2005: Kola was signed to Box Fresh Pictures as a director alongside Anthony Mandler. Many of her first videos were done with this company, including videos for artists such as Beans, J-Status and Tony Hussle. At the same time she was also writing music video treatments for established directors such as Anthony Mandler, Lenny Bass and Dr. Teeth. She wrote the treatment for Common's video "Testify" which starred Taraji P. Henson and Wood Harris. During the same time, Kola styled and modeled for the clothing line Billionaire Boys Club. 2006: She was asked to re-vamp the company of Island Def Jam as director of creative services. Antonio "L.A" Reid, president of Def Jam, said she would be "the one to keep the building cool, someone in tune with downtown cool and pop mainstream." That year Kola also started an monthly '90s party with her friend Oscar Sanchez called "1992". Playing only music from the late '80s and early '90s, the event brought out a mix of tastemakers and celebrities including Dave Chappelle, Jay-Z, Ne-Yo, Jermaine Dupri, Patrick Ewing, Redman, DJ Premier, The Clipse, Maxwell, Chanel Iman, Zoe Kravitz, Grand Puba, Lord Finesse, and KiD CuDi. Although its residency is in New York City, the party has taken place in Miami, Paris and Amsterdam. In 2008, 1992 was nominated for Best Party at the Paper Magazine Nightlife Awards and also received press in The New York Post,i-D, Trace, Paper, and a feature in The New York Times. 2008: Kola started her own clothing line, VIOLETTE. With an official debut in fall 2008, the clothing was described as "a mix of opposite worlds: uptown and downtown, hip-hop and rock, feminine and masculine, casual and couture". The following year, Vibe listed the "31 Most Stylish People Under 31" with Kola coming in at 23rd. She was also featured in Nylon as part of their lineup of "It Girls". In this year Kola was interviewed Sean "Diddy" Combs for Supreme Magazine, which was photographed by Terry Richardson, and was included in the Nike Destroyer Campaign alongside Dee & Ricky and Scott Campbell. In 2010, she was featured in a Rachel Roy campaign. Later that year, she became the first female to collaborate with Brand Jordan on her own Jordan sneaker. The shoe was offered at select boutiques nationally, most of which sold out in the first few days. Publications including Women's Wear Daily, Footwear News, TeenVogue.Com, Complex, and The Source covered the occasion. In 2011, The New York Times did a feature on Kola. In 2015, Kola wrote, directed and starred in an art film for Drake's Hotline Bling video. She also starred in the reality documentary television series3AM, which aired for seven episodes on Showtime.
