Acquiring Minds

Buying for Brand (Then Growing 4x)


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Matt Orley wanted to enter the short-term rentals space. Buying a business — and a brand he admired — was his way in.

Register for the webinars:

  • DO’s and DON'Ts of the LOI -  TOMORROW!! - https://bit.ly/3YtLIvp
  • From W2 to Owner Mindset: How to Think About Your Take-Home Pay - Jan 15th - https://bit.ly/4qJ1Xk5

Topics in Matt’s interview:

  • Investment properties as a side hustle
  • Evolving short-term rental ecosystem
  • Difficult transition with the seller
  • Influence of Airbnb on customer expectations
  • Importance of clear communication
  • Rolling up property management companies
  • Concentrating on one region of the country
  • Difference between urban and rural markets
  • Launching a membership program
  • Putting the brand first when making decisions

References and how to contact Matt:

  • LinkedIn
  • Instagram
  • Red Cottage

Get complimentary due diligence on your acquisition's insurance & benefits program:

  • Oberle Risk Strategies - Search Fund Team

Get a free review of your books & financial ops from System Six (a $500 value):

Get a complimentary IT audit of your target business:

Connect with Acquiring Minds:

  • See past + future interviews on the YouTube channel
  • Connect with host Will Smith on LinkedIn
  • Follow Will on Twitter

Edited by Anton Rohozov
Produced by Pam Cameron

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Acquiring MindsBy Will Smith

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