So What Do You Do, Reggie Ossé, Host of The Combat Jack Show?

Combat-Jack-WP-artReggie 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.