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Discussion – 


Discussion – 


How to Invest and Run Multiple STR Units in Different Markets (Ep. 339)

Is it too much trouble to manage multiple short-term rentals (STRs) in different markets? If you have the opportunity to invest in Airbnb properties, but you know you’d have to run the units remotely, there are tactics and tools you can use to make the job easier.

Karen Chenaille is the real estate investor and vacation rental host behind Star Gazer Stays, a STR business with properties in Vermont, Tennessee, Mississippi and Florida. She is also an active member of our STR Profit Academy and works full-time as a program manager for a Fortune 500 defense contractor.

Today, Karen joins me to explain how she grew her portfolio to 11 properties, discussing what she looks for in a STR market and how she manages those units remotely. She shares her experience as a host through COVID-19 and describes how Profit First helped her build the cash reserves to navigate the crisis. Listen in for Karen’s insight on leveraging a CEO mindset as you expand your STR business and learn what tools you can use to run multiple Airbnbs in different markets!

Topics Covered

How Karen grew a portfolio of 11 STR properties

  • Use extra space in own 5BR house
  • Added condo near ski resort
  • Sold convenience store to expand

What Karen looks for in a STR market

  • Vacation rentals have been around long time
  • Local governments pro-STR and make money

How Karen finds cleaners + maintenance staff in new markets

  • Stay in local Airbnb, contact host/cleaner
  • Ask for referrals from local realtor

The benefits of using Wi-Fi locks for self check-in

  • Only valid for period from check-in to checkout
  • Know what’s going on and stay in control

Karen’s vision for the future of her STR business

  • Grow Airbnb revenue for next six to eight months
  • Decide whether STR can be main source of income

Karen’s experience as a host through COVID-19

  • Lost $20K in five days on Tennessee properties
  • State of Vermont blocked calendar through 7/1

What bookings look like for Karen now

  • New properties in Florida booking like crazy
  • Tennessee Airbnbs picking up (at higher rates)
  • Guests choosing drive-to destinations

How Karen applies the principles of Profit First

  • Pay yourself and taxes first, then use rest to operate
  • Narrow down and prioritize expenses based on ROI

How Karen built the cash reserves to survive COVID

  • Leverage YNAB cashflow management tool
  • Set aside money to pay off expenses in 10 months

How Karen is implementing the CEO mindset

  • Only do things good at, outsource rest
  • Develop systems + use automation when possible

Karen’s advice for STR hosts

  • Don’t feed into hysteria and panic
  • Still much opportunity in STR space

Connect with Karen

Star Gazer Stays

Star Gazer Stays on Facebook

Karen on Airbnb


STR Profit Academy

Get Paid for Your Pad by Jasper Ribbers and Huzefa Kapadia


Remote Lock


Profit First by Mike Michalowicz



Mike Michalowicz’s Podcast: Entrepreneurship Elevated

Clockwork by Mike Michalowicz

The 4-Hour Workweek by Timothy Ferriss

Email jasper@getpaidforyourpad.com