[4][5][8] Weiland studied economics, Spanish literature, and business management at Vanderbilt University before moving to the fashion and design industry.

[10] Weiland, creative director of the Timo Weiland brand, and Eckstein, design director, climbed up the DJ circuit under the stage name "Timo+Alan" and have performed at New York City hotspots such as the Soho Grand Hotel, the Red Egg, The Brooklyn Museum, The Met, The Museum of Arts and Design, Jumpin Jack’s, David H. Koch Theater, and the Lincoln Center.

[14][15][16][17][18][19] In the summer of 2018, Weiland cofounded The Lead, a vertical media company designed to help fashion and lifestyle retailers find business opportunities in the technology market.

[27][28] It was announced in September 2015 that Weiland would be working with Banana Republic to produce a capsule collection for the Spring 2016 line.

[30] Later that same year, Weiland's company was named the style director for Crowne Plaza and debuted a line of uniforms for the hotel chain.