Transcript, Episode 100: Carlos Watson on braving big changes

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This episode of Hello Monday, "Carlos Watson on braving big changes," originally published on Monday, March 15, 2021.

Jessi Hempel: From the news team at LinkedIn, I'm Jessi Hempel. And this is Hello Monday. It's our show about the changing nature of work and how that work is changing us. Welcome to our 100th episode. Truly. It's been nearly two years since we launched. 

You know, we expected to go deep with our guests on how jobs were evolving, how the work itself was changing, but that is not what happened. Instead, our guests have brought stories about how they transform, how they rise to the challenges of navigating new career paths, balancing work within their lives and finding meaning. 

These stories, they inspire me. They show me that I can change, too. And that's what I hope they do for you. So for our 100th episode, I'm bringing on a guest who's transformed his career over and over again.

Carlos Watson: I've been an entrepreneur. I've been a journalist. I've worked in business as a management consultant and as an investment banker. I've worked in politics. I've managed campaigns. I was a grocery boy at Publix where "shopping is a pleasure.” I was the mail boy in a legal office. So I've done lots of different things.

Jessi Hempel: That's Carlos Watson. Carlos built and sold an education company before he was 30. He's worked in business and politics. He's been a host on CNN. Eight years ago, he founded OZY Media to uncover rising voices before they went mainstream. Think podcasts, TV shows, massive festivals.

Last summer, in the midst of the Black Lives Matter protests, Carlos launched The Carlos Watson Show where he interviews high profile guests. Carlos has great advice about how and when you can make changes. Here's Carlos. 

Carlos Watson: Two things I think have helped me be willing to try new things. One, as simplistic as this sounds, something good happened to me that I had nothing to do with: I ended up with a really wonderful mom and dad - mom especially - who really affirmed early on that, "I love you no matter what,” like "I'm on your team, no matter what." And so, so often it's hard. I think for parents and other loved ones to really embrace people, taking a chance because you want the best for Jessi. You want the best for Carlos, for Sarah, for whomever. And so the idea that they're going to now take a risk, that's really hard.

And my mom, for whatever combination of reasons early on, just gave a big warm hug. Not, "I can promise you it's going to work out,” but that, "you're bright. Hopefully you're interesting. You're going to be hardworking.” And, "You should go for it." And, "why not?" All of that, I think has been helpful to me in ways I probably won't even ever fully fathom.

Jessi Hempel: Well, I love that you started there, Carlos, because from what I understand that you grew up in Florida, right?

Carlos Watson:  I did. Miami. Yeah. 

Jessi Hempel: And you grew up in a, it wasn't a terribly wealthy or upper-class family by any stretch. 

Carlos Watson: I wish it was. I wouldn't have minded. I would have been very happy. That would have been fun.

I wouldn't have minded. Would've been good. 

Jessi Hempel: It seems like your, your family gave you a lot of the skills and tenacity that have led to great success. And your mom was an educator. Was it her background in education that gave you the runway to try different things? 

Carlos Watson: I think that was part of it. I think when you're a teacher, you see the different ways different children learn.

And so I think she brought that appreciation to the table. And so she had us in... She basically had four kids between the ages of 36 and 41, which again, in that era was, I don't even know what that would be like. That'd probably be like, today, 46 to 50 or 51. Right? So, um, I know you're having a number two, but it'd be like, you were starting on number one and you were just beginning the journey.  

Jessi Hempel: I'm tired just thinking about it. 

Carlos Watson: Well, you know, she always, uh, you know, she had a great sense of humor. And so I think her teaching background was part of it. The other really interesting thing, Jessi, is that my mom grew up in the segregated South in Virginia, which I guess now it almost seems like a nice way to say it. It was worse than that.

But, uh, she grew up with super loving parents who believed in her. She was the second of seven. She went off to college, graduated college, came out, looked for a job. And Jessi, she would keep getting hired over the phone and by letters in those days, um, and Cincinnati, Ohio, and then when she would show up, all of a sudden, miraculously, this Black woman no longer had a job. That was two plus incredibly difficult years. That's a long time, you can imagine. 

And then Brown v. Board happened. And so sometimes we read these things in the history books. They don't mean anything to us, but in my family, what it meant was that, for the first time, my mom could get a job. And she got a job and she started teaching and she really appreciated that.

And a couple of years in a woman who had gone to college, uh, with a guy named "Marty King,” as in Martin Luther King Jr. um, came by her church, uh, to say, Angolans, as in the children of Angola, went to learn. Who will teach them. And my mom always said she sat there in church that day and thought, well, I, Rose, want to teach.

And no one will let me teach and these kids want to learn and no one will teach them. Maybe, we should go together. And so she did something incredibly daring before there was a Teach For America before there was, um, the Peace Corps, before there were easy, regular, Intercontinental flights, she took the bus up to New York from Cincinnati, Ohio, and, uh, stepped foot on a boat and set sail for Portugal and ultimately, a for Angola.

And, uh, she taught there for several years and then later came back to the States and met my dad and married and had a family. But I say all that to say, Jessi, that, that the other piece of it, for her, was not only being a teacher, but she had taken a chance. She had taken a very bold chance and she had taken a bold chance that paid off that made her a broader person, a more interesting person, a more dynamic person, a more worldly person.

And she, I think, brought that warmth to other people's passions and pursuits, even if they weren't conventional. And maybe, especially, if you can't be in charge of who your mom is, because I just won the lottery. But what you can do is what I call, surround yourself with angels and really make sure that, not that you're around people who are gonna agree with everything you do, but we all know the difference between someone who fundamentally is bringing positive Juju and positive energy into your circle and those who, for whatever reason, aren't able to sit with you and hear your dreams, not their dreams, your dreams, and help you think about your dreams and your next steps.

And so, you know, I got a lucky deal in being around, being born to someone like that and being around. And I always say that I wish it for other people in whatever form it may take, whether it's a neighbor, a roommate, a best friend, cousin, and aunt and uncle, whatever it can be, that that's a good deal when you can find it.

Jessi Hempel: You know, Carlos, I think that's such a beautiful point because I do think that the people that you choose to surround yourself with reflect back to you, your expectations and hopes for yourself and what you're capable of and the Mark that you can make on the world. Right? 

Carlos Watson: Yeah. And you and I both know Jessi, that there are moments when not only do you need good advice and good encouragement, but sometimes you need people to nudge you. You know, I heard Ta-Nehisi Coates say the most beautiful thing about his wife. He said, "She believed in me, even when I didn't believe in myself." He had gotten fired. He said from his umpteenth, uh, writing job. I think it's Time. It was Time Magazine and he was embarrassed to come home and tell her about it.

And he said, when he came home and he said, "Maybe, I should go ride a taxi." And he looked up to see what she thought. And he said, "What do you think?" She said, "I think you should write more. And that was it. And, and thank goodness she said that. Huh? Thank goodness for all of us that she said that.

Jessi Hempel:  You know what I love about that story? I think, and, you know, Carlos, I spent so much time talking to amazing successful people, like yourself, about their careers and the assumption before the conversation is always that it goes like up into the right, like first a good thing happens, then a great thing happens, then a really great thing happens.

It seems like maybe the truth is more like you stumble forward and you try to find your way and some things don't work. And then, if you're lucky, something really works. 

Carlos Watson: Sometimes you just need someone to stay close through that really tough part. And it's a good thing when it happens. And as you said, it may not work out up and to the right. It may work out some other interesting curve, but, but yeah, it's nice to see it. Especially if, if someone then is willing to pay it back, somehow, or pay it forward. 

Jessi Hempel: Well, so, Carlos, how did your education inform what you thought you would do initially for your career? 

Carlos Watson: I was a kid of the 70s and 80s in Miami, Florida. And kids like me who had two parents who were teachers: you probably thought a lot about being a lawyer because we saw lawyers like Thurgood Marshall and others as hopefully helping do things like Brown versus the Board and trying to right wrongs. And so, I thought a lot about law for a lot of like junior high and high school. That's what I thought. 

When I finally got this job summer of my senior year, I’m at the biggest law firm. I'm dressed up nicely, like my mom said I should be, and I'm showing up there and I'm handing out the mail. And then I see these guys aren't enjoying it and then a really nice guy who was a summer associate there, Mike. Mike, if you're there, hello. I think he kind of like, saw me, like, peeking around the corner and like, curious. And so he kinda like waved me in and you know, we just started having conversations during the summer and he would tell me a little bit about the job, what have you, and he balanced it out a little bit and he made me think, "Okay, well, maybe there's a way", but I wasn't sold on it.

But those were the things that were in my head. Things like law, things like journalism, things like politics were the main things. And it wasn't until I went to college, and my favorite professor, Martin Kilsten, may he rest in peace. It wasn't until Professor Kilsten made me start thinking about business as well, and about being an entrepreneur, that I even started to expand more. So I guess I had lots of influences all along the way, starting with my parents, but running up through, you know, the summer jobs and these good professors and these other kinds of people who I'd read about or, or watch. 

Jessi Hempel: In the time that I have known of you and followed your career, you've seemed like such an obvious entrepreneur. I'll say it's like part of the fabric of who you are. Um, but you didn't come to it right away. And I'm curious if when you were 19, 20, 21-years-old, if that was even on your radar, or if you knew people who were entrepreneurs. 

Carlos Watson: I, in retrospect, did know some people were entrepreneurs, but we didn't call them entrepreneurs. My Uncle Clinton, in small town Virginia, ran a little, one-room convenience store. And I remember he used to say, with a little bit of an accent, "Sto' business is slow business” because it wasn't very exciting. And so, and so he was an entrepreneur. 

My dad always had it on his mind, before they used the phrase flipping houses, he kind of knew that, but he couldn't quite get that right. Miami also is a place where we've got lots of not fully legal entrepreneurs and so that was in my mind a little bit. And then I went off to college and I got interested in it because Professor Kilsten said to me, who's, who's a politics professor that we needed more, uh, integration of entrepreneurship and that people like Ross Perot, who you may or may not remember, who was an entrepreneur and could afford his own campaign, had more of an ability to shape things than people who didn't. And so he kind of had that in my mind.

In those days, I was still focused on journalism though, and I was writing during the summers for the Miami Herald and the Detroit Free Press. And in Detroit, there were a couple of brothers from Arkansas who, um, who were the biggest drug dealers in town. And I very unwisely decided to call them up because I saw what they were doing was all the stuff that I was studying at Harvard, like all the stuff from Harvard Business School, like buy one, get one free, bringing in lower price workers, giving credit so people could buy more, um, you know, incentive system. Like it literally was all the stuff that they taught at Harvard Business School except, you know, they were doing some different. And so that was another thing to me. That was interesting. And I started thinking about entrepreneurship. Even more broadly and, uh, certainly, didn't pursue it. 

Jessi Hempel: No. Did that culminate in a series of stories? I mean... 

Carlos Watson: You know, but it did not because I realized when they did pick up the phone and they were shocked that I had called and they asked again for, "What did you say your name was?" that that would have been kind of a dumb idea. But it was, you know, all of those things made me aware of entrepreneurship and then you started to have more different kinds of entrepreneurs. 

You had a guy named Reginald Lewis who was an entrepreneur, uh, who recently was a lawyer, um, and who then, uh, got into business and bought a big billion dollar company and it was a big deal at the time. And so you heard his story a little bit and then, Silicon Valley still wasn't fully hot yet. I mean, people knew Steve Jobs and Bill Gates, but they weren't household names in any way. 

So, um, this is my very long way of saying entrepreneurship started to bubble, I'd say in college with Professor Kilsten. I'd get these other little, uh, interesting notes here and there, but nothing thickened quite yet until I actually moved out to Silicon Valley and then I thought, "Oh, That sounds kind of fun to be a part of creating something new."

Jessi Hempel: We're going to take a quick break here. When we come back, we'll hear more from Carlos Watson. 

(Our podcast midroll ads happen here.)

And we're back with more from the entrepreneur and media star, Carlos Watson. After college, Carlos got into politics.

Carlos Watson: Back to Florida, and I worked as chief of staff and campaign manager to a young up and coming, uh, guy. I like to say he was Obama before Obama, and he was a guy named Darryl Jones. Very talented, charismatic guy. And then I went back to law school in part with his encouragement and my parents. And then this business firm, McKinsey came and started recruiting, not at business schools, but at law schools and medical schools and the military and other places. And so I went and I joined them, but I had begun to think about doing something entrepreneurial and I ended up quitting after two years to start my first company, which was an education company with my sister and my best friend. We all three lived in one small apartment until my sister's decided that was a bad idea to live and work together.

So she left us, but we all still work together. And we built that company over a number of years. And you know, when we sold it, some weird, wonderful happenstance happened. And I had done some guest appearances on TV when I was running the company and people saw that I now had more time. They started to ask me to do more TV and I started doing guest appearances and then hosting shows and then, you know, got a chance to anchor, which was, uh, which was fun.

Jessi Hempel: You know, a lot of folks, they spend their entire professional lives trying to position themselves so that they will land in that anchor spot. You did that and then you left that. So, talk to us a little bit about that transition. 

Carlos Watson: Yeah. So there were a number of things. First of all, I was lucky to do it and I love to do it. And it was a lot of fun and I did it and I had some good success. And I got a chance to do it at some fairly significant places, but my mom got very sick and she, we didn't know it. In retrospect, we should have known sooner, but it moved my parents to the Bay area. And then I'd left the Bay area after we sold the company and I'd moved to New York to do TV. And she got very sick, Jessi, but we didn't know until too late. 

And so, and she had late stage cancer, late stage kidney cancer. And so I quit and I left and I moved back out to try and take care of her. And so that brought me back out to the Bay area for the second time. And it was in the process of being back out here. She was a lifelong teacher. She always believed in learning and growing. And we were sitting at Stanford hospital one day and she looked at me and she said, "You know, you're too young just to be in the doctor's office all the time. We gotta get you busy again." 

And so, yeah. On our way home. I'm one of these people just, I think out loud, I'm always writing on whiteboards or note pads. And so we stopped by a little Office Depot. We bought a whiteboard, put it in her house. And so I started thinking out loud and I realized that as much as I had loved what I was doing at CNN and MSNBC and other places, I felt like sometimes I was repeating a lot of the times I was repeating the same four or five stories ad nauseum. Not that those stories weren't important, but I just felt like the world was way more expansive. And there was more that I thought people should get to see and hear, and I wanted to be a part of doing that. 

And so I started to think, what would different look like? Like if you were going to re-imagine news and culture and ideas for curious people, what would you do? And so I started writing a business plan, uh, kind of with my mom watching close by. And I remember the first day we got our OZY office. There's a nice picture of, uh, my folks came and you know, my mom wrote in saying "Mom and Dad were here." We were building Ikea furniture, uh, with my business partner. 

And it really was kind of a, even in the midst of a difficult time, it was a family adventure. It was something that everyone believed in. She was super excited about it, very proud of it. And so I definitely would not have done that if that hadn't happened. And I would rather that she had not gotten sick, but, but you know, it ended up creating a new chapter and, and a good chapter. And you know, one that, that, you know, I still love to this day.

Jessi Hempel: Well, Carlos, what I really appreciate about that story, and thank you for sharing it, is that the personal choices we make and the professional choices we make are so entwined, we can't actually decouple them. And it's so clear to me that you made such a smart choice in choosing to take that moment and go back to the West Coast. 

In the moment that you were making it, was it very clear to you? Or was there any confusion around banking it?

Carlos Watson:   I think it was relatively clear. We have a pretty close family. We were all pretty close. I think there was always that sense of everybody's responsible for everybody, if that makes sense. And we very much came from a kind of a very sharing culture and perspective.

So, no, it, it, it probably was. Yeah, not as hard for me as it may have been for other people. I think, I think for me, I, I had both had some good things happen in my career, so I probably had greater comfort. I probably, financially, was at a more solid place maybe than other people. So it might, that also would facilitate me making that decision.

And then also I want to believe even if neither of those were true, but who knows, that my mom is just a good mom. She was, she was a good mom. She was good people. And, you know, I think our perspective as a family was always whatever you can do to help. So that was, that was not as hard. And Jessi, as you said, it was, I was fortunate.

I mean, they originally thought you'd only get to live for six months and then she lived for nearly three years. And so that also occasion, probably a different set of conversations that I would have had with her, otherwise. You know what I mean? And a different set of experiences than I would've had with her otherwise. 

Jessi Hempel: I look at your career and you have these exceptional degrees and I'm curious the degree to which they freed you up to feel like you had the privilege to make choices, because there was a backdoor or another way to, to explore another opportunity because of those, those pieces of paper. 

Carlos Watson: Yeah, I probably, those degrees both in the underlying knowledge they gave me, the confidence they gave me, that when exposed to other talented people, that I didn't somehow feel like there was, you know, at least to me an obvious mismatch. Maybe, I just wasn't aware enough of it, but I think there was, and then it probably gave me some sense of job flexibility. Again, not that you could get exactly the job you want, but that they're probably, you know, as long as you're a reasonably good person reasonably on it, that there was, there were going to be some opportunities.

So those things probably did give me for better, for worse, probably more confidence to take chance than maybe I would have, if I didn't, if I didn't have those experiences and those societal validators.

Jessi Hempel:  So we're catching up with you right now, Carlos, at a time when OZY (Media) is a force. It is not the startup it was when I first learned about you launching it. Um, but it exists out in the world and puts out a set of stories and voices that you might not see otherwise. And I want you to tell us a little bit about it.

Carlos Watson:  I always say that OZY was started with love. You know, today OZY's a broader media company, but when it started, the idea was that for curious people, there was lots of places you could go to get caught up on the news, but discovering the new and the next wasn't always easy. To discover a young comic before everyone knew Trevor Noah's name or a bartender before she was AOC or a college kid before she was reading poetry at the inauguration, like that wasn't always easy.

And I thought that there was a magic to that, that I thought it was both interesting, but also it could be inspiring. And it could give people more confidence to live differently the more they read about this woman, Jennifer Downs, who was doing research on CRISPR before she won the Nobel prize.

 It's just, the more that you could come across a publicist who is becoming Ava DuVernay or whomever that there was that there was a little magic in that. So that's how we started a morning newsletter and afternoon newsletter and I really wanted to be a part of helping people see more so that they could be more and do more. And, and, and bringing people the new and the next, not in large quantities because I didn't ever think that we could be a place that could bring you 3000 stories. But I felt like if we could bring you eight to 10 every day that were really good and different and might have a young Trevor Noah or a young AOC or a young Aaron Judge, or Dua Lipa or whomever that there'd be something special there.

And for us, I think part of that, the. Malcolm Gladwell-esque tipping point came when some of the TV network heads started to approach us and say, you know, "Books become movies. Would you be open to those articles becoming TV shows?" And we sold a show called The Contenders and then breaking big and defining moments and soon we had about a dozen TV shows on the air, and that became a big part of us. Something similar happened on the podcast side, when. Our articles or series became the thread and flashback and OZY Confidential and these others. 

Um, and then for me, in many ways, Jess, even though we can't do it right now, the most fun part was OZY Fest. And so I'm going to be excited when that, so I, you know, OZY is reaching people all over the world. Uh, these days, I think we reached 75 million people every month, which is hard for me to believe and think about it, uh, anymore, but it's great.

 And I hear from people who listen to our podcasts or watch our shows or people, or read our newsletters and. You know, sometimes they're happy, sometimes they're not, but I feel like our audience is really thoughtful and they care and they push us and they ask us to be better. And I love it. I feel like I at least feel like I learn every day and I hope that, uh, you know, I hope lots of other people are too. 

Jessi Hempel: So Carlos, you know, OZY is at this point, a very big media company with a lot of different voices coming into it. Um, but at the center of it still is you. You play a big role in the company and a big, active role in interviewing. And the reason I was actually the most excited to talk to you is because I think that you are a very good interviewer. So I wonder if you might just take a moment to share with me, like what makes an interview work for you. You get people to share amazing things.

Carlos Watson:  Oh, well, thank you for that. Um, and I liked doing it. I feel like I genuinely feel like I'm learning. I have gotten a lot out of people who wanted to be there and that's important because not everyone always wants to be there. I've tried to meet people where they are in that moment. I mean, I prepare. And when I read about you and learn about you, but I want to meet you where you are. So when George Lopez came on, he wasn't there that day to make a lot of jokes. He was like in a very different space or Danica Patrick, the race car driver, came on the other evening. She was kind of in a very different, she wanted to go. She wanted to drive somewhere new and you know, and I wanted to be right there with her and kind of go with her. 

I hope people always feel like I cared and I prepared, but that I also was willing and to let it go and go there. And I, for me, Jessi, I find that the better time they have the better time it is, if that makes sense.

Jessi Hempel: Yeah. 

Carlos Watson: And so I really want to make it in my mind. This will sound completely hokey, but I always ask myself like Priyanka Chopra or Bill Gates or interviewed all the time, how do I make this interesting and worth their time? How do I make them want to be here and want to be in this space? And like, what would, how would that look? And so those are some of the things that I try to do. 

Jessi Hempel: It makes me think about how time is really our only truly finite resource. You know, we have a certain amount of it and then we don't. And as somebody who makes media myself, maybe you feel the same way, I feel so appreciative of the time that people choose to spend with me.

And so of course you have to invest everything you have in making sure that Carlos, your time here with me on this Monday night as well spent, and that we wrap it up and deliver it to the people who choose to spend that time with us in a meaningful way. 

So if I catch up with you in a decade or so, and I sure hope I catch up with you before a decade or so, what are you going to be doing? Law? Entrepreneurialism? TV? Teaching? 

Carlos Watson: Jessi. I'm so late to the, uh, to the kid game, but I hope I actually have a kid or two. So, uh, cross your fingers for me. That'd be a good thing. And I hope that I'm still learning and getting to do things. And I believe so deeply in this coming decade. Like I really, Jessi I tell all my team, I think the 2020s are going to be the new 60s... that I think that this is going to be such a time a fundamental rethinking of so many basic things from love to marriage, from race to work, from tech to capitalism, from war to robots, and what, at its best, what a wonderful time to like refresh and reset and make things bolder and more vibrant and more fair and more open. And, um, if OZY could be a part of that and like a really important part of shaping how people live in the world, like, I'd feel really... I'd feel really good. 

Jessi Hempel: I love that. Thank you, Carlos. This is great. 

Carlos Watson: Thank you for having me. 

Jessi Hempel: That was Carlos Watson. Check out his daily YouTube series, The Carlos Watson Show; he's a great interviewer. 

And this week on Office Hours, we'll be taking on career changes. We especially want to know about the big swings people who set out about moving into one field. And then after a while, did something entirely different. What kind of training did you need? What was the most important thing about the process? What would you advise someone else? Let's reflect on it together this week and also, let's celebrate our hundredth episode. 

Join us for Office Hours to chat through it all. Wednesday afternoon at 3:00 PM. Eastern, we'll be on the LinkedIn News page, and you can find us by following LinkedIn News or emailing [email protected] for the link.

If you like the show, please take a moment right now to rate us on Apple Podcasts or wherever you listen. I know I always ask and there's a reason each rating helps us surface the show to more people. It's a really easy way to help us a lot. 

Hello Monday is a production of LinkedIn. The show is produced by Sarah Storm. Joe DiGiorgi mixed our show. Florencia Iriondo is Head of Original Audio and Video. Dave Pond is our Technical Director, Michaela Greer, Samantha Roberson, Carrington York and Victoria Taylor remind us we're capable of anything. Our music was composed, just for us, by the Mysterious Breakmaster Cylinder. You also heard music from Poddington bear. Dan Roth is the editor-in-chief of LinkedIn. I'm Jessi Hempel. 

Our show is back next Monday. Thanks for listening.

Carlos Watson: I want to take OZY Fest to Mississippi, to Arkansas, and to Montana. I don't know why, but something tells me that is going to be so warmly received there and people are going to look forward to it and it's going to be a thing 

Jessi Hempel: Well, please bring OZY Fest there, and I will be the first to be there and cover it. And may that also mark the end of the pandemic.