Berra’s first sponsor was Blockhead, which led to his experience with the “Blockhead House”, where he met fellow skateboarder Jason Dill. He then moved onto the 101 skateboard brand, owned by Natas Kaupas, and he has since stated that “I didn’t have a good time on 101”. Before Kaupas could assign Berra the status of a “professional” team rider, Berra quit 101 and joined Tony Hawk’s Birdhouse company. While with Birdhouse, the 23-year-old Hawk was a mentor figure to Berra, leading to Berra’s initial forays into acting. In 1992, Berra left Birdhouse and since admitted that his departure was due to being “young, misunderstood, and silly.” Several months later, Berra joined the Foundation team, skating in the company’s 1993 video, Super Conductor Super Collider.

In 1998 Berra returned to Birdhouse to create the skateboarding video The End. In one of the notable scenes in the movie, Berra’s death is simulated in a decapitation scene (filmed with the aid of a dummy).

Berra has maintained an interest in acting since the age of 18. He was a series regular on the short-lived Fox drama 413 Hope St., portraying Quentin Jefferson, a young man infected with HIV. Berra has also held brief roles in the television shows Felicity and Nash Bridges, as well as a minor role in the 1999 film Anywhere but Here.

In 2003 Berra struggled with severe ankle pain that prevented him from skating for most of the year and he underwent reconstructive surgery in January 2004. Footage of Berra entering ankle surgery is featured in the DVS Shoes (formerly DVS Shoe Co.) video, Skate More, a production that he managed to film a full part for.

Berra grew up in both Nebraska and Missouri and he explained in 2007 that his family was poor: “I was considered poor when I was growing up. I didn’t have a phone.” Berra was bullied at school for skateboarding and struggled as a student, with Berra stating that he “was the kid who everybody assumed was a complete lost cause.” It was at the age of 14 years that the isolated Berra, who had a small number of friends at the time, decided that a professional skateboarding career was his aspiration.

The Berrics concept was primarily conceived by Berra, who enlisted close friend, Koston, to invest in the premises that contains the training facility. Located in Los Angeles, U.S., the facility’s name is an amalgamation of the pair’s individual names: Berra + Eric = Berrics. In 2009, skateboarding journalist, Chris Nieratko, gained entrance to the skate park and its cardinal rule: “You have to film while you’re skating The Berrics.” The footage is later posted on The Berrics website, TheBerrics.com. TheBerrics.com grew to become one of skateboarding’s most popular websites in only several months: “In January, the site had more unique visitors than sites for all of the major skateboarding magazines, and ESPN.com’s action sports page, according to comScore, a market research firm.”

As of August 15, 2013, Berra has not been filmed with his two children on the Berrics, or any other media, but he responded to a fatherhood question in 2009 in the following manner:

As of 2013, Berra regularly appears on the website venture The Berrics that is co-owned with professional skateboarder Eric Koston. As of March 2013, Berra is no longer a member of the Alien Workshop team and his sponsors are DC Shoes, Grizzly Griptape, Skullcandy, and The Berrics.

Following the commencement of a new chapter of the Berrics project in early 2013, whereby a new premises was officially opened and the website was reconstructed, Berra has collaborated with professional skateboarder Paul Rodriguez on numerous projects, such as the Network A series “LIFE” and a Mountain Dew commercial entitled “Progression”.