The Three Questions with Andy Richter - Tony Dokoupil

Episode Date: May 2, 2023

Tony Dokoupil (CBS Sunday Morning) joins Andy Richter to discuss his father's career as a weed dealer, accidentally catfishing Andy, learning the ropes of broadcast news on air, and much more.

Well, alright, let's get started. Hi everyone, Andy Richter here with another episode, edition, I don't know, episode, I guess, of the three questions. And today I am talking with Tony D'Ocapil. You were close. I'm going to jump in. I'm going to jump in, Andy, and don't feel bad for a second about what I'm about to do here because my last name was mispronounced at my graduation in high school. That's complicated the name the name is uh is never and as a result i continue to i don't because people always screw my name up and i'm good with it i have i'm very carefree about other people's names which turns out they get upset about it they like when i write news in the news business they really want you to say it right but i so

the copal uh yes okay my yeah my uh my ancestors would be very happy if i if i continued with the proper czech not slovakian pronunciation of the copal the copal yes yeah it's the copal and and yeah it's it's a czech word uh anyway it's a it's a really it's an what does it mean it means it means um i sold it all or or sold out all gone uh which was an a fitting a fitting last name for my father who as you may know was uh for his only professional career as a grown-up a drug dealer um yes so selling it all was a great thing we will get to that well i was also going to say it's also good for somebody that's on television i don't know you know anything in the in the vicinity or ballpark of selling out. I don't know. Maybe that could be used against you.

It's OK. I don't think there's anybody on television that can feel like they haven't leveraged their soul in some in some small way. There are compromises. Yeah. Dozens of times a day you do it. You know, it's if you if you do this for a living in a capitalist society, there's going to be some amount of selling your art. And and you might as well just kind of get used to it and then feel your way through to like what feels right and what feels wrong. And, you know, but I just you know, I mean, I came from I went to film school and I came from a bunch of guys that are like, I would never sell out. And it's kind of like, why not? We should, we should, we should, we should disclose to people that I'm actually paying you for this interview for this publicity. Yes.

Yes. Can we, can we talk about what we just talked about, about with Katie? Yeah. You want to repeat that? Yes. Yeah. So I don't know, maybe a year ago or so uh when we were in full full zoom times i you know i wasn't doing any in-studio interviews and i reached out to your wife katie turr on uh twitter

we are mutuals and i said hey would you ever want to you know would you ever want to be on the podcast and i'm a fan of you and your husband and and then tell them what happened so well uh unbeknownst to you i was right here where i am right now like 20 feet from the naked cowboy in times square and uh you know i don't get a lot of sleep uh because i'm on a morning show and i read her direct messages because i've been like sock puppeting her on on uh on twitter with authorization because she's been off of it from like before it was cool. So it wasn't working for her, but she still had a professional need to check the messages every now and then. So I was the one doing it.

And so we got the message from you and me being a fan, read it, very excited for Tony and wrote back. Oh, my God, that's going to be amazing. Tony's going to be so excited and then what did you say to tony unbeknownst to you that tony was the one you were talking to i said oh i'm so sorry i maybe i wasn't clear i only want you on the podcast something along i think it was like never in a million years actually but i uh yeah no checks no we have no check policy oh man the name is too hard to say i just don't trust myself with it katie told me then i think later she she mentioned it to me or you did you mention it to me i thought she did i don't know it came around and and you became aware of it i thought it was i tucked it away as a funny story, but I also thought in my back, back my mind,

like, you know, I get it. I've been with Katie for almost eight years now. She's always been the more well-known of the two people in the household on TV. And so like, if you never invited me on,

I would have felt no ill will toward Andy Richter. I would have been, well, no, I was, I was happy to find out that you were a fan. And then when I talked to her, she told me what a fan you are of this podcast, which is always nice to hear because I don't ever, I'm always surprised when someone

just out in the world says, hey, I like your podcast and I listened to it. So the reason I like it is actually because it doesn't have a clear, like, this is where it's going. There's not an agenda when you come on. It's an unstructured conversation. And out of that, It's not an agenda when you come on. It's an unstructured conversation. And out of that, it's sort of like letting yeast work in bread. Like it leavens itself and it finds interesting places. And what you do, that's really great as an interviewer that I wish I could do, you know, in broadcast television, but we never really can. You can't have the time.

You let the conversation breathe and people come to you. Yeah. I've done a lot of dishes listening to Andy. Well, thank you so much. I mean, that is like very, very gratifying to hear. So. All right. So you are originally a Florida boy, correct? I'm a Florida boy. I'm kind of a southerner in general. You know, we were talking earlier with a couple of your colleagues about like words that are hard to say for people on TV or on broadcast. And like, you know, I really struggle with the word W A T E R, which a lot of people think has a T in it, but I say it W A R D E R water, water, water, which is

kind of a South Florida, Maryland thing. Yeah. There's it's like on the wire when it's like water or Philly, you know, there's, yeah, there's weird ones there. But yeah, I grew up in Florida, Maryland thing. Yeah. There's, it's like on the wire when it's like Wooter or Philly, you know, there's, yeah, there's weird ones there. Uh, but yeah, I grew up in Florida. Uh, you know, didn't wear a shirt or shoes until I was like 14. Um, uh, and I really actually terribly miss, uh, Florida. I, um, uh, I, we moved away when I was in fifth grade and, um, it just was like fractured the whole thing in two. And I always, I often think even to this day in my forties, like, I wonder how my life would be different if I continued to be a Florida boy. Cause it's such a distinctive place.

It's a very distinctive place and it can be really wonderful. And then, and then all, but also be this sort of like the Florida that we really, that is screaming from the headlines today. Yeah. Yeah. I should clarify for people that like, you know, Florida is a big place and I'm not from North Florida, which people talk about being like distinct from the South. I'm from South Florida. Right. So I grew up in, in, uh, in Miami, uh, in, in South Miami really. And, um, when you're a little kid there, like it was a genuinely wild place. Like you would, you would take a right hand turn down a road by your house, and then the road would end, and then it would just be gravel, and then it would be jungle.

And then you would feel like a dinosaur from Jurassic Park is going to come around the palm frond. It feels primordial, which was great. And you mentioned that your dad was just a major weed dealer, And you say he never had any other job? No, this is a guy, not in true adult life, right? So this is a guy who went to college, you know, classic baby boomer, went to a Catholic private school, born in New York and then New Jersey,

and could have done really anything with his life. But it was the 70s and weed seemed, if if you could remember back, most people can't like we'd actually had a moment in the early 70s where it seemed like it was edging toward legality. Time magazine, Newsweek, they were putting it on the cover with questions like, is it time for legalization? States were decriminalizing. And he felt like, hey, you know, I love doing the stuff. Love it. It makes people happy. Right. Love, love spreading happiness. And it feels like this is becoming legal. So maybe I should get in on it. Right. It'd be like if ice cream was being legalized today, you'd be like, Oh wow, I should start selling ice cream. I get a truck right now. Sure. Sure.

And then, so he started doing it for five years, six years, seven years. And then, you know, before you know it, it's no longer the early 70s. It's the late 70s. And the attitude toward pot has completely reversed. Reagan is coming into power. You know, the devil weed is now what people view marijuana as. And by that point, though, he's in his 30s. He's done nothing else with his life.

And so he has no choice really but to continue in this one and only profession. And we lived in Miami, uh, only for the kicks, like his, his market was, uh, Maryland and North. That's where he sold. And, but he lived in Miami, just like, you know, it's like, if you're in finance, you live in New York. Like that's where the good bars are. Like in Miami, if you were a drug dealer in the 80s, it was like, that's the place to be. You know, I'm going to go to the Colony Hotel. I'm going to have a boat in the harbor. I'm going to get my dock siders and I'm not going to wear a shirt and I'm going to have

a good time. And how did he get the weed up to Maryland then? So he had a great system with his partners where there was one guy who would go to columbia and then the guy in columbia would get it on uh a big uh seagoing tanker which is used to to bring fresh water between the islands in the caribbean that guy would bring it to you know point a uh and then sailboats from the north that were going uh you know rich people's sailboats that were going between the islands and like you know nantucket uh they would be filled up unbeknownst to their owners with weed uh and then sailed up the coast and then my dad would pick the landing spots from maryland all the way up to maine and he was the guy in the tall grass you know at 3 a.m waiting for the boat to come in

and with the truck pulled up to the dock uh and then they'd go to a safe house uh it was already cleaned you know no seeds um it was been it been worked on uh and then was it wrapped because how do they keep it the smell you know because oh my god they called it the green elephant uh yeah because it was a real craft because the smell was so bad um yeah it had bugs in it you know like tarantulas would crawl out of it you'd get bitten by things uh it the the smell was everywhere the birds would come after it if it was the summertime i mean like like there was one one story in particular where they filled a barn in connecticut with it and then they all went to sleep or passed out you

pick and then the next morning it was like birds had built nests all over the barn and there was like basically no pot left and a lot of evidence everywhere and very mellow birds and the birds were singing bob marley tunes it was amazing yeah that's i mean that's incredible because you you know, I mean, out here in LA, there's, you know, there's, there's dispensaries everywhere. And I'm living in East LA right now. And there's one right where the five and the 10 meet. And you can, you know, you see the building from the highway, but driving by on the, on the five at 60 miles an hour, you can smell weed. And that's not with the windows open. That's just like through the vents coming through. Maybe people were just so naive. You know, like maybe these rich people were like, oh, it smells a little skunky around here today.

I mean, I think part of it was that the weed today really is more potent. It's stickier. It's stickier. It's stickier. It's more fragrant. If you get a High Time magazine off of eBay, High Times was like the playboy of pot, right? Like the centerfold, instead of a naked lady, it was like naked pot.

It was a big bud. Yeah, it was a bud. If you get a High Times from the 70s or early 80s and you look at the quality of the weed, it looks like something you scraped off your lawnmower on a wet day that that is true yeah it just was different and in fact it's so different that my dad you know after doing federal time for dealing uh now lives in in boston or in cambridge in massachusetts and it's legal there now. And he's gone to a

dispenser and he's bought it. And he's like, for him, it's like heroin. He's like, I can't even, I just sit on the couch too strong. Did your mom, was your mom aware of what your dad did for a living? Yeah, no, they were all in, it was a whole family business. Uh, my mom got a loan from her, from her father to buy the first kilo. kilo uh and my uncle was involved and you know they really felt and history has actually proven this out that they were on the right side of the law ultimately and that they were spreading happiness and um yeah they got no shame about it i don't think they should i mean as you say it's been borne out that now it's a grown-up substance but it certainly doesn't warrant the kind of demonization that it that it had to go through for all those years you know

yeah and all that nonsense about a gateway drug it's like as i've said before it's a it's a gateway drug to carbs past 10 p.m that's the only thing it's yeah it's a it's a gateway to bad philosophy uh yeah did you feel like was there like a sense of insecurity in your house because of that because you know your dad doesn't it's not really a job and it's you know and it's it's it's always got there's always got to be stress involved when you're making your money 100 illegally illegally. Totally. I mean, I think it, you know, they may have been like, you know, spreading happiness and, and, uh, and, and, and all the rest with their friends, but it was like, it fucked me up pretty good. Uh, and you know, to this day, even because, um, you know, it's funny when I, when I meet people for the first

time here, I'll do, I'll name drop for you here. This will be fun. Yeah. All right. So last weekend, Katie and I were in London and we were on vacation and we were in a hotel having a meal and Chris Rock is there. Have you heard of Chris Rock? He's a former... I have. He's a former host of the Oscars. Yes. Anyway, he watches our show.

He's the slap guy. He's the slap guy. Yeah, yeah. He comes over anyway he watches our show he's the slap guy he's the slap guy yeah um he comes over because he watches our our morning show he was like i mostly watch gail but you slide in there and i was like thanks chris real confidence booster um uh but he's he's kind of a news junkie right so he sits down and we end up talking for a long time and he starts making some points about various things in the news and one thing that he made a point about was like, you know, everybody should be treated in the eyes of the law as though they were you. And he's making reference to me because when he sees me, he doesn't see he sees a guy who, you know, has has every level of privilege you can imagine in society. Right. Like, yeah, full head of hair of hair you know looks like he was a general

in the military in the 1950s and played a sport um and and like people think that my dad is jfk or like my dad is the dean of middlebury college you know like they yeah yeah and in fact i'm always like i so the world sees me as a guy who's like been winning. But in fact, my childhood was, was pretty rocky because of how, you know, dad was, he was selling, but he was also using, he was showing up and then not showing up, you know, middle of the night stuff, weird people in the house. Like it was. And then when we, when we left, we had lots of money when things were going good as you do.

But then when he got busted, the money just vanished. And that is like a really shaky. Yeah. That's a confusing thing when you're 11 years old. And then the other thing that's really was confusing is the, the whole side of my family, my grandmother, my cousins,

my uncles that were part of our network down in Florida, not in the business, just regular people. I never saw them. Like I never saw my grandmother again because we were fleeing. What happened was my dad went to prison. To make it really complicated, my stepfather, who was his partner, marries my mom to lock her off as a witness. We flee from anybody who could find us an exact retribution for my father telling tales because he cooperated with the feds. So it was a really rocky upbringing.

And so when I walk into a room today, people see me one way. But like my my emotional reality inside is very different because my upbringing was in other ways like quite disadvantageous, let's say. Yeah. Yeah. So your mom married your stepfather. Let's say. Yeah. Yeah. So your mom married your stepfather. Was it was they were situation once my dad was out of the picture that my stepfather was somebody she could be completely open with. When she, and this literally happened, we got into Winnebago and we drove to New Mexico from Florida and we dug up a cooler of money that my dad had buried in the base of a house where some cousins lived. When we did that, that's something she didn't have to keep from my stepfather because he knew what was going on. Whereas if she's just dating some guy she met

in Coconut Grove, she'd have to make up a story about why we're going to New Mexico. Wow. It was convenient, too. Can't you tell my love's a-growing? Did you ever get a sense from your mom that she felt bad for the life that she was giving you? What I've come to realize now, as a parent myself know, I work in the news industry, it's chaotic. Uh, we're not always our best when we're home. We're not always fully present. We're not like the perfect parents. We'd all like to be all the time. Nobody is, you realize that she was doing the absolute best that she could.

And on top of that, you don't have to be the greatest parent of all time. You just need to be good. Right. And she was she was very good. You know, she was loving. She was present when I needed her amidst all the turmoil around us. She was steady. And and I ended up devoted to her. And that was a way that I was able to kind of find my path in life. It was I wanted to live up to her expectations, which is actually a great motivator.

So, yeah, she was good. Are you an only child, by the way? I'm an only child. They were never married. They were doing tons of drugs. They didn't even think they could get pregnant. I was like, well, that's a nice thing that, you know, we didn't think that you could make it through the drugs, the sperm, you know, whether the sperm or the egg, whichever one

was very strong. That's exactly the anecdote. You know, they just sort of gets told over wine. You're like, oh, wow. Not how I would have done. That's not how we do it these days, mom. But oh, my gosh, that's amazing. Well, how I mean, does it at a certain point, does it settle down?

I mean, do you how long are you sort of on the lam? For my entire teenage years, that whole part of the family is gone and we have no money. My nickname, you know, I'm going to a good public, I go from private school to a public school and from having money to being a kid that my nickname in high school is literally poor boy. You know, it's all relative. There's definitely people that are worse off. But it only begins to shift when I get into journalism and I have this like sense of instability inside. I don't know where it really comes from because I don't have answers to what was really going on with my family. And I when you become a journalist, one of the things you learn is like how to call the

federal government and get court cases. And so I called on a whim and asked for the case, any cases tied to my last name, which as you know, is pretty unique. And I, I got a fax back. This is in the days of faxes from the federal archive, like the big archive, the one that has like Al Capone's records in it. They don't't keep everything they only keep the two percent of stuff that's really important and it was the indictment that brought my dad in uh and it was for 17 fucking tons of marijuana in one job it was a 10 million dollar wholesale job in 1986. And, and I was in New York.

I was working for the old newsweek magazine and I was like, flabbergasted. I was like, holy shit. Like I knew they were into stuff. I didn't know they were into this. Yeah. So I called my mom and I was like,

mom, I'm looking at an indictment here from, he ended up getting arrested in 91, but the job was 86. I was like, I'm looking at an indictment here from 91. it says big tony sold 17 tons of marijuana in a single job do you know anything about that and she was like oh honey we were gonna tell you and i was like when were you going to tell me i i'm almost 30 i'm almost 30 it's. We're saving it for our deathbed confession.

It was amazing. Yeah, it was quite a it was quite a moment. It was like reporting on your own family. Yeah. Yeah. And I mean, was it the size of the of that particular shipment or was that was that like sort of one of many of similar? One of many. That's they would bring in one major job every year and that job in particular uh it was enough marijuana to roll a joint for everybody in college in america at that time and it was actually covered it was it was actually it was actually covered in new york magazine uh because prior to that there had been a huge crackdown by the Reagan administration on home grows, like the domestic market. They were ripping up every plant in

California. That was beginning to be a thing that people did grow in America. They ripped everything up. And New York Magazine had a big story about how there was reefer sadness in New York City. And then my dad and his partners, they, they turn that frown upside down with their 17 times just blizzard. Oh, wow. What, what room is there for you and your identity in this, in this childhood with all this stress going on and this, you know, all these like adults, like they're not evil or anything but there are like they're not providing a fertile environment for a healthy emotionally mentally healthy child what is young tony or were you little tony since he was big tony i was little i was little tony yeah like like true like a true

mob family there's big tony little tony well what was i mean what was little tony did little tony make himself known did little tony try and or did little tony just kind of keep quiet and to get along kids always rebel it seems against their parents and if you're most times your parents are you know dentists and insurance brokers or whatever and then you're the one that goes crazy and wild. But when your father is the one going crazy and wild, you end up being quite a straight edge. So I was real serious about getting a college scholarship. And then I got one. And then I, I was, I went to the school that gave me the most money to be responsible. And then I worked really hard. And like, so I was like this really tight ass rule follower. They used to call me the, uh, the white sheep of the family.

In other words, like they're all black sheep. Sure. Sure. I'm the white sheep. Yeah. What were you afraid would happen? I mean, were you just trying to not be like them because they, yeah. Cause I just, there's a lot of anger that you have.

I don't have it anymore. You know, cause now like it actually, it actually ended up being the best possible like training for what i do now uh because we moved i met a lot of people uh it forced me to develop skills with new people i was good with conversation like the things it all is well that ends well and like everything is golden now right i can't believe how well it's turned out and I feel great. And so I don't have any anger, no bitterness anymore. But for a long time, there was a lot of anger. And I felt like, you know, when I was broke in my 20s and I didn't have anything going professionally and I didn't have any introductions, I didn't have any connections.

Yeah, there's a lot of anger and frustration with them. And I felt like I couldn't enjoy my 20s the way other people did because i also felt like my dad was such a good example of a guy who had advantages and then tried a couple doors and behind those doors there was drugs money and girls and he just like basically lost his life to it you know yeah uh and so i didn't want that to happen uh but now it's like now it's hilarious so you know ultimately i wrote a book about this and in the book there's like all kinds of weird sex with my with my parents which is a very strange thing to report on as a journalist an even stranger thing to then write and then i sent the book to my father and my father read the

whole thing and and then he called me and he was like, Tony, I like the book. I do. But there's not enough hookers. Okay, dad. I'll let the publishing house know. We need to get some more hookers in there. Yeah. There's a five-some in there, dad.

Is that not enough for you? No. Oh, my goodness. And this is your parents are sharing all of this yeah like they shared all of yeah well ultimately oh i mean once once you keep a secret more or less for 30 years and then someone comes waving the indictment and the in the court case then you kind of have to come to the table and be like okay son we'll we'll answer some questions and i'm actually i owe them an apology 100 because like when when they were talking and when I was writing the book, this was definitely me like exacting bitter revenge.

And now we're like 10 years on. And and I love them both dearly. And I and I have kids of my own and I feel stupid for being as hard on them as I was. It was like an aggressive airing of their laundry. It was like an aggressive airing of their laundry. Yes, it was like you kept this for me and you and you and my life was really chaotic and confusing as a result. And so now I'm going to just, yeah, I'm going to air it all and I'm going to get paid for it. And and and it was like it was not the book succeeded as journalism. It failed as memoir because it didn't have any genuine reconciliation and wisdom about like life is complicated and nobody is perfectly good or perfectly bad yeah but then

again they didn't need to tell you about fivesomes like did you press them to tell you about fivesomes no i didn't press them it wasn't you know a grilling uh but my my my father is you know i have a theory about criminals in general and he really is like the criminal of the group uh that that they actually love what they're doing and they're proud of it and they want their exploits to be known and that's ultimately why they get caught and so like he was he was happy to talk about you know all the all the blow and the hookers and the lost money and the Mercedes and the, you know, the cruising yacht and all the shit that, that, you know, frankly, people go get into that business in the eighties in Miami to enjoy. Like that was kind of the point, not a, it wasn't like a

regrettable side effect. No, that was why you do it. Yeah. Do you think he was a criminal before he was a criminal or being a criminal? You know what I mean? Like, did he, did he have a kind of criminals mentality growing up? You know, do you? Like, did he, did he have a kind of criminals mentality growing up? You know, do you think that's who he was? That's a really interesting question. Um, I think he was in love. I think at some point he was a very literary guy. He read a lot of books. Uh, he was an English major in college and I think he fell in love with the old idea of the American outlaw. And he, and so the, you know, the outlaw is like is a bad guy, but also kind of a good guy. Right.

And so that's the perfect role for him as a drug dealer, particularly a dealer of weed. Yeah. Yeah. Yeah. Right. Yeah. Because it's, you know, it's the soft and cuddly drug dealer. Yeah.

It's like, you know, like the life ruining drug dealer. Yeah. Yeah. When do you start to sort of gravitate towards journalism? When do you start to think, like, I want to be a journalist? And what was it about it that made you feel like it was the thing you wanted to do? So I played baseball in college. And I played in three different college summer leagues.

Went around the country with that. Met a lot of people. And when I started reading a lot on like the buses the bus rides are like 12 hours long and uh i did a lot of reading so then i started like thinking oh maybe i'll be like a big swashbuckling non-fiction writer or something and then i realized oh well you could just get paid for writing magazine articles so i got interested in doing that and and got an internship at newsweek which at the time like people forget it basically newsweek is like owned by a cult now i don't

even know who it's like the saddest uh it's very weird it's i don't really know what's going on i know it's it's so sad it's like uh you know that's where i spent my formative years in journalism but at the time like john meachum was the editor mark whitaker before that uh and like everybody who i ever read and loved growing up worked there and and they sent me everywhere uh and i got to meet all these all you know additional people and i fell in love with just like not celebrity journalism not talking to famous people not splashy pieces but like just regular like general, wander the country and find interesting stories, journalism. And I ended up being like one of the last people in that old era of media who got paid to go to all 50 States and do interesting stories. Uh, and, and it,

and I just fell in love with it. And now I get to continue a version of that with television. Um, yeah. And it's, it's, it it's really like i can't uh it's like part part show business because you got to get people in tents yeah you gotta get people interested yeah and it's television it's part theater still television yeah yeah it's still television it's part theater because you're you know you've got to ad lib a lot and you're like kind of you know you're scripting things in your head and trying to perform it. But then it's also like kind of teaching. It's almost like educational or preaching even, you know, like you want people to understand something and you, you deeply want them to get it. Um, so I just, it hits on so many levels. I love it so much. There's sort of a

pursuit of truth. Is that the, is that the, you know, is at the center of it. And do you think that was in reaction to your upbringing? No, I don't. Cause I actually don the, you know, is at the center of it? And do you think that was in reaction to your upbringing? No, I don't. Cause I actually don't, you know, one kind of, there is one type of journalism that is pursuit of truth with a capital T and defense of democracy with a capital D, you know, for love of country almost. And, and that, that's not the kind of journalism that I, I, you know, that's an important component of it, but journalism is also

anything of interest to people, literally any news is anything that people want to talk about telling stories. And, and, and, and so, um, you know, I like doing pieces on, uh, not exposing things or, you know, pinning people down or making people look stupid. Uh, I like trying to elucidate something that's complex. There's lots of examples. Also, just crazy adventure stories. I went to the bottom of the Pacific in a freaking submarine. I did space training.

I camped out on a glacier in Alaska with special operations on a training mission. I went the whole length of the Keystone Pipeline. It's like I've done crazy stuff. I went and gambled in Monaco. Like all like just either just experiences that you then bring to people in a way that is kind of documentary. And do they need to know about it?

They don't need to know about it, but hopefully you make them want to know about it, you know? Yeah. I mean, you kind of touched on it. It does kind of seem that the sort of rootless upbringing allows you to be comfortable

in these kind of constantly that the sort of rootless upbringing allows you to be comfortable in these kind of constantly changing scenarios, because I think, you know, a lot of people would be, you know, kind of too intimidated to do all these different things, you know? Yeah. And I'm very, it ended up being very chameleon like, and, you know, you can go into any place, you know, because my background is so kind of checkered any any assignment that i have i can walk into somebody's home and there there's going to be some part of my my background that will connect with their background and i found that to be true across racial cultural social lines and it's just such a valuable point of connection uh yeah it's it's a great it's a great it's a

great gig it really is when when did you kind did you start to feel the transition between print and television? Here's some stories. This was not a planned thing. I didn't think TV was going to be in my future. Then the internet came and just torched everything that was made of print. That whole world went away. I had kids i had kids by then i needed to pay bills um so i started doing i went over to msnbc uh and i started doing internet television like streaming before streaming was a thing uh and then that went south pretty quickly and then, finally I got an assignment where I was like covering some early primary

in Arizona down by the border. Nobody in the TV world was offering me any kind of deal. And frankly, I was not good on TV. I mean, I was bad, but Katie, uh, was like, look, Tony, I know TV. Oh, so you guys were already together at this point? Yeah. I mean, I mean I skipped over like I condensed like three years there but like we met in 2015 and she was like she was at

that point I was doing some television but I was terrible at it and I had no contract that was just sort of like basically if like everybody else had a dentist appointment. They were like, Tony, go out there and do that. Substitute teacher of reporting. Totally. Totally. This was back. This was when MSNBC was going through like a let's put digital writers on, you know, that'll work.

And so I was I found myself in Arizona covering something there on the border. And Katie was like, look, you need to take your chunky i'm a writer glasses off and you need to get rid of your corduroy jacket like you're a professor because you don't work for a magazine anymore you work for tv now you need to wear a black t-shirt and before you go out to the border you need to do 100 push-ups and then you need to put your hair up real big and see how that goes and i was like all right i'll see how that goes. And I was like, all right, I'll see how that goes. So I did that. I don't even remember what the story was. It was probably terrible. But that very day, ABC News calls. They're like, can we talk to your agent? We loved your reporting down in Arizona. Wow. It's a it's a shallow business on some level. It's a look at your business. They they they liked something about, you know, maybe it was my my deep and insightful coverage of whatever the hell I was talking about in Arizona., maybe it was my deep and insightful coverage

of whatever the hell I was talking about in Arizona or maybe it was the push-ups. You don't remember. Maybe it was the push-ups and the big hair. And then one of these ridiculous no one trusts their own judgment ways. ABC takes me on for a tryout,

but I'm still at MSNBC. And then MSNBC suddenly is like, oh, they want to make an offer. We want to make an offer too. We love you also. We have always loved you. And I was like, come on. And then I called CBS and I was like,

hey, you know, your competition's offering me stuff, you know, but I really think I actually fit with you. And they were like, we'll offer you something, but's gonna be the cheapest and i was like i'll take it oh wow you had the sense uh you know to know that that's where you wanted to be well because when my book came out uh i was a character on sunday morning so they covered i got to see what's what's what cbs did with my actual story. And I really respected it. And then I watched a lot more of the coverage.

I got into the history of it. And I was like, wow, if there's a place where I feel like I fit, it's CBS. And so I literally took tens of thousands of dollars, which is a lot of money to me still is and less money to work here. Cause I felt like it was the right home for me. And, and it was, it was the right choice. I'm having a great time.

Was it a very much an on the job kind of training in terms of like learning God on cameras? Or did you have to complete? Oh my God. Well, I had Katie. I had Katie who, who Katie is like,

you know, as you may recall, she's like the Mickey Mantle of television. And I say that not because she's a Hall of Famer, although I think she's amazing, but because the story about Mickey Mantle, the baseball player, is supposedly that his dad threw a ball into the crib at baby Mickey and just hit the baby in the face until Mickey learned how to catch a ball and then forced the baby in the face until mickey learned how to catch a ball and then you know like forced the kid to be good and katie grew up in a house with two journalists who were very

intense and they basically made her just be really good she gets it on a deep level um and so like yeah i had her but otherwise i didn't have anything and i remember my first story here at cbs um there was a guy you remember like in august of 2016 there was a guy with suction cups who was climbing trump tower yeah i do remember that it was august so everybody was on vacation uh i just started at cbs so the evening news was scott pelly dignified prestigious broadcast that it was sent me to cover it. And I was the guy who just come from Arizona with the big hair and the pecs. And I did not know how to be on the evening news. So I went out there in a lime green linen shirt on button to like here, uh, the big hair, like I

was going to Friday,iday drinks on the rooftop somewhere and um and to me it was like a fundamentally unserious situation it's like some joker he's climbing the building but like evening news saw it as a possible terror situation you know this guy's running for president uh donald trump is like we don't know what this guy's doing they led this was story a one yeah um and this and i am tony lime green linen of my tony lime green linen uh with the big hero who's never been on network tv before he's never been on network tv before uh he has no idea uh and when he came to cbs it was because of the morning show and and sunday morning not evening he didn't know what evening was like i did not know what i was doing uh and they they come to me first

and i start talking with like a grin on my face and i start kind of like you know playing it almost for laughs and then to make things worse not only was i didn't look right my report was wrong but the producer who was with me she in the middle of my report yells, no. And I think, oh, I must, I'm sorry. I must be confused. I must be talking over somebody or I got a bad cue. So on live television to at that time, 8 million people, I just stopped dead and put my hands in my pocket. And I just look at nothing. I'm like, as though I'm rehearsing. And then like the control room goes crazy. It turns out she wasn't yelling. No, she was giving me a late cue saying go.

Cause they, they'd bumped something up. It was such a bad hit on, on all those three levels that I was banned. I was, I was, it was not an official ban, but like, they did not ask me back on the evening news for many, many months. But it ended up being a really good thing because then it did allow me to do the things that I thought I could I could really make an impact with. That sounds like so corny, but like it let me do the things that I was good at, which was feature stories for the morning show and cover stories and big things for for Sunday morning. And like it ended up being great. Yeah, well, I mean, they kind of did. You know, they dropped you right into the fire. It kind of on them and i hope they understood that yeah yeah no i'm gonna get

an email again every time i tell this anecdote they're always like there was like stop talking about that you weren't banned i was like well okay show me show me it was a coincidence well show me when i next appeared on Evening News. Yeah. What do you want out of your future? Where do you see yourself heading? I mean, what kind of, you know, the 10 years from now, what kind of picture do you see of yourself i want to stay in the job i have for as long um as i can i really enjoy it uh i love gail i love nate um i love our whole team here uh and it feels just like there's not a better job

in journalism like i can't imagine moving to another job in journalism where I have the same camaraderie, the same freedom to pursue stories, the same reach, which sounds funny because like, you know, broadcast TV is changing. Like if Joe Biden watched our program tomorrow,

that would lower the demo. Like that would lower the age group, the average viewer age you know it's it's not yeah yeah but but it's still millions of people um and it's a lot of people the other privilege of this job is because it's broadcast and not a podcast or cable you know a decent portion of our viewers fell asleep the night before watching some crime drama. And like, they just woke up in the easy chair and are the news that they see on my talking face might be the only like straightforward, just the facts news that they catch all day. And that's actually a great thing. I love that. Yeah. Um, so yeah,

I want to keep doing this job you know you know to avoid the long-term brain damage of getting up before 5 a.m in my 50s and beyond you know like 10 15 20 years from now i i know and katie also like it we would love to spend some time overseas yeah uh my mom the one of the great gifts i think uh she she's she can get me italian citizenship so she's going can get me Italian citizenship. So she's going through the process like that would be cool. Oh, wow. That would be cool.

I don't know. That's just sort of what do you want to do, man? You answer the question. God damn it. What do you want to be? Well, I mean, I kind of have talked about it on here a little bit because I mean, I'm getting married. I got a new daughter that, you know, I, I, my fiance was a single mom when I met her. And so now I have a three-year-old daughter. I have a 22-year-old son,

a 17-year-old daughter, and then a three-year-old, um, which is kind of, yeah, it's a big gap and it's kind of Peter Segal, the guy that hosts, uh, hosts an NPR game show that I'm forgetting the name of right now. And he wrote a great piece about being a dad later in life, having kids, you know, there being a span of time and then having babies late later in life in the Atlantic. And it was really, it, it's a little saddening because you do feel like as with anything, the more you do it, the kind of better you get at it. And having raised teenagers now to go back to baby is, it's not that it's easier, but I'm just calmer. I'm more centered. I'm more patient. I'm more present. And I don't think I did like a bad job with my first two kids, but I do kind of feel like I was not as settled in myself, which is just the nature of life. I think. How could you be right? You're in your, you must've been in your early thirties with the 22 year old or mid thirties.

Yeah. Yeah. I'm getting married in june we bought a house together that we're remodeling that we're you know that we're renovating that i have no idea how we're going to pay for all of it you know i mean i'm i'm and and i and i'm kind of you know the the conan show ended on tbs i'm doing this podcast and I'm putting lots of irons into, you know, kind of lukewarm fires to see if they'll maybe not go ice cold. So I have no idea. I, you know, I had five years ago, I had a future in mind, you know, that was one of the, that's one of the things about getting divorced.

I don't know if, you know, I had a future in mind. It was, I didn't know exactly, but I had a pretty good picture of what it was going to be like. It was, I didn't know exactly, but I had a pretty good picture of what it was going to be like. It, it's not that anymore. It's, it's, it's different and I don't know what it is. So I'm kind of rewriting my own future. So, you know, it's, yeah, it's easy for me to sit here and say, what, you know, what do you want out of the future? But, you know, I mean, healthy and happy, I guess, you know, it's kind of, you know, those kind of things. You're what you say about divorce, though. I mean, you know, divorce really is like it is like a forest fire in your life.

Like it just takes all the vegetation. Everything is the landscape is scarred and changed. And then like everything has to grow back anew. At least that was my experience of it. And so, yeah, one thing where I hope to be like i love my wife and i intend to be a good husband uh you know it's not that i was a bad husband before but like i was definitely a youthful stupid person in ways that i'm not anymore katie always talks about how like she tells her older friends she's like she's like stop looking stop excluding from the dating pool

guys who have been divorced because in fact they've learned their lessons they are better they can cook now they're they clean better like they're yes they're better humans well you know this podcast you know the last question what have you learned uh you know like what do you what do you think what wisdom can you impart to my hungry viewers listeners whatever what have i learned oh my god i'm gonna this. No, there's no flubbing. No, I think there is flubbing, you know, cause I actually don't feel like I've learned anything, which is the hardest part. And I've been living in fear of the, the, the, this big close, uh, all morning because I don't, I don't feel like I'm at an end. And so I feel like, uh, this is an unscheduled exam. And as a result, I don't have the wisdom ready. And so maybe there's wisdom in that, that what I've learned in my career is the worst moments and biggest fuck ups have had a way of becoming advantages and opportunities.

opportunities. And that same thing is true in my personal life. The biggest disadvantages of my childhood, the biggest fuck-ups in my personal life have become, in the full sweep of time, advantages and opportunities. And that keeps me excited about the future. So that's what I would impart to your viewers. Well, and see, that's good. You didn't flub anything. Remain open and, you know, make lemonade out of lemons. That's, you know. That's a really, that, did you just come up with that? Make lemonade out of lemons? Yeah, I did. I did.

That's really good. I did. It's a good one. Yeah, yeah. Well, I have a line of lemonade coming out, so it's all subtle marketing. Are you still taking angel investors on that because um i'd love to get in on absolutely absolutely you can get in on the ground floor for 150 bucks or if you know somewhere that where there's an unguarded lemon tree then uh you're in you know

you know one other thing i've learned i'll add is that when I die, I want to become human compost and have a lemon tree grown with the soil that was me. This sounds crazy. Yeah, it sounds nuts. Yeah. But there's a lady in Washington state who has come up with a way, an alternative to dying as we know it. Not cremated, not tombstone burial, but human composting. I think that's great. It'll never be a morning TV segment, but it can live on this podcast.

I endorse human composting. Yeah, there we go. Tony DeColpo of CBS, The Mornings. Yes, yeah. And tune in. And it would be very helpful if you were under 70 when you tuned in. Yeah. It would be really good for Tony because, you know.

The advertisers, apparently, they don't want, they want the young demographic. Yes. 65, 58, you know. Right. Feeling it. Feeling their oats. That's the age they're looking for. The people that don't need a catheter just yet.

Yeah. Catheter advertisement. But soon. That's for cable. We're broadcast. Oh, well, ooh la la. All right, Tony. Thank you so much.

And thank all of you out there for listening. And I'll be back next week. Bye-bye. The Three Questions with Andy Richter is a Team Coco production. It is produced by Sean Doherty and engineered by Rob Schulte. Additional engineering support by Eduardo Perez and Joanna Samuel. Executive produced by Joanna Salitaroff, Adam Sachs, and Jeff Ross. Talent booking by Paula Davis, Gina Batista, and Maddie Ogden.

Research by Alyssa Grahl. Don't forget to rate and review and subscribe to the three questions with Andy Richter, wherever you get your podcasts. Can't you tell my loves are growing? Can't you feel it? Ain't it showing? Oh,

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