Mailbox Money Show

Achieving Financial Freedom Through Short-Term Rentals with Tim Hubbard


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In this episode, we are joined by Tim Hubbard, founder and CEO of Midtown Stays, a short-term rental accommodation company which has successfully accommodated over 15,000 guests with excellent reviews from all over the world. Tim began his real estate career as an investment broker, selling multifamily and commercial properties in Northern California. The five-member team he led completed more than $2 billion in transactions. He has been personally investing in real estate for the last 10 years and has since acquired a multi-million-dollar portfolio comprised primarily of small multi-family properties in multiple markets.

With the help of his team, he continues to expand and manages everything remotely from his home in Medellin, Colombia. His intent is also to teach others how to do the same and increase their income 3,4, or even 8x by implementing the right strategies to convert existing long-term rentals into nightly rentals through his live events and podcast.


In this episode, we explore:

00:36 – Guest introduction

02:36 – Tim’s Real Estate background

04:45 – Big opportunities in short-term rentals

08:35 – Passive investments | Attaining financial freedom

11:48 – How lease arbitrage works

13:30 – Establishing management teams

16:30 – Passive income opportunities

18:14 – Short-term rental taxes

20:48 – Short-term rental regulations in different places

25:15 – Life as a passive investor

26:06 – Personal development tools: podcasts, books,


Connecting with the Guest:

Short Term Rental Riches Podcast: https://podcasts.apple.com/us/podcast/short-term-rental-riches/id1488518397

Website: https://restmethods.com/, www.midtownstavs.com

Facebook: https://www.facebook.com/restmethods

Instagram: https://www.instagram.com/restmethods/

Youtube: https://www.youtube.com/channel/UCe1dEeJ-kH91-I9YZIPh-tA/videos

Linkedin: https://www.linkedin.com/in/midtownstays/

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