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Rich Rudy started their career in the real estate industry in the mid-1980s as a Licensed Real Estate Broker. Rich worked as the VP/Division Manager of a home building operation, responsible for land procurement, subdivision, development, and construction of up to 125 homes per year. In 1989, they founded The Pinnacle Real Estate Company, Inc.

In 2014, Rich Rudy founded Manor Ventures LLC, a company that acquires residential properties and renovates them to create beautiful homes for families in Maryland and Southern Pennsylvania. Additionally, Manor Ventures has a social mission of providing employment opportunities to individuals recovering from alcohol and substance abuse. The end dates for both positions are not provided.

Rich Rudy received their Bachelor of Science (BS) degree in Business from the University of Maryland, where they attended from 1979 to 1983. Rich also obtained a Bachelor's degree from the University of Maryland, although the specific details regarding the duration and field of study are not provided. Additionally, Rich Rudy obtained a certification in "Guy Kawasaki on How to Rock Social Media" from LinkedIn in August 2018.