STR Investing, The Podcast

Discover a treasure trove of insights for short-term rental projects! Learn how to work with professional designers for free, ensuring your space blends style with durability. The Wayfair Project Solutions team shares tips on sourcing furniture that meets both hospitality and residential needs, avoiding common pitfalls, and accessing high-quality goods. Explore how detailed staging and thoughtful design can transform your rental into a booking magnet, while navigating the evolving market landscape and leveraging social media to engage with potential guests.

Taylor sits down with Nico, a former tech sales executive turned short-term rental entrepreneur, to unpack one of the most creative and strategic STR journeys we’ve heard.Nico shares how he:Went from selling software to CFOs of billion-dollar tech companies to flipping homes in AustinUsed STRs to offset a major tax bill after a liquidity event—and never looked backBought and converted a 110-year-old Piggly Wiggly grocery store into a cash-flowing Airbnb duplexBuilt a 12-unit portfolio, including midterm arbitrage units for corporate travelersLaunched Live in Luxury, a white-glove service for high-earning W2 professionalsPartnered with data-driven operators to scale his business and serve busy investorsLeveraged cost segregation and depreciation to legally eliminate his tax burdenIf you're looking for ways to optimize your tax strategy, generate consistent cash flow, and invest in memorable, high-performing STRs, this episode is packed with insight. Learn more: LiveInLuxury.co___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

Sean Moore, a real estate veteran with 25 years of experience and founder of Vodyssey, shares invaluable insights from his journey in the short-term rental industry. He discusses how he stumbled upon STRs in 2006 and emphasizes the importance of authenticity in building a coaching community. Sean reveals the three pillars of success: location, experience, and marketing, while cautioning against common costly mistakes. He advocates for unique guest experiences and long-term investment strategies, inspiring both newcomers and seasoned investors to think intentionally.

John Bianchi, co-founder of STR Search and known as the Airbnb Data Guy, shares his expertise in identifying lucrative short-term rental properties. He discusses how to analyze key revenue drivers like amenities—think hot tubs and pickleball courts—that can significantly impact profitability. From strategic capital allocation to presenting Airbnb listings with high-quality photos, he reveals practical tips for maximizing ROI. Bianchi’s insights on avoiding bad buys and focusing on effective data analysis make this conversation invaluable for both new and seasoned investors.

Mark Lumpkin sits down with Shaun Shirazian, the new CEO of Lodgify — one of the biggest tech names in the vacation rental industry. Shaun shares his journey from hosting in San Diego to leading a global company from Barcelona, and breaks down the major shift happening in tech: from Software as a Service (SaaS 1.0) to Service as Software (SaaS 2.0).You'll hear about:How Lodgify plans to make hosting easier through automationWhy customer obsession is at the heart of Lodgify 2.0What’s changing and what’s not in the STR industryHow Sean’s first 100 days shaped the future of the companyInsights on global markets, regulations, and what's next for hostsWhether you're a new host or scaling your portfolio, this episode is packed with real talk, future-focused insights, and a behind-the-scenes look at a major player in STR tech. Don’t miss it!Contact Shaun: shaun.shirazian@lodgify.comFollow him on LinkedIn: Shaun Shirazian Learn more about Lodgify: lodgify.com__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

Pedro Rivera, Head of Acquisitions at Summer OS, brings a wealth of expertise from hotel acquisitions to the short-term rental space. He highlights the unexpected parallels between the two markets, emphasizing the critical role of data in making informed investment decisions. Pedro discusses how accurately assessing competitive sets and lot features can enhance STR performance. He also unveils innovative tools for revenue tracking and the importance of being hands-on with operational strategies, paving the way for success in a highly competitive landscape.

In this episode, Mark Lumpkin sits down with Jay Ullrich, STR operator, tech founder, and CEO of HostBuddy.ai - to unpack his journey from cold-calling landlords and scrubbing his own units to managing 45+ short-term rentals and launching one of the most advanced AI guest communication tools in the industry.Jay shares:How he built a thriving STR property management company without outbound salesWhat he learned scaling from 1 arbitrage unit to 45+ managed homes in San DiegoWhy HostBuddy.ai was born out of late-night guest message fatigue, and how it worksHow today’s AI tools can help you reduce stress, automate communication, and increase profitsWhy HostBuddy stands out from every other AI chatbot in the spaceThe challenges of scaling and how to maintain trust as you growHow to test HostBuddy live on their site (no signup required!)Whether you’re just starting in cohosting or you’re managing dozens of units, this episode is packed with firsthand experience and future-focused insights that can save you time, money, and headaches.Try HostBuddy's AI for yourself → https://hostbuddy.aiConnect with Jay: jay@hostbuddy.ai | @hostbuddy_ai on Instagram—Enjoyed the show? Subscribe, share, and leave a review for the STR Investing, The Podcast so more hosts can scale smarter.__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

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 👋)What setup, reset, and guest playtime actually looks likeHow families, friends, and even company retreats are using it to connect and create memoriesIf you’re looking for an easy, low-lift way to upgrade your guest experience (and boost your bottom line), this one’s for you.Learn more at QRClue.com or email them at hi@qrclue.com Like what you hear? Subscribe, share, and join us again next Friday!__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

Dive deep into the art of selling like a pro! Discover why believing in your product is key to closing deals. Learn about innovative scheduling tricks that enhance client commitment and the importance of emotional intelligence in sales interactions. Uncover the powerful 'cancer pill' mindset and techniques like 'choice of two positives' to change your approach. The episode even highlights the underrated brilliance of Men's Wearhouse strategies. Ultimately, the big takeaway? Authenticity is your secret weapon in transferring emotions to close those deals.

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__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