In this special live episode, Mark and Taylor sit down in person to riff on one of their shared obsessions: sales. But this isn’t your typical sales 101 chat. It’s raw, real, and full of battle-tested strategies that have helped them close deals from cars to real estate to STR investments.

Here’s what they dive into:

• Why “assuming the close” only works if you believe in your product
• The “cancer pill” mindset that will transform how you sell
• How to uncover and use the power dynamic in two-person sales conversations
• The underrated brilliance of Men's Wearhouse sales strategy
• Why you should never book client calls at 12:00 or 12:30
• “Choice of two positives,” “calendar closes,” and other tricks you’ll want to steal
• When and how much pressure to apply—and how to make it match your personality
• The one universal reason someone doesn’t buy from you
• Why storytelling beats pitching every time

Whether you’re running sales for your STR business, pitching investors, or just trying to close more life deals—this episode will sharpen your edge.

Biggest takeaway? Sales is just a transfer of emotion. So be real, believe in your offer, and go close.

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