In 1985, Faena followed in his parents footsteps into the textile industry and founded the fashion label Via Vai at age 19. He launched the brand with 50 colored shirts he funded himself. The brand expanded to include ready-to-wear collections and a denim line. Faena sold the company in 1996

He was a fashion designer for over ten years before beginning a career in real estate development in 2000. He partnered with Len Blavatnik, Philippe Starck and Foster + Partners to redevelop abandoned docklands in the Puerto Madero neighborhood of Buenos Aires, Argentina. Foster + Partner's residential condominium in re-development was their first project in South America. The Faena Hotel designed by Starck opened in 2004.

The Faena District, which is estimated to be a $200 million development, is the most valuable real estate in Buenos Aires. The Faena Arts Center, a converted flour mill located in the center of the district, opened in September 2011 and displays the work of local and international artists. In November 2011, German artist Franz Ackermann exhibited the results of his voyages around Buenos Aires with the largest mural of his career in the center. The Cuban duo Los Carpinteros debuted their first solo exhibition in Buenos Aires at the arts center in May 2012.

He expanded his brand to Miami Beach with a $1 billion project to develop a six block waterfront property. Construction on the Miami Beach Faena District began in 2013. The project includes the restoration of the 1948 Saxony hotel, and an arts center, Faena Forum, by architect Rem Koolhaas and OMA and residences by Foster + Partners. Baz Luhrmann and Catherine Martin are also involved in the project as designers for the interior of the Faena Hotel Miami Beach. The district will be landscaped by Miami-based firm Raymond Jungles. The Faena House, a 18-story residential unit, is the project's first building scheduled for completion.

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