SSTIR Crazy Month 2025: Let’s Learn, Grow, and Succeed Together!
When I started CottageLink Rental Management (in 2001) 23 years ago, it was a very different landscape to what property managers experience today.
Back then, the short-term rental industry wasn’t the collaborative and resource-rich environment we know today. There were no webinars on building trust with your guests, no downloadable checklists for safety audits, and certainly no gamified training events. I learned the hard way—through trial and error, long nights solving unexpected crises, and plenty of missteps along the way.
But here’s the good news: we don’t have to do it that way anymore.
The short-term rental community has evolved into a network of shared expertise, where the answers to your most pressing challenges are just a click—or a conversation—away. That’s what SSTIR Crazy Month 2025 is all about: equipping you and your team with actionable knowledge, real-world examples, and the tools to take your rental business to the next level.
Why SSTIR Crazy Month is a Game-Changer
Think of SSTIR Crazy Month as the ultimate training event for short-term rental professionals. Running from January 27 to March 2, it’s a five-week program that dives into the key pillars of our industry: trust, safety, insurance, regulations, and sustainability. And it is entirely free.
Each week follows the journey of StayWise Rentals, a fictional family-run property management company navigating the kinds of challenges we all face: rebuilding guest trust, ensuring properties are safe, finding the right insurance, staying compliant with regulations, and embracing sustainability without breaking the bank.
This isn’t just about sitting back and watching. It’s about participation. It’s a masterclass in running a rental business, wrapped in a fun and engaging format.
Learning From Experience—and Each Other
Looking back, I wish something like this had been available when I was growing my business. I remember struggling to build trust with guests, wondering if my insurance policies were enough, and scrambling to meet new regulations. It was isolating, trying to figure it all out on my own.
SSTIR Crazy Month is the antidote to that isolation. It brings together the wisdom of industry experts, the camaraderie of peers, and the power of interactive learning. Whether you’re a seasoned operator or just starting out, there’s something here for everyone.
What’s in Store for 2025?
This year, the program is packed with resources and opportunities to learn:
- Weekly Themes: Each week, StayWise Rentals tackles a major challenge:
- Week 1: Building trust with guests.
- Week 2: Ensuring safety across properties.
- Week 3: Navigating insurance pitfalls.
- Week 4: Staying ahead of regulations.
- Week 5: Embracing sustainability to cut costs and attract eco-conscious guests.
- Expert-Led Content: Every week features insights from top industry professionals like Chris Maughan on trust and Justin Ford on safety.
- Interactive Challenges: Teams can audit their own websites, inspect properties for safety hazards, and review insurance policies—all with guidance from the program.
- Gamification: Earn badges like “Trust Builder” or “Safety Champion” as you complete tasks, climb the leaderboard, and compete for prizes.
- Live Q&A Sessions: Get your questions answered directly by experts during weekly panels.
Why Not Make It a Team Effort?
Here’s an idea: Use SSTIR Crazy Month as a structured training event for your team. Set aside time each week to go through the content together. Assign challenges that align with your business’s needs, then come back to share insights and solutions.
It’s not just about checking boxes. It’s about creating a culture of collaboration, learning, and continuous improvement within your organization. Plus, the competitive leaderboard element adds a little fun to the mix—who doesn’t love a bit of friendly rivalry?
Let’s Build the Future, Together
The short-term rental industry has come so far since I started, and it’s events like SSTIR Crazy Month that showcase how much we can achieve when we work together. It’s an opportunity to not only learn but to connect, share, and grow as a community.
So, gather your team, register for SSTIR Crazy Month, and let’s tackle trust, safety, insurance, regulations, and sustainability—one challenge at a time. Together, we’ll build businesses that thrive, protect our guests and owners, and lead the way in this exciting industry.
I can’t wait to see you there!
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