The Money Mondays - Money Talks: Terrence J Breaks Down Wealth, Real Estate, and Giving Back 💵 E160

Episode Date: February 16, 2026

The Money Mondays is a business podcast here to teach you how to make money, invest money, and donate money by showcasing some of the world's most successful people and how they do the same. Hosted by serial entrepreneur Dan Fleyshman, the youngest founder of a publicly traded company in history, this money podcast gives you an exclusive behind the scenes look at how the wealthiest celebrities, entrepreneurs, athletes and influencers make, invest and donate money.If you want to learn more business and investing while you work to improve your financial life, you're in the right place!In this episode, Dan sits down with Terrence J—host, actor, producer, and investor—to unpack the business side of building a career in entertainment and turning that momentum into real wealth. Terrence shares the hustle story behind landing 106 & Park (including the bold move that changed everything), why he chose to pivot to E! News at a peak moment, and how he learned to protect his brand by only saying “yes” to opportunities that align.Then they get straight to the money: Terrence breaks down how he accidentally fell into real estate through his first home purchase, how he evaluates investments (including restaurants and operator-led businesses), and why financial literacy is the difference between keeping wealth and losing it—especially for athletes and creators. They also talk mentorship, long-term planning (trusts, life insurance, and protecting family), and why giving back becomes even more important as your life and priorities evolve. The AI inside HighLevel is booking 250,000+ appointments every month without a human touching it. Voice AI answers missed calls and schedules meetings. Conversation AI handles lead follow-up 24/7. Over 2 million businesses run on this platform. Try it free for 14 days → danhighlevel.com/ai

Ladies and gentlemen, welcome to a special edition of the Money Monday, Monday's podcast. We cover three core topics, how to make money, how to invest money, how to give away to charity. I'm very excited because I actually have someone here that's been on camera for decades. So I'm actually going to ask him advice and questions after we film this because he has a zillion hours of experience on camera behind the scenes, in front of the scenes, and everything in between on stages, award shows. It's mind boggling how much time he's put into this industry. and I'm very excited to ask them questions. As you guys know, this episode will be under 40 minutes because the average workout is 45 minutes. The average commute to work is 45 minutes.

This episode will be between 34 and 38 minutes for your listening pleasure. Also keep in mind, this podcast is not just for you. It should be for your friends, family, and followers. You liking, commenting, and subscribing is very useful for our charity. It's very useful for our podcast. It's very useful to spread the message about money because too often we grew up thinking it's rude to talk about money. We want to change that narrative. That's why this podcast is in the top 50.

all over the world every single week because of your help. It's very important for us. And also keep in mind, this podcast might be for someone from your past, present, the future. You might be sitting somewhere four months from now and be like, wait, I remember that thing he said, I should forward that episode. So as you're listening to these things,

it's not just for you. Think about the people in your life. Without further ado, Mr. Terrence, Jay, give us a quick two-minute bio, so we get straight to the money. What's up, Dan? Thank you so much for having me on your show. The Money Mondays, I'm so happy to be here.

I have, like you said, a long career starting in media and entertainment. I started my first big national show in 2006. I was there. Yeah, you were there, yeah, which would have been 106 in Park. Went on to do a string of movies that generated over $100 million in the box office. Got behind the camera, produced films as well, and then started producing a bunch of television, a bunch of different movies. And then really got into financial literacy.

And so now my portfolio encompasses real estate, investments, and yeah, just a bunch of experience on stages. And yeah, just happy to be here with you, man. All right. I got so many questions. So let's start from the beginning. Normally I don't do storylines, but your storylines involve a lot of things that go on

with this ecosystem of talking about money. 106 and Park. Yeah. This became a phenomenon. Yes. When you first went on, how did they pick you? How did you decide? And then as you're like, okay, now it's year three, your four, you're five.

They're like, okay, well, they need me now. Like, just talk us through the business side of getting on to a TV show. Okay. So, yeah, the year, I graduated from college in 2004 with a degree in broadcast journalism. I then took a job working in at NASCAR. I was working in there, diversity marketing department. And I enjoyed it, but it wasn't really what I was passionate about. So while I was working a job and, you know, trying to stack up some money, I auditioned for a bunch of things.

I mean, I probably auditioned for a hundred things. Really? Yeah, just a bunch of, I mean, I auditioned to be in, I think it was Spider-Man at the time. Like, just all types of things, not as Spider-Man, but just all types of extra roles, everything. that you could want to do in Hollywood. And I got turned down and got told no, a bunch. Eventually, they had a open casting call at BET. And I went to New York City from Florida, and I stood in line.

I was probably number 500 in line. Wow. Yeah, there were thousands of people out there. Wow. And I remember going through the first round of auditions. I was nervous. I messed up. I didn't know what to expect.

And I came out of the room and I bombed it, right? But the guy that was standing in front of me in line while we were waiting to get in, he came out like, yes, I made it to the second round. And I was like, damn, if he could just make it to the second round, why can't I? So my goal was not to build the whole wall. I just had literally, I was like, I got to make it to round too. This guy wasn't that much. You know, he wasn't, you know.

And so I drove. from New York to Atlanta to audition for the same thing the next day. Wow. And when I got to the next audition, I had, I almost missed the next call because I had driven down. They were closing the doors. I was able to slip in because I had my name badge from New York. From the day before. And I went through round two, then round three, because now I had the confidence.

Now I knew what to expect. and getting and landing that job completely changed the trajectory of my life. Sure. So you created the butterfly effect. Yeah, yeah. You not driving to Atlanta would have changed my life. Like I literally went to, I was at 106th of the park. I used to bring my t-shirts out in the parking lot out front and the street.

Like I was giving them out. You coming. It means so much. And hearing these stories now of how it impacted people, how it, you know, motivated people, inspired people. At the time, you know, in 2006, everything was changing, right? Facebook was just created in 2004. YouTube, I think, came out in like 2005. Media was changing. Technology was changing. And this was just the perfect storm of ingredients that show. And, you know, from New York to Japan to London, it really was a cultural phenomenon that changed the game. And that's something I'm proud

be a part of that history. So I used to stand outside because there was a line, a couple hundred people waiting to go inside as the audience. And I would offer to give on my T-shirts for free as long as they put it on right now. Wow. And all I was doing is hoping for the pickup. As they would show the crowd, Terrence was hosting with Roxy. And sometimes they would pan to the crowd to show the live audience. And so some people were wearing my shirts or my hats, I would get a little bit. It was only for a second, but it was free. And my only rule was, if you take it, you got to put it on right this second. You got it for free. Otherwise, you've got to pay 20 bucks. Okay. Okay.

You also did E-News. Yes. This is one of the biggest names in the world. You even mentioned it earlier. Talk to us about getting on to E-News, which was literally one of the biggest that there was. So I had, at that point, I had been on 106 for seven years, I believe. And, you know, we were at a point where I think it was time to renegotiate.

I had did some movies in between. So Think Like a Man was largely successful. You know, I was in a great place in my career. Roxy was crushing it as well. And it was a pivotal moment because we had to make decisions. How long do you stay, you know, do you leave when you're on top or do you wait, you know, to sit in the club so they turn the lights on, right? And for us, we decided to leave, you know, leave the restaurant before you're the last person at the table. And so going to ENews, it was a gamble at the time, right?

I ended up becoming, you know, the lead anchor, but a lot of people didn't understand why I would leave, you know, such a cushy, great situation to go after something else. But, you know, I had something to prove, you know, I wanted to show that it wasn't just hip-hop music videos that I could do. I could conjugate a verb and I could be on the red carpet. And, you know, I can interview Jay-Z and, you know, Kanye West, but I can also interview Leonardo DiCaprio and. and Tom Cruise. And so I went on to Enews and, you know, did what I had to do. And yeah, man, it was just an incredible run. So when you get TV shows, movies, hosting, stages, award shows, you get bombarded by different

options. Yeah. How do you decide that you're going to put your personal brand on, not just the paycheck part, but like, how do you decide, like, you know what, I will host that award show or I will do that movie with Kevin Hart or maybe I will do it with this person or that comedian? You know, in the beginning, I took a lot of. of things, right? It was, you know, paying off your college loans and getting yourself out of, you know, when I started, I was pretty much living on a couch. So I didn't come from a television

background. I didn't have much. And so building wealth was something that was very important to me. I didn't ever want to go back. I didn't want to go back to being poor. I didn't want to go back to nothing. So I took a lot of different opportunities in the beginning. After, you know, becoming established and really getting my foot in the door, then I really started to appreciate doing what I'm passionate about. And so now I'm in a place of my career. I don't leave the house unless it's something that I believe in, unless it's something that aligns with my brand. I can't take any check now, right? I have too many people that depends on me and too many businesses that would would fall apart if I did things that, you know, jeopardize my integrity,

right? So you got to focus on things that align with your spirit, focus on things that align with your personal brand. That takes a while to develop. But yeah, in the beginning, you got to take things to pay the rent. So I think overall, through the ebb and flow of this economy and through this, you know, this world, you got to, you got to be careful with what you take. You got to be careful with what you turn down. And ultimately, you've got to follow your gut. You got to follow your instincts on those things. So someone out there is listening.

They're an aspiring comedian, actor, DJ, rapper, singer. They want to be out there. They want to get on to that stage or behind that camera. What would you say to them to make themselves stand out to get picked or to showcase their actual personality? That's a load of question. You know, as we talk about and we celebrate, you know, 20 years, the world is changed, right? When I first started, there were only a few outlets that had the opportunities in place to do what I wanted to do. And in addition to that, equipment was really expensive.

So you couldn't just put up and start doing your own thing. Now you can create your own destiny, right? There are a lot of different opportunities, but they might be harder because they're more competitive, but you can create your own landscape like this, right? You can visualize this show and you're able to touch millions of people through your concept that you completely have creative control over your complete autonomy over and that's a beautiful thing as well so what i say to people is this follow what you're passionate about if you're going to start your podcast right and you like golf then focus your podcast on golf for sure don't try to emulate somebody else or because you've seen, hey, a lot of people are successful doing fitness videos.

Now I'm going to start doing fitness videos, but I don't care about fitness. People will see right through that. People love authenticity. People love specificity, right? So if you're really into food and you love cooking and you love wine, then your show should be focused on cooking and wine, right? Don't try to go in a direction of something that you're not passionate about because the audience. will see right through that. We've seen a lot of people start to make money in different industries.

But sometimes we hear about the NFL and other categories where they leave the league and five years later they go bankrupt. You started talking about financial literacy and that's part of your passion now. What do you think that happens or occurs that make people that make a lot of money start to lose it or if not worse, lose all of it after they make that money? You know, I think it begins with our school system. I think that, you know, we, the way our education in our country is broken down through a child and a student's matriculation, the focus on finance, the focus on financial literacy is not in place, right? When we grew up, we didn't even have a podcast like this.

We didn't have relatable people sitting, talking about money. It was almost a thing that our parents' generation, and especially, you know, the generation before, they never. never really had those money conversations, especially as route, especially in public, right? And such a crabs in the barrel, competitive, you know, type of thing where young people didn't discuss it because we're all fighting for the same types of jobs, right? So I think the lack of financial literacy that a lot of these young athletes, a lot of young people, period, go into, not knowing how to invest, not know, not understand. understanding real estate, not understanding taxes. So, you know, you're a young athlete and you've

heard the breakdown a million times. You know, you get your first million dollar check. You don't account for the IRS. So, you know, 30% is gone. 40% if you live in California, right? You got your agents. You got your managers. You got your squad. Your training. Your baby, all of those things. You add all of that up. And, you know, you might be taking home 300K for every one million made right your your career has a shelf life right you all of us aspire to have the longevity of lebron james but that's one in a billion right and so as the the the years go on so many of them that that don't properly uh put their money where they need to you know they become bankrupt in the in the years that follow i think the the biggest key is information uh you know on our

phones right now is more access to information than all of human civilization ever, right? Right now on our phone. And so I think, you know, podcasts like this, you know, I do invest fest with the earn your leisure guys and do a lot of stuff with them. You know, I have my own podcast that talks about financial literacy. There are so many incredible people out there that are giving information. You can't look on this. Damon John's page without him telling you something that that can help you out, right? And so, yeah, I think it's, it's, it's on us to educate and help our, you know, our friends and our people. And it's on everybody to understand, you know, the price of Bitcoin right now,

to understand what's going on in the stock market, to understand real estate and know the interest rates and knowing they, they drop and when they rise and when's a good time. So it's the information's out there and it's up to us, you know, because these next few years are going to be pivotal. You put that thing on your Instagram the other day, talking about AI and how fast it's coming. You know, it's, yeah, it's time. It's showtime right now.

So what was the turning point when you decided, okay, started to make some money, did a couple shows, did a couple of movies, got some good award shows, things have been going good now. I can actually finally put aside, when was that moment? You're like, you know what? I want to make my first real estate investment. I want to invest into my friend's new restaurant,

or my friend's nightclub or my friend's music label or my friend's clothing line or the stock market like when was that turning point you know i i i call myself a student of life um you know all of those things have different answers for real estate i really fell into it by accident i bought the my dream home and my dream home uh in l a mansion that i you know threw a bunch of parties at and had a great time at when it was time to move, I looked up and it was a great investment. And I think over COVID, when everybody started renting and, you know, the arrival of technology like Airbnb and making rentals and short-term rentals and option, I was really able to capitalize off of that. So the success of buying my first home led to me buying a second property that was

an investment property. And then once I got a hold of that, you know, I was able to be. I probably did $20 million in real estate over a three-year span. And then, you know, then once you learn what you like in the real estate market, you can kind of adjust, right? Airbnb is in a much different place than it was. The economy is in a much different place than it was. Short-term rentals and, you know, mortatoriums on markets like Palm Springs and Miami. It changes.

So you got, have to adjust with all of that. So real estate is, you know, it's an ebb and flow. It's a market like anything else that I've had to adjust to. Learn, you know, with restaurants and businesses that I invest in, I always go after what I like. So I'm an investor in an incredible restaurant called Last Lap here in Miami and in New York. And it's a, it's a restaurant and a bar that I like to go to. You know, our location here has chef Kwame, one of the top chefs in the world, right? So I'm not investing in things that I don't like to enjoy because I know when I, if I like something,

I know somebody else will like it too, right? So even when I buy cars, even when I buy, you know, watches or anything, I go after what I like. And then, you know, you hope that the market will adjust and have a resale value for it if you decide to opt out of it. But that's why I always go back to passion. I meet so many people that do things just to do things or do things because they see somebody else doing things. I like to invest in things that I like, that I'm passionate about, or that I find somebody that is passionate about that I can align with. So if you're not going to be the person that can create the technology, you can be the Steve Jobs that gets next to Wozniak, right?

If you're not over there making the best hamburger, you can be Ray Kroc and still be, you. you know, behind McDonald's, because you align, right? So I also look for incredible CEOs, incredible people that I can invest in because, you know, and I've learned a lot of that from you. I mean, you're an incredible, you have an incredible eye for talent. And that's something that I've really learned to appreciate over time.

So when you're a public figure and a lot of people become public figures, even when they only have 10,000 followers, 50,000 followers, etc., they said to go bombarded with requests. Instagram, Facebook, LinkedIn, TikTok, Snapchat, freaking carrier pigeons. They're getting hit up by everyone to invest into deals. Hey, invest in my pizza shop, invest in my hair salon, invest in my this, invests by that.

How do you say no to people? You know, I don't have the bandwidth to do too much, right? I am hyper-focused on what I consider the A-Bs and C of my life, right? my core business and then the ancillary businesses that surround that. And I recently got married. So for me, I'm at a place in my life where, you know, my relationship and where building a family and those things, you know, have taken precedent over some of the stuff that I would have done, you know, 10 years ago, right? So for, for me, it's the opportunity, it has to be fully vetted. It has to be the right thing. And I got to be, again, I

go back to passion a lot. It has to be something I'm passionate about. If you come to me with an idea about a space that I don't care about, I'm going to be much less likely to invest in it. Because we've all been burnt so many times. There's so many times where somebody will come and say, oh, you have to invest in this technology or you have to invest in this. And it's something that I don't understand. And then, you know, you end up losing. When I do understand it, I usually end up, you know, with an upside. So I really try to be careful and not spread myself too thin because I already got my eggs in a lot of baskets and I try to be careful with investments for sure.

Comedian just gets signed to be on a Kevin Hart movie. Okay. And man, they made some money. Movie takes off, becomes a big success, and now they just made $2.5 million. Wow. And they've only been making $50 grand a year before that. What would you say to that person? They saved up a couple million dollars all of a sudden.

They have this newfound wealth. What would you tell that person to protect themselves from not blowing it on investments? Ooh, you know, that's a great question. You get your first $2.5 million and you worked with Kevin Hart. Well, the first thing I would do as a career thing is, you know, when you get the steam off of one of those, right? When you align yourself with somebody like Kev or somebody that, you know, is booming in the box office, you want to set yourself up with work things that help, you know, lead to longevity in your career, right? You don't want to be a one and done. We've seen so many people come and you have a big hit movie or you have that one big TV show, but you're not quite able to capitalize off for a long time.

So investing in yourself is always my, you know, one of the first things, making sure. that you're making the right moves and putting together a nest egg so that you can take the right jobs and that you can create your own platforms and your own tools for success. So that's number one. Now, with the actual money, right, I try to put percentages of it in different things, right? So I'll put a percentage of my money possibly towards a real estate investment, right? So if you got $2.5 million and now you want to buy a house, we'll do very simple math. and let's say you're buying a $1 million property that you want as an investment property.

You got to put, what, 30% down depending on where you're at with it. So that's $300,000 of your money now put into that, right? So now you have your property. Hopefully you can get, you know, a renter that comes in that can help with your income. And again, a million dollar property is, that's incredible, right? That's super ambitious. But we're breaking down to 2.5, right? So I put a little money there.

Now I would take a little bit and stack it away so that I have it either in something that's very safe, like an IRA or just, you know, a very safe investment. And then I would put it in, you know, a good portion of it into the market. And I think understanding and learning the market, it's very volatile, right? You want to invest like Warren Buffett. You want to put as much into those blue chip stocks and investments. You know, the S&P 500, you want to, you want to just, you want to put it in places where your money can work for you. We are now entering a time in the world where your hard work is not going to be enough to sustain your retirement and your long-term wealth. You have to park that money somewhere where your money is going to yield the rewards for you.

It's just, the economy is too fucked up. We're not in a position where your social security is going to be able to take care of you for the rest of your life. My father, my dad passed away two years ago. And when I really got to see the end of life things that happen with Social Security and insurance, all of those things. It's insane how we've set up, you know, our elderly and how we've set up the elderly and how we've set up the country, right? And so I, you know, I learned so much from that experience and I want to make sure I educate as many as possible. Having a life insurance policy is something that a lot of us don't really talk about and not educated on, putting our money into trusts, setting our

family up for success. So I would definitely, with that $2.5 million, and the biggest thing, if I got $2.5 million, you want to talk to Kev. Right. Right. You call Kev after. Kev is one of the smartest investors and one of the nicest guys. To this, you know, there's never a time where I call Kevin and he don't pick up the phone. It's like, yo, T, what's up?

What are we doing, right? You want to use your relationships. You want to use, you want to have people as mentors in your life. I oftentimes call people that I look up to that I feel like are very successful to this age, to this day. and I always ask questions, hey, I'm thinking about investing in this, or I'm thinking about exiting this, or I want to sell this houses.

What do you think about this price? You have to use your relationships. Let's put on our charity hats. Why do you think it's important for people, for their household or for their company, for their employees, their kids, etc., to see them do some type of charity work? I don't know if anything is more important than charity.

you know, as we get older, I think, you know, in my 20s, I really had something to prove. I really wanted to, you know, be the best and do the most and make a lot of money and, you know, have success and show off and, you know, all those things and buy the Lamborghini and buy this house. And, you know, that kind of goes into your 30s as well. once you get that emotional intelligence, once that 40 hits and you realize how finite our time on this planet is, and you realize how precious this opportunity that we have is called life, you realize how important it is to help others, right? How important it is to give back. how important it is to help the next generation not make the same mistakes that our generation made, how to set them up for success in ways that we never saw, right? So, you know, I do charity in a multitude of different ways. I've given charity back. I'm on several boards. I love education

and I went to historically black college, North Carolina A&T State University. And so I'm very active with my university, from actually donating money from a financial standpoint, to working with the young people there, to doing a ton of work with all types of organizations from the NAACP to United Negro College Fund. You know, so a lot of that educational part is part of my life. And then to working with people like yourself, being a part of your toy drive with your foundation and Trina's kids is something that is going to always be on my life. list. When I get calls to do charity events, it's always on my list, making sure that I'm spending

time giving back. I've really gotten into animals as well. So I've been like going to local dog shelters and and working with, you know, animals as well. And I just think that's part of our mission. I think part of our, what we're seeing, you know, with all the fragments that are going on in the news every day we wake up, there's wars all across the world. There's financial, worry. There's a lot of things. I hope that this time will bring us all back to a level of connectivity and humanity where we can really focus on giving back, loving each other, helping each other. And I think, again, bringing it back to money, financial literacy and financial freedom are ways to do that. And that's why this is your show is so important. And I'm so happy we

got to spend time today on it. So there's only one question I ask on every single. single episode and out of hundreds of times I've asked it I've never gotten the same answer. Okay. You guys are building a family together with your new wife. At some point you'll have one child, maybe two, maybe three, who knows what's in the store for little baby J. But along the way, you build up movies, might end up creating a film studio investing in companies, products, exits, and you have hundreds of zillions of dollars later on the future. What percentage of your net worth you leave to those future children?

Yeah, that's a great question. You know, so right now it's all set up. You know, it'll go to my wife and my mom. If I went today, knock on wood. Because that's my family now. When I have kids, hmm, I would hope that I'm in a position where I can leave them enough, but also teach them and educate them enough so that they can make a ton. and, you know, then the rest give to charity and give to people that needed, give to foundations

that that means something to me, give to, you know, my team and the people that have supported me. You know, I have a great, you know, management team and, you know, Fred and Yanle and people that have been with me for years. I want to, you know, give the money away to the people that I love the most and the people that I can help the most. and yeah one day when I have kids that'll be a different question we'll come back and do the show when I have kids and then I'll see how much but I'm hoping that I can teach them to be billionaires too so that we can continue the cycle of giving back are there any projects that are coming up for you

anything that people should be looking out for yeah a ton of films um the the soonest one that I think will drop me and TI just did a really funny romantic comedy together so so that will be the one that'll be dropping. I'm producing and hosting the red carpet for the N. N.A.C. Image Awards. So I'll be back out in LA. I don't know where this airs. But tons of red carpets, tons of TV shows. And I'm really excited. I'm producing and hosting a show called Marriage Box. Right. I loved, there were obviously rest in peace and

to everybody that lost their life during the pandemic. But during the pandemic, my experience was eye-opening, no technology, being just, you know, off the grid. And so I created a show. We're going to put three couples in a box. And we're going to see if they can. Say a box. Explain it.

Like a tiny home, like just a box, no phones, no TV, no internet, no Wi-Fi. Every day they survive, the challenges in the box. we'll give them $1,000, and then the winner, they'll get a big prize. So that shows called Marriage Box. So I'm currently in production for the next few months shooting that. And then, yeah, just, you know, back to it. Working, keeping the hustle alive, brother. I love it.

Where can people find you on social or any of your company's products, shows, anything? Everything is at Terrence J, my Instagram, my Facebook, my TikTok, Terrence J. And then my financial literacy podcast is Money Talks. So make sure you check out Money Talks. Dan has an incredible episode on there. So watch Dan's episode on my podcast too. All right, guys, as I mentioned earlier, this is important for you to think about to share.

It might be three months from now. It might be three years from now. Of someone that might be an aspiring actor, comedian, TV star, they might be talking about investing. There might be something that hits in your mind in that lunch, breakfast, dinner, whatever, with your friend, and you share this episode with them.

liking, commenting, subscribing is what helps us keep in the top 50 in the world. It's because of you guys. Appreciate you guys. We'll see you guys next Monday here at the money Mondays.com.