Reggie Ossé (more commonly known as Combat Jack) has a devotion to and passion for his craft that is undeniable. And it’s likely why his weekly hip-hop culture podcast The Combat Jack Show attracts listeners as wide-ranging as a 70-year-old “ride-or-die” fan and two-time Academy Award nominee Jonah Hill. He and his motley crew of singular personalities discuss hip-hop, culture and current events, and interview their guests honestly, with an entertaining mix of equal parts irreverence and respect. The show recently incited some media furor because an episode with retired NYPD Deputy Inspector Corey Pegues revealed his criminal past — controversial to some, but standard fare to those familiar with his show’s candor.
A former entertainment attorney whose past clients include industry heavyweights like Jay Z and Diddy, Ossé remembers driving his kids to school in the mornings and listening to former Hot 97 host Star and thinking, ‘I wish I could do that. I wish I was as brave and fearless and carefree.’ Walking away from his law practice to pursue a more creative path initially meant writing a book, then spinning captivating behind-the-scene yarns on his blog Daily Mathematics, and then eventually co-hosting The Combat Jack Show, where it’s clear that he is having the time of his life bringing the stories of people he admires to the world.
Here, Ossé shares his advice on making it in the podcast world and offers wisdom on how to make your passion your reality.
Name: Reggie Ossé
Position: Host, Internet personality
Resume: Began his career at Def Jam’s business and legal affairs department, then worked as an associate at West Entertainment Services. Was co-founder and managing partner of the entertainment law firm Ossé & Woods, which became Wade, Ossé & Waldon in 2001. Worked as VP, audio/music DVDs, at MTV Networks; then co-authored Bling: The Hip Hop Jewelry Book. In 2009, began writing as Combat Jack for his Daily Mathematics blog and went on to write for sites like XXL.com and Complex.com. Was a managing editor at The Source. Started The Combat Jack Show in 2010 as a hip-hop culture Internet radio show, now a podcast, that also concurrently ran as a video series on Complex TV in 2013. Co-founder of Loud Speakers Network, home of podcasts The Read and The Brilliant Idiots.
Birthday: July 8, 1969
Hometown: Brooklyn, NY
Education: BS in industrial labor relations from Cornell; JD, Georgetown University Law Center
Marital status: Married
Media mentors: “I kind of jumped into this, so I don’t have a mentor, per se, but… the two [media personalities] that really inspired me are Howard Stern and Star from Star & Buc Wild.”
Best career advice received: “When I interviewed Jessica Rosenblum, she said the best career advice she got was from her late mentor Chris Lighty: ‘Stay in your lane and master your craft.'”
Guilty pleasures: Hip-hop group Migos, comic books, Byron Crawford
Last books read: Queens Reigns Supreme, by Ethan Brown; and The Isis Papers by Dr. Frances Cress Welsing
Twitter handle: @combat_jack
When you look back on your professional life, were there any singular events or experiences that foreshadowed that you’d one day be Combat Jack?
Initially, when I started practicing law, I was very intimidated by my inability to write or to tell a narrative or to really communicate in words. And after years of writing letters and agreements and going back and forth with attorneys and record labels and managers, when I started blogging 10 years ago I was like, ‘Oh s–t, I can write.’ So [I gained] the ability to write through all my years as an attorney without even realizing that that was the skill I was gaining. My listeners say the way I ask some of my questions is as if I’m interrogating somebody like an attorney. But as an attorney, you’re trained to really get as much of the facts as possible out of someone. When I would get a new client and they would be telling me what situations they were involved in or what deals they had, I would try to get as much of their life story [regarding] that issue as possible, and I realize I’m doing the same thing now.
The Combat Jack Show has a very personal feel and because of that you’re really good at getting people to open up. How do you prepare for your interviews?
Well, another thing that I benefit from as an attorney is that I’m very anal with my research. So I study almost everything that I possibly can about my upcoming subjects. I’ll buy any books online immediately about anything that pertains to my subjects. I go over almost any accessible interview that they’ve done over the past 10 to 15 to 20 years so I can [find] things that are not necessarily well known about them as well as events or topics that have already been covered so I can avoid them. I put in hours of preparation for almost each and every guest. Being armed with all that information [makes me] very confident. I’m also pushing the interview to be a conversation.
What did you learn from the experience of bringing The Combat Jack Show to Complex TV?
[I learned] that bringing the podcast to the television medium is possible and that it is something that I do want to do and investigate further. People are calling me the Charlie Rose of hip-hop, and I’m really honored by that. [I’m] taking something and really bringing depth and intelligence and human interest to it. So I really want to continue on that trajectory, but I also realize that it’s very difficult to expand my brand to other mediums. I think Complex did a good job, but there was a huge backlash from my core audience initially. So I really can’t jump at every opportunity that comes my way because it’s a check or a broader platform. Not saying that that’s what I did with Complex, but I learned through my experience that I have to be more mindful. Being on a podcast platform, you really develop a unique, intimate relationship with your audience, and it’s so intimate that if you deviate even slightly it could damage that relationship. And that relationship, really, is all I’ve got. So if tomorrow I was offered millions of dollars to do a nightly talk show, my main concern would be, ‘How do I still deliver quality content on The Combat Jack podcast?’ You can’t alienate your core audience.
So let’s say in a perfect world that you were able to do this without alienating the core audience. How do you envision your own late night show?
I would strip it down and it’d be the Charlie Rose show. Me, my subjects and the guests. That’s it. I do like the look and the tone of Oprah’s Master [Class] series. It’s still one-on-one, but with a little bit more flexibility in its presentation.
What advice would you give someone who wants to be in your shoes someday?
The great thing about social media right now is that it provides a platform for anyone who is passionate to find their voice. So find your voice and don’t be afraid to fine-tune, even publicly, what that voice is. The Combat Jack Show has changed its format several times on air, and we’re still trying to figure it out. There’s no formula. In this age where transparency is a premium you have to be honest. You also have to find something that speaks to an audience. In the podcasting world, you have to train your audience and be as consistent as possible. If you’re going to be a weekly show, be a weekly show — even if no one’s listening to you, or you think no one’s listening to you. And be good. Not everybody’s meant to speak publicly.
The cost of entry right now is so easy, but because it’s so easy everybody now wants a podcast. You have to find a way to make your show stand out from the hundreds of thousands of podcasts that are out there. I’m in my 40s. I lived through the ’70s, the ’80s, the ’90s. I’ve worked in the music industry. I’m still a big kid. All of that makes my voice unique. I’m an attorney. I grew up in the hood but I’m also Ivy League educated. That’s unique.
You’ve thanked Kanye West before for showing you how important it is to believe in yourself. How do you maintain that belief in yourself?
I can humbly say that I’m changing the game because I wholeheartedly believe in what I’m doing. I remember hearing an early Kanye talk to me about how he’s going to be respected as one of the greatest rappers in the world and I’m looking at him like, ‘You’re crazy.’ But he was crazy and that insanity was that he believed that and it worked out.
I’m a very spiritual person, so I definitely believe that [your] thoughts become your words, and then what you speak about becomes your reality. So even early [I was] watching [people] like Biggie and Tupac and even Jay Z and the paths that their lives took. Tupac’s so rebellious and just ‘thug life’ — and I’m not saying that’s all that his art consisted of, but his voice reverberated so much on a certain frequency that eventually, I think, it led to his demise. Biggie also. He was so visceral with regard to gun violence. And then you’ve got Jay Z, who nobody believed in but is talking about all of this success — even at a time when I was looking at him and was like, ‘Man, you’re out of your mind.’ And then years later look at what his thoughts, his words and his actions manifested.
Even now a lot of people are saying, ‘You can’t do this. You can’t do that. You’re too old. Your subject matter’s not engaging. Your shows are too long.’ I still get a lot of ‘can’ts.’ The biggest obstacle I faced towards the end of 2013 was, ‘Well, you’re not right for the millennial audience.’ I just [dug] in deeper because at this point in my life this is all I have. Other than my family and just living and breathing, this is the only thing I’m passionate about 24/7. This is what I want to do for the rest of my life.
Janday Wilson is a storyteller based in the greater New York City area. You can find more of her work at jandaywilson.com
This interview has been edited for length and clarity.