In this episode of STR Investing, we welcome Eric Goldreyer, founder of BNB Finder—a direct booking platform designed to help guests find their next short-term rental without the high fees of traditional OTA platforms. Eric shares his inspiring journey from BedandBreakfast.com to Turnkey Vacation Rentals and now BNB Finder. We dive into the benefits of direct bookings, professional property management, and the future of the short-term rental industry. Whether you’re a newbie or a seasoned pro...

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36:32

STR Listing Optimization and Revenue Strategies with...

STR Investing, The Podcast ·

2024/05/23

Sabrina x2 on this episode! Join us for an insightful episode of STR Investing, where Sabrina Guler welcomes Sabrina Calnan, an expert in short-term rental revenue management and listing optimization. Sabrina Calnan shares her journey from the corporate world to mastering the art of Airbnb, discussing strategies to maximize revenue for individual hosts and property managers. This episode is packed with valuable insights for both seasoned investors and new entrants in the short-term ...

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41:37

From Boats to Millions: Jeremy Werden's Journey to a...

STR Investing, The Podcast ·

2024/05/17

In this episode of STR Investing, Taylor Jones welcomes Jeremy Werden to share his incredible journey from investing in his first short-term rental just three years ago to now owning a portfolio of 25 Airbnb listings and 7 boats, generating over $1,000,000 per year. Jeremy built his portfolio from scratch with minimal startup capital, documenting his entire journey while growing an audience of 200,000 on social media. Within a year, he was able to go full-time and achieve financial freedom, a...

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69 results

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