About Richard Montgomery

Richard Montgomery

Richard Montgomery

Richard Montgomery has experience in a wide variety of real estate related businesses. His involvement with methods to improve the real estate consumer experience over 30 years provide a unique perspective to his no-nonsense real estate advice.

Montgomery is the co-founder of PropBox, an AI-powered platform designed to help homeowners sell their properties without traditional agents or commissions.

As CEO of Corporate Relocation Services (CRS) from 1985 to 2010, Montgomery led a team of people to provide real estate consulting services to large corporations with national operations.

These companies regularly relocated employees to serve business purposes in different locations. In this role as consultants, the CRS team worked with thousands of employees, real estate agents, appraisers, mortgage lenders, inspectors and specialty contractors throughout the United States.
Founded a real estate company in 1989 that was organized and developed to deploy a totally innovative business model for real estate services that significantly improved the customer experience. This model transformed the traditional real estate model to be very much similar to the way most other businesses in other industries deliver their products and services to the market. It ultimately failed to break through the marketing clutter as this was before the modern internet, the iPhone, applications, and a startup culture.

Montgomery began his career as a real estate agent. He credits his early success to a strong mentor who taught him to treat buyers and sellers as he would treat his parents. Montgomery founded his company in 1970. It grew and prospered utilizing the identical methods in use today.  The company became one of the leading 25 companies in the Electronic Realty Associates(ERA) franchise system and a market leader in the local community. It was during these years in the field his observations of the real estate industry shaped his belief that reforms are necessary to improve consumer outcomes in real estate transactions.

Read his column here.

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How to Force a Home Sale When Your Co-Owner Refuses Dec 16, 2025

Dear Monty: I would like to know the pros and cons of moving out of a home that you own with another person who refuses to sell the property to divide the assets. We have a mortgage, but we are not married. We co-own a house together. Monty's Answer:... Read More

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Save for Down Payment or Upgrade Before Selling Your Home? Dec 09, 2025

Dear Monty: I live in a lower-value area in Jacksonville, Fla. I want to move to a nicer area. My question is, should I even bother to do upgrades to my current house to make it more "attractive" to the buyer? Or should I use that money towards a dow... Read More

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Should You Add That Master Bath? The ROI Reality Check Dec 02, 2025

Dear Monty: We have a split-level, three-bedroom, two-bathroom house with one bathroom on the first floor and one in the basement. All the bedrooms are on the first floor. We are considering adding an additional bathroom, specifically as a master bat... Read More

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Choosing Your First Brokerage in the AI Era Nov 25, 2025

Dear Monty: I have just passed my salesperson exam and would like to know what to look for when determining the most suitable brokerage company for 2025. Any direction will be appreciated. Monty's Answer: The AI real estate market has grown from virt... Read More