INTERVIEW: Harry O Speaks On Calculated Communication, Reputation, New Book + More

Summary

The Breakfast Club: Harry O Speaks On Calculated Communication, Reputation, New Book + More (June 10, 2025)

In this compelling episode of The Breakfast Club, host DJ Envy, alongside Charlamagne Tha God, delve deep into an enlightening conversation with Harry O. The discussion spans Harry O's journey from his beginnings in hip hop to his current role as an entertainment executive and college professor. Central to the conversation are themes of calculated communication, reputation management, and insights from his newly released book, It's Beyond Words. This summary encapsulates the key points, insightful discussions, and profound conclusions drawn during the episode.

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Introduction to Harry O

The episode kicks off with DJ Envy introducing Harry O (Harold Wilkerson), highlighting his multifaceted career. From his early days as a rapper in the Bronx to becoming a respected entertainment executive and educator, Harry O’s diverse experiences set the stage for a rich discussion.

Notable Quote:

Harry O [02:20]: "What's going on Eve? What's going on everyone? Thank you for having me."

From Music to Executive: Harry O's Journey

Harry O recounts his transition from the music industry to the business side of entertainment. Starting in the eighth grade, his early involvement with Uptown Records and collaborations with iconic figures like Puff and Ja Rule shaped his path. Despite not achieving mainstream success as a rapper, Harry O emphasizes the importance of adaptability and building a sustainable career.

Notable Quote:

Harry O [06:30]: "I view it as I came into the entertainment business in eighth grade. I made a life out of it. I'm sitting here doing an interview on The Breakfast Club."

The Art of Calculated Communication

At the heart of Harry O’s philosophy is calculated communication—a strategic approach to building and maintaining relationships. He underscores the necessity of genuine interactions over transactional exchanges, emphasizing that trust and intentionality are paramount.

Notable Quote:

Harry O [08:51]: "I just can't pick up the phone and say, hey, I have a bunch of deals for you. She doesn't even know who I am yet. We have to build trust."

Building and Sustaining Relationships

Harry O illustrates his communication strategies through anecdotes, such as his interaction with Lauren LaRosa. He distinguishes between "farming" (nurturing relationships over time) and "hunting" (targeted, goal-oriented interactions), advocating for a balanced approach depending on personal versus professional contexts.

Notable Quote:

Harry O [28:53]: "We have to be those barriers because in hip hop, we could be the heroes or we could be the villains."

Reputation and Media Manipulation

A significant portion of the conversation delves into reputation management and the impact of media portrayal. Harry O discusses how a solid reputation precedes personal interactions and the dangers of media manipulation, which can distort self-perception and lead to real-life consequences.

Notable Quote:

Harry O [17:05]: "People meet your reputation before they meet you. Your reputation is in this room before I walked in."

Hip Hop's Influence: Blessing and Curse

Reflecting on his roots in hip hop, Harry O acknowledges both the positive and negative influences of the genre. While hip hop was instrumental in his self-actualization, he also critiques its role in perpetuating harmful stereotypes and self-destructive behaviors.

Notable Quote:

Harry O [30:35]: "Hip hop aided me on a path to self-actualization... But there's things in the music that's villain like that can cause you on the wrong destruction."

Reflections on Irv and Murder Inc.

The conversation takes a poignant turn as Harry O discusses the passing of Irv Gotti, a close associate from Murder Inc. He shares personal sentiments on Irv's role as a family man and the profound impact his loss has had on him and others in their circle.

Notable Quote:

Harry O [25:21]: "Irv was the hero of the family. Watching his passing made me come closer with my family the way Irv was with his."

Educational Insights: Rethinking College Curriculum

As a college professor, Harry O critiques traditional communication courses, advocating for more practical and contemporary subjects like entrepreneurship, AI, and real estate. He emphasizes the need for education to evolve to meet the demands of modern industries.

Notable Quote:

Harry O [37:19]: "There should be more entrepreneur courses in college. We're going to need AI courses in college... They can build games. They can do all the things that I would never even thought of art school."

Perspectives on Seductive Communication

Addressing a query about seductive communication, Harry O explains it as the ability to seduce someone's mind to navigate interactions effectively. He clarifies that it doesn't pertain to sexual seduction but rather to influencing and persuading through strategic communication.

Notable Quote:

Harry O [35:35]: "Seductive communication is like knowing how to seduce someone's mind to navigate in a certain way."

Conclusion and Book Promotion

Wrapping up the interview, Harry O promotes his book, It's Beyond Words, available on Amazon. He shares the genesis story of his relationships within the NBA and WNBA, highlighting how intentional communication led to significant business deals.

Notable Quote:

Harry O [40:00]: "I leave deals with the WNBA and closed deals with the NBA because of strategic and intentional communication."

Final Thoughts

The episode concludes with light-hearted banter and promotional segments. However, the core of the conversation remains anchored in Harry O's insightful perspectives on communication, relationships, and personal growth.

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Key Takeaways:

1. Intentional Communication: Building genuine relationships requires strategic and thoughtful interactions beyond mere transactions.

2. Reputation Matters: A strong, positive reputation opens doors and facilitates trust in both personal and professional realms.

3. Media's Dual Role: While media can empower, it also has the potential to distort self-image and societal perceptions, necessitating mindful consumption and creation.

4. Educational Evolution: Modern education should incorporate practical and emerging fields to better prepare students for the future.

5. Influence of Hip Hop: The genre's impact is multifaceted, serving as both a catalyst for personal growth and a source of challenging stereotypes.

Harry O's discourse offers valuable lessons on navigating the complexities of communication in today's fast-paced and media-saturated world. His experiences and strategies provide actionable insights for listeners aiming to enhance their interpersonal skills and build lasting reputations.

Transcript

[Unknown Host]

This is an iHeart podcast.

[DJ Envy]

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[Harry O]

Panoramic moonroof, ambient lighting, bows and massaging leather. Appointed seats are optional features.

[Lex Borrero]

Welcome to the youe versus you podcast. I'm Lex Borrero inviting you to go beyond the titles and the accolades of the world's most successful entertainers. Each week we take off the cape and get real about the inner battles, childhood stories and the moments that shaped our guests. Get inspired to become the best version of you. Listen to youo vs you podcast on the iHeartRadio app or wherever you get your podcast.

[Unknown Host]

I also want to address the Tonys. On a recent episode of Checking in with Michelle Williams. I open up about feeling snubbed by the Tony Awards. Do I? I was never mad. I was disappointed because I had high hopes to hear this and more on Disappointment and Protecting youg Peace. Listen to Checking in with Michelle Williams from the Black Effect Podcast Network on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.

[Harry O]

I know a lot of cops. They get asked all the time, have you ever had to shoot your gun? Sometimes the answer is yes. But there's a company dedicated to a future where the answer will always be no. This is Absolute Season one Taser Incorporated.

[Unknown Host]

I get right back there and it's bad.

[Harry O]

Listen to Absolute Season 1 Taser Incorporated on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.

[Charlamagne Tha God]

Wake that ass up early in the morning. The Breakfast Club.

[DJ Envy]

Morning everybody. It's DJ Envy. Just hilarious. Charlamagne the guy we are the breakfast club. Lauren LaRosa is here as well. And we got a special guest in the building. We got the good brother, Harold Wilkerson.

[Harry O]

I don't think anybody gonna know who that is.

[DJ Envy]

Harry O, ladies and gentlemen. What's up brother?

[Harry O]

What's going on Eve? What's going on everyone? Thank you for having me. LL Lauren. What's up Harry O.

[Charlamagne Tha God]

Got a new book called It's Beyond Words which is out right now. And you talk about the art of calculated communication.

[Harry O]

Yes.

[Charlamagne Tha God]

What is that?

[Harry O]

Great question. So the art of calculated communication. Let me just rewind a little bit for the room who may not know or those who don't know in the room, that besides an entertainment executive, I'm also a college professor, and I've been teaching communication courses for maybe 10, 12 to 13 years.

[DJ Envy]

I know that if you're gonna go that far, let's go all the way.

[Unknown Host]

Back then, I didn't either.

[DJ Envy]

You know, Harry O started off as a rapper.

[Harry O]

Yes.

[DJ Envy]

That's how I originally know Harry O. He's from High bridge. He's from the Bronx. He started up as a rapper and was signed to the Ink. Yes, signed to the Ink. You was a hype man for Ja Rule for many years, and then you stopped rapping. And now break it down. Well, first of all, how did you meet Irv and everybody and go through that whole list of things?

[Harry O]

Great question. So let me rewind. Right. So first, I started the entertainment business. I had a deal with Uptown RA Records first with Andre Harrell and everyone over there. God bless the Debt.

[Charlamagne Tha God]

My favorite label level, favorite, favorite.

[Harry O]

Right. Best for r B music. All right, so I was maybe, like, in eighth grade. So that came. Went. Then I was working with Puff for a rap for a while. Whoa. Oh, that bad boy. Yeah. Listen, I know my guy's going through a lot, but I got to give him a lot of credit for helping me of where I'm at today. Like, I have to give him his credit because I probably wouldn't be here without the image of him.

[Charlamagne Tha God]

You can't take away what he did professionally.

[Harry O]

Professionally and what he did for me in my life personally. He did a lot for me. And I, you know, tell you about if I have time. Like, he stuck up for me plenty of times when executives tried to blackball me and things like that. Puff found out about it, step in like, nah, you're not doing that to my guy. So I got to give him his credit. So from there, we transitioned quick. I had to deal with Motown and had to deal with Murder, Inc. How.

[DJ Envy]

Many deals did you have?

[Harry O]

About four deals.

[DJ Envy]

Okay.

[Unknown Host]

Starting at eighth grade.

[Harry O]

Started in eighth grade. Started in eighth grade. Like, I've been doing entertainment for a long time. So now fast forward. Let me just tell you as far as me and Ja, I met Ja on the set of a movie called Turn It Up.

[Charlamagne Tha God]

I remember Turn It Up.

[Harry O]

Right. You're not gonna remember me in the movie because they edited me out the movie. So you're not gonna remember me, but if you look at the credits, you'll see me in the credits or whatever. So the movie was shot in Canada. So we travel to Canada, right? I'm there with my manager. We're trying to get into Canada. My manager at the time, he gets arrested. For some reason, he can't get into Canada. You know how that goes. So now I'm just. I'm young. I'm in Canada about to shoot this movie. I'm by myself. I'm a little nervous. So my trailer is right next to Ja's trailer. But I would always see Ja in the Violator office because we was working with Violator Def Jam, but we never really, you know, knew each other. We saw each other. We pass. So I'm in a trailer. He knocks on my trailer door. So I opened up. He go, yo, you sign a Def Jam, you signed a Violator. I'm like, nah, my guy, my son is. And we doing work over there. He go, man, I hear you here by yourself and your manager got arrested. Listen, anything you need, come to my trailer. If you need weed, if you need Hennessy, if you need anything. Ja has been trying to get me high since I met him. Right, right. But, yeah, I don't do any of that. So from there, Ja and I had a connection. That was his first album, like, right before his first album came out. After his album came out, he, like, blew up and took off. And, you know, my career was going wherever it was going, but anytime we would see each other, it was like we would stop everything and give each other love. And then I met Chris Gotti, Irv's brother, somewhere in the club. And he knew I did music. He said, listen, why don't you come down to the studio? Went to the studio, started recording records with Irv, Records with Ashanti Records, with Ja. The next, you know, a brotherhood formed where, although me and Ja came in through entertainment, that's more my brother. Like, that's. That's my guy. And I said before, my company, Chase Republic, we serve as, like, an independent agency for him. We close a lot of different deals, like I do with you, Ian. We talk about made a lot of money together, but more importantly, that's. That's my brother. That's my guy.

[DJ Envy]

So now. So now you. You get out of music, and music never takes off.

[Harry O]

I see. It's. You can look at it that way, right?

[DJ Envy]

You tell me.

[Harry O]

Well, I had to transition. I always say this, right? Somebody can ask you, like, how do you view success Right. So in your eyes, you may say, Harry, yo. As an artist wasn't successful, and that's fine. You can see it that way. I don't view it that way. I view it as I came into the entertainment business in eighth grade. I made a life out of it. I'm sitting here doing an interview on a breakfast club. I'm not a rapper. I'm not.

[Charlamagne Tha God]

I always known you as an executive. Like, that's how I always looked at Harry O as an exec. I never. I never even knew anything about no.

[Harry O]

Rappers like the E being a dj. Yeah. There's been plenty of times where, like, I would have to wait for E outside of the radio station, try to get music played. Like, we have that relationship. You and I met later on in life as being an entertainment exec. It's same thing with Lauren. Like, you and I met, first conversation I had with you, it says, listen, I could possibly make some money with you. Right?

[Unknown Host]

Yeah.

[Harry O]

And that's how it went. But E just knows a little bit of the backstory. But yeah. So it all depends on how you want to look at it as far as you're not being successful. But I made a life for it. My daughter, listen, I paid her tuition for entertainment. Do you understand? Her private school tuition, which we all know is very expensive, all through entertainment. So someone asks, hey, you weren't successful? I don't know. I wouldn't say that. I say, I think pretty well, you.

[Unknown Host]

Probably about to ask this. Then I'm interested to know. So from the artist perspective, then you transition into the executive side because of the relationship. And what is that transition? Because you started at 8 and executive is an adult making real adult decisions.

[Harry O]

Right. Well, it's two folds to it. Right. As I said, I've been a college professor teaching communication courses. Now with communication, I understand the art of connecting with others, but first connecting with yourself and what we talk about. Once I understood and fully came of who I am, a higher sense of awareness of me, I understood my abilities. I understood how I can build relationships. So I just started to build and form credible relationships with people, building trust, but in a strategic way. Not in a manipulative way, just very strategic. And like, I can talk a lot about me and Envy because Envy and I made some money together and our relationship built and I was intentional on how we're building our relationship. So what I did was I just merged the world between entertainment and education and made a life.

[Charlamagne Tha God]

So. So what is the art of calculated communication and how has that helped you Navigate through all those different worlds.

[Harry O]

So the art of calculated communication. And to make. To make it short, because we can talk about this all day, but what I would do is this, right? Say with Lauren, for instance, right? I met Lauren at the Brooklyn Nets event. Now, you said, hey, Lauren's on her way here. Can you send somebody to get it in immediately? I'm like, all right, I know who she is. I absolutely know that we can probably do business with her.

[DJ Envy]

Lauren was two hours late, by the way.

[Harry O]

I wasn't gonna say driving to Brooklyn.

[Unknown Host]

Is like driving to another planet.

[DJ Envy]

Okay.

[Unknown Host]

And it was raining. But what do I always do? I will pull up for y' all later. Not.

[Harry O]

Yeah, we had an event in the Barclays center for the Brooklyn Nets, which are one of my partners, and I hire E to do different events. So E, While we're there, he's like, listen, Lorman's on the way. Can you send somebody to get a. You know how difficult it is to get someone inside the Barclays center when it's closed? Like, it's really closed at this point. But I understand I have to be a little bit strategic. I want to build a relationship with this young lady and possibly do business. So we send an executive to go outside and figure it out to get her in. Now, as she's in, I understand it takes more than one encounter for us to start building some type of relationship, but we have to have that first encounter. It has to be a genuine encounter. It has to be. Maybe someone can help build that bridge between you and I. And I used June. June, Emmy's manager, whoever's listening, I said, june, do me a favor. Let her know. Stamp me right. Let her know. So June went to you and said, hey, Harry. O. This is my guy. That's all I needed to start building some type of communication with you. Now, to make it a little bit shorter, in order for Lauren and I to build a relationship, I have to get her to peel back her layers. I have to try to get to know her. The closer I get to her, the more of a chance I have of doing great business with her. I just can't pick up the phone and say, hey, I have a bunch of deals for you. She doesn't even know who I am yet. We have to build trust. So I have to get her to peel back layers. I have to ask her questions. But if she never responds, like, say. If I say, hey, as simple as this. Lauren, how was your day today?

[Unknown Host]

Great so far, besides dealing with charlamagne.

[Harry O]

But other than that, I'm the best.

[Charlamagne Tha God]

Father of her day.

[Harry O]

Best father of the day. What are your plans tomorrow?

[Unknown Host]

We have a flight. We're going to LA for the BET Awards. Me and the team at the Breakfast Club.

[Harry O]

Wow.

[Unknown Host]

Well, not them, but the producers and stuff.

[Harry O]

You have a lot of work at the BET Awards.

[Unknown Host]

We do. The latest with Lauren LaRosa is in the radio room for the first time ever for two days.

[Harry O]

Pretty cool. Congratulations. I love that. Now check this out. Right? So I would have to work a little bit harder now with Lauren because although I asked her these questions and I know we're on air, there's a lot going on. I asked her how was her day, right? And she said how her day was. She didn't say how was yours too?

[Unknown Host]

Oh, shoot. Sorry.

[Harry O]

So that's.

[Unknown Host]

I'm anticipating the next question.

[Harry O]

I know it's fine. I'm interested in knowing about her day, but I want to see how much interest she's holding in me to know about me as well. And sooner or later that will come. This is our. Maybe like our second encounter. But if I can't get you to have that exchange with me, I have to work a lot harder and be more strategic and to get you to communicate with me. And if you never do that, it's like, all right, this person doesn't have any interest in building with me in this area.

[Unknown Host]

I think also too, in business, I've never had a business interaction where my first thought is to say, how was your day? Like, most people come to you just like, so, like, this is what I want, this is what I need. So you just kind of sit and listen and then you try and think through, can I even do that with everything else that happened?

[Harry O]

And that's the problem with communication, where I don't want any communication with anyone to feel transactional. And I'm only using Emby as an example because we made some money to get me through business. NBA and I have a relationship where NBA called me at 5 o' clock in the morning and we're talking about dance. We're not even talking about business. We're talking about dance. She's like, do you do this with your daughter? Look at these classes. Check this out. How did it get there? It got there through strategic communication and connecting and building. If every time I see E is just, hey, I got A, you got B. Sooner or later, if I don't have A anymore or I'm in a downside, I can't get E to really pick up my calls because we don't have a connection if I'm making sense here.

[Charlamagne Tha God]

Yeah, you are making sense. But I will say I hate small talk, right? So when I hear that conversation with you and Lauren, I'm like, okay, what does he want?

[Unknown Host]

That's what I was thinking too.

[Charlamagne Tha God]

I'd rather you just get to it. And I don't think there's anything wrong with transactional conversation. Like, you know, if you have something to offer me and you think that I'm a person that can help you execute something, bring it to the table. That's intentional conversation.

[Harry O]

Now here's the thing that may work in your professional world, it may not work in your personal life though, because communication, listen to, understand communication will be the key to your professional and your personal life. That may be okay for your business relationship, but not every personal relationship. Not somebody that's just trying to build a genuine friendship with. You don't want it to feel transactional.

[Charlamagne Tha God]

So that's what you're trying to. You're trying to build a personal relationship with Lord.

[Harry O]

Well, for me, my success comes when I'm building a relationship with a person where we have some type of friendship.

[Charlamagne Tha God]

Got you.

[DJ Envy]

Gotcha.

[Harry O]

If we have some type of, some kind of friendship, like, we don't have to talk at 5 o' clock in the morning, but if we have some type of connection, some type of friendship is a higher ratio that we can do great business together.

[Unknown Host]

I think people, there are some people that would argue against that though, because, I mean, I think too, it's kind of like the background that you have, like knowing the type of like music and era that you come from, you value that. But a lot of people don't have values today. So it's like, I don't want to be your friend. If we're going to do business, we'll do it. And then we determine what that looks like after.

[DJ Envy]

I will say this though. The one thing for people listening to me, Harry O. Is like Steve Stout, right? And when I say, like Steve Stout.

[Charlamagne Tha God]

That might not be a good thing for some people.

[Harry O]

No.

[DJ Envy]

Well, let me tell you, I'm going to tell you one more politician that. I mean, he connects businesses to people, to talent. So for instance, he had a. One of his clients was East New.

[Harry O]

York, which was a show that was.

[DJ Envy]

On channel nine or whatever it was. And he called me one day and was like, e, I have a part for you in this show. I'm like, bro, I'm not acting. I've taken acting lessons a long time. He was like, nah, I really want you to read the script and try it.

[Harry O]

Right.

[DJ Envy]

And I'm like, because of our relationship, I was like, you know what? Let me give it a shot.

[Unknown Host]

Right?

[DJ Envy]

And when I did it, it went well. They love me. They wanted to bring me back for more episodes. But what impressed me more was I know Harry O from a street rapper, like from the Bronx, like gangster rapper. But to see him being a guy that's in the middle of East New York. And me, we're in the trailer, but he's teaching a class in the middle of me shooting as a professor. And I'm like, this is amazing because you see how people evolve. You know what I mean? And a lot of people don't evolve. A lot of people still want to be the toughest, hardest rapper at, you know, whatever age. And it just doesn't make sense. And I appreciated that. I'm like, cuz he revolved. But that relationship, like you said, was the reason why I trusted you to try East New York.

[Harry O]

Yeah, absolutely. And to Lauren's point, listen. Yeah. When we discuss in communication, Charlotte and everyone, it's all theoretical. Like, what I'm saying may not work with you or resonate with you. It just happens that it resonates with me and it's been proven to be successful for me. And like I said, I'm glad E like, mentioned that, because he is a testament to what I'm saying as far as how we built this relationship where it's trust. I call him and say, envy, I'm gonna put you on tv. It's a network. We're doing this cop show. Want you to act in it. All right, cool. After we discuss whatever the logistics are. He doesn't even have to think anymore because he's like, you know what? I trust Harry O. But we built our relationship to that point. And I was intentional about that.

[Charlamagne Tha God]

Yeah, I get what you're saying. Like, to establish a real connection. I think to establish a real connection has to be some form of real communication.

[Harry O]

Yes, absolutely. Absolutely.

[Unknown Host]

And I think God too depends on. Because, like, there are certain times where, like, if people approach me, do certain things, and they say that they've worked with Charlemagne or Envy, I'll call them and say, hey, do you know this person? Like, is it because nowadays too, because you turn to this chapter or page in your book, you talk about, like, the influencer. You talk about, like, media being the beauty and then the beast being society because of the way that things are distorted or, like, shown online with people in business. You never know what's real and what's fake. So it's like you gotta kind of like hold up what you want before you even be like, let me allow you to enter what I've worked on.

[Harry O]

Right, absolutely. And for me is building your reputation. I'm not sure if you heard the saying, people meet your reputation before they meet you. Yeah, right, Your reputation. My reputation is in this room. Before I walked in, that's the only reason I was able to get it. So I know building my reputation, that's a form of knowing how I connect with myself, knowing how I see me and how what I project for others to see. And if my reputation is solid, people will vouch for it. So. Yes, absolutely. And we represent me. I mentioned media and manipulation in the book as well, which is really, really important. If I have some time, can I touch on it?

[Charlamagne Tha God]

Of course.

[Harry O]

All right. Because in the book I mentioned. I brought up Shine in the book and the shooting that happened X amount of years ago. And this is really important that I don't want it to seem as like I'm poking a hole at Shine or picking at wounds, anything like that. Now, Sean was arrested for what? Like, what did he get arrested for? What did he do?

[DJ Envy]

So it was assault or some man shooting a gun.

[Charlamagne Tha God]

Look it up.

[Harry O]

Okay. I just want somebody else to say, that's all.

[DJ Envy]

Yeah, that's what I believe. Discharge an illegal firearm, I think.

[Harry O]

All right, so what happened? Meaning what led him to do that? And it's not only that Sean that have these issues or that had these issues. A young. A lot of young people in our hip hop culture had these issues. Now let me connect it to media manipulation and representation. Media, how we describe it is any way you receive information, any way you receive thoughts. Right. So it could be the movies you watch, it could be the music you're listening to. So if you are young and you're not understanding exactly who you are yet, you're not connecting with yourself. But every time you see you, it's in the wire, it's on these shows of these criminal shows. All the music you're listening to is telling you who you are. You have to be this, you have to be that.

[DJ Envy]

You.

[Harry O]

All of these images and media creates a distorted image of who you supposed to be.

[Unknown Host]

Yeah.

[Harry O]

And. But that distorted image can cause a real life consequence for you. So when I look at somebody like Sean and others and I can recall, like Sean saying and reason why I brought it up, because I was. I was there. Like, I was. I was there for this whole thing. I remember Sean saying to someone, not going to mention the person's name, but he said, I need people to see me and respect me the way they respect Jay Z, right? And it's like, all right, but what you know of Jay Z is, yeah.

[Charlamagne Tha God]

You don't get that from busting your gun.

[Harry O]

But something manipulated him to feel that way, right, to do that. So. But it's all about what he's seeing in the media, in the music you're listening to in a TV show you're watching. All of this is polluting how you feel about you and who you think you have to be. I have to be this. I need you. No, I'm not Rick Ross the officer. I'm Rick Ross. I need you to see me like that. But all of that is manipulating you. And if you're not understanding who you are, it's gonna cause a real life consequence for you. And that's what happened with Sean. So. Hey, what up, y' all?

[DJ Envy]

It's DJ Envy. The first few months of 2025 have been quite a year. Work deadlines, group chats you can't escape, and your weird cousin's latest overshare. It's a lot, but here's some good news. You don't have to bring that stress into your car. The all new Nissan Murano is your piece on wheels, thanks to its available features. Imagine sliding into the relaxing, massaging seats that feel like they were made to melt your tensions. Take in the skyline views that let sunlight pour in and watch as your day brightens. I have a special playlist that always gets me right. And with the Bose premium sound system, you too can vibe like you're at your own private concert. Plus, with your 64 color personalized lighting option, you can set the mood any way you want, be it romantic, chill, or in a straight up do not disturb mode. Let the Nissan Murano be your oasis in a chaotic world. Because sometimes the greatest rush isn't rushing at all. Drive the all new Nissan Murano today.

[Harry O]

Panoramic moonroof, ambient lighting, bows and massaging leather. Appointed seats are optional features.

[Lex Borrero]

Welcome to the you versus you podcast. I'm Lex Borrero and every week we sit down with some of the biggest names in entertainment to talk about the real stuff, struggles, the doubts, and the breakthroughs that made them who they are. We go deep exploring childhood trauma, family, overcoming loss, and the moments that shape their journey. These honest conversations are meant to take the cape off our heroes with the hope that their humanity inspires you to become a better you and therefore set you free to live the life of your dreams. Here's a sneak peek.

[Harry O]

I'm trained to go compete. I'm trained to be like harder.

[DJ Envy]

But sometimes that mentality stops you from.

[Harry O]

Stopping and smelling the flowers in your own garden.

[Lex Borrero]

Is it wrong to want more?

[DJ Envy]

We migrate.

[Lex Borrero]

Our family migrated here.

[DJ Envy]

I'm like second generation.

[Lex Borrero]

Listen to you versus you as part of Michael Tuda Podcast Network. Available on the iHeartRadio app, Apple Podcast, or wherever you get your podcasts.

[Harry O]

Over the past six years of making my true crime podcast Hell and Gone, I've learned one thing. No town is too small for murder. I'm Katherine Townsend. I've received hundreds of messages from people across the country begging for help with unsolved murders. I was calling about the murder of my husband. It's a cold case. They've never found her and it haunts me to this day. The murder is still out there. Every week on Hell and Gone Murder Line, I dig into a new case, bringing the skills I've learned as a journalist and private investigator to ask the questions no one else is asking. Police really didn't care to even try. She was still somebody's mother.

[Unknown Host]

She was still somebody's daughter.

[Harry O]

She was still somebody's sister.

[Unknown Host]

There's so many questions that we've never.

[Harry O]

Gotten any kind of answers for. If you have a case you'd like me to look into, call the Helen gone Murderline at 678-744-6145. Listen to Helen gone Murderline on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. What happens when we come face to face with death?

[Lex Borrero]

My truck was blown up by a.

[Harry O]

20 pound anti tank mine. My parachute did not deploy. I was kidnapped by a drug cartel. I just remember everything getting dark. I'm dying. When we step beyond the edge of what we know, to open our consciousness to something more than just what's in that western box. And we turn I clinically died. The heart stopped beating, which I was.

[DJ Envy]

Dead for 11.5 minutes.

[Harry O]

My name is Dan Bush. My mission is simple. To find, explore and share these stories.

[DJ Envy]

I'm not a victim. I'm a survivor. You're strongest when you're the most vulnerable.

[Harry O]

To remind us what it means to be alive. Not just that I was the guy that cut his arm off, but I'm the guy who is smiling when he cut his arm off. Alive Again. A podcast about the fragility of life, the strength of the human spirit, and what it means to truly Live listen to Alive again on the iHeartrade app, Apple Podcasts, or wherever you listen to your favorite shows. Like, when I look at you, right, this is the brown girl grinding, right? It's important that I brought my daughter here today to see what we see in this box. What we see, this is a beautiful brown sister who bullied her way onto the show, who's making noise, making moves. She's covering the Diddy trial and she's killing it. Her outfits are crazy. Crazy in a good way. What I mean, crazy in a good way. Crazy in a good way.

[Unknown Host]

I knew it.

[Charlamagne Tha God]

No, no, Harry O got me now.

[Unknown Host]

You know, he.

[Harry O]

I like what he said.

[DJ Envy]

I'm buying 10 books now.

[Harry O]

So, no, as we are viewing her in media, we're looking at her. This image is important because a brown girl is watching and seeing that. And that reality is something that she can obtain and is something that's authentic. Outside of that, it can cause a disruption, if you understand what I'm saying.

[DJ Envy]

So now I gotta ask, you were with Murder Inc. For a long time. How was the passing of Irv have affected you? Cause you know Irv in and out, and we've had conversations about it and conversations about his health. So how has that affected you?

[Harry O]

Well, with the passing of Irv is still like in disbelief, right? When I'm talking about Irv or up in conversation to say, all right, rest in peace, Irv. Got it. Like, it's really weird still now the passing of him, I see how it affects me and everyone around. Like, I am very, very, very close with Ja, right? And Irv and I were really cool, but I'm closer with Ja. It affect me because in this way, no one may not know this outside of his family. Irv is such a family, family man, right? I have never seen a family as close as his in my life. I've never seen it. So. And he was like the hero of the family. And for. And no disrespect to anyone else in the family that's doing great things, but he was like a hero. And so for the hero to pass and see how that affects the family dynamic, it made me. How it affects me. It made me come closer with my family. Like, Irv is the type where, listen, if it's holidays, his house is packed with the whole family, not just him and the kids. It's nieces, it's nephews, it's aunts and uncles. It's like 30 people running around his house. And it was just a loving, loving, loving family. A lot of people didn't see that side of him. You see Murder Inc. You see the music or you see the problems with the 50 cent or whatever, so on and so forth. But the guy was an amazing family man. And to watch that. And as a father, yeah, it affects me because, like, I want to be closer with my family the way Irv is with his family. So that's how I would say it affects me.

[Charlamagne Tha God]

You know, it's interesting when you talk about the art of communication. Like, I like the way Irv communicated. It may have rubbed some people the wrong way, but I like it because it's direct. Like when we talked about how, you know it was intentional, he wasn't the small talker. It was this, what we doing? This how we doing it. This how I think it should go.

[Harry O]

Right.

[Charlamagne Tha God]

I like that.

[Harry O]

No, listen, absolutely. It's something to be admired there. Everyone has different strategies on how they communicate. Irv being direct may work for him with certain people, but I'm quite sure it didn't work with. It didn't work with everyone. Right. So it all depends on what your style is. And I was thinking about something. Yeah. Some people don't like small talk, and that's fine. Like in the book, I mention a term called farming and hunting. Those are different ways of nurturing a relationship. When we're cutting the small talk out, I'm hunting. I know exactly what I want. I know what you have. We know we can make that work. But every relation doesn't work like that. Sometimes we have to farm, we have to plant seeds. I don't know where the relationship may go, but I know we can possibly build. So I'm going to plant seeds. Then we just water the seeds. Water the seeds, and next thing you know, we're eating off the fruit from the seeds. And it's really important. Yes. I'm an entertainment executive. So all we're talking about is how these theories affect. In business, it's in your personal life as well. If a young man is trying to get to know a young lady, or vice versa, it's ways you go about that. You have to be intentional. You have to be strategic. Yes. What is your goal by dating this woman? That's transaction. Cut the small talk. It doesn't work like that in your personal life. Right. You have to farm. Your daughter is seeing someone. Your oldest daughter, they're not engaged or nothing like that?

[DJ Envy]

No.

[Harry O]

All right, I'm sorry.

[Charlamagne Tha God]

She's 23.

[DJ Envy]

She's 23.

[Harry O]

Right. But that young gentleman, he had to farm the Relationship with Madison. Right. He had to farm. It wasn't a transaction or a hunting relationship. It doesn't work like that. He had to be intentional. Farm plant seeds, whatever those seeds are, check up on it, Know her birthday, know her dad's birthday, so on and so forth. So farming and hunting are two different ways of building a relationship.

[Charlamagne Tha God]

And you talk about the difference between intrapersonal and interpersonal.

[Harry O]

Oh yes. So the first form of communication, the most important form is your intrapersonal I n T R A. That's the conversation within how you see yourself, how do you connect with yourself, what do you think about yourself? How do you evaluate yourself? If you can't evaluate, if you don't possess the ability to self evaluate, then you're at a disconnect with you. So everything how I feel and think about me, that's my intra will depict my inter, my interpersonal relationship. So, you know, Charlamagne, you say something that hurt people. Hurt people. You say that a lot, right? It's something internally that's at a disconnect. So since they're at a disconnect internally, they add a disconnect externally with others. So when you understand who you are in your intra and you're reaching the highest level of who that person is, you understand who you are, you understand what you can do. And I understand how to connect. I can connect with others better because I connect with myself at a certain level. So intra depicts how your inter will turn out.

[Unknown Host]

You also talk about in your book hip hop and how it shaped you as a man, both good and bad. How does that speak to your communication?

[Harry O]

Wow. All right. So yes, hip hop aided me on a path to self actualization of being the man who I am today. And I mentioned this in the book and I'm gonna give the gentleman credit where I heard the term. And I tell you, yes, hip hop got me on this path. But I have to have accountability and understand that also some of that content in the music could have caused a self destruction, some form of self destruction. Like some of the artists we were, you know, I was mentioning in the book, I mentioned, are we the heroes or are we the villains? And I heard this term through a pod know it was a TED talk by the guy Lecrae and we're gonna make a documentary about it. Salute to him. Yeah, salute to him. So I want to give him his credit. He mentioned hip hop. Are we the heroes or are we the villains? Are we Reason why I mentioned this? Yes, I'm a child of hip hop. I have to Credit hip hop for being, taking me where I am. But also there's things in the music that's villain like that can cause you on the wrong destruction, wrong path. We glorify the person that's coming home from jail before we glorify the person that's going away to college. Right? We do a lot of that in this music. So are we the heroes or are we the villains? Now what's the difference between a hero and a villain? A hero has the same attributes as a villain, but a hero becomes a person, becomes a villain through trauma. Some type of trauma can make you become a villain. You look at anything in nonfiction or fiction. Batman, his parents got killed and he became this. If you seen the joke or something happened, he became a villain for these reasons. What turned hip hop music villain like the crack epidemic? The crack epidemic, as far as in my theory, in this documentary we're shooting, the crack epidemic shaped and destroyed hip hop music into the way where it turned into more villain like in the music and the content that's in it. So are we the heroes or are we the villains? I understand that hip hop made me a hero, but I also understand some of it could have made me a villain as well.

[Charlamagne Tha God]

In my last book, Get Honest or Die Lying, why Small Talk Sucks, I have a whole chapter with basically the same thing. I'm just exploring hip hop's ability to be a positive and self destructive force. Listen, like literally, like, I think that if you come, if you're a certain age, at some point we gotta have some accountability.

[Harry O]

At, at some point I'm glad we feel the same way because at some point you have to have accountability. I'm never disrespecting my hip hop music. It made me who I am. But yes, there are images. It's things that we put up on a pedestal. If we don't have accountability, we are causing poison if we don't know how to steer that ship in the right direction. But is it also how it's cultivated? Right?

[DJ Envy]

And the reason I say that is if I put a gun on the table and you use a gun, that could be a negative thing. But if I teach somebody how to use the gun the proper way and the right way and what to use it for, it's a positive thing. Same thing with hip hop, right? Yes, hip hop, all those images we've all seen, all seen. But my parents, especially my dad cultivated me to look at things a certain way. I never sold crack, I never sold drugs. You know, I never used coke or crack or Nothing like that. Because my dad cultivated to me to like, no, this is what this is for. These are messages from here. But that's not you. Yeah, don't make that you.

[Harry O]

Right.

[DJ Envy]

You see what I'm saying?

[Harry O]

So it's two different sides with your daughter.

[DJ Envy]

Your daughter dances, she listens to hip hop music. And I'm sure she might dance to some stuff that's a little salacious, but you tell her this is cool for this. But that's not.

[Harry O]

You listen. And there's a job, like you just said, your dad, your dad was there. Like I always say, you know how you take a kid bowling and they got to put the barriers up so the ball can go down? That's what parents are, right? We are the barriers. And we need both. We need both because you can have one parent and that ball could still gutter that way. Right? We are the barriers to keep the kids going forward. So your dad, was that to let you know, like, yeah, this is what the world is, but that's not what's good for you. Listen, there were times, yeah, my daughter dances and she dances to hip hop. And she's not gonna remember this. We'll get in the car and I wouldn't play no hip hop in the car at all. None whatsoever. When she was younger, when she was maybe 4, 5, 6. It's not gonna be certain shows on TV, no disrespect to any of the shows, but certain shows, excuse me, certain shows wouldn't be on television. Cause I'm trying to shape her mind to see a certain way. Now, we can listen to certain music because I see that the barriers are working. I see who this young lady is. So, yeah, we could listen to hip hop. And I'd rather her listen to, you know, Drake than over some other artists. But yeah, we have to be those barriers because in hip hop, we could be the heroes or we could be the villains.

[Charlamagne Tha God]

That is a fact. Seductive communication. You leave that chapter blank in the book.

[Harry O]

Yeah. Why?

[Charlamagne Tha God]

It just has to be continued, Right?

[Harry O]

So when I first wrote the book, I wrote the book in 2020 during the pandemic when I started. Now, as a college professor, there's different chapters in the book, right? So I'm gonna answer your question quickly. We start off with intra personal communication, the conversation within. So if I'm teaching a class and it's the first day of the semester, and I say, all right, Charlotte, welcome to my class. Did you take any communication courses before mine? And you may say, yeah, I took a leadership and communication Class, I'm like, that was your first communication class. Communication should be taught with prerequisites in a certain order. Right. So the first order is intra. Then I go into inter. Then I speak about culture and communication. I speak about media and communication, power and leadership. I'm taking you on a journey seductive. Communication is sort of like the final level of the book on how you use seduction to communicate. And not seduction in the sense of a sexual form. Just knowing how to seduce someone's mind to navigate in a certain way. And the reason why I left it blank, because it has to be a part two to the book now. Come on. It gotta be a part two to the book.

[DJ Envy]

Now. As a professor. Right. You know, I look at college courses as sometimes outdated.

[Harry O]

Yes.

[DJ Envy]

Right. And that bothers me a lot, especially with my kids, you know, going to college because a lot of things that they want to learn or that they're into, a lot of times these colleges don't necessarily teach. Right. My first major was communications. I left communications and went to business management and marketing. But for me, what I wanted to learn for communications wasn't helping me with what I wanted to do.

[Harry O]

Right, right.

[DJ Envy]

Communications was a lot of reading, a lot of intro, a lot of this, a lot of that. But I wanted to be hands on with this stuff like that. So talk about some of the courses that you think should be in college and some of the things that should be taken out of college.

[Harry O]

Right. That's a. That's great.

[DJ Envy]

Because I have no disrespect.

[Harry O]

A lot of the algorithms that I.

[DJ Envy]

Learned in college I don't use. I've never used. And if I have to, I have a computer that will do it for me.

[Harry O]

Absolutely. Now it's two parts I want to get into. Now, some of the courses that are in college, I have to be really careful because I'm still a college professor and I don't want the college to be listening right now. So I do believe there should be more entrepreneur courses in college. We're going to need AI courses in college. We're going to need real estate courses in college. You're going to need these things in colleges Now. I believe certain colleges are doing it. Ja Rule's son shout out to Jordy. He just graduated from SCAD in Atlanta.

[Charlamagne Tha God]

That's Savannah.

[Harry O]

Savannah, yeah. I'm sorry. Savannah. And he was home for his sister's wedding. And we were in the kitchen at Ja's house and he was saying how all these different courses that he's taken, it was never available. To me as a student. So some of the courses that we're talking about e, like, we've been out. We've been removed from college for a little bit. Some of these colleges are doing that, like, teaching him how to code. He can build games. He can do all the things that I would never even thought of art school.

[Charlamagne Tha God]

I know, because my daughter's been talking about. She, like, that's the one school she's looking at.

[Harry O]

But, like, even when Josh talks, he's like, listen, I visited the campus, and I'm like, I've never seen a school like this. So, yeah, I do think we need those particular courses. Now. Let me just rewind. As far as, like, a communication course I mentioned in the book, I credit Eddie Murphy to where? To one of the reasons I'm here today in the movie Boomerang, Like, Boomerang is one of my favorite movies. You seem like he was a marketing executive. He garnered so much attention from women. He was smart. He was. He was everything. I'm watching this, and this goes back to my representation. I'm watching this movie. I'm like, I want to do that. I want to know how to do that. So I was in college at the time. So I went to my counselor. I said, listen, in this movie, this guy, Eddie Murphy played Marcus Graham. He's a marketing executive. How do I get into marketing? She said, well, you need to understand what communication is to understand what marketing is. I said, well, sign me up for all communication courses. X amount of years later, I'm doing marketing strategies for my own company. So I needed that course. I needed these courses to be able to do what I'm doing now.

[DJ Envy]

Gotcha. Gotcha. Well, tell them where they could get this book, brother.

[Harry O]

You can get the book on Amazon, right? If you're listening, you could just type in Harold Wilkerson. Cause if you type in Harry O, nothing's gonna come up.

[Charlamagne Tha God]

If I was not gonna come up, it'd be a bunch of y' all. You as homies from death row.

[Harry O]

People always make that mistake, too. But that's a different story. Yeah, but you can get the book on Amazon in the search engine. Just put in it's beyond words by Harold Wilkerson, and then it'll pop up. So please get the book. And one of the lessons I want you to understand and learn, I leave it off. I closed deals with the WNBA and I closed deals with the NBA for going over six. Six or seven seasons now. And it all started for me attending one basketball game. I attended a game. And it went from the person who handed me my ticket to go sit on the floor. And through strategic and intentional communication, I started closing deals with the CEO of the New York Liberty, the CEO of the Brooklyn Nets. Like it went from attending like how do you attend a game? And then fast forward you closing deals with the owners and CEOs of WNBAs and NBAs. And you hear all that when you pick up the book.

[DJ Envy]

All right, Harry O ladies and gentlemen.

[Harry O]

Pick up the book.

[DJ Envy]

It's beyond words. Available now.

[Charlamagne Tha God]

Yes sir.

[DJ Envy]

Appreciate you brother.

[Harry O]

Thank you. Do I get like the whole thing when they be like, yo, tomorrow I'm going to be on the Breakfast Club.

[DJ Envy]

Can we close out the show first?

[Harry O]

I'm sorry O It's the Breakfast Club.

[DJ Envy]

Good morning.

[Charlamagne Tha God]

Wake that ass up early in the morning.

[Harry O]

The Breakfast Club. Does friendly have a taste? If it does, it's probably like hello's peppermint flavored anti plaque and whitening toothpaste. Brush away plaque, show tartar who's boss and remove surface stains to naturally whiten. Hello's thoughtful and flavor forward products make.

[Unknown Host]

Brushing your teeth feel like a confetti.

[Harry O]

Filled bathroom dance party. So say hello to hello with the always cruelty free, never tested on animals to toothpaste that's made to spread smiles. Visit helloproducts.com and let hello add some everyday yay into your life.

[Lex Borrero]

Welcome to the youe versus you podcast. I'm Lex Borrero inviting you to go beyond the titles and the accolades of the world's most successful entertainers. Each week we take off the Cape and get real about the inner battles, childhood stories and the moments that shaped our guests. Get inspired to become the best version of you. Listen to youo vs you podcast on the iHeartRadio app or wherever you get your podcasts.

[Unknown Host]

I also wanna address the Tonys. On a recent episode of Checking in with Michelle Williams, I open up about feeling snubbed by the Tony Awards. Do I? I was never mad. I was disappointed because I had high hopes to hear this and more on disappointment and protecting your peace. Listen to Checking in with Michelle Williams from the Black Effect Podcast Network on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.

[Harry O]

Why is a soap opera western like Yellowstone so wildly successful? The American west with Dan Flores is the latest show from the Meat Eater Podcast Network. So join me starting Tuesday, May 6th where we'll delve into stories of the west and come to understand how it helps inform the ways in which we experience the region today. Listen to the American west with Dan Flores on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.

[Unknown Host]

This is an iHeart podcast.