SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips

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


Listen Later

Ever Dealt With a Water Damaged 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 water damaged 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:


  • Water Damaged Nightmare and Insurance Savior - Jason and Rory's experience with a water damaged 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


    Follow Us!


    Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show!


    SmartStay Show Website and on Instagram and YouTube

    Prideaway Stays Website and on Facebook and LinkedIn

    Straightforward Short-Term Rentals Website and on Instagram

    Attorney Rory Gill on LinkedIn

    Jason Muth on LinkedIn


    Hospitality.FM

    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!

    ...more
    View all episodesView all episodes
    Download on the App Store

    SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting TipsBy Airbnb Superhost Jason Muth + Rory Gill

    • 4.9
    • 4.9
    • 4.9
    • 4.9
    • 4.9

    4.9

    39 ratings


    More shows like SmartStay Show - Short Term Rental Counsel + Coaching | Airbnb Hosting Tips

    View all
    BiggerPockets Real Estate Podcast by BiggerPockets

    BiggerPockets Real Estate Podcast

    16,770 Listeners

    Real Wealth Show: Real Estate Investing Podcast by Kathy Fettke / RealWealth

    Real Wealth Show: Real Estate Investing Podcast

    399 Listeners

    Rental Income Podcast With Dan Lane by Rental Income Podcast

    Rental Income Podcast With Dan Lane

    827 Listeners

    Get Rich Education by Real Estate Investing with Keith Weinhold

    Get Rich Education

    610 Listeners

    Passive Real Estate Investing by Real Estate Investing with Marco Santarelli, Investor and Entrepreneur.

    Passive Real Estate Investing

    975 Listeners

    Tax Smart Real Estate Investors Podcast by Hall CPA

    Tax Smart Real Estate Investors Podcast

    413 Listeners

    BiggerPockets Money Podcast by BiggerPockets

    BiggerPockets Money Podcast

    3,068 Listeners

    Real Estate Investing with Coach Carson by Chad Coach Carson

    Real Estate Investing with Coach Carson

    609 Listeners

    Thanks For Visiting by Airbnb Superhosts Annette Grant & Sarah Karakaian

    Thanks For Visiting

    579 Listeners

    Real Estate Rookie by BiggerPockets

    Real Estate Rookie

    1,843 Listeners

    Short Term Rental Secrets Podcast by MICHAEL SJOGREN

    Short Term Rental Secrets Podcast

    16 Listeners

    PassivePockets: The Passive Real Estate Investing Show by PassivePockets, Jim Pfeifer, and Left Field Investors

    PassivePockets: The Passive Real Estate Investing Show

    137 Listeners

    The Short Term Show by 8 Figure Airbnb and Short Term Rental Real Estate Investor Avery Carl

    The Short Term Show

    441 Listeners

    On The Market by BiggerPockets

    On The Market

    894 Listeners

    The David Greene Show by David Greene

    The David Greene Show

    690 Listeners