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How to lead by listening: What growing up on MTV taught JoJo Simmons

Reality TV star, music producer, and serial entrepreneur JoJo Simmons on the power of listening and the massive benefits of switching off.
A black-and-white portrait of JoJo Simmons is centered between an image of a film camera on the left and a close-up of a hand adjusting audio mixing controls on the right.
Last Prisoner Project / Ben Collins / Getty Images / Unsplash / Big Think
Key Takeaways
  • JoJo Simmons grew up in a family with its own reality TV show and has become a serial entrepreneur.
  • “If you know how to speak to people,” says Simmons, “you can close any deal, walk into any room, make anything happen.”
  • Here, Simmons reveals his tips for better communication and offers an essential nugget of advice for young entrepreneurs.
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For JoJo Simmons the road to leadership was not exactly conventional. But the lessons he has picked up along the way, shared here with Big Think, are packed with valuable insights that resonate across a broad swath of common ground. 

Simmons grew up in a family with its own reality TV show — and one that enabled him to build a legacy of his own. After starring on six seasons of MTV’s Run’s House — where viewers were invited inside the home of his father, ordained Pentecostal minister Reverend Run, an original member of hip-hop group Run-DMC — Simmons went on to found two companies: record label Whos House Entertainment, and 3isFor, a content strategy and media production firm focused on telling stories about mental health and personal growth.

Continuing his family’s humanitarian streak, Simmons also became involved with numerous non-profits, serving as an ambassador for the Last Prisoner Project, as well as the manager of Whos House Ballers, an amateur basketball team for underserved youth from Queens. He currently hosts the For Good podcast, where he invites his guests — including rapper Lil Eazy-E and psychologist Cheyenne Bryant — to chat about topics such as overcoming adversity and living with purpose.

In the following interview, Simmons reveals what allows him to juggle so many different projects, why everyone should go through a rebellious phase and “bump their head,” and how he keeps his private and professional life in balance.

Big Think: Growing up in a family with their own reality TV show probably comes with some unique challenges. Did you feel pressured to live up to people’s expectations?

Simmons: My TV career started when I was about 14 or 15 years old. Before then, I didn’t feel much pressure. We were seen as both a prestigious Black family, and a church family — a family that walks the straight path. As you grow up, you experiment with things, and I definitely felt pressure to make sure that I upheld the family name.

I felt I always had to live up to my father’s standards with regards to how he wanted us to behave publicly. As a kid, you don’t understand how big something is. Your parents just tell you that it’s bigger than you, and you need to act accordingly.

I think I handled it well for a while, but then I went through a bit of a rebellious phase, and started doing what I wanted. Later, when I took a step back, I finally saw for myself just how big it was. At the same time, I realized that the only pressure on me was the pressure I put on myself.

Big Think: So, you think that rebellious phase was necessary to get you to where you are today?

Simmons: For sure. I’m not promoting it, but I think everybody has to go through a phase where they bump their head a few times. You think you know what you’re doing, only to learn that your way may not be the best way. Going through that stage educated me on how I should approach situations and use my energy.

Big Think: You wear a lot of different hats in your professional life. What’s your big time-management secret?

Simmons: I’m a routine guy. I find that the most successful people are people of routine. They know what they want to do and use their time wisely, splitting it up so everybody feels served.

On most days I wake up early, before the rest of the world. That way, I give myself some mental space. I go to the gym for about an hour and a half to two hours, to get the physical activity that helps my mental activity. Afterwards, I make sure that my kids are fed and off to school, and then I start work, hopping on phone calls and talking to clients.

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I don’t procrastinate. I used to be a big procrastinator back when I was in high school. However, I learned quickly that procrastination never really does anything for you, so I like to get things done right away. Not rush them, but get them done.

Sometimes, passionate and ambitious people struggle to maintain a sustainable work-life balance. 

Big Think: Clearly, you get a lot of pleasure and energy from your work. Does that make it difficult to draw the line?

Simmons: I actually make sure I prioritize myself, because if I’m not doing good, then nothing around me can be doing good. Not the companies, not my family. Every day when I wake up, I take care of myself so I can take care of everybody else. I just went on a family vacation for a few days. When you work hard, you have to make sure you relax hard, too. If you don’t, you crash. You’re not relaxed, you’re not confident, and you’re not the best version of yourself.

Big Think: Are there any particular leadership styles you subscribe to?

Simmons: I like to lead by listening. I like to listen to everyone around me, and especially to the people we hire and trust to do their job. Of course, I give input and step in when needed, but I think leadership is about instilling confidence. If people feel valuable and appreciated, they’ll work hard for themselves and for you.

The biggest thing — and this is something that a lot of young entrepreneurs need to understand — is that it’s OK to pick up the phone and call somebody who knows what they’re talking about.

Growing up in the TV and music industry, there were so many mentor figures around me: my dad, my uncle, and people like Steve Lobel, who I always give a shout-out to because he was a big help when I started my music production company. He showed me how to move in that space, which a lot of people assume I learned from my dad and my uncle, but it wasn’t just them. I also looked outside the home to see who else I could learn from.

The biggest thing — and this is something that a lot of young entrepreneurs need to understand — is that it’s OK to pick up the phone and call somebody who knows what they’re talking about. It’s not embarrassing or shameful. It’s empowering for them when they realize you respect their knowledge enough to learn from them. And you get real, valuable answers that way. I’m indebted to anyone who picked up the phone for me whenever I needed them to.

Big Think: Do you think that the business side of your professional life requires different skillsets or personality traits than the creative side?

Simmons: I’d say I’m still the same person, but when I’m in creative mode, I’m in that quirky, goofy, think-outside-the-box space. I pull inspiration from everything and just throw ideas around. When I’m in business mode, I’m more organized, more put together. That’s when it’s not just shooting things at the wall.

Big Think: You work with young artists and kids from marginalized communities — how do you help them become the best version of themselves?

Simmons: The only way is to instill confidence, tell them the truth, give them the harsh reality, but also keep them focused and on the swivel. With young kids — we’ve all been young, so you know how it is — it can be hard for them to listen to older people, because they think they already know everything. The key is showing you relate to them, that there are other options, other paths.

The same goes for the players in the basketball team I help manage. We show them that basketball isn’t their only route. Even the best players on the team, the ones that score 30 points a night and win trophy after trophy, we teach them teamwork, community, discipline — things that apply to not just basketball, but life in general.

Big Think: You’re a great communicator and public speaker. Did you learn those skills on TV, by acting, or somewhere else later in your professional life?

Simmons: TV helped, but I don’t know if that’s the main thing. I remember maybe in 4th or 5th grade, I had an English teacher, Mrs. Manners. I did a paper, and she told me I was good with words, that that was one of my strengths: I knew how to write, how to speak. That made me feel empowered as a kid, and led me to enjoy writing and speaking to people, to move and inspire them by choosing the right words and saying them in the right manner.

I’m not big on fluff. I’m big on clear communication, speaking from the heart.

And there’s a difference between speaking well and sounding like you’re something smart or interesting when, in reality, you’re not saying anything at all. I’m not big on fluff. I’m big on clear communication, speaking from the heart: genuine. Sometimes I wing it, and maybe I shouldn’t, but my team knows I don’t like over-prepping. Give me the subject, and if I’m passionate, I’ll speak for an hour, passionately. People can hear that.

And if you know how to speak to people, you can close any deal, walk into any room, make anything happen. We all love a great conversation, and it starts there. If you can hold a great conversation, that’s half the battle.

Big Think: AI is quickly changing both business and entertainment. How have you been using it in your work?

Simmons: Personally, I’ve dabbled, and it’s pretty cool. I always tell people: use it, but don’t let it handicap you. AI will never personalize like humans can. Creativity comes from people. Working with a creative company, sometimes you don’t know what your clients want. AI gives you options, but nothing hits as hard as a real person putting in the work.

Big Think: What did your experience in entertainment teach you about confidence — and overconfidence?

Simmons: When I was younger and on TV, I wouldn’t say I was cocky, but I definitely felt I had everything together, and when people found out I didn’t, that was a real ego check. The way I dealt with that, though, was to sit back and make myself understand that everybody goes through failure and everyone gets their ego checked. The only thing that matters is what you do moving forward. You can’t keep repeating the same patterns. You’ve got to learn to leave your ego at the door and just do the best you can, every day.

Now, I don’t move with ego anymore. I don’t need everyone to know I’m the boss when I walk into a room. I don’t need people to see me as powerful. I just want them to relate to me. I’ve learned to live without ego, because it’s the only thing that’s stopping us from achieving success.

Big Think: Are there any big mistakes you’ve made over the course of your career that ended up teaching you a valuable lesson?

Simmons: I don’t know if I can pinpoint any, as I’ve made a lot of mistakes. I discovered artists I probably should have signed but didn’t, who went on to become some of the biggest stars in the world.

Out of loyalty and love, I always helped people, even when — in hindsight — I maybe should have looked out for myself a bit more. I don’t regret anything, though. I’m happy to see the people I’ve helped succeed, and I still support all of them. I wouldn’t call those mistakes, but there are things I’d have done differently.

I always say I should have taken more advantage of the opportunity when I had the spotlight on me to really solidify my own legacy. I’ve talked about this a lot — I was a child on reality TV, and I still wanted to live that childhood, hang with my friends, be a teenager. If I had solidified the JoJo Simmons brand earlier, who knows. But we’re building it now.

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