SSTIR Crazy Month is an exciting five-week online event designed for short-term rental professionals to tackle the industry's most pressing challenges in Safety, Sustainability, Trust, Insurance, and Regulations (SSTIR).
Guided by expert mentors and brought to life through the engaging story of StayWise Rentals—a fictional property management company navigating these hurdles—participants will gain actionable insights and solutions they can apply to their own businesses.
With gamified elements like weekly challenges, mystery clues, leader boards, and exclusive rewards, SSTIR Crazy Month combines education with entertainment to inspire growth and innovation in the vacation rental industry.
Join us and transform how you manage your rentals!
Join us in a month-long adventure with StayWise Rentals, a fictional property management company navigating the highs and lows of rapid growth. This year, SSTIR Crazy Month 2025 brings you an engaging, story-driven program that mirrors real-world challenges in the short-term rental industry.
StayWise Rentals started as a family business but is now at a crossroads, tackling pressing issues in Safety, Sustainability, Trust, Insurance, and Regulations. Each week, you’ll step into the shoes of Sarah and Mike Chen as they face these hurdles head-on, guided by industry-leading experts. Will they emerge stronger or falter under pressure? You decide!
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Follow StayWise Rentals through weekly episodes highlighting challenges and innovative solutions.
Learn from top minds like Chris Maughan, Justin Ford, Nick Massey, Bob Garner, and Dana Lubner, and others, as they mentor the StayWise team.
Earn badges, solve mysteries, and climb the leaderboard by participating in challenges that reflect real business scenarios. Participate to win some great prizes.
Discover strategies you can implement in your own rental business, from trust-building techniques to sustainability practices.
The story of StayWise Rentals is more than fiction—it’s a mirror of the obstacles and opportunities every rental operator faces. Through engaging content, live panels, Q&A sessions, and challenges, you’ll gain practical knowledge and tools to elevate your business.
Be part of the journey. Be part of the solution. Are you ready to help StayWise Rentals thrive?
Register today and start earning your first badge!
Enjoy some of the content from 2024 below
Heather Bayer hosts a great panel discussion and you can now watch the recording and join industry leaders, Neely Khan, Dave Goodfellow, and Harshad Harania who dive into the essential topic of Trust and how it pertains to guests, community and staff.
Discover expert insights and valuable tips for building trust in the vacation rental industry. Stay ahead in the competitive market with I-PRAC certification and trust signals.
Enjoy some of the content from 2024 below
A great panel discussion and you can now watch to the recording and join industry leaders, Justin Ford, Catherine Ratcliffe, and Humphrey Bowles, who dive into the essential but often overlooked areas regarding safety in the vacation rental industry.
Discover the importance of effective guest screening in significantly reducing the likelihood of problem rentals thereby safeguarding your short-term rental business.
Enjoy some of the content from 2024 below
Insurance is a no-brainer for a Short-Term Rental Business but have you looked at all the aspects that need coverage? Business, Property, Liability, and Travel Insurance are your 4 key pillars to ensure the financial security of your business and most policies don’t cover all the bases.
Insurance often takes a back seat in conversations about building a successful short-term rental property management business, but it has such critical importance, we have to pay more attention to it.
Enjoy some of the content from 2024 below
Learn key terms, effective strategies, and best practices for navigating short-term rental regulations. Connect with decision-makers and influence regulatory decisions in your favour while staying ahead of changes and prepare for the future of regulations.
Learn key strategies for navigating short-term rental regulations and advocacy in this insightful podcast episode with expert Rolf Blizzard.
Enjoy some of the content from 2024 below
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Learn about sustainability in vacation rentals and responsible tourism in this insightful interview with Marc Ribail. Discover tips for implementing eco-friendly practices in your business.
We will notify you of all upcoming events as part of SSTIR Crazy Month 2025 and also your standings in the competition to win our grand prize.
