STR Investing, The Podcast
Unlock financial freedom through short-term rental investing with hosts Taylor Jones and Mark Lumpkin. Each week, they sit down with the biggest names in the STR industry to uncover what’s working right now — from acquisitions and design to operations, marketing, and scaling portfolios.
Taylor has helped acquire and manage over 500+ STRs, while Mark brings years of hands-on experience transforming properties into high-performing investments.
Together, they break down real strategies, real numbers, and real stories that help investors grow smarter and faster.
Whether you’re buying your first Airbnb or expanding a multi-market portfolio, this show is your roadmap to building wealth and freedom through short-term rentals.
Subscribe and start turning your STR goals into results.
STR Investing, The Podcast
Helping With The Trashy Side STRs - Can Monkey
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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
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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
