STR Investing, The Podcast
Welcome to STR Investing, The Podcast, where hosts Taylor Jones & Mark Lumpkin reveal the keys to financial freedom through short-term rental investing. Whether you're taking your first step into this lucrative market or looking to expand your portfolio, this podcast is your ultimate resource for success.
Taylor, who has successfully acquired over 200+ properties, brings not only his personal experiences but also sits down with industry experts to share insights and stories from every corner of the STR world. From sharing insights of building 9 figures of STR businesses, to staying on top of the latest trends in acquiring, designing, furnishing, and operating profitable short-term rentals, he covers it all.
But that's not all. We're also lifting the veil on the challenges and triumphs of entering the industry, offering invaluable advice that you won't find anywhere else. Whether it's navigating regulatory changes or finding the perfect property, STR Investing, The Podcast is your trusted guide at every stage.
Join Taylor & Mark as he shows you how short-term rental investing can lead to financial freedom. Don't just dream about it - make it a reality with STR Investing, The Podcast today.
STR Investing, The Podcast
Helping With The Trashy Side STRs - Can Monkey
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
__
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
