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