In this episode, Alex and Annie are joined by Alex Shapiro, CEO and Co-Founder of CanMonkey - the very first Trash-To-Curb Service that handles the waste and recycling can duties of your vacation rental properties.
CanMonkey started 4 years ago with a business model that’s similar to Uber and DoorDash - employing gig economy drivers to ensure a seamless service across 13 different states. What differentiates them from Uber’s business model is that they’ve achieved profitability as a bootstrapped startup, instead of relying on funding and burning through cash.
Before Alex made the decision to go all-in, he chose to first see CanMonkey drive results in their local market. Luckily, this market was Scottsdale, AZ - one of the most thriving markets in the rental property space. His A-HA moment was during a meeting with a client who was converting his long-term rental into a short-term rental and had expressed his frustration with his current waste management setup. This conversation unlocked a deal that effectively doubled their business overnight - and Alex knew it was time to fully bet on CanMonkey.
This hasn’t been an easy journey so far. As with any bootstrapped startup, the founding team needed to put on many hats, and fulfil all the needs of the business without excessive hiring. Where this approach has truly shined is in their go-to-market strategy - instead of a spray-and-pray sales approach, they’ve been very intentional about organic social and building strategic partnerships with key players in the vacation rental space.
One of the reasons why property managers choose CanMonkey’s services are the benefits that they bring to the managers relationship with their HOA. With their data-driven approach, they’ve been able to bring peace to the mind of the communities they serve, and even overturn HOA fines, which is no easy task.
The way CanMonkey develops their service has been a key factor in their rapid growth. Alex has always approached product development with flexibility and feedback in mind, letting their clients be the ones who inspire their product development strategy and ultimately choose how they’re best served.
Another key factor has been their sublime approach to marketing. During the conversation with Alex, it’s apparent that his wheels are always turning when it comes to new ways to market their business. His approach to finding relevant and fun ways to create social media content stems from conversations he has with clients, and the tidbits that come through during those interactions. He’s also not afraid of “poking the bear” and creating campaigns that might receive negative feedback, which can often be a phenomenal strategy to gain brand awareness through a tiny sprinkle of controversy.
Alex is as business savvy as they come - the formative years of his career were spent working in revenue teams at Fortune 500 companies, which has given him a good understanding of how to scale, and has influenced how he’s made decisions about potentially acquiring investment.
The one thing he’s had to learn is how to manage spend, as his typical previous working environments would provide million dollar budgets for new initiatives, which just isn’t the case for an early stage, bootstrapped startup.
CanMonkey looks to be a perfect storm. With their leadership, go-to-market approach, and vast total addressable market (everyone has trash!!) There's really no limit to how far CanMonkey can go. Plus, since there’s no labor shortage in the gig economy, it seems like they truly have everything figured out, and we are excited to see what their future holds.
Tune in to the full episode to learn what it takes to successfully scale a service-based business!
This episode is brought to you by Casago, Guest Ranger, and Good Neighbor Tech.
Visit AlexAndAnniesList.com to view our top picks for the best suppliers in vacation rental technology and services.
Special thanks to Rev & Research for being the presenting sponsor of Alex & Annie’s List.
Connect with Alex:
Connect with Alex and Annie:
