I got the chance to sit down with a man of many talents, Tom Flanagan. He’s worked making TV shows, commercials, concerts, launched TV networks, gaming companies, magazines and he even writes music. He worked with some of the Jackass guys on MTV, skaters from Berricks and helped rock stars climb mountains for cancer. He started a beer brand, and won awards for making fun of Crocs shoes, and they paid him to do that. 

He was at Cannes Creativity Festival launching a cool gaming career company called The Kickback which is “an educational, entertainment, and media platform with a series of live stream events focused on gaming culture. It’s mission is to cultivate innovation, creativity, and ensure career opportunities for the next generation of diverse students, including those attending HBCUs”.

After his endeavors working for different companies, he decided to open up his own holding company Irish Boy Ventures and also he has some secret stuff happening with car brands that I wish I could tell you.

I had a lot of fun during this interview, and learned a lot about versatility.

Rio Damata: So, what's your name and what do you do for a living?

Tom Flanagan: My name's Tom Flanagan, and I build media and entertainment properties.

Rio Damata: Do you work for a company or do you own a company?

Tom Flanagan: For many years, I worked for a lot of big companies in the advertising space. Since we're at Cannes, I'll mention Leo Burnett, where I started as a consultant 24 years ago. I later became an executive, ran Leo Burnett New York, and helped open offices in Los Angeles. I also oversaw global entertainment marketing, which included music, fashion, action sports, and similar areas at Leo Burnett.

Rio Damata: What is Leo Burnett?

Tom Flanagan: Leo Burnett is one of the leading advertising agencies in the world. I believe there are about 96 offices around the world at this point.

Rio Damata: What do they do as an advertising agency?

Tom Flanagan: As an advertising agency, we worked on big global clients like McDonald's and Samsung, among others. Over the years, they've made acquisitions and become part of the Publicis Holding Group, which is based here in France and is one of the largest holding groups. I left to pursue various other things, and now I have my own company.

Rio Damata: What's your company called?

Tom Flanagan: It's called Irish Boy Ventures. We're essentially a holding company, and we partner with and invest in various media and entertainment companies. We aim to build our own media and entertainment properties, focusing on niches such as gaming, luxury automotive, and sports. Our strategy is called "stacking niches," where we focus on fans of specific lifestyles and build experiences around those lifestyles to help them celebrate and elevate their experiences.

Rio Damata: That's interesting. Can you elaborate on what you mean by "niches"?

Tom Flanagan: Sure. For example, in gaming, we realized there was a need for HBCU (Historically Black College and University) schools. There's a great company in Atlanta called Community, spelled with an "X" instead of an "O" (CXmmunity). They launched the first esports league for HBCU schools, enabling black students to recognize what's possible in gaming and esports. Despite a high percentage of young black kids playing video games, less than 5% of black people have careers in the video game industry. 

To address this, we started something called "The Kickback." It's a live event that we film, where we invite students from HBCUs and high schools—initially focusing on Atlanta—to learn about career opportunities in gaming. Executives from gaming companies speak to the kids about potential careers, and we end the event with a celebratory hip-hop concert, sneaker culture, and other elements the kids are passionate about. Essentially, it's a career fair disguised as a lot of fun.

Rio Damata: That sounds really interesting. What's your advice to anyone who wants to be in the marketing field or your field?

Tom Flanagan: My advice is to become a Swiss Army knife. Be curious about every role there is to play. In advertising, I've been fortunate to have every job you can possibly have. I started as an account manager, dealing with clients, creating reports, and ensuring they got what they needed from the agency. I moved on to sales, digital, creative, and eventually became the boss, running the agency. This versatility allows me to mentor people in various aspects of their careers, whether in advertising or producing television shows, films, and commercials.

Rio Damata: So, your basic advice is to be versatile?

Tom Flanagan: Yes, be very versatile. By doing that, you'll find what you love the most and can focus on that. For instance, I didn't enjoy account management, but I'm glad I did it because I learned a lot. As I progressed, I discovered my interests lay elsewhere in the industry. Some young people make the mistake of fixating on a single role, like being a creative director, without understanding the other roles within the company. This can hinder their career advancement because they don't fully grasp how the entire company works.

Rio Damata: That's interesting. Well, thank you very much for joining us. I appreciate it.

Tom Flanagan: You're welcome. Thank you for having me.