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