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 Austin
• Used STRs to offset a major tax bill after a liquidity event—and never looked back
• Bought and converted a 110-year-old Piggly Wiggly grocery store into a cash-flowing Airbnb duplex
• Built a 12-unit portfolio, including midterm arbitrage units for corporate travelers
• Launched Live in Luxury, a white-glove service for high-earning W2 professionals
• Partnered with data-driven operators to scale his business and serve busy investors
• Leveraged cost segregation and depreciation to legally eliminate his tax burden

If 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 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

In this episode, Mark sits down with Shawn Moore, a 25-year real estate veteran and founder of Vodyssey, to unpack two decades of lessons in the short-term rental space. Shawn shares how he stumbled into STRs in 2006, built a thriving portfolio, and eventually launched one of the most respected coaching communities in the game: all while staying rooted in authenticity and real results over flash.

You'll learn:

• Why post-COVID investors often learned all the wrong lessons
• The three pillars of a successful STR: location, experience, and marketing
• How Sean approaches investing with long-term appreciation in mind
• Why uniqueness and guest personalization are the ultimate revenue drivers
• Mistakes that cost thousands and how you can avoid them

This is one of our most honest and wisdom-packed conversations yet. Whether you're scaling or just starting out, Sean's mindset and experience will inspire you to build intentionally and invest wisely.

Learn more about Sean and Vodyssey at vodyssey.com
Connect on LinkedIn: Sean Moore
___

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

In this episode, Taylor Jones sits down with the “Airbnb Data Guy” himself, John Bianchi, co-founder of STR Search and the brain behind hundreds of profitable short-term rentals. They unpack John’s exact process for identifying high-performing properties, avoiding bad buys, and why analyzing revenue drivers like pickleball courts and hot tubs can mean the difference between $80K and $200K.

You'll learn:

• How to reverse-engineer success in any STR market
• What “table stakes” amenities top listings always have
• Why cheap debt beats a fancy kitchen
• How to efficiently allocate capital for max ROI
• The secret sauce behind STR Search’s data models

This is one of the most practical and entertaining data breakdowns we've ever recorded. Whether you’re buying your first property or optimizing your tenth, don’t miss this one.

___

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

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 automation
• Why customer obsession is at the heart of Lodgify 2.0
• What’s changing and what’s not in the STR industry
• How Sean’s first 100 days shaped the future of the company
• Insights on global markets, regulations, and what's next for hosts

Whether 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: [email protected]
Follow him on LinkedIn: Shaun Shirazian
Learn more about Lodgify: lodgify.com

__

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

In this episode of the STR Investing Podcast, Taylor sits down with Pedro Rivera, Head of Customer Success at Summer OS, to explore how his unique background in hotel acquisitions and build-to-rent communities shaped one of the most powerful tools in the short-term rental space.

Pedro shares:

• The key differences (and surprising similarities) between hotel and STR investing
• What institutional real estate gets right—and wrong—about short-term rentals
• How Summer OS was born out of frustration with unreliable data and plug-and-play tools
• Why accurate competitive sets, lot size, and submarket awareness are critical for STR success
• What most investors miss when projecting revenue and tracking performance
• Why operators must keep their hands on the wheel—set-and-forget doesn't work
• What’s next for Summer OS, including real-time variance analysis and revenue trend forecasting

If you’re scaling your STR portfolio, building underwriting systems, or struggling to trust the data, this episode is a goldmine.

Explore Summer OS: https://www.summeros.com

__

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

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 sales
• What he learned scaling from 1 arbitrage unit to 45+ managed homes in San Diego
• Why HostBuddy.ai was born out of late-night guest message fatigue, and how it works
• How today’s AI tools can help you reduce stress, automate communication, and increase profits
• Why HostBuddy stands out from every other AI chatbot in the space
• The challenges of scaling and how to maintain trust as you grow
• How 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.ai

Connect with Jay: [email protected] | @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 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

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 creation
• Why 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 collection
• Why it’s designed only for vacation rentals (sorry, hotels 👋)
• What setup, reset, and guest playtime actually looks like
• How families, friends, and even company retreats are using it to connect and create memories

If 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 [email protected]
 

Like what you hear? Subscribe, share, and join us again next Friday!

__

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

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 product
• The “cancer pill” mindset that will transform how you sell
• How to uncover and use the power dynamic in two-person sales conversations
• The underrated brilliance of Men's Wearhouse sales strategy
• Why 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 steal
• When and how much pressure to apply—and how to make it match your personality
• The one universal reason someone doesn’t buy from you
• Why storytelling beats pitching every time

Whether 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 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

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 idea
• Why homeowner rejection opened the door to a thriving STR market
• The secret sauce behind Can Monkey’s explosive growth
• What it really takes to manage a trash route across hundreds of cities
• The 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 ops
• Can Monkey’s next chapter: 10,000 properties and software that could shake up the space

If 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.com
Contact Alex: [email protected] or connect with him on LinkedIn

__

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

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 business
• Why “being a good neighbor” is the foundation of sustainable short-term rental success
• The origin story behind Revnest: a marketplace built to buy and sell STR-ready properties
• How Revnest is changing the game with verified revenue data, instant communication, and regulation insights
• A first look at Revnest’s newest tool: a crowdsourced, constantly updated short-term rental regulation map
• Why this regulation tool could become one of the most powerful resources for STR investors and how you can contribute
• How Stefan’s team is partnering with local experts and brokers to deliver hyper-accurate compliance data at scale

If 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.com
Contact Stefan: [email protected]

__

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