Digital Jeff (Castillo) Just Might Be Instagram’s Favorite Photographer

Leaders Create Leaders and Legends Train are just two of the media machines associated with prolific content creator “Digital Jeff” Jeff Castillo. He boasts an impressive resume that features work with some of the biggest names in entrepreneurship such as Gary Vaynerchuk, Suzy Batiz,and long-time collaborator Gerard Adams. 

Jeff developed a passion for photography early on in his life in his hometown of Laredo, Texas where he would make the 90s version of viral videos with his VHS camera.

“The reason I think I fell in love with film making was that I was able to bring over my friends from around my neighborhood [to watch my videos] and there was one time where night after night people wanted to re-watch the same one.”

— Digital Jeff Castillo, videographer and speaker at Miami Art Summit.

When Jeff was 17, his life took an unexpected turn when he married his girlfriend that was expecting their first child. Unconvinced that he would be able to support his family with his paychecks from Pizza Hut, Jeff saved up enough money to buy a new camera and got to work. After some paid gigs, he was able to open his own studio and by age 20 Jeff knew that he would be able to provide for his family through his photography.

Eventually, Jeff enrolled in college and opened his agency, The Digital Republic, after graduating. In 2015, despite the success of his business, Jeff found himself feeling unhappy and dissatisfied — so he decided to close down his studio to pursue his dreams. 

Digital Jeff, known for gritty, acerbic New York street-scapes.
The hustle

Jeff decided that he was going to travel to New York from Laredo to film a documentary called “Hustle New York” with a list of 12 different people that he wanted to feature in the film. After tracking down Gary Vaynerchuk for an interview at a Jets game, Jeff met his future business partner Gerard Adams. Initially, Jeff had just planned on interviewing Gerard for the documentary but they quickly became friends. The two began collaborating on videos together for Gerard’s YouTube channel and they ended creating an online series called Leaders Create Leaders.

Leaders Create Leaders has since evolved into so much more than just a webseries. Recently, Leaders Create Leaders has developed a two-day workshop program geared towards the most promising entrepreneurs of the future. In addition to all of his endeavours with Leaders Create Leaders, Jeff has created a fitness coaching brand with his wife, Suzy, called Legends Train. Together they offer bootcamps, online coaching, merchandise, and weight-loss programs through their website. They also provide the public with motivational content through their social media platforms. 

In Miami for Miami Art Summit? Hear Jeff Castillo speak on all things digital, art, and the videographer life in conversation with Grit Daily’s Jennifer Matthews at 5:25pm – 6pm on Jeff Castillo & The Art of Instagram.


Samuel Loetscher is a Columnist at Grit Daily. Based in Miami, he currently works in e-commerce and writes about Latin America and South Florida.

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