How to lead by listening
By Tim Brinkhof | Published: 2025-09-08 13:00:00 | Source: Business – Big Think
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For Jojo Simmons, the path to leadership wasn’t exactly traditional. But the lessons he learned along the way, which he shares here with Big Think, are full of valuable insights that resonate across a wide range of common ground.
Simmons grew up in a family that had its own reality TV show, which allowed him to build a legacy of his own. Having starred in six seasons of MTV’s hit show Ran’s house — where viewers are invited inside the home of his father, Pentecostal pastor Reverend Run, an original member of the hip-hop group Run-DMC — Simmons went on to found two companies: the record label Whos House Entertainment, and 3isFor, a content strategy and media production company focused on telling stories about mental health and personal growth.
Continuing his family’s humanitarian streak, Simmons has also been involved in several non-profit organizations, serving as an ambassador for the Last Prisoner Project, as well as the director of the Whos House Ballers, an amateur basketball team for underprivileged youth from Queens. Currently hosting For good podcast, where he invites his guests — including rapper Lil Eazy E and psychologist Cheyenne Bryant — to chat about topics like overcoming adversity and living with purpose.
In the following interview, Simmons reveals what allows him to juggle so many different projects, why everyone has to go through a rebellious phase and “bump their heads,” and how he maintains a balance between his private and professional life.
Think big: You’ll likely grow up in a family that has its own reality TV show with some unique challenges. Did you feel pressure to live up to people’s expectations?
Simmons: I started my television career when I was about 14 or 15 years old. Before that, I didn’t feel a lot of pressure. We were seen as a prominent black family, a church family – a family that walked the straight path. As you get older, you start trying things, and I definitely felt the pressure to make sure the family name was kept up.
I felt like I always had to adhere to my father’s standards regarding how he wanted us to act in public. As a child, you don’t understand how big something is. Your parents told you that it’s bigger than you, and you have to act on it.
I think I handled it okay for a while, but then I went through a rebellious phase, and I started doing what I wanted. Later, when I took a step back, I finally saw for myself the extent of it. At the same time, I realized that the only pressure I had was the pressure I was putting on myself.
Think big: So, do you think that rebellious phase was necessary to get you to where you are today?
Simmons: certainly. I’m not promoting it, but I think everyone has to go through a phase where they bump their heads a few times. You think you know what you’re doing, then you discover that your path may not be the best. Going through this stage taught me how I should deal with situations and use my energy.
Think big: You wear a lot of different hats in your career. What is your big time management secret?
Simmons: I’m a routine man. I find that the most successful people are routine people. They know what they want to do and use their time wisely, dividing it up so everyone feels served.
Most days I wake up early, before the rest of the world. This 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 keep me mentally active. After that, I make sure my kids are fed and going to school, then I get to work, making phone calls and talking to clients.
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I don’t procrastinate. I was a huge procrastinator when I was in high school. However, I quickly learned that procrastination never helps you, so I like to get things done right away. Don’t rush them, get them done.
Sometimes, motivated and ambitious people struggle to maintain a sustainable work-life balance.
Think big: You obviously get a lot of enjoyment and energy from your work. Does this make it difficult to draw the line?
Simmons: I actually make sure I prioritize myself, because if I don’t do good, nothing around me will be able to do good. Not companies, not my family. When I wake up every day, I take care of myself so I can take care of everyone 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’ll crash. You’re not comfortable, you’re not confident, you’re not the best version of yourself.
Think big: Are there any particular leadership styles you share?
Simmons: I like to lead by listening. I love listening to everyone around me, especially the people we employ and trust to do their jobs. Of course, I provide input and step in when needed, but I believe leadership is about instilling trust. If people feel valued and appreciated, they will work hard for themselves and for you.
The most important thing – and this is something a lot of young entrepreneurs need to understand – is that it’s okay to pick up the phone and call someone who knows what they’re talking about.
Growing up in the TV and music industry, there were a lot of mentor figures around me: my father, my uncle, and people like Steve Lobel, who I always credit for being a huge 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 father and uncle, but that wasn’t the case for them. I also looked outside the house to see who else I could learn from.
The most important thing – and this is something a lot of young entrepreneurs need to understand – is that it’s okay to pick up the phone and call someone who knows what they’re talking about. It’s not embarrassing or shameful. It is empowering for them when they realize that you respect their knowledge enough to learn from them. You’ll get real, valuable answers that way. I am indebted to anyone who picked up the phone for me whenever I needed it.
Think big: Do you think the business side of your career requires different skills or personality traits than the creative side?
Simmons: I would say I’m still the same person, but when I’m in creative mode, I’m in that weird, goofy space and thinking outside the box. I draw inspiration from everything and just come up with ideas. When I’m in business mode, I’m more organized and more collected. That’s when it’s not just shooting things at the wall.
Think big: You work with young artists and children 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 their feet. With young children – we’ve all been little, so you know how it is – it can be difficult for them to listen to older people, because they think they know everything already. The key is to show them how much you relate to them, that there are other options, other paths.
The same goes for the players on the basketball team I help manage. Show them that basketball is not their only path. Even the best players on the team, the ones who score 30 points a night and win trophy after trophy, we teach them teamwork, community and discipline – things that apply not just to basketball, but to life in general.
Think big: You are an amazing communicator and public speaker. Did you learn these skills on television, through acting, or elsewhere in your career?
Simmons: TV has helped, but I don’t know if that’s the main thing. I remember maybe in fourth or fifth grade, I had an English teacher, Mrs. Manners. I prepared a research paper, and she told me that I was good with words, and that that was one of my strengths: I knew how to write, and how to speak. It made me feel powerful as a child, and led me to enjoy writing and talking to people, to move and inspire them by choosing the right words and saying them in the right way.
I’m not big on fluff. I’m interested in clear communication and speaking from the heart.
There’s a difference between speaking well and sounding like you’re an intelligent or interesting person, when in reality, you’re not saying anything at all. I’m not big on fluff. I’m all about clear communication, and speaking from the heart: real. Sometimes I do, and maybe I shouldn’t, but my team knows I don’t like to over-prepare. Give me the topic, and if I’m emotional, I’ll talk for an hour, emotional. People can hear that.
If you know how to talk to people, you can close any deal, walk into any room, and accomplish anything. We all love a great conversation, and it goes from there. If you can have a great conversation, that’s half the battle.
Think big: Artificial Intelligence is rapidly changing the business and entertainment sectors. How do you use it in your work?
Simmons: I personally tried it, and it’s great. I always tell people: Use it, but don’t let it hold you back. AI will never be as personalized as humans are. Creativity comes from people. Working with a creative company, sometimes you don’t know what your clients want. AI gives you choices, but nothing is more difficult than a real person doing the work.
Think big: What has your experience in entertainment taught you about confidence and overconfidence?
Simmons: When I was younger and appearing on TV, I wouldn’t say I was conceited, but I definitely felt like I had it all together, and when people found out I didn’t, it was a real test of my pride. However, the way I dealt with it was to sit down and make myself understand that everyone goes through failure and everyone checks their ego. The only thing that matters is what you do moving forward. You can’t keep repeating the same patterns. You have to learn to leave your ego at the door and do your best every day.
Now, I don’t move with ego anymore. I don’t want everyone to know I’m the boss when I walk into the room. I don’t need people to see that I’m strong. I just want them to relate to me. I have learned to live without ego, because it is the only thing that stops us from achieving success.
Think big: Are there any big mistakes you’ve made throughout your career that ended up teaching you a valuable lesson?
Simmons: I don’t know if I can pinpoint anything, because I made a lot of mistakes. I discovered artists that 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 probably should have taken care of myself a little more. I don’t regret anything, though. I’m happy to see the people I helped succeed, and I still support them all. I wouldn’t call those mistakes, but there are things I would have done differently.
I always say I should have taken more advantage when the spotlight was put on me to cement my own legacy. I’ve talked about this a lot – I was a reality TV kid, and I still want to have that childhood, hang out with my friends, and be a teenager. If I had promoted the JoJo Simmons brand earlier, who knows. But we’re building it now.
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