Santi was born in the Dominican Republic. His parents moved the family to Passaic, New Jersey when he was two and then Salem, Massachusetts when he was five. After graduating from Salem High School he earned a Communication degree from Endicott College in Beverly, Massachusetts.

During his sophomore year at Endicott, he began an internship at JAM'N 94.5 doing audio production. Santi was hired as an associate producer in 2003. "I worked when they needed me, unpaid, and I made myself very visible. I learned whatever I could and I stayed in front of people's eyes. Santi started performing stunts. The show host gave him the nickname "Krazy Kulo" and subjected him to relentless bullying and often assigned him preposterous tasks to carry out live on-air. "I do it for the people, I do it for the entertainment, I do it to make him a sympathetic character.”

Santi worked his way up to co-producer and in 2007 was promoted to Executive Producer of the morning show. "You have to be able to do anything, and don't be afraid to ask questions," Deoleo says. "People love to talk about themselves so if you ask them how they would fix a problem, they are always willing to help you out and explain it."

In December 2012, morning show co-hosts were let go by Clear Channel Communications. The show was renamed " The JAM'N 94.5 Morning Show," which saw Deoleo take on a more prominent on-air role as himself, rather than Krazy Kulo. In January 2013, Real World star Ashlee Feldman was named co-host of the revamped morning show.

On July 22, 2015, Santi was released from the station, and Ashlee Feldman and a new host would host the show beginning the following Monday.

After several months off the air, mainly heading into 2016, in April, Santi was hired at another radio station and company where he worked for the next few years... Until now.

“I’m back where I belong! Sometimes a break in a relationship turns out to be the best thing for it.”

In April 2012, Santi was named one of Stuff Boston's sexiest Bostonians, "a lineup of lovely, lust-worthy locals who represent a broad range of sexy styles".

Deoleo has run and completed The New York City Marathon twice and the Chicago Marathon, as well as competed in numerous triathlons. He is active in Crossfit, a "high-intensity strength and conditioning" fitness program.