Carlos Watson is the CEO and Co-Founder of Ozzy Media, which is killing right now. He was a former CNN, MSNBC journalist who decided, this is not how I want to live. This is NOT how I think the news media world should be, and I m just going to go out there and do it differently.
00:00:37.160He hosts The Carlos Watson Show, which is a podcast and on YouTube.
00:00:41.340He's also a co-host with my pal Katty Kay of the BBC.
00:00:44.560She's sweet and fun, and they do their own separate podcast together.
00:00:48.540But listen, this guy is really interesting.
00:00:50.460He's 51 years old, born and raised in Miami, parents were teachers.
00:00:55.580He is a kid who openly says he was a black boy dubbed difficult in school,
00:01:02.260who somehow managed to overcome the many challenges thrown his way to wind up at Harvard and then Stanford Law School.
00:01:10.060And now he's a media executive doing really well.
00:01:13.160He's interviewed everybody, everybody from Barack Obama to Bill Clinton, Ta-Nehisi Coates, Malcolm Gladwell.
00:01:18.420I could go on. He gets people from all sides of the spectrum because he's open minded and he he's not he's not ideological.
00:01:26.720He's not particularly partisan. He used to work in dem politics, democratic politics.
00:01:30.280But and I think he definitely means more liberal, but you'll see for yourself that it's possible to to be in that place and to still be open minded to other ideas,
00:01:39.260to have beliefs like I definitely don't share when it comes to the cops and systemic racism, possibly in other issues, but to still be open minded to discussion.
00:06:41.020If you wanted to be heard in your family, you had to learn the art of conversation when you're living with so many women.
00:06:46.520Well, and not only that, so many women who we didn't share the same interest.
00:06:51.320And like trying to convince my sisters – we had one big TV – to let that TV be on the playoffs, NFL playoffs or what have you, that was the ultimate art of negotiation.
00:07:02.920So, yes, I definitely learned a thing or two about – I always say how to compromise and how to surrender gracefully.
00:07:11.060I'm still working on that, both of those things.
00:07:14.580Now, walk me through how a kid from what you describe as a relatively humble, relatively modest home outside of Miami grows up to get into Harvard, goes to Stanford Law School, and winds up running a big media company.
00:07:32.460I mean, your company is just killing it right now.
00:07:50.680I didn't appreciate that at the time, and certainly they will tell you that I didn't always show my appreciation as a kid.
00:07:56.000But when all is said and done, while no one's perfect, like I ended up with a really good deal, and I think having good, creative, loving parents who are generally positive people I think was a big help.
00:08:12.140And that was especially true when I had some rockiness early on.
00:08:16.160I had some issues in school and some other things.
00:08:19.200I had a very bad accident when I was 11.
00:10:00.520But although it just, this also may be TMI, but it wasn't because my eggs were actually fine when I started to, you know, try to have children.
00:10:08.140But this is really a lot of information.
00:10:55.080But I do try to mention it sometimes because anybody else who's out there, because there's precious little on the internet about that issue.
00:11:00.820So, like, when you Google it, you're like, I'm the only one.
00:11:03.240I'm deformed and I'm never having kids.
00:11:09.280And your mom, back then, she would have had to do it, you know, the old-fashioned way because they didn't have IVF back in the late 60s, 70s.
00:11:17.500And, you know, she was fortunate to have.
00:11:21.780But C-section, indeed, I was the first of several C-sections.
00:11:29.860And, you know, I like, though, that you talked about the T-shaped uterus and the whole journey to pregnancy because it's funny.
00:11:38.780I started having lots of conversations with people about this in part because I had several younger sisters who have been thinking about this.
00:11:46.720And it is such a positive thing, not just for women, but for men, too, to hear this conversation and for people to get information, to get hope.
00:11:59.560And I think your girl, did Erin Andrews tell me that she was talking to you about this?
00:14:25.580I'd get sent to the principal's office.
00:14:27.600They would ask my mom to come pick me up.
00:14:30.040And in those days when there were no cell phones and women were just beginning to take on more white-collar professional jobs, for her it was super embarrassing because no sooner did she drop me off at school and gone to work, then there was a message waiting for her.
00:15:54.700And they didn't think two plus two equaling yellow was very funny.
00:15:58.520So they would ask me to leave the building.
00:16:01.700And so and once you start to become the bad kid that happened, and I think even more so, and there are lots of studies on this, I think particularly for a lot of black boys, unfortunately,
00:16:13.580and certainly in my era in the 70s and 80s, you could easily like end up getting pigeonholed and getting down a bad road.
00:16:25.140And so they would start to say, well, what is wrong with this kid?
00:16:29.860And there was a young Ph.D. student, Carol Bernstein, who was doing her Ph.D. at the University of Miami.
00:16:37.660And as the story goes, she was in the teacher's lounge, and she was doing her Ph.D. on like disruptive kids.
00:16:44.360And she heard all the teachers talking about this bad boy, Carlos Watson.
00:16:48.180And she thought, oh, my goodness, he would be like the perfect example for my dissertation.
00:16:55.160And so when the new year came, she met this bad boy, Carlos Watson, who all the teachers didn't want in their class and were worried about.
00:17:02.840And she was the one who came to my parents and said, you know, I actually think he is probably just a bored, bright kid.
00:17:12.480You should go get him tested at the University of Miami where she was studying.
00:17:15.880And there was a child psychiatrist, Dr. Shogi, who, you know, normally it was a very expensive thing to have a kid test it.
00:17:25.400And God bless him, Dr. Shogi or his kids, if you're listening, thank you.
00:17:29.660He kind of waved it and said, you know, let me, you know, let me test him.
00:17:34.480And, you know, they came back and said, you know, I do think he doesn't have a learning disability.
00:17:39.320I think instead he's a bright kid who's bored.
00:17:41.820Let's see if you guys can challenge him a little bit more.
00:17:44.120And that actually really helped me, Megan, because you can imagine as parents, you know, the last thing you want to hear is this early in the game.
00:17:56.020And yeah. And you're hearing that every day and you're having to go to school to pick him up and you're worried and you're like, oh, my goodness, what's going to happen?
00:18:03.860And so to finally see a little bit of light that maybe there is something better for your kid here was a big relief.
00:18:11.500And to my parents credit, they like latched on to that and they began to say, hey, is there a different school environment where he could do better?
00:18:18.240Or are there other things we can do to make sure that we channel his energy well?
00:18:23.000Wow. That's amazing. And a testament to your parents paying attention when the information came in, when you told me the story, when you mentioned Carol, I got I got a chill because you could just see this is like the turning point in your story.
00:18:35.900In the story of bad boy, Carlos Watson, who turns out to be this brilliant kid, as as the credentials and your life, your life's work would prove.
00:18:44.420And it reminds me of my friend Nancy Armstrong, who's amazing. She's coming out in the fall.
00:18:49.300She's going to come on then with a documentary on ADHD.
00:18:53.580That doesn't sound like you had ADHD, but it's a lot of the kids who struggle with this get get labeled as just problematic.
00:19:00.480They get kicked out of the classroom. People don't want to deal with them. They're annoying.
00:19:03.640And if we if we look at it differently, like at the number of stars and academics and like Thomas Edison, all these people have had ADHD or so we think it can be turned.
00:19:15.700Right. If it's recognized, you have somebody who cares about you intervene.
00:19:18.940It can be turned into an asset. And a kid who was just thought problematic can be seen in a totally different lane and achieve endless, endless ends.
00:19:28.040Well, you know, the other piece of it that my mom said as well, she got because I talked to her about it later on in a really grateful way.
00:19:35.720And and it was interesting because I think about some of the kids I grew up with.
00:19:40.540We lived in kind of a working class neighborhood. And and so I was able to see very clearly thinking about my next door neighbors kind of just very different routes.
00:19:52.800I could have gone down. Megan, I asked my mom, I said, you know, why, you know, why did you do the things you did?
00:19:59.320She said, you know what? She said it was good that I was an older mom.
00:20:02.360She said, if I'd been a younger mom and I was getting that much criticism and it was that much of a struggle and I was having to leave work all the time, she said I would have gotten overwhelmed.
00:20:11.400But she said the fact that I was an older mom made me thankfully not give up and navigate the system better.
00:20:18.680And so I often think about that, too, you know, back to your story about, you know, coming to motherhood later, that probably, you know, so many different benefits to having some of that life experience.
00:20:30.120Mm hmm. That's true. I mean, I do think it's easier to keep your temper.
00:20:33.680You know, it's like, yeah, this is really worth getting getting upset about.
00:20:36.960And also, like you, I was thinking about it with respect to covid, because I think some people some people share too much with their children.
00:20:45.820They overshare and the children don't need to be frightened about covid, frankly, about school shootings, about any of that stuff.
00:20:53.280They they don't they have enough to worry about.
00:20:55.320And so I do think sort of being older, you've seen more, you know, as Brit Hume used to say, your give a shit meter changes and for the better, you know, for the better.
00:21:04.940And so you telegraph less worry and I don't fright about life.
00:21:10.500And what is a dangerous society than you otherwise would have?
00:21:13.680Coming up next, I'm going to ask Carlos about what John McWhorter said.
00:21:17.060He thought the top four prescriptions for improving some of our inner city communities, some of our inner city black communities would be remember that with McWhorter the other day.
00:21:25.840So I'll put him to Carlos. And he's actually got some interesting additions for that list.
00:21:31.080What you said about your mom is reminding me, you know, we had John McWhorter on the show recently and we were talking about, you know, forgive the term, the black community, because I realize there's not really a black community.
00:21:43.860There's not a white community. I don't know what the hell that means.
00:21:45.460But, you know, there are some problematic items, things that we need to talk about inside inner city Chicago and places like it.
00:21:52.700And he said four things. And I'm just going to say them quickly because he was much more articulate than this.
00:21:58.620He said, end the war on drugs. If there were no black market and hard drugs, he said there would be a revolution in the black community.
00:22:05.580Normalized trade school. He said it's absurd to keep telling black America that the ideal is to go to four years of college and pretend like you like Shakespeare.
00:22:14.120Hey, that applies to more than just black America. Just FYI.
00:22:16.480Um, improve reading education. He's a linguistics guy, so he wants he wants reading to be taught with phonics.
00:22:22.980He thinks it's really important. And then he said broaden access to contraception to make family planning much more accessible.
00:22:29.200So, I mean, you know, you talk about sort of how you how you pulled yourself up and your mother's example and attention to you.
00:22:37.540What do you think of that? And what do you think about sort of this?
00:22:40.880I mean, there's a lot of there's a lot of young black boys who are labeled problematic, who do not wind up at Harvard and Stanford Law School.
00:22:49.000Yeah, I a number of the things he said there I like and I think makes sense.
00:22:55.380I think the drug point that that's interesting about about what revolution would ensue if that were the case.
00:23:04.580Um, uh, what was the second thing he said? He said trade school, um, you know, I would tweak that a little bit because I think they're more modern versions of trade school,
00:23:15.440um, whether that's computer coding academies, right, or or other sorts of things.
00:23:20.940So I would I would I would think about what it meant.
00:23:23.660But but but but the notion that a four year college is an option, but not the only option, um, I think makes sense, by the way, not just in inner cities, but broadly speaking, I think there are absolutely many ways forward.
00:23:37.320And, and, and I no longer think also that we will just launch, I think that most of us will have many different careers, right.
00:23:45.520And so thinking about schooling, not just as something you do from five to 21 or five to 22, but that there's going to be continuous learning and continuous resets and continuous opportunities to pivot.
00:24:01.140I mean, look at you going from the law to broadcasting to, you know, I would call you an entrepreneur now.
00:25:05.400One of the things I've been talking to folks a lot about is, um, what would happen if we thought not only about some of the challenges of the moment,
00:25:12.580but we thought about the next 250 years of America, and if we had effectively a new constitutional convention,
00:25:19.420and if we broaden the people who were at the constitutional convention, uh, as we would, uh, this time around,
00:25:27.160meaning that in addition to Washington and, you know, Jefferson and Hamilton, you had Kelly and Coates and Gladwell and Lakshmi and all sorts of folks who were part of the conversation.
00:25:39.000And what kind of creative things would we think about in a world that will have robots and will have AI, right?
00:25:46.020And so I think that that's my long way of saying, if we want to make big, dramatic, social and economic, uh, change and improvement,
00:25:57.960we have more tools in this moment than we've like ever had, right?
00:26:02.880And, and we could make a lot of changes in communities, including the black community.
00:26:07.660And some of the things John said, I think are part of it.
00:26:10.500I don't know that I would make that all of the things that, that I would do that.
00:26:15.140I do think that there are real issues around, um, uh, uh, uh, um, uh, what are some of the other things I think that I would do that I think would make a substantial difference?
00:26:27.420I, for example, um, uh, would have a thousand new schools across the country that were super high quality and that were super open to a wide variety of people.
00:26:40.620I would, um, uh, I would think, uh, more ambitiously about, um, facilitating entrepreneurship, meaning, um, more bank loans and even more than what the SBA does to really stimulate that.
00:26:56.460And I would have not only, um, accelerators or kind of startup boot camps in wealthy places like Silicon Valley, but I'd have them in lots of other places like East St. Louis and, um, uh, and other parts of the country and, and create businesses out of, out of there and facilitate that probably a more ambitious, aggressive ways.
00:27:16.900And I think we sometimes do, uh, even when we say we're going to do that.
00:27:20.360Is it Kevin Hart who's doing, he's doing something like this.
00:27:23.700I think he's going, um, to underserved communities and trying to explain to young people how they can get their own business started, how they can get a loan, like to make it simple, to put it in very simple terms.
00:27:35.160Because, I mean, I'll tell you, even, even I, as a law school graduate, and it's overwhelming when you try to deal with the paperwork, you're like, how do I set up a company?
00:27:50.420And, and, and, and by the way, it's not for everybody, but, but, but, but yeah, I'm definitely a believer in, in not only breaking it down, but then having almost like a, a team and a collective.
00:28:03.020I mean, you see people do that, Megan, when people start running, right?
00:28:06.240They do running clubs and get people going and when they're going to do their first marathon or what have you.
00:28:10.420And I, and I would treat a startup kind of similarly, which is, which is, I would not only give people advice, but I'd put them like on a team of other entrepreneurs who are all, you know, trying to break through.
00:28:23.640But, but, but Megan, I, I do, you know, I feel strongly that we can do better and that it doesn't necessarily have to take a generation or two or three.
00:28:35.640And, and I would love to see our leaders just be way more ambitious.
00:28:42.840Like I live in Silicon Valley and I see companies like Zoom and DoorDash and Uber and Tesla and Airbnb, all companies that sounded ridiculous.
00:28:53.820I'm sure the first time someone told someone about them, right?
00:28:56.520Like, wait, you're going to rent out rooms in your house to random strangers over, you know what I mean?
00:29:01.800Online or wait, wait, you're going to compete against the taxi industry that no one knows how to crack.
00:29:07.440And people literally are shooting at each other over medallions.
00:29:10.800And, and so if we can be that ambitious there, I'd love to be that ambitious about, um, about social policy in whatever dimension.
00:29:20.320Um, and, and I feel like sometimes the ideas we talk about are more modest and I would love something that was really going to change things, you know, pretty significantly.
00:29:32.600Well, you're up against people's general resistance to change, to big change, you know?
00:29:36.120And in fact, I was just reading, um, we just said on Adam Grant, who I know you've had on.
00:29:40.200And, um, one of the, I think, I think this is from his book, but one of the, one of the things that was espoused was when trying to convince somebody that your idea is a good one, one of the things you might consider reassuring them of is the things that will stay the same, right?
00:29:56.480Like I got this big change to propose and, but like, here's a one through nine that's going to stay the same.
00:30:01.600And I just like 10, 10 is going to go away, you know?
00:30:05.400And I thought it was a really interesting persuasion technique, but let me pick up on something else you said.
00:30:13.280And I, and I think that's what you're doing right now with founding your own media company, um, and putting out your own show on YouTube and as a podcast, which has been hugely successful.
00:30:22.740And I love it, of course, cause I'm doing something similar though, not as ambitious, I think not yet.
00:30:28.220And, um, I wonder what you think about what's happening right now in our media.
00:30:32.660You've been, uh, just so our listeners know, you've been at CNN over time.
00:31:04.880Like he was like, you know what I mean?
00:31:07.160Like it was really a wild idea and I still remember, uh, first hearing about Rupert Murdoch and hearing about the Fox channel and then eventually Fox news and some of these other things.
00:31:17.220And so they were really, uh, kind of creative pioneers, but, but, but yeah, I mean, I think that in the same way that currency is changing, meaning crypto and tech is changing, meaning kind of robots and everything else.
00:31:30.860And, you know, how we date, how we work, where we live, all of that is changing.
00:31:37.920And I, I think that there's a window here where there will be three or four really significant new media companies by the end of the decade that really are among the 10 most important in the world that weren't household names, you know, today.
00:31:53.780And so I hope that Ozzy ends up getting to become one of those.
00:31:57.740I think that to really capture, not just the attention, but the commitment of curious people, I think you can't be smart and boring and you can't be flavorful, but empty, but I think you have to be both smart and flavorful.
00:32:12.500And I think you have to meet people where they are.
00:32:15.200And I think that it can't just be digital as great as digital is, but I actually deeply believe in live events.
00:32:21.500Well, I know you said that one of your goals for your show or one of your personal goals is to be like Oprah.
00:32:27.840And I understand, I used to love Oprah.
00:32:29.440I love her less now, I confess, because she got political and I was just like, oh, she kind of got so rich and so out of touch.
00:32:35.280I was like, I've kind of lost you and you've lost me.
00:32:38.860But I understand the point, you know, big interviews with anybody.
00:32:43.680Incidentally, she was just saying her big mistake in one of her interviews was she had Sally Field and she said she made the mistake of asking Sally Field whether Burt Reynolds sleeps with his toupee on.
00:33:01.540Wait, why did she say that was a mistake?
00:33:03.600Well, because apparently Sally Field did not like that and shut down.
00:33:07.760She went totally cold on Oprah and Oprah said she couldn't get back in.
00:34:07.180And because it was remote, I couldn't actually see her clearly enough.
00:34:11.740But all of a sudden you could feel that it had changed.
00:34:14.220And I know that if I had been there, I feel like something – I would have had a second chance with it, but I didn't.
00:34:20.620So some people are a little more reserved.
00:34:25.600And even though they are public figures, you know, in their heart they come to conversations on the defensive a little bit if that makes sense.
00:34:32.460And so there's not that same kind of just ease, I'm here.
00:34:38.180And so there's already some of that going on a little bit.
00:34:42.940And so if something throws them off, then I feel like it is tougher for them.
00:34:48.780Whereas there are other people who, you know, they're going to laugh with you almost, you know, almost –
00:34:54.700You know, I think about former President Bush who's, you know, 43 who, you know, he's going to laugh with you almost no matter what.
00:35:05.720I think he would laugh with you even if he didn't like you.
00:35:08.860I think – I mean obviously certain scenarios wouldn't allow him to laugh.
00:35:12.040But he in general is someone who would just assume that people would be laughing and that there would be jokes flowing.
00:35:21.740And our media has gotten so polarized and so, frankly, nasty that when people don't know the anchor or the host and they take a risk by going on, especially in a long-form podcast situation, it's like it's not a three-minute one-and-done situation.
00:35:38.140I mean like I've been on the other end of that where I've like this caricature of me has been painted in the media that doesn't match up at all with who I am.
00:35:46.920And you consider the invitation saying, okay, why is that person having me on, right?
00:35:51.420Do they think that this is going to be a gotcha or this is – you know, it's just you've got to – you do have to carefully navigate the waters because not everybody is like you.
00:35:59.940You are an open-minded, kind and generous interviewer.
00:36:03.380I think other people are more looking to advance their own star.
00:36:09.300I – and maybe part of that is also the reality era that we're in, right, and some of the competitive survivor-type games and mentality I think that people see and go after it in that way.
00:36:22.900Or maybe some people would argue some of that even goes back to the early days of 60 Minutes and Mike Wallace and the rest.
00:36:30.360But now social media – social media rewards that behavior.
00:36:56.120And you're always going to end up being surprised, right?
00:36:59.420Like, you know, and if you stay in it and you're just with the person, they're going to share something that reminds you that most of us are contradictions, right?
00:37:12.040What did Dr. King used to – he loved that quote that – there was a famous quote that he used to say, there's enough stuff in me to make both a gentleman and a rogue, right?
00:37:21.200And I think very few of us are only one thing or the other.
00:37:25.440And so I actually – I like the contradiction.
00:37:27.720And I'm more interested in someone who has contradictions and who's willing to allow that to be part of how we get to know each other.
00:37:46.120I don't know much about her, but God, she gets killed in the press, right?
00:37:48.840She says controversial things, but there are a lot of people out there who say controversial things, you know?
00:37:53.500It's like why would you say that makes me uninterested in speaking with them, you know?
00:37:59.200Or I just want to have them on so I can beat the hell out of them.
00:38:01.820Now, if they say something really stupid and they're a politician, game on, right?
00:38:04.980Like that you put yourself out there, especially if it's a short-form interview and you just – you know, they come on just to explain the thing.
00:38:10.420But in podcasting, it's fun because you get to – you get the layered pieces of a person, you know, where none of us is all good or bad.
00:38:19.080None of us comes to this world with a presumption of, you know, evil or all goodness.
00:38:39.700But first, I want to bring you a feature we have called From the Archives here at the MK Show, where we look back into the history of the show, the show's library, now with more than 100 episodes.
00:38:52.900I've been thinking about that and using it.
00:38:54.680Just like there's something about just the woo without the who that's appealing.
00:38:57.820Anyway, we will be bringing you a clip today that you should go and check out if you haven't heard it yet, or you can listen to the whole episode.
00:39:04.120You can listen again if you already have listened to it.
00:39:06.380And today we're going all the way back to episode 28 in November of last year for my conversation with my pal Dave Rubin.
00:39:13.280I can't believe he was only episode 28.
00:39:16.200Like, I cannot believe that we're already at 100 and Dave was 28.
00:39:19.520It just seems like it's all going by so quickly.
00:39:23.900It did very well, and he and I had a great conversation about politics, about his own political journey from the left to the right, about gay marriage, about his own marriage.
00:39:34.200But listen, it's Monday, so let's have some fun.
00:39:36.320Near the end of the episode, we got into two stories that had us both and my entire team cracking up.
00:39:41.700They had to do with sperm banks, Donald Trump Jr., Dennis Rodman, and my nana.
00:39:56.660So the day we were, when we were deciding to do all this, it was a few weeks before.
00:40:02.140We had been planning on it for a long time, but when we were finally ready to, like, deposit the sperm and actually begin the process, it was right as the lockdowns were starting.
00:40:10.600And our fertility doctor called us, and it was Friday.
00:40:14.420He said, you've got to get here in the next hour because we could be closed for months.
00:40:18.740Like, you've got to deposit this sperm now.