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From Law to Rentals – The Unconventional Path to Real Estate Success with Mike Stone

In this episode, we sit down with Mike Stone, a trailblazer who transitioned from a successful legal career to become a dynamic real estate entrepreneur specializing in short-term and medium-term rentals. 

When you realize that you’re in the wrong field, it takes a ton of courage and conviction to make a career pivot early in your career.

We’re diving into Mike’s fascinating transition away after working as an attorney full-time, detailing why he decided to step away from a profession that he spent many years of legal training (and thousands of dollars in tuition) to enter.

Mike details how he got started in short-term rentals and eventually found success in medium-term rentals by directly contacting insurance companies instead of individual renters.

You’re going to learn a ton about authenticity and taking calculated risks during this episode. Mike’s ebullient personality and passion about real estate investing, hospitality, and coaching others shine through during our discussion.

Mike is terrific at building valuable relationships and leveraging mastermind programs to build his business and help others with his new coaching program.

This episode is a very insightful look into Mike’s journey and strategies for diversifying rental income streams.

Things we discussed in this episode:

  • How Mike went from the top of his law class to burning out as a defense attorney.
  • Why personal development books sparked his interest in investing and real estate.
  • His strategy of “contract first, then the door” to eliminate arbitrage risk.
  • How he pivoted to directly co-hosting properties instead of arbitraging.
  • The difference between short-term and medium-term rental seasonality.
  • Why he recommends buying your first investment property before quitting your job.
  • Contacting insurance companies directly instead of relying on platforms.
  • Negotiating higher nightly/monthly rates with entities vs. individuals.
  • Leveraging masterminds for ongoing learning, coaching, and networking.
  • How to negotiate higher rates with entities versus individuals.

Get in touch with Mike:

Website /



Join Jason Muth of Straightforward Short-Term Rentals and Attorney / Broker Rory Gill of NextHome Titletown and UrbanVillage Legal in Boston, Massachusetts for another episode of The Real Estate Law Podcast!

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The Real Estate Law Podcast 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!