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

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]

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: [email protected]
Website: boxabl.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

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 $200K
• How he tripled the revenue of an existing STR
• Using a cash-out refi to scale faster
• The power of personalized guest experiences—handwritten notes, welcome screens, and more
• Partnering with developers to create STR-ready homes

Derek 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!

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!

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!

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/

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.