Casting a memory back to 2011 isn’t difficult for longtime Television Producer & Fashion Entrepreneur Chuck Holliday: the New York City native was freeing himself from the fallout of a messy breakup that spilled into public view in the middle of New York Fashion Week, which resulted in the overall opinion changing overnight for the usually private Holliday.
Chuck believes he has finally gotten his reputation back, although he acknowledges that his preference for keeping his personal life private has still left a taint on his image.
He was a fixture in NYC’s fashion/social scene during the early 2010’s and was best known for his obnoxious behavior and cold stare-down on the ‘Brotherhood’ themed reality series “TLNA: The Late Night Alumni” (Holliday also served as the show’s producer). He had a ruinous relationship with fitness model & one-time TLSR writer Valencia Garcia, which ended badly… and very publicly.
Later in 2011, Holliday, while shooting for a pilot in Jamaica, allegedly witnessed the aftermath of a fight shortly after arriving to his hotel. That ensuing fight resulted in what he claims was loud gunshots heard on the property. Less than 2 hours later, the producer headed straight for the airport and flew back to the U.S., making it clear he wouldn’t be back. His departure scuttled the pilot, costing the cast and production crew sizable paychecks. He was later fined $10,000 and suspended for 7 years by his union (eventually reduced to 5 years).
He shifted gears in 2016 when he relocated to Charlotte and launched a Men’s Fashion Accessories Line called Made Lifestyle Collection. The reviews weren’t initially great, but it got him away from the negative stigma that followed for 5 years. He has since gained a Perfumer’s License and creates custom Fragrances as part of the collection. Holliday says the line is cash flow positive.
While never ruling out a return to Television Production, the 46 year old has embraced a new career that came out of left field: Podcast and Radio. “The Match Off” is a weekly Syndicated Radio Show slated to debut in the Fall 2022 in 25 markets (a distributor has not been announced, but is rumored to be Audacy) and is based on his successful dating Podcast, “The Date Sheet-Exes+Owes,” hosted alongside former Publicist turned Film Producer Shanda Foster.
In this new show Chuck Holliday will employ the trademark insight, humor and humanity that has made him a surprise hit as a Podcast host. Holliday hopes the new show will help listeners make sense of the current dating and social climate through spirited, agenda setting conversations with entrepreneurs and executives, as well as other industries.
The Lifestyle Republic: What do you want listeners to takeaway from your new syndicated radio show “The Match Off” that may be of use in their dating journey?
Chuck Holliday: First off, I’m not a relationship expert. I never claimed to be, never will, and have no desire to run around in a cheap suit & tie sitting on platforms doing stupid hot takes that are disrespectful and onerous. I wanted to do a show that celebrates the spirit of dating and Work/Life Balance. Today’s social and dating climate is so predicated on how a toxic rapper perceives women that we all forget that a normal dating life isn’t as bad as people make it out to be these days.
The Lifestyle Republic: Do you feel you’ve missed out on close friendships due to your workload?
Chuck Holliday: No. I look at my scheduling for major moments in my life or someone else’s life and just say, ‘I can’t,’ or, ‘No, it’s not going to work.’ And I never had the thought to be able to bend for that.
The Lifestyle Republic: What kind of mark do you want to leave with this new radio show?
Chuck Holliday: I’ve never thought about it. I will say that it’s wild how black men have completely changed the opinion of how dating works according to them. You have some men who will say that the strong independent thing has destroyed some women and that having kids makes them undesirable. Who on earth says that with a straight face and believes that? How is it that a successful football player who loves his wife and lives by a desire to be good in life is viewed and labeled corny and a square? Some of the issues start with my community being comfortable with embracing hopelessness and shunning the desire to do better. Remember when Nick Cannon was considered corny just a few years ago because he never got himself caught up in any gang dealings? Now he’s celebrated for announcing he’s having new kids every week, which is something my community identifies with more than him wanting to maintain a gang-free image.
I want this radio show to remind people that we once used to celebrate upward mobility and encouraged it amongst friends and colleagues. That concept in my community is mostly gone outside of the old guard, and it’s why we are perceived outside of it as aloof and clown-ish.
The Lifestyle Republic: In the era of social media, it can be challenging for some to really put in the work to carve out their own lane — When did you realize it was best to pave your own path and avoid the trends with this radio show?
Chuck Holliday: Trends are just what they are – trends. This is real life and that deserves more than just a quick social media footnote. I try and do what I do from the mindset of the everyday viewer on TV or listener in audio. Even when I did ‘TLNA’ years back, I wanted the presentation to feel like the average man leaving his job and going for a drink with his friends. I thought the show presented that perfectly, regardless of how the episodes later played out.
The Lifestyle Republic: How do you handle the losses or ideas that don’t work and what is your message to people who may feel defeated on the path to chasing their dreams?
Chuck Holliday: Everyone has ideas and sometimes it doesn’t work. This brand we’re currently doing this Q&A for has undergone 2-3 name changes since 2005, and it’s perfectly okay. For every reality show like ‘The Singles Project’ and ‘Brooklyn 11223’ that broke through, there’s a ton of shows that failed. For every concept that I’ve done that has worked, there’s 2-3 others that I launched beforehand that didn’t work out. It’s okay when something doesn’t work out, but the most important part about it is taking the teaching lessons from that and going back to the lab stronger than you were before. People don’t realize how difficult it is to create a fragrance. You’ll see the cologne bottle and the finished product, but you won’t see the 12-15 formulating bottles in the lab of drafts that didn’t smell right and therefore had to be re-created from scratch all over again. Even with the process of launching this upcoming radio show, some of the women I had in mind as co-hosts made it known early on that they didn’t really desire to do the work involved with co-hosting a show and just wanted to show up, fearing that if the numbers aren’t good, it’s a clean walk and no one will see it. That’s sad that we’ve become this now rather than just challenging ourselves to do the work. I’m someone who takes pride in professionalism, so I’m always on time, prepared and focused on doing my best work. I get ridiculed for that, but in the end, no one can say anything about me doing my job with dignity and pride.
The Lifestyle Republic: How would you describe your business model and the work that you do?
Chuck Holliday: What I’ve done is create a lane that works specifically for me, and I can be the guy who produces a show for video, co-hosts a Podcast or Radio Show and then works on Fragrance without having to be that guy all in the same week. I keep a clean image and I don’t care about having to be front and center or having to have a spotlight put on me. Beyond any level of talent, my biggest attribute is being extremely passionate about the work. All of these things have allowed me to be successful and continue thriving through changing times. I don’t ever have to worry about potential roadblocks with referrals given to me based on behavior or constantly arguing with people on places like Twitter. Everyone wants to manifest something yet won’t do the actual work that comes with it outside of smiling on camera or trying to look good on social media.
You also have a group of people who constantly argue on Twitter, and that gets them nowhere but posting hope quotes because no programming directors want anything to do with them based on their toxic behavior on social media. If I’m a programming head and I’m seeing a rising talent constantly bickering on social media, I’d steer clear of that, much like what most programming directors are doing these days anyways. Memorable moments may always last, but reputations always stain. I’m blessed to have had a long career in Television and can return if I wanted, but thankfully I’m always looking for a new challenge.
When you just do the work that’s put in front of you with pride and dignity, everything else always works itself out in due time. And that’s all that matters in the end.