I had a nice sit down with Oscar Santana over at the Wonderland Ballroom outside on the patio on a cloudy Sunday evening. Santana’s friends dubbed him the “Prince of Podcasting” and it is understandable. He is part of the DC based Big-O and Dukes Show, The Mike O’Meara Show, and Tech 411. All of these podcasts combined have achieved over 10 Million downloads. Please be aware that what you are about to read is a tale so epic that you will never use the word “epic” to describe how good your burrito was.
Santana was born in Bolivia and came to D.C. with his family when he was three years old. His father was part of the Pan American Health Organization and got a contract to work in the Nation’s capital. The contract was originally only supposed to be six months, but it turned into a permanent gig and Santana grew up in the United States. “I really grew up riding the metro hitting the city my parents. My mom got a job in the city as well. I was a D.C. kid. While I respect my roots and I love the fact that my parents were able to carry that from La Paz, it’s the best of both worlds. This is my home.”
Santana discovered his passion for radio at West Virginia University. “I loved radio ever since freshman year in college.” His parents were not too excited to hear about his dream to find a career in broadcasting. “They were super old school. Three things mattered to them. Doctor, lawyer, or engineer.” He explained that his parents did not understand any other way to make a living other than these career paths, so Santana compromised and chose to pursue a degree in marketing and get an internship in radio. “The whole time I was there I was working on my degree just as much on my radio career. I would do overnight shifts and morning show shifts.” He got a gig being the hip hop DJ at one point and enjoyed hearing from his listeners that were permanent residents at a prison near the station. “I was getting an email or a letter from someone that’s locked up for life saying, ‘Please play this song.’ I felt a connection with the audience and it was always glorious.”
Santana was about to do another summer internship at the station in West Virginia when his station manager encouraged him to try out for an internship position with WHFS in Washington. “That’s a legendary rock station.” He made the trip back home the next day to apply for the spot and got it. His role at the station turned into a part time job after he graduated, but he had to keep his dream of being a talk show host a secret from his parents. “I was studying for the LSATS, pretending that I was going to do something with law.” What he was really doing was working at the station. “I was just stacking boxes and driving vans. I wasn’t on the air. Every opportunity I had I just grinded to get one more step into that studio.”
Two years later he is 25-years-old and saw an opportunity to fill in for a evening jock that couldn’t make it to work. “I was with my assistant programmer and said, ‘I’m ready to do this.” The assistant station manager took a good hard look at Santana and then looked at his phone and quickly called two other jocks to see if they could fill in the spot. No one was available. Again he took a hard look at Santana and asked him, “Do you know who Wally Pip is?” Santana had no idea. His station manager then explained “You don’t know who Wally Pip is because Lou Gehrig stepped in his place.” Santana interpreted the story as the station manager telling him to “Go and be great!”
Santana stepped up to the challenge and modestly told me “I did a decent job.” He became a fill in for jockeys that could not make it to work, but then a seismic shift in jobs at the station happened and everything changed. “I was trying to keep my head above water.” After all the change he landed a full time spot on a morning show called Junkies in the Morning. He gained a new job and, unbeknownst to Santana, was about to meet a lifelong friend and radio partner. “They brought some guy that was part time. Chad Dukes. We got pinned against each other. Two guys on opposites.” I was thinking about Lethal Weapon when Santana described to me how they partnered him and Dukes on the show. It was just like Murtaugh and Riggs.
The Junkies noticed that the two had good chemistry on the air as the two worked together more and more. They became friends and just like in Lethal Weapon, one day Santana found himself on a toilet with a bomb on it. Wait. I’m getting lost in the metaphor. That didn’t happen. “We ended up putting a demo together over a dominoes bacon cheeseburger pizza in a small studio. We thought that is was great and gave it to the program director who didn’t listen to it for seven months.” After the long wait they finally got their show, which started at midnight and ended at one in the morning on Sunday nights.
They both were super excited to have the opportunity. “Wow we have a show!” Then the guy who gave them their shot was fired and a new program director from KROQ in Los Angeles took his place. “Lisa Warden came along and said ‘It’s not every day that a van driver and an intern get their own show on a major market radio station.’ As hurtful as it was it was true, because I was a promotions guy and Chad was an intern. Slowly but surely she warmed up to us and gave us direction. She was a great mentor.” Warden helped them hone their skills and then an evening slot opened up on Friday evenings. “This is our big shot.” Santana explained that in traditional radio you don’t need two people to run the evening shift, but the two wanted to work together during that time slot. Things got intense.
“They split us up and pinned us up against each other and then they made us work together. It was like you are fighting your best friend.” Meanwhile, the station tried out people from all over the country for about four months to get the evening slot filled. “We thought we’re never going to get this gig, but the one thing I learned in college is you have to make a bigger splash.” Santana got the idea to rent a mobile billboard company to promote their show. He paid for it with the little saved money he had at the time. The sign read “Big “O” and Dukes the Future of WHFS is Now!” Dukes and Santana drove to Warden’s house the day after they got the sign around 6:30 in the morning and called The Junkies while they were on the air to tell them to call Warden.
The Junkies woke her up on the phone and instructed her to look out her window. “She opened it and right outside was our two big faces.” They got the full time gig to do nights in D.C. and all was well, but in just six months the station flipped to Spanish. “I remember when it happened. I had gotten in my car and turned on the radio and it was Spanish music.” He further explained, “Radio is a cruel mistress. She will treat you well and it’s like you’re in love and you’re going to be married forever. But anybody that’s ever gotten into radio will tell you that you are not really into radio until you get fired”.”
Did I mention that this is an epic tale? That means that there is more to come. Check out “Podcasts of DC: Oscar Santana Rises Reloaded!”