Evolving Creativity & Storytelling at the Pace of Pop Culture: Insights from Ira Madison III



If you want to be a successful creative, Madison III recommends surrounding yourself with creative friends


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In our digital-first world powered by social media, change is fast and constant—and there is a continual pressure on marketers and their partners to keep up (or miss out on critical opportunities to grow and engage with target audiences).

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During #SMWLA, Ira Madison III sat down with Grey West‘s Bevan Mahaney for a conversation around staying relevant by drafting off or creating for pop culture — and how to maintain your voice and message in the process.

The creative process & stay abreast of pop culture trends

On Keep It! Madison III and his two co-hosts cover a wide variety of topics spanning race, sexuality, and celebrity gossip and get the opportunity to interview and interact with funny and fascinating faces every week.

In discussing how he identifies people to host and what topics will be covered, he described “it’s basically what happened..we’re pretty topical…we find out what’s trending, what people are talking about and go through each story over the weekend and by Monday we decide what we’ll talk about the next day.”

More generally, as much as possible he tries to follow the practice of steering clear of topics he isn’t genuinely interested in. The one exception being ‘mega news,’ but even then if it’s big enough news there is a likelihood you’ll develop a curiosity to discuss what it is.

When asked for his secret in staying ahead of the latest pop culture trends, Madison III had a simple answer: “I’m glued to my phone…it’s hard to take media breaks, even when you’re on vacation…you want to be politically and culturally literate.”

Keeping a positive vibe

If you want to be a successful creative, Madison III recommends surrounding yourself with creative friends. He says that this is reflected in his conversations on Keep It!

“If you’re a creative person, specifically in LA and the industries we work in, it’s easy to get wrapped up in your work and the idea of trying to keep up with the Jones’ of the industry. It’s great when you have friends as creative as you and as interested in the same things you’re talking about.”

He went on to describe that a lot of the conversations that he engages in on a non-professional, everyday life basis serve as an inspiration and help formulate the opinions he’ll ultimately deliver on the podcast. When this happens, “it doesn’t feel like work – rather it’s preparation for the show,” he explained.

Beyond serving as fuel to continue delivering high-quality podcast episodes, Madison III also added this is important in avoiding your own “echo chamber.” In other words, pushing yourself to look outside of your own perspective before fully formulating your thoughts on a given story. As examples of who he particularly looks to, he mentioned Allison Davis, Wesley Morris, and Jenna Wortham.

“You read their works and you get them coming to you as opposed to seeking out the entire website,” he added.

None of this is to say there isn’t a level of healthy competition amongst Madison IIi and his friends, “if there wasn’t any at all, we probably wouldn’t be who we are,” he said. The differentiating factor is that they feed off one another and in turn, push and build each other up to be greater together as opposed to bringing one another down.

The role of bloggers/commentators/podcast hosts in pop culture

In the context of red carpets and fashion, Madison III expressed “there’s this idea that people bonk against criticism…there’s someone you don’t know judging you but you have to think of it as a push and pull and how criticism creates the culture and a necessary part of it.”

Taking this example further, he articulated that there are celebrities and reporters who are talking about whether they look good or not in this dress or outfit, but it’s also the fact that they’ve been provided the wardrobe for free and wore it because the designer wants people to see and critique it. ”If you’re participating in this you have to participate in the other part.”

“Criticism is very good in terms of television, and films and books and other culture because you constantly can’t have …a culture as I said earlier that’s an echo chamber and a lot of people now have built their own echo chambers where they don’t hear any criticism.”

The role of brands

When posed with the question as to whether or not brands have a role in cultural movements and conversation Madison III explained, “whether or not they’re doing an ad or tweeting, they have a voice. If a brand wants to advertise on Tucker Carlson for instance, that’s having a voice whether or not they know it.”

He added that if your brand wishes to be engaged with a community and is interested in supporting a cause at one point in the year, support it year round. Be proud about your brand’s beliefs and you’ll attract the right people.

“Instead of creating an activation around a tent pole because this is the moment we celebrate Pride for instance if that’s the community you want to target, support Pride year-round not just in June – that’s when you see what a brand truly represents,” Mahaney added.

In short, prove to your audience there’s authenticity behind your dedication to them and make them feel heard and seen outside of the confines of a given month, day, or week that may be devoted to them.

As a piece of parting advice for creators looking to kick off their own podcasts, he shared, “pretty much anyone can do a podcast.” The key requirements: the ability to record it, edit it, and have the tenacity to keep going until you develop a following.

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