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In November 2011, Manwin became an operating partner of Playboy, managing the brand's online and entertainment business Playboy Plus Entertainment, which operates a number of television channels and online services based in the UK and Benelux.
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Manwin also created 3DXSTAR in a partnership with Funky Monkey Productions. In June 2011, Manwin bought all adult related assets of Carsed Marketing Incorporated, including Twistys, Twistys Cash Affiliate Program, GayTube, SexTube, and TrannyTube. In May 2011, Manwin acquired the pornographic video sharing website YouPorn. The 2010 Manwin purchases accounted for US$130 million in debt and the company raised US$362 million in financing from 125 secret investors including Fortress Investment Group, JPMorgan Chase, Cornell University in 2011. In December 2010, Manwin entered into a partnership with Wicked Pictures to manage Wicked Pictures' paysites.
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In November 2010, Manwin introduced celebrity news website (now defunct). In September 2010, Manwin acquired EuroRevenue, which owned various niche pornography sites. In June 2010, Manwin opened non-adult video sharing website (now defunct). Manwin went on an acquisition spree of other popular pornographic entities. Thylmann also bought in a separate deal during the same period. In March 2010, Thylmann bought the assets of Mansef and Interhub, and merged the properties into a new entity called Manwin. The domain name was first registered in August 2007. Between 20, Thylmann bought three more websites: MyDirtyHobby, Webcams, and Xtube. Mansef was run as a familial business with several of the company managers being related to each other Manos, Youssef and Keezer later wanted to sell the companies, looking to move onto other ventures. Matt Keezer started PornHub in 2007 under Interhub in which Mansef was also a partner. In 2006, Thylmann sold his shares in the company that controlled NATS and used the proceeds to purchase the Privat Amateure website. It later launched Brazzers and a porn production company among various other pay sites. Mansef was funded by Concordia University graduates Stephane Manos and Ouissam Youssef (Mansef a portmanteau of the two's surnames) in 2004 as the holding company for various " thumbnail gallery post" websites and an affiliate network. In the late 1990s, German-born Fabian Thylmann created NATS (Next-Generation Affiliate Tracking Software), which was used for marketing pornography across different websites.