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: 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 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 hi@qrclue.com

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

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: alexander@canmonkey.com or connect with him on LinkedIn

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: stefan@revnest.com

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 hour
• The RV loophole that bypasses permitting and building code bottlenecks
• Ways Boxabl homes are already being used for disaster relief, workforce housing, and STRs
• Plans to expand into larger homes, townhouses, and multi-unit developments
• Why Boxabl is considering becoming its own real estate developer
• How ADU-friendly laws in states like California and Arizona are opening doors for investors
• Ideas for turning Boxabl units into high-performing Airbnb properties, roadside motels, or couples’ getaway communities

If 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

__

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

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 properties
• The power of data when choosing a market
• Why operational density matters—and how to achieve it
• What makes a short-term rental truly “differentiated”
• The hard lessons from new construction vs. heavy renos
• Building a property management company (even when you didn’t plan to)
• How to operate a U.S.-based STR portfolio from Europe with precision

Whether 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.

🎧 Tune in, take notes, and get ready to think differently about scale, systems, and strategy.

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 on
• How the pandemic became an unexpected growth accelerator
• The scrappy early days of doing everything solo
• How a remote cabin in Pennsylvania changed everything
• Why not every investor is in it for cash flow—and why that’s okay
• His approach to building relationships, earning trust, and growing organically

Whether 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.

🎧 Tune in for one of the most down-to-earth origin stories in the space.

→ Learn more about Landon and his team: bnbbreeze.co/our-team
→ Attend Landon’s upcoming STR Summit in 2025 (use code strcribs10 for a discount): The STR Summit – Keys to Cash Flow

__

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