DiscoverSmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting TipsOur $130k Flood Claim - How Proper Insurance Saved Our STR Lake Home! | Darren Pettyjohn
Our $130k Flood Claim - How Proper Insurance Saved Our STR Lake Home! | Darren Pettyjohn

Our $130k Flood Claim - How Proper Insurance Saved Our STR Lake Home! | Darren Pettyjohn

Update: 2025-01-14
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Ever Dealt With a Flooded Rental Property? This Could Save You Thousands.

As short-term rental owners, Rory and I have seen it all - from the good, the bad, to the downright disastrous. One fateful night, we got that dreaded 2am call about a flooded property, and let me tell you, it was a nightmare. 

But what happened next is the real story. In this episode, we sit down with Darren Pettyjohn, the co-founder of Proper Insurance, to unpack why short-term rental insurance is so crucial - and how their specialized coverage saved our bacon when disaster struck.

Darren pulls back the curtain on the unique challenges facing vacation rental owners, the sneaky tricks some insurance companies use, and the innovative solutions Proper has pioneered. If you own a short-term rental property, or are thinking about getting into the game, you won't want to miss this. 

It could be the difference between a minor headache and a total nightmare. Click play and find out how Proper Insurance can give you the peace of mind to focus on being a 5-star host.


Things we discussed in this episode:



  • Flood Nightmare and Insurance Savior - Jason and Rory's experience with a flooded short-term rental property and how Proper Insurance stepped in to help.

  • Specialized Insurance Policies - The need for niche insurance products tailored to specific industries like short-term rentals.

  • Proper Insurance's Unique Features - Endorsements like bed bug coverage, squatters insurance, and no limit on guest-caused damage.

  • In-House Claims Administration - Proper Insurance's ability to control the claims process from start to finish, leading to better customer service.

  • Differences Between Short-Term Rental and Standard Homeowner's Policies - The multi-use nature of short-term rentals and the need for a combined homeowner's, landlord, and commercial policy.

  • Positive Claims Experience - Jason and Rory's praise for Proper Insurance's transparent communication and their ability to make the claims process smooth.

  • Risks of Misrepresentation - The potential consequences of homeowners misrepresenting the use of their properties to insurance companies.

  • Worcester Insurance - Proper's sister company providing business policies for professional property managers.

  • Wave O - Proper's guest damage protection solution, offering an alternative to traditional security deposits.

  • Importance of Employee Engagement - Darren's insights on the challenges of managing a growing business and the value of maintaining personal connections with employees.




Get in touch with DARREN:


Facebook - https://www.facebook.com/propervacationrentalinsurance

Instagram - https://www.instagram.com/properinsurance/

Website - https://www.proper.insure/


#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #AirbnbManagement #ShortTermRentals #ShortTermRentalInsurance #PropertyProtection #ClaimsManagement #VacationRentalOwners #RiskManagement #PropertyManagerInsurance #GuestDamageProtection #EntrepreneurialInsights #InsuranceInnovation #PeaceOfMind


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SmartStay Show is part of Hospitality.FM, a podcast network dedicated to bringing the best hospitality-focused podcasts to those in and around the industry, from Food + Beverage, Guest Experience, Diversity & Inclusion, Tech, Operations, Hotels, Vacation Rentals, Real Estate Law, and so much more!

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Our $130k Flood Claim - How Proper Insurance Saved Our STR Lake Home! | Darren Pettyjohn

Our $130k Flood Claim - How Proper Insurance Saved Our STR Lake Home! | Darren Pettyjohn

Airbnb Superhost Jason Muth + Rory Gill