STR Investing, The Podcast

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Welcome to STR Investing, The Podcast, where hosts Sabrina Guler and Taylor Jones 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. Sabrina, co-founder of an 8-figure STR fund, and Taylor, successfully acquiring over 150+ properties, bring not only their personal experiences but also sit down with industry experts to share insights and stories from every corner of the STR world. From sharing their insights of building 9 figures of STR businesses, to staying on top of the latest trends in acquiring, designing, furnishing, and operating profitable short-term rentals, they cover it all.But that's not all. We're also lifting the veil on the challenges and triumphs of entering the industry, offering invaluable advice that you won't find anywhere else. Whether it's navigating regulatory changes or finding the perfect property, STR Investing, The Podcast is your trusted guide at every stage.Join Sabrina and Taylor as they show you how short-term rental investing can lead to financial freedom. Don't just dream about it - make it a reality with STR Investing, The Podcast today.

Sabrina Guler & Taylor Jones


    • May 30, 2025 LATEST EPISODE
    • every other week NEW EPISODES
    • 34m AVG DURATION
    • 35 EPISODES


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    Latest episodes from STR Investing, The Podcast

    New Amenity You Have Never Heard Of!

    Play Episode Listen Later May 30, 2025 28:36


    What if you could give your guests a memorable, screen-free experience and stand out in a crowded short-term rental market—without adding a $10K hot tub or building a pickleball court?In this episode, Mark sits down with Rachel from QR Clue, a former property manager turned entrepreneur who's on a mission to turn everyday rentals into unforgettable guest experiences. QR Clue is a ready-to-go, interactive mystery game—part escape room, part storytelling adventure—that guests play using subtle, QR-coded items placed throughout your property.You'll learn:The “aha moment” that sparked QR Clue's creationWhy this amenity can be installed in any STR (with just a kitchen + bedroom)How hosts are using QR Clue to drive more bookings, 5-star reviews, and guest data collectionWhy it's designed only for vacation rentals (sorry, hotels

    Sales Advice From the Worlds Best Salesman

    Play Episode Listen Later May 23, 2025 52:50


    In this special live episode, Mark and Taylor sit down in person to riff on one of their shared obsessions: sales. But this isn't your typical sales 101 chat. It's raw, real, and full of battle-tested strategies that have helped them close deals from cars to real estate to STR investments.Here's what they dive into:Why “assuming the close” only works if you believe in your productThe “cancer pill” mindset that will transform how you sellHow to uncover and use the power dynamic in two-person sales conversationsThe underrated brilliance of Men's Wearhouse sales strategyWhy you should never book client calls at 12:00 or 12:30“Choice of two positives,” “calendar closes,” and other tricks you'll want to stealWhen and how much pressure to apply—and how to make it match your personalityThe one universal reason someone doesn't buy from youWhy storytelling beats pitching every timeWhether you're running sales for your STR business, pitching investors, or just trying to close more life deals—this episode will sharpen your edge.Biggest takeaway? Sales is just a transfer of emotion. So be real, believe in your offer, and go close.__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

    Helping With The Trashy Side STRs - Can Monkey

    Play Episode Listen Later May 16, 2025 40:30


    It started with a simple problem: take the trash out, bring it back in. But that tiny pain point? It turned into a full-blown logistics revolution for short-term rental hosts nationwide.Taylor Jones dives deep with Alex Shapiro, co-founder of Can Monkey, the tech-powered trash service that's now serving over 5,000+ properties across 28 states and 475 cities. What began as a favor for a friend became one of the most unexpected wins in the short-term rental game.Inside this episode:How a random lunch and one smelly STR mishap sparked a business ideaWhy homeowner rejection opened the door to a thriving STR marketThe secret sauce behind Can Monkey's explosive growthWhat it really takes to manage a trash route across hundreds of citiesThe unexpected power of timestamped trash photos (yep, they can save you from fines)What makes a great “can runner” (spoiler: it's not driving a BMW)The surprising blend of tech, trust, and trash - and why it matters for STR opsCan Monkey's next chapter: 10,000 properties and software that could shake up the spaceIf you're in the STR world or just love stories of scrappy entrepreneurship, this episode delivers a goldmine of insights, operations hacks, and growth strategies you'll wish you heard sooner. Hit play now, you'll never look at trash day the same way again.Learn more at canmonkey.comContact Alex: alexander@canmonkey.com or connect with him on LinkedIn

    STR Regulations with Revnest

    Play Episode Listen Later May 9, 2025 39:19


    Host Mark Lumpkin sits down with Stefan St. Marie, founder of Revnest, to unpack how his journey from first-time Airbnb host to tech entrepreneur is helping solve one of the short-term rental industry's most frustrating pain points: transparency in regulations and property data.Here's what you'll learn in this episode:How Stefan turned a wild first guest experience into a thriving property management businessWhy “being a good neighbor” is the foundation of sustainable short-term rental successThe origin story behind Revnest: a marketplace built to buy and sell STR-ready propertiesHow Revnest is changing the game with verified revenue data, instant communication, and regulation insightsA first look at Revnest's newest tool: a crowdsourced, constantly updated short-term rental regulation mapWhy this regulation tool could become one of the most powerful resources for STR investors and how you can contributeHow Stefan's team is partnering with local experts and brokers to deliver hyper-accurate compliance data at scaleIf you've ever struggled to figure out STR rules in a new market, or wished there was a better way to vet listings and verify numbers, this episode is a must-listen.Learn more and explore the map: Revnest.comContact Stefan: stefan@revnest.com

    Folding Houses That Can Be Built In 1 Day with Galiano Tiramani

    Play Episode Listen Later May 2, 2025 20:34


    Taylor is joined by Galiano Tiramani, co-founder of Boxabl—the groundbreaking housing company known for building foldable, factory-made homes that can be deployed in under a day. From military housing to backyard ADUs and Airbnb-ready tiny homes, Galiano walks through how Boxabl is shaping the future of modular living and short-term rental opportunities.What you'll learn in this episode:How the “Casita” unit is built, shipped, and set up in as little as one hourThe RV loophole that bypasses permitting and building code bottlenecksWays Boxabl homes are already being used for disaster relief, workforce housing, and STRsPlans to expand into larger homes, townhouses, and multi-unit developmentsWhy Boxabl is considering becoming its own real estate developerHow ADU-friendly laws in states like California and Arizona are opening doors for investorsIdeas for turning Boxabl units into high-performing Airbnb properties, roadside motels, or couples' getaway communitiesIf you're in real estate, hospitality, or just love innovation—this is one to bookmark.Connect with Boxabl: Email: hello@boxabl.com Website: boxabl.com

    Transatlantic Host: Managing Your U.S. Airbnb from Italy with Chris Van Arnam

    Play Episode Listen Later Apr 25, 2025 26:26


    We sit down with Chris Van Arnam, an STR operator who's not just building high-performing short-term rentals in the Smoky Mountains, but doing it while living halfway across the world in Italy.Chris walks us through how he built a 10-cabin portfolio rooted in data, operational efficiency, and design differentiation. He opens up about why he sold off part of his portfolio, how he pivoted into new construction, and what it's really like managing from a different continent.We unpack:How Chris sourced and scaled his first 10 propertiesThe power of data when choosing a marketWhy operational density matters—and how to achieve itWhat makes a short-term rental truly “differentiated”The hard lessons from new construction vs. heavy renosBuilding a property management company (even when you didn't plan to)How to operate a U.S.-based STR portfolio from Europe with precisionWhether you're just getting started or are in the thick of growing your portfolio, this episode is packed with real-world insights from someone who's quietly built a scalable STR business from scratch.

    Investing in STRs with Amish with Landon Schlabach

    Play Episode Listen Later Apr 18, 2025 37:25


    From Handwritten Checks to Managing 115+ STRs Across 14 States w/ Landon SchlabachIn 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 the pandemic became an unexpected growth acceleratorThe scrappy early days of doing everything soloHow a remote cabin in Pennsylvania changed everythingWhy not every investor is in it for cash flow—and why that's okayHis approach to building relationships, earning trust, and growing organicallyWhether you're just getting started or scaling your STR business, Landon's story is packed with lessons on grit, trust, and jumping in before everything's perfect.

    Mastering the Guest Experience with Derek Gisriel

    Play Episode Listen Later Apr 4, 2025 34:53


    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—handwritten notes, welcome screens, and morePartnering with developers to create STR-ready homesDerek and his wife turned their passion for travel and design into a profitable STR business. Tune in to hear their journey and get practical tips to optimize your own rental!

    Drive 60% Direct Bookings with Mark Simpson

    Play Episode Listen Later Mar 21, 2025 41:52


    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 entirely on OTAs.Simple but powerful strategies to drive direct bookings—including a game-changing messaging tactic that can land you instant reservations.The biggest mistakes hosts make with pricing and why some direct booking sites charge more than Airbnb (and how to fix it!).The top tools and tactics for increasing direct bookings, including Get Directo and other must-have resources.How to structure your OTA listings to drive traffic to your direct booking site without breaking platform rules.Mark Simpson has helped set up over 1,000 direct booking websites, and he's here to share his playbook on how to make your short-term rental business thrive.Connect with Mark Simpson and get the exact template he uses to generate bookings: DM him “template” on Instagram @boostlyuk.Don't forget to like, subscribe, and share this episode with your fellow hosts.Let's take control of our bookings!

    Secrets To Paying Less Taxes With Airbnbs Featuring Nathan Sosa

    Play Episode Listen Later Mar 11, 2025 37:26


    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 minimize your tax burden.Don't leave money on the table—tune in and learn how to make tax laws work in your favor!

    Insider Information on Airbnb From a Former Employee with Paul Kromidas

    Play Episode Listen Later Feb 14, 2025 44:14


    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 strategies in today's evolving market. Whether you're just starting out or looking to scale your portfolio, Paul's journey provides a powerful roadmap to achieving long-term success in short-term rentals. Check out his website here: https://www.summeros.com/

    North Georgia Isn't Dead: Finding Cashflow in the Toughest Markets with Connor Cushman

    Play Episode Listen Later Feb 7, 2025 36:34


    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 opportunities. Drawing on his experiences in North Georgia's competitive market, he breaks down the importance of smart property selection, strategic amenity upgrades, and keeping an eye on market fundamentals like interest rates and ROI. Whether you're a budding investor or a seasoned pro looking to 10x your results, this conversation is packed with actionable insights to elevate your STR game. 

    Super Mom: Growing a STR Portfolio While Working Full-Time and Raising Kids

    Play Episode Listen Later Jan 29, 2025 38:26


    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 how her new company provides hosts with free, high-quality products to delight visitors. Tune in as Mark dives headfirst into the world of STR podcasting, gleaning real-life lessons in hospitality, financing, and long-term wealth building from an investor who's living proof that success in vacation rentals is within anyone's reach. 

    Investing in STRs, Boutique Hotels, & Management Companies in South Carolina with Josh Hatter

    Play Episode Listen Later Dec 20, 2024 28:29


    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 team and technology to support sustainable growth. Josh also offers a preview of his new educational venture aimed at helping investors bypass industry hype and access proven, expert-driven strategies. Whether you're just starting out or looking to refine your approach, this episode provides a reality check on what it takes to succeed in a more mature, data-driven short-term rental market.

    Direct Bookings Made Easy with Gil Chan (CEO of Crafted Stays)

    Play Episode Listen Later Nov 1, 2024 52:20


    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 understanding your ideal guest, building a differentiated product, and utilizing effective, simple strategies for direct bookings. This episode is packed with insights on staying competitive in STRs by focusing on core customer needs, design, and efficient operations. If you're ready to take your STR game to the next level, this episode is for you!Tune in to hear practical advice and inspiring stories from two seasoned STR operators.

    Scaling Airbnbs in the "Bourbon Capital" of the US with Jay Bowman

    Play Episode Listen Later Oct 11, 2024 28:09


    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 duplexes into high-performing short-term rentals. Jay also provides insights into the challenges of hospitality as an asset class and his future plans to explore other markets and unique investment opportunities.

    Buying Raw Land in Oklahoma & Building Luxury Airbnbs with Max Gagliardi

    Play Episode Listen Later Sep 23, 2024 31:19


    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, marketing, and direct bookings could be the key to multiplying your income and building your own resort community.

    Inspiring Moments In The Wild with Eric Moeller (CEO of Freewyld)

    Play Episode Listen Later Sep 6, 2024 33:02


    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 touches on the challenges of adopting new technologies in the industry and the strategic pivot towards integrating hospitality with real estate to enhance guest engagements and property management. Join Eric and Taylor as they explore the nuances of sustaining growth and innovation in the evolving landscape of short-term rentals. 

    Building a Portfolio of Short Term Rentals Before Legal Drinking Age with Brett Deas

    Play Episode Listen Later Aug 9, 2024 25:26


    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 properties and his effective direct booking approach using social media and content creators to enhance visibility and profitability. Tune in for insights on finding undervalued properties, the power of content marketing, and the evolving landscape of short-term rentals. 

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

    Play Episode Listen Later Jul 12, 2024 29:38


    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 without any upfront cost. Ben discusses the evolution of the market, the critical role of content marketing, and the strategies that transformed his business. Tune in to learn how Ben's unique approach to social media and direct bookings can revolutionize your own rental business.

    How I Turned a $55,000 Drug House Into a $1.5M Airbnb with Tyann Marcink

    Play Episode Listen Later Jun 27, 2024 28:35


    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 not and underscores the profitability of creative real estate investments. Tune in and learn from Tyann Marcink's incredible journey to elevate your short-term rental game.

    Transforming Airbnb Expenses Into Revenue Streams with Allen Meringolo

    Play Episode Listen Later Jun 19, 2024 30:36


    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're a seasoned Airbnb host or just starting out, this episode is packed with actionable tips and valuable knowledge to help you elevate your STR game. Tune in and learn how to make your Airbnb expenses work for you!

    How to Turn 1 Airbnb into 3 with One Transaction: Featuring Rob Leventhal

    Play Episode Listen Later Jun 10, 2024 22:20


    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 to short-term rentals or looking to enhance your investment strategy, this episode is packed with valuable insights and practical advice. Tune in to hear Rob's story and gain inspiration for your own investing journey.

    Unlocking the Future of Direct Bookings with Eric Goldreyer, CEO of BNB Finder

    Play Episode Listen Later May 30, 2024 37:16


    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, this episode is packed with insights to elevate your rental business.Episode Highlights:- Eric's journey and the creation of BNB Finder- Advantages of direct bookings and professional management- Future trends in the short-term rental industryWhere to Find Eric:Website: [BNB Finder](https://www.bnbfinder.com)  Email: Eric@bnbfinder.comTune in for expert tips and advice!

    STR Listing Optimization and Revenue Strategies with Sabrina Calnan

    Play Episode Listen Later May 23, 2024 36:32


    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 rental market. Don't miss this deep dive into the nuances of listing optimization, revenue strategies, and the evolving landscape of Airbnb.00:59: Sabrina's journey from investment banking to short-term rentals3:05: Transition to long-term property management and entry into Airbnb4:55: Passion for Airbnb and creative side of the business5:50: Discussion on individualized property revenue management07:55: Evaluating properties and market deep dive13:09: Common investor mistakes and market assumptions20:33: Comprehensive revenue management components23:58: Art and science of short-term rental business26:47: Service offerings and ideal clients for BNB ExcellentConnect with Sabrina Calnan on LinkedIn: https://www.linkedin.com/in/sabrinacalnanLearn more about her work: https://www.bnbexcellent.com

    From Boats to Millions: Jeremy Werden's Journey to a 7-Figure STR Portfolio

    Play Episode Listen Later May 17, 2024 41:37


    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, allowing him to pursue a life and career that excites him every day.Jeremy also introduces his new startup software venture, BNBCalc, which is helping thousands of short-term rental investors analyze potential deals. He believes that short-term rentals are the best avenue for anyone looking to quit their job, enjoy a comfortable retirement, or build generational wealth.Join us as we discuss Jeremy's unique investment strategies, including short-term rental boats and alternative assets beyond traditional properties. Tune in to learn valuable insights and strategies for creating a 7-figure portfolio in the STR market. Don't forget to follow Jeremy for weekly tangible tips on building short-term rental businesses from the ground up, and check out his podcast, "Short-Term Rental Pros." Join us today!

    Unlock Creative Financing: Buy STRs with No Down Payment & at Half the Current Interest Rate

    Play Episode Listen Later May 9, 2024 34:24


    In this episode of STR Investing, host Taylor Jones interviews Aidan Groll and dives deep into innovative financing strategies that will help you acquire short-term rentals without the need for a hefty down payment. Learn how savvy investors are leveraging creative solutions to secure properties at half the current interest rate. If you're eager to expand your STR portfolio, this episode is a must-listen!

    From $0 to $76 Million in STRs: Q&A Deep Dive with Founder Sabrina Guler

    Play Episode Listen Later May 3, 2024 37:33


    In this unique episode of STR Investing, host Sabrina Guler departs from the usual interview format to answer some of the most frequently asked questions she receives. Sabrina shares insights from her transition from working at Apple to starting her journey in short-term rental investing. Covering topics from her first property purchase challenges to strategic advice for new investors, this episode dives deep into the practicalities and personal experiences behind successful STR investing.TIMESTAMPS:00: Q1 - What was the hardest thing for you when buying your first property?4:51: Q2 - Why did you pick short-term rentals and did anyone help you?9:33: Q3 - How do you find good markets and good properties?14:53: Q4 - What tools and platforms do you use?17:10: Q5 - What are the key metrics that you look for?19:33: Q6 - What is the biggest mistake you've seen or made in this asset class?21:26: Q7 - What are the toughest lessons you've learned on your short-term rental journey?23:52: Q8 - Is there still an opportunity on Airbnb or is the market too saturated?26:08: Q9 - How did you know it was the right moment to quit your job?30:37: Q10 - Are there any red flags that I should avoid at all costs and how do I avoid a bad investment?33:03: Q11 - What if I fail?PLEASE LEAVE US A REVIEW! Taylor and I are trying to grow our podcast show, it always helps - and most importantly, it helps other investors! :)

    Property Management Deep Dive: Tips on Managing Remotely with Brooke Rigolini

    Play Episode Listen Later Apr 26, 2024 31:03


    In this insightful episode of "STR Investing," host Sabrina welcomes Brooke Rigolini, head of property management at Techvester, to dive deep into the nuances of property management within the short-term rental industry. Brooke shares her extensive background in hospitality and property management, emphasizing the importance of guest experience and proactive communication. Listeners will learn about handling unexpected issues, enhancing guest stays through thoughtful gestures, and the impact of maintaining high standards on revenue and reviews. This episode is packed with actionable tips for new and seasoned investors, focusing on the critical role of a personalized approach to managing properties and ensuring guest satisfaction.Timestamps to help you skip along!00:21 - Introduction to the episode and guest Brooke Rigolini.00:57 - Brooke discusses her role at TechFester and her approach to property management.03:12 - Key strategies for enhancing guest experience and handling complaints.07:06 - Scenario discussion on how to handle unexpected issues like hot tub malfunctions.10:03 - Brooke's advice for new investors on choosing between external property management and self-management.12:16 - Importance of having a reliable network of vendors and handymen.15:00 - Differences between external property management services and in-house management.18:56 - Challenges of managing properties with boots on the ground and how to mitigate them.22:03 - Recommendations on leveraging technology in property management.26:44 - Discussion on how property owners can inadvertently hinder their revenue potential.30:00 - Final advice for new investors in the short-term rental market.

    Cohosting 101: Become Profitable Without Owning Property with Austin Palacios

    Play Episode Listen Later Apr 15, 2024 29:56


    Join us in this insightful episode as Taylor sits down with Austin Palacios, a pioneering short-term rental (STR) investor from West Palm Beach, Florida. With a rich background in wealth management, Austin made a significant career pivot in 2021 to focus full-time on short-term rental investments. He co-founded a dynamic management company tailored to the unique demands of the South Florida vacation rental market.Throughout the episode, Austin shares the innovative systems and processes he developed while building his management company, strategies that not only streamlined operations but also accelerated client acquisition, enabling rapid scaling of the business. These methodologies became the cornerstone of his latest venture, Co-Hosting Acquisitions, a mentorship program dedicated to coaching upcoming STR investors on how to effectively gather management clients.Tune in to discover Austin's top strategies for cohosting, and learn how new investors can embark on their own successful paths in the competitive world of short-term rentals. Whether you're a seasoned investor or just starting out, Austin's insights offer valuable guidance on maximizing profitability and efficiency in this lucrative market.Check this episode out on Youtube: https://youtu.be/okcnPYjIdeY

    Expert Renovation and Installation Insights with Mark Lumpkin

    Play Episode Listen Later Apr 9, 2024 30:26


    Join us on the "STR Investing" podcast as we chat with Mark Lumpkin, head of Sales at STR Cribs. Mark is an expert in transforming properties for short-term rentals and has overseen the installation of over 500 rentals in his career. He shares practical tips for property renovations, cautionary tales to avoid, and essential advice for first-time owners. Whether you're a new investor or looking to enhance your portfolio, don't miss Mark's wealth of knowledge. Connect with him on LinkedIn at https://www.linkedin.com/in/mark-lumpkin-84b173142/ and explore STR Cribs' services at strcribs.com to elevate your rental game!

    Unlocking Revenue Potential: A Deep Dive into STR Investing Strategies with Austin Weinerman

    Play Episode Listen Later Mar 13, 2024 26:21


    In this episode of STR Investing, The Podcast, host Sabrina Guler sits down with Austin Weinerman, the Head of Revenue at Techvestor. With a wealth of experience managing over $20 million in revenue across various portfolios, Austin delves into the crucial strategies for maximizing revenue in short-term rental (STR) properties.From the get-go, Austin emphasizes the importance of listing the right photos and understanding the pivotal role amenities play in attracting guests. He shares invaluable insights on identifying and investing in amenities that truly resonate with guests, ultimately leading to higher bookings and increased revenue.But that's not all. Austin takes listeners on a journey through the intricacies of pricing strategies, shedding light on how tools like PriceLabs can be leveraged to optimize pricing based on seasonality and demand fluctuations. Understanding how to price your property effectively can make a world of difference in revenue generation, and Austin breaks down the process in a digestible manner.Whether you're a seasoned investor or just dipping your toes into the world of STR properties, this episode offers practical advice and actionable tips to propel your revenue to new heights. Tune in to gain a competitive edge in the STR market and unlock the full potential of your investment properties.

    Buying the Right STR Property, Tips from Expert Taylor Jones

    Play Episode Listen Later Mar 12, 2024 29:20


    In this episode, we're joined by Taylor Jones, the Head of Acquisitions at Techvestor and the co-host of the STR Investing Podcast.With a remarkable track record of helping Techvestor acquire over 150 successful STR properties, Taylor Jones is a seasoned expert in the field. Join us as Taylor shares his wealth of knowledge and insider tips on purchasing the perfect STR property.Throughout the episode, Taylor dives deep into the strategies and considerations that have contributed to his success in acquiring STR properties. From identifying high-demand locations to evaluating property metrics and negotiating deals, Taylor provides invaluable advice tailored to both novice investors and seasoned pros.As the STR market continues to evolve, Taylor discusses emerging trends, innovative technologies, and key factors to consider when selecting the right property for investment. Whether you're looking to diversify your portfolio or launch your journey into real estate investing, Taylor's expertise will guide you towards making informed decisions and achieving your investment goals.

    Mastering Markets: Data-Driven STR Buying with Expert John Bianchi

    Play Episode Listen Later Mar 9, 2024 33:41


    Dive into the world of data-driven short-term rental investing in this insightful episode of STR Investing, The Podcast, where host Sabrina Guler is joined by John Bianchi, known in the industry as "The Airbnb Data Guy." As the founder of STR Search, a service dedicated to helping investors find profitable, hand-picked properties across the nation, John brings a unique perspective on how to leverage data for strategic investment decisions.In this episode, John shares his expert analysis on identifying the most lucrative markets for STR investments, using a blend of tourism trends, regulatory insights, and economic indicators. Listeners will gain an understanding of how to navigate through complex data to pinpoint locations with the highest potential for returns, avoiding the pitfalls of oversaturated markets.John also discusses the importance of understanding local and national data trends to make informed purchasing decisions, whether you're making your first investment or expanding your portfolio. With his guidance, you'll learn how to utilize STR Search's resources to uncover hidden opportunities and make data-backed investments that align with your financial goals.Join Sabrina and "The Airbnb Data Guy" for a deep dive into the strategies that can empower you to buy in the right STR markets with confidence. This episode is a must-listen for anyone looking to harness the power of data to enhance their investment strategy and achieve greater profitability in the short-term rental space.

    Designing for Profit: Kaitlyn Rowsey (Ex-Airbnb) Shares Expert Strategies

    Play Episode Listen Later Mar 9, 2024 37:27


    Join us on STR Investing, The Podcast, where host Sabrina Guler sits down with former Airbnb insider and short-term rental design expert, Kaitlyn Rowsey. In this enlightening episode, Kaitlyn shares her invaluable insights into how strategic design can significantly boost the profitability of your short-term rental. Drawing from her rich experience at Airbnb, she reveals the design secrets that not only enhance guest experiences but also ensure your listing stands out in a crowded marketplace.  Whether you're just starting out or looking to optimize your existing rental, this episode offers a wealth of knowledge on elevating your property's appeal and maximizing returns. Don't miss out on these expert strategies to transform your short-term rental into a high-performing investment. Tune in now and take the first step towards a more profitable rental journey.

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