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Mr. Kleinmann was the President of Freshpair.com from 2001-2011, an online retailer of mens and women's undergarments which he started running from his bedroom and grew into a well established and respected company. A signature achievement was creating National Underwear Day. This annual event came to include multiple underwear fashion shows and an all-star event with celebrity guests garnering press coverage on The Today Show, Good Morning America, CNN, and thousands of other media outlets worldwide. In 2011, Mr. Kleinmann sold Freshpair to start The Underwear Expert, a site that covered the global men's underwear industry, created content, and covered the 600+ brands. The site quickly became the largest men's underwear site in the world and Mr. Kleinmann was quoted in Men's Health Magazine as well as The New York Times. In 2015, Mr. Kleinmann decided to use his expertise in the industry and evolve The Underwear Expert into an underwear of the month club. This subscription model company curates underwear based on the customers personal style, giving them controls to fine tune their monthly box as well as providing access to underwear brands around the globe in an expertly curated platform.