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Masekela was born in Los Angeles, the son of a\\xa0Haitian\\xa0mother and South African jazz musician\\xa0Hugh Masekela.\\xa0Masekela is also the older half-brother of\\xa0Survivor: Cook Islands\\xa0contestant Nathan Gonzalez. He was raised in\\xa0Staten Island,\\xa0New York\\xa0in the same class with rapper\\xa0Method Man\\xa0and\\xa0Carlsbad, California, where he attended\\xa0Carlsbad High School. Masekela is the co-founder of Berkela Motion Pictures with Jason Bergh. When he was a teenager, Masekela\'s upbringing brought him to Southern California, where he was first exposed to surfing, snowboarding and skateboarding.

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His career began as an intern at Transworld Publications in 1992, home of\\xa0TW Snow,\\xa0TW Skateboarding\\xa0and\\xa0TW Surf\\xa0magazines. He served as an NBA sideline reporter for\\xa0ESPN\\xa0during the 2003-2004 season. Masekela was co-host of\\xa0The Daily 10, a countdown of the day\'s "top 10" entertainment stories, on the\\xa0E!\\xa0network until it was cancelled on Sept 27, 2010 (last show Oct 1, 2010).\\xa0He was also host of both the\\xa0X Games\\xa0and Winter X Games on\\xa0ESPN\\xa0for 13 years but left in 2012 to work for NBC and NBC Sports Network through a contract with Red Bull Media House.\\xa0He appears in the "Green" episode of Yo Gabba Gabba singing the song "Hello World" which aired on Nick Jr. on April 22, 2009.

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In 2010, he was hired by ESPN to help as a correspondent in its coverage of the\\xa02010 FIFA World Cup\\xa0in\\xa0South Africa.\\xa0While working as a correspondent, Masekela was featured, with his father, Hugh, in a series of videos on ESPN. The series, called "Umlando - Through my Father\'s Eyes", aired in 10 parts during ESPN\'s coverage of the FIFA World Cup in South Africa. The series focused on Hugh and Selema\'s travels through South Africa. Hugh brought his son to the places where he grew up. It was Selema\'s first trip to his father\'s homeland.

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A native of New York, Masekela travelled the world in his youth with his father, South African jazz musician\\xa0Hugh Masekela.\\xa0Masekela\'s own band, Alekesam,\\xa0shares the name of his first film which chronicles his relationship with his father and their connection through music, which premiered at the Tribeca Film Festival in 2012.\\xa0Alekesam\'s music has been featured on\\xa0Entourage\\xa0and\\xa0House of Lies, with their newest single, "All Is Forgiven", featured on the season four premiere of the\\xa0Showtime\\xa0hit. Masekela has hosted live events, including YouTube\'s Brandcast in New York and Paris, YouTube Live on Stage from the Kennedy Center and Google\'s Zeitgeist.

In February 2014, Masekela made his\\xa0Olympic\\xa0broadcasting debut from the\\xa02014 Winter Olympics\\xa0in\\xa0Sochi, reporting features for NBC\'s nationally syndicated Olympic Zone.\\xa0He joined the Emmy-award-winning investigative series VICE on HBO as a correspondent and executive producer in 2015.\\xa0That year, he also appeared in the remake of the cult classic Point Break.

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From April 2016, Masekela appeared as the host and executive producer of\\xa0VICELAND\\u2019s docu-series,\\xa0VICE World of Sports.\\xa0The series took viewers all over the world to explore each location\'s people, politics and culture through sports. The series premiere at the\\xa0Tribeca Film Festival\\xa0on April 22. Masekela is also involved in the production company UX Entertainment. Based in Los Angeles, UXE specializes in film, commercials, music videos and animation work.

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Masekela has a clothing company, Art of Craft, which donates a percentage of every sale to charity