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870. - Tom Freston

Nicholas
@nicholas

Tom Freston was a co-founder of MTV who later led MTV Networks’ global expansion and served as CEO of Viacom. His great new memoir, Unplugged, is out next week. We chat with him from his home in New York about travelling overland to the Middle East in the 70s, his early ad man days, how to manage a business that's heading downhill, he has no time for audiobooks, his favorite podcasts, Trump calling up for VMA tickets back in the day, how brands took over entertainment media, our favorite Unplugged episodes, how MTV spread from middle America to LA and New York, getting fined by the American government for having lunch with Fidel Castro, when Vice was Vice, and his favorite restaurants in NY. instagram.com/tomfrestonunplugged twitter.com/donetodeath twitter.com/themjeans howlonggone.com Learn more about your ad choices. Visit megaphone.fm/adchoices

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Full transcript

Showing the full transcript for this episode.

Chris Black

[upbeat music] How Long Gone, uh, it is, uh, an overcast rare Thursday, uh, recording. Um, we've had to adjust our schedule because we have the GQ Man of the Year Awards tomorrow night. I'm in Los Angeles, and so is Jason.

Jason Stewart

Mm-hmm.

Chris Black

I gotta say, big bro, I needed, I needed sun and I'm not getting it, and I'm not gonna get it from what I understand.

Jason Stewart

We got a little rain tomorrow, got a little... Like I said, you just missed it, bro. 87 degrees yesterday or whatever it was. So you, you're at the Chateau, and our listeners should know your, your suitcase with your podcasting equipment is being held hostage because they're setting up a red carpet in the little area for some dumb event tomorrow. So-

Chris Black

[laughs]

Jason Stewart

... that- that's why you hear Chris's voice-

Chris Black

I, I don't think it'll sound, I don't think it'll sound that bad, to be honest

Jason Stewart

I, I don't, I don't... I didn't say it's gonna sound bad. I'm gonna say it sounds different.

Chris Black

Different. I, well, the, the... Yeah, the um... I ran into Will in the lobby and he was like, "Yeah, we're getting, um... They're saying it's an atmospheric river vibe tomorrow, so we've decided [laughs] to make, we've decided to make a few changes to the layout to, to make sure everything's covered. Um, but he didn't, he didn't-

Jason Stewart

The atmospheric river, I forgot about that phrase

Chris Black

It's such a great descriptive term. It really says so much. Uh, but he, he seemed... he didn't seem stressed, so I'm not stressed, you know?

Jason Stewart

Yeah, we'll throw a little money at that problem. You know, it doesn't have to be all indoors. I mean, all outdoors, right?

Chris Black

It do- no, it doesn't. It really doesn't.

Jason Stewart

Yeah, I'm excited. After this I'm gonna hop in the sauna, head over there. We got some table reads, feeling very writers' room-y. I can't wait to get the, uh, the Chex Mix going and the whatever we or- the Sweet Green orders, protein play.

Chris Black

Don't worry, I, I already r- I already ran into 15 producers, uh, that said hello, um, that I recognize from our Zoom calls, so they're ready.

Jason Stewart

I hope talent walking.

Chris Black

They've got the gummy, they got the gummy worms out in cups already-

Jason Stewart

[laughs]

Chris Black

... somewhere, somewhere in this fucking behemoth.

Jason Stewart

Are you a Red Vine or a Twizzler household?

Chris Black

[laughs] Oh, that's why those motherfuckers get fat. The writing room don't pay enough to put on 20 from eating all the snacks.

Jason Stewart

Right.

Chris Black

You gotta... Like, that's, that's... They should give you the, the GL- the option is GLP-1 or snacks. You can't do both.

Jason Stewart

GLP-1 or a PB&J, whichever one. [laughs]

Chris Black

[laughs] That, that's it. In the writer, in the writer... I see the, like... All y'all do is eat. That's all you do.

Jason Stewart

Yeah.

Chris Black

Writers, I feel for you. I know it's tempting. I, I have the same... Look, I'm... You put cheese in front of me, it's gonna be tough.

Jason Stewart

Don't leave them around you.

Chris Black

Don't leave your cheeses around me. True eater for real.

Jason Stewart

Chris, as famously known as a real eater, of course.

Chris Black

[laughs] Oops.

Jason Stewart

Um, yeah, sorry about the weather. I'll be in New York this weekend DJing a wedding. Pray that, let's pray that we get wheels up. I feel good about it, though. I'm not worried about it.

Chris Black

I, I honestly, dude, I mean, I, honestly it was business as usual today at JFK.

Jason Stewart

It's a crap shoot.

Chris Black

And it was busy. Like, it was busy.

Jason Stewart

Mm-hmm.

Chris Black

Like, it was... You know, it wasn't... It didn't feel different in that way. But yeah, I... The, the-

Jason Stewart

Not a lot of crying, not a lot of people sleeping on cots and, and waiting in bread lines or anything like that this time.

Chris Black

No, but there's, there's a lot of, um... Now that winter's hitting, I think people are trying to put those masks back on. [laughs] And-

Jason Stewart

Oh, you mean because it's like a-

Chris Black

Cold season

Jason Stewart

... cold season. What a little bitch.

Chris Black

D- you know what, Jason? It's shocking to me that people don't... I trust my immune system. I feed my immune system. I'm nice to it. I coddle it. I keep it warm. I cool it down.

Jason Stewart

Pause.

Chris Black

If you take care of the system, it should work fine, you know? Like, obviously there's, there's o- other factors involved, but I just noticed... Like, I went to the, uh, Wednesday show last night at Brooklyn Steel, and of course there were some masks in that audience. You already-

Jason Stewart

Yeah, yeah

Chris Black

... you already know there's some ma- But that audience, it seemed-

Jason Stewart

They got masks that ain't even out yet up in that bitch

Chris Black

They got [laughs] the new shit. They got... But there was a... I saw a g- I saw a lot of masks at that show, but also the people wearing the mask, and this is disappointing, closer to our age than college age.

Jason Stewart

Mm-hmm. When, when I went to that all-ages Electroclash-

Chris Black

Yeah

Jason Stewart

... and Slowdive Festival, I saw a lot of people wearing ma- It was, it was really... But it was, like, one or the other. There was no gray area.

Chris Black

Yeah, yeah, yeah.

Jason Stewart

Like, like with adulthood, it's really all over the place and some people are, are hypochondriac-y than others, and some people have actual illnesses, and blah, blah, blah. But when I was there, it was either, like, I have an emotional support backpack that's also a panda bear, and I have my mask, and I have my ear muffs, and I have my-

Chris Black

[laughs] Yes

Jason Stewart

... you know when, like, the horse, they have to wear the little thing on the horse so they don't get spooked from the side?

Chris Black

[laughs] Spooks.

Jason Stewart

They got that shit on. It's either those people, where if you, like, walk past them they go... Like, just by, like, being in... Or it's either that or just people, like, puking on the floor or just like, "What up, dude?"

Chris Black

Yeah, they're like-

Jason Stewart

"My name's Brad. You guys wanna, like, fuck later?"

Chris Black

I'm wearing a d- [laughs] I'm wearing a tank top and have a septum piercing and smoked a whole pack of cigarettes. I don't know what day it is.

Jason Stewart

Uh-huh.

Chris Black

Yeah, that is the-

Jason Stewart

I brought my dad here. He's chill.

Chris Black

That is sort of the... That is kind of what a lot of shows are like now, I think. That, that divide of like-

Jason Stewart

But I, but I like that everyone with... young people at least, everyone gets along and no one is-

Chris Black

Oh, yeah, yeah, for sure

Jason Stewart

... no one i- I mean, it, it's different if, depending on the show. At a Wednesday show it's a lot of nice people, probably less right-wing conservative.

Chris Black

I would say zero of the... I lit- maybe zero.

Jason Stewart

Been very respectful of everyone's space. It wasn't, you know, we're not getting our-

Chris Black

Actually, you know, I was standing, I was standing on a little balcony and they, they weren't super respectful of my space, if I'm keeping it 100 with you. I think they were like, "This big cis bitch is in my way. I can't see over..." I just, I was kinda trying to keep my little spot as the show started, and I felt like I was getting a little-

Jason Stewart

They were encroaching.

Chris Black

I feel like some baristas were edging me out.

Jason Stewart

When, when we're, when we were at the Addison Rae show in the balcony, if somebody tries to encroach, guess what? No, no dice.You gotta crawl down on your ha- Chase Sui Wonders gotta crawl down on the floor, hands and knees

Chris Black

Luke, [laughs] Luke gotta s- sniff my nuts if he wants to see SN Ray, and he might like it.

Jason Stewart

Mm-hmm.

Chris Black

That's the fucked up part.

Jason Stewart

Okay. Over at Wednesday, you're saying they felt a little more entitled.

Chris Black

They felt entitled, and I, I, I... And y- I mean, you suffer from this way more than I ever would, but I, I, I am, uh, aware of my size and that I am probably obscuring someone's view, and I wanna be respectful of that.

Jason Stewart

Earth master over here.

Chris Black

Yeah, exactly. [laughs]

Jason Stewart

[laughs]

Chris Black

I wanna be respectful of that because, you know-

Jason Stewart

Yeah

Chris Black

... they paid the money to see the band they love, you know, as much as I did, so.

Jason Stewart

I wanna donate to Greenpeace too. I wanna do a lot of shit, Chris. I know.

Chris Black

I wouldn't do that. No.

Jason Stewart

[laughs]

Chris Black

Don't, don't put that on, don't put that on my jacket, big dog.

Jason Stewart

But all, all I'm saying, I wanna see what happens at a show that has a little more rowdy energy. You know what I mean? Or I wanna see some- I wanna see you rip someone's N95 off in the pit.

Chris Black

Oh, don't worry.

Jason Stewart

You know what I mean?

Chris Black

When American Nightmare plays at Rough Trade record store, I'm about to go fucking crazy.

Jason Stewart

Okay.

Chris Black

Don't even worry about it.

Jason Stewart

Okay.

Chris Black

There's no masks. I don't think there's any masks there. But I went-

Jason Stewart

[laughs]

Chris Black

So before the show, Jacob and I went to Bernie's. I'm sure you've heard of Bernie's. It's a restaurant in Greenpoint.

Jason Stewart

Mm-hmm.

Chris Black

And I'd been there once or twice for an event, and I, I have to say, and I told the owner this, but second-best veggie burger in the world maybe, after, after Houston's.

Jason Stewart

Really?

Chris Black

It was ve- it was... And I, I... Yeah, it was very, very good. I was really impressed.

Jason Stewart

So does it go Houston, Bernie, then Superiority?

Chris Black

Y- I, I love Superiority's sandwiches. The burger isn't my favorite thing.

Jason Stewart

Mm, mm-hmm.

Chris Black

Do you know what I'm saying?

Jason Stewart

Mm-hmm.

Chris Black

Like, the sandwiches are so good, and there's a lot of them that are really good, but the, the burger is fine. This burger was multi-patty.

Jason Stewart

[laughs]

Chris Black

And I f- exactly. And it felt... It just felt like-

Jason Stewart

Are, are you saying more than two?

Chris Black

I think it was two, but with shredded-

Jason Stewart

Okay

Chris Black

... lettuce, American cheese, sesame seed bun.

Jason Stewart

Okay. Standard, standard.

Chris Black

And very-

Jason Stewart

No, no funny shit

Chris Black

... no funny shit.

Jason Stewart

No fig jam, no blue cheese.

Chris Black

No. But I told, I told Oliver, I was like, "Bro, this thing is really fucking good." The fries, every... It was just a, it was a, a great-

Jason Stewart

What farm was the shredduce from?

Chris Black

You know what? I am gonna inquire about that because I was like, "Bro, is this shit all vegetables?"

Jason Stewart

[laughs]

Chris Black

He's like... He looked at me like, "Yeah, you fucking idiot. Of course." And like, look, I don't know, man. There was... Do you remember how popular fake meat was for, like, a three-year period? I feel like it was-

Jason Stewart

Of course

Chris Black

... but it's over. It's, like, kinda over.

Jason Stewart

Yeah, I mean, I still see Impossible every once in a while, but it feels very... It's giving phased out.

Chris Black

I'm referring more so to Beyond.

Jason Stewart

Mm-hmm.

Chris Black

I feel like that was a s- a fucking rocket ship, and then it just fucking... People were like, "Wait, this is actually terrible for you? I don't... Like, I'm not gonna eat this."

Jason Stewart

A lot of, a lot of undigestible gluten-

Chris Black

Yeah

Jason Stewart

... i- in play.

Chris Black

Look, I was just... I made the trek to Brooklyn last night, and it was a success all around, and that makes me feel great.

Jason Stewart

Okay. You've been doing good over there in, in Brooklyn lately, bopping over to Tame, w- over at Strange Delight.

Chris Black

Yeah.

Jason Stewart

Now Bernie's with Wednesday.

Chris Black

I saw, I saw Strange, I saw Strange Delight guy at Allison Roman's book party, and I, but I didn't get to say what's up to him, and I, I wanna... I was like, "Oh, that's my..." He was wearing the hat, so it was a giveaway, but-

Jason Stewart

Sure

Chris Black

... good restaurant.

Jason Stewart

Good guy.

Chris Black

Good restaurant.

Jason Stewart

Okay. Well, the next time I'm in New York, we can try to do one more cool re... We'll, we'll do a noodle pudding and-

Chris Black

I'm, I'm ready to go. If I have to hear about it one more time before I eat there, I might kill myself, but I'm going to eat there.

Jason Stewart

I don't care if Jack Antonov lives upstairs-

Chris Black

[laughs]

Jason Stewart

... and it only because Lena-

Chris Black

No, I'm gonna-

Jason Stewart

... went, used to go there

Chris Black

... I'm gonna go up on Ja- I'm gonna knock on Jack's door and be like, "All right, let's see what you really got, bitch. I want a hit. Like, let's get in here. I wanna get in the l- I wanna get in the lab."

Jason Stewart

Oh, not a, not a fight. You want him to write a hit. Okay.

Chris Black

My, my, my... I've had a long-

Jason Stewart

I thought you meant like, "I'll let you have first punch."

Chris Black

No. I mean, I would let him have first punch.

Jason Stewart

[laughs]

Chris Black

It ain't... I can take a l-

Jason Stewart

Man, the, the photo of, of Margaret sitting on his lap where he's wearing the, the NBA basketball shorts-

Chris Black

That's sick

Jason Stewart

... and the wife beater.

Chris Black

A lot of people are like, "You guys don't get it. This is the perfect... This is how all Jewish couples..." They're like, "This makes so much sense, actually. You don't understand." It was really funny.

Jason Stewart

He's been pulling like this since day one.

Chris Black

Yeah. I wanna, I wanna go knock on it. I think that's an idea for us too, is that we show up at Emil's house or Mark Ronson's house or Jack Antonov's house, and like, "All right. All right, Wyatt, Andrew Wyatt, we got 12 hours. Let's, let's see what we got. Let's see what we can do here."

Jason Stewart

Okay. So it's a little Scared Straight-

Chris Black

Exactly

Jason Stewart

... Sabotage. It's a little Room Raiders.

Chris Black

Yeah, it's a little Room Raiders.

Jason Stewart

I'm, I'm gonna do the white glove test-

Chris Black

Yes

Jason Stewart

... on the NS 10s.

Chris Black

[laughs]

Jason Stewart

Please believe.

Chris Black

Nah, you know I'm not white gloving anything at Emil's.

Jason Stewart

[laughs]

Chris Black

No, no, no, no, no.

Jason Stewart

[laughs]

Chris Black

No, but yeah, I think this is, this is an idea I've had for a while where I'm like how good these... I think of these guys as geniuses that are such a big part of the process and really are the ones-

Jason Stewart

Mm-hmm

Chris Black

... doing it. But, like, if you and I show up at Tobias Jesso Jr.'s fucking farm, and you're out picking carrots, and I'm like, "All right, bi- what do you got, bro?" Oh, Olivia Dean can do it, but I can't?

Jason Stewart

You, I, I pull the MPC out of the suitcase and say, start cooking. I feel like Fred Again would be able to do this more-

Chris Black

Yeah

Jason Stewart

... than almost anyone else.

Chris Black

No, it's true.

Jason Stewart

Because all these other people, it's kinda like showing up at Jack Kerouac house and, and be like, "All right, give me a nice little story about the American struggle off top." [laughs]

Chris Black

[laughs] I need, I need, I need a 2,000-word story about the American struggle on site, like right now.

Jason Stewart

Mozart, I need a Verizon jingle.

Chris Black

[laughs]

Jason Stewart

My desk, sundown.

Chris Black

Oh, it's so funny.

Jason Stewart

There's an extra 1,500 in it for you if you can give me the stems.

Chris Black

Oh, God. That's so fucking funny. It's so good.

Jason Stewart

[laughs]

Chris Black

Uh, all right, yeah, so anyway, we're, we're here. Watch us on the live stream tomorrow. What time is the live stream?

Jason Stewart

Yeah, 7:00 PM PST if this comes out before then.

Chris Black

Thursday night, 7:00 PM PST on the live stream. Hopefully we'll cut it up for YouTube. We're gonna be talking to all of our favorite men and, uh, women additionally of the year.

Jason Stewart

Gotta give it up to the men.

Chris Black

Thank you to our GQ family, uh, Will Welch for, for inviting us to do this. We're happy to be here. Uh, I think that's it. Jason, I'll see you in a couple hours for, uh, more, uh, reading.

Jason Stewart

Do you still wanna get dinner after our table read, just to keep it all the way Hollywood with it?

Chris Black

We should. And there's also some, uh, there's some partying happening at one of your favorite places that has also been, uh, added to the slate, just if you're interested.

Jason Stewart

The slate for tonight?

Chris Black

Yeah, yeah. A little pre, you know, some, a little something, something light.

Jason Stewart

I have a facial at 8:45. How's this gonna work?

Chris Black

Yeah, that's the whole point. That's... It fixes it, the problems.

Jason Stewart

I'm so glad we had this convo. Okay, what's the party? I'll bleep it.Got it

Chris Black

... you know.

Jason Stewart

Okay

Chris Black

And I was like, "I think Jake's gonna b- I think Jake's gonna be here," so we'll see. I don't, I don't... I'm gonna feel insane, I'm sure.

Jason Stewart

Is this a USB situation for me?

Chris Black

I mean, does Asad use vinyl or does he use USB?

Jason Stewart

[laughs] I think he can handle both. That's a good point.

Chris Black

Go take, go bump him and his silk shirt out of the way and see what you can put a little Madonna on for the heads.

Jason Stewart

I'll, I'll blaze Asad a little ass-

Chris Black

[laughs]

Jason Stewart

... tonight.

Chris Black

Uh, no, thank you guys for listening, howlonggone.com, and, uh, we'll see you on the World Wide Web. Thank you.

Jason Stewart

Wagwan.

Unknown speaker
Probable ad read (98%)

This episode of How Long Gone is brought to you by a new podcast from The Guardian, Stateside with Kai and Carter. This is covering a lot of our bases, Jason. It's, uh, it's trying to slow down the news and wrestle with the questions we all have about what's happening in the world. And I know you particularly have quite a lot of questions.

Jason Stewart

A lot of questions, but how often? 'Cause we do this podcast three times a week, and that's a sweet spot. How many times do they do?

Chris Black

Three times a week, and I, I, I have a feeling just based on the platform and these talking points that they're maybe gonna be covering different stuff than we do. That's just a guess.

Jason Stewart

The Guardian is not some billionaire-owned platform. They're not afraid to say what they wanna say, brother.

Chris Black

Yeah, Rupert ain't sniffing around in, in what, uh, journalists Kai Wright and Carter Sherman are up to over there at, at, uh, Stateside.

Jason Stewart

Mm-hmm.

Chris Black

But yeah, listen wherever you get your podcasts. You can watch on YouTube. It's three times a week, and, and who couldn't use more news? You know, especially, especially when it's, when it's not, you know, from here, let's say.

Jason Stewart

[laughs]

Unknown speaker
Probable ad read (99%)

Give, give it a, give it a listen. Give it a listen. This episode of How Long Gone is brought to you by our best friends at BetterHelp. Jason, we're, we're deep into May, which is, uh, Mental Health Awareness Month, and this is just a reminder that whatever you're going through, you don't have to go through it alone. Life is a damn journey. Some days feel good, and others feel overwhelming. Whatever's keeping you up at night, it's easy to feel like you have to figure it all out on your own. But the truth is, no one has all the answers. Well, and no journey should be alone. Having someone with you to listen, to understand, and to support you can really make all the difference.

Unknown speaker
Probable ad read (99%)

I agree, Chris, and sometimes, you know, it, it's nice to be talking to somebody even if they're not even listening, even if you don't even get to s- be in the same room with them because what you're doing is you're admitting these things to yourself and that's the most, that's the most rewarding thing you can do sometimes. So, you can have a great little therapy sesh with your perfect therapist at BetterHelp. Choosing between over 30,000 people so you can get the right one just for you. Over six million people globally are using it and, you know, have some breakthroughs, go on that walk after your BetterHelp sesh, you know, whatever it might be. Get a nice little lunch all for yourself, maybe a non-alcoholic kombucha, and just think and be like, "Damn, I really am him." You don't have to be on this journey alone. Find support and have somebody with you in therapy. Sign up and get 10% off at betterhelp.com/howlong. That is betterH-E-L-P.com/howlong.

Chris Black

All right, Tom. Look, thank you for joining us on How Long Gone. You, are you in your study? Is this an office? It looks like we're-

Tom Freston

This is, uh, where I work. This is my office, but it's in my home. I'm, I'm in Manhattan. I'm in New York, so I'm just working a worker bee here.

Chris Black

[laughs] Sure. Sure. Sure. Sure. So you don't, you don't need to, at this point in your life, you don't feel the need to separate sort of, uh, home and work with an office that you have to commute to? You're happy to stay at home?

Tom Freston

It's a mixed blessing, for those of you with home offices. It, when you used to leave, uh, that was like a punctuation mark, leaving the office and, you know-

Chris Black

Yeah

Tom Freston

... when you have it in your house, it's sorta like, you know, a monkey on your back. It, you know, you can always twin b- back in there. But yeah, it's convenient.

Chris Black

Yeah.

Tom Freston

It's an easy commute.

Chris Black

If nothing else. Are you uptown? Are you an uptown guy?

Tom Freston

I'm an uptown guy now. I lived in Tribeca for, like, 20 years, but I moved uptown, and, uh, here I am.

Jason Stewart

Okay. You, so you s- you describe yourself as a worker bee. At this point in your, in your life and career, what are we diligently working away at?

Tom Freston

You know, there's an old maxim that, uh, work will expand to fit, to fit the amount of time you had if work was y- always your default position.

Jason Stewart

Mm.

Tom Freston

So, I do a bunch of things. Uh, the, the main thing I'm doing these days is, [laughs] uh, is promoting this book.

Chris Black

[laughs]

Tom Freston

But other than that, I, I've been the board chair of this thing called the ONE Campaign, which is this anti-poverty advocacy group, focuses on Africa, does RED.

Jason Stewart

Shout out to Bono.

Tom Freston

Yeah. S- so I've been doing that. I'm the board chair for 18 years, and, uh, you know, in the wake of a lot of the Trump cutback, I'm really bus- that takes up a lot of my time.

Jason Stewart

Okay.

Tom Freston

Uh, I've been working with these TV networks, uh, in Afghanistan. I went back there ev- and they're still trying to see how we can survive and-

Chris Black

Yeah, I wanna get into your relationship with Afghanistan 'cause I think you're the only person I know that has been there voluntarily.

Jason Stewart

Let's get the charity stuff out of the way at the head, at the, at the beginning, Tom.

Tom Freston

Well, that is charity stuff-

Jason Stewart

[laughs]

Tom Freston

... 'cause I'm working there for free, you know? I-

Jason Stewart

Yeah, yeah. I know. I know

Tom Freston

... I'm h- I b- I was helping them set up the first commercial thing after the fall of the Taliban, you know, and the idea was this was gonna help build tolerance. They never really had television. Help socialize and civilize people, connect them to each other, all of that.

Chris Black

They never really, they never really had television?

Tom Freston

No, no, no.

Jason Stewart

So now, uh, now you kinda pivoted that to educational stuff for the, for the Afghanistan people?

Tom Freston

That's right.

Jason Stewart

No politics, just math and stuff, I'm assuming.

Chris Black

[laughs]

Tom Freston

Yes, that's right.

Chris Black

Yeah.

Tom Freston

You know, w- and we, we had, like, 250 advertisers when things were booming. Now there's one.

Chris Black

Okay, so we've cut the ad rev-

Tom Freston

I- it's like Red Bull, Red Bull. [laughs]

Jason Stewart

[laughs]

Tom Freston

'Cause it's like these energy drinks 'cause there's no alcohol.

Chris Black

Okay.

Tom Freston

People just wanna get jacked up doing s- [laughs]

Jason Stewart

It's a, it's a little cardamom Red Bull or whatever-

Tom Freston

Yeah. [laughs]

Jason Stewart

... Zoran's drinking. That's what they're selling ads for.

Tom Freston

They have their ver- or they have their versions of the Red Bull. Uh, but it's that. We get money from foundations like Malala and Gates to do educational programming for Afghan women who've been marginalized, you know?

Chris Black

When's the first time you went there, though, like the '60s?

Tom Freston

I went there in '72.I went there in '72 and, uh, fell in love with the place.

Chris Black

But you were just on, like, a vibes mission at first?

Tom Freston

I was on a, I was on a vibe mission. I was-

Jason Stewart

What was her name, Tom? What was her name?

Chris Black

[laughs]

Tom Freston

Susan. Susan.

Jason Stewart

Got it. [laughs]

Chris Black

A famous Afghani name, Susan. [laughs]

Jason Stewart

[laughs]

Tom Freston

Yeah. No, I was advised to go there. I was, I was, uh, I had been in advertising in, in this, in New York, was work- they had tried to get me to work on Charmin toilet paper, and I, I quit. That was the last straw for me, and I went at this woman said, "Come and meet me in, uh, Paris. We're gonna cross the Sahara Desert." I did that, stayed with her a couple months, and then I kinda went everywhere. And then I met this Susan in Greece, who told me, "India, that's like the Holy Grail, the greatest show on Earth." So I went over land and stopped in Afghanistan after being in Iran and Lebanon and so forth, and-

Jason Stewart

Mm-hmm

Tom Freston

... I, I just got a fascination with the place. It really struck me. It was beautiful. People think of Afghanistan now as a, this barbaric place where everybody's fighting all the time. But back then, I, I mean, they, they had a tourist poster. They didn't have many tourists, but you say, "Visit Afghanistan and see the world's friendliest people."

Jason Stewart

And, and, and you can attest to that. You agree that they are the friendliest people?

Tom Freston

I did. It was, they were very hospitable.

Jason Stewart

Mm-hmm.

Tom Freston

It was a beautiful land. It was exotic. It was like I was stepping out of time. It was intoxicating.

Jason Stewart

Okay.

Chris Black

What did, what was your look at the time?

Tom Freston

I, it was a little hair. I, I, I-

Chris Black

[laughs]

Tom Freston

... had a different haircut, you know?

Chris Black

I imagine the hair was a little longer, but was there any... What, what was the look as far as the, the tattered rags?

Jason Stewart

Yeah, I'm-

Chris Black

Oh

Jason Stewart

... I'm, I'm imagining a Jay Peterman from television Seinfeld.

Chris Black

[laughs]

Jason Stewart

You know? Trekking from, from Manhattan to Timbuktu.

Tom Freston

I spent a year on the road with two changes of clothes, so by the time I got there they were a little ragged. But, you know, I would pick up clothes along the way.

Jason Stewart

Sure.

Chris Black

Okay, so we were traveling, we were traveling light.

Tom Freston

I was traveling [laughs] light, uh, with a duffle bag, yes.

Jason Stewart

Okay. Hitchhiking down the Silk Road.

Tom Freston

I did.

Chris Black

[laughs]

Tom Freston

I, I hitchhiked there.

Jason Stewart

And what was the, what was the Hindu Kush looking like over there in Afghanistan at the time?

Tom Freston

Well, they were always, like, 20,000-plus-foot mountains covered with snow. They were beautiful. There was no pollution 'cause there was hardly any cars. Now it's a whole other story, so.

Jason Stewart

I'm talking more about the Kush-

Tom Freston

Oh, the Kush

Jason Stewart

... that might have a little crys- crystal on snow cap, different kinda cap on the mountains.

Tom Freston

Afghanistan had the best hashish in the world.

Jason Stewart

Yeah. Oh, oh.

Tom Freston

And they, they were, they were proud of that. And it was called... But no one called it Hindu Kush, it was a Kush variety. That kinda came about when those California botanists got into it.

Jason Stewart

Mm-hmm.

Tom Freston

You know, started naming strains.

Chris Black

Yeah, these nerds.

Jason Stewart

Wiz Khalifa took that and ran with it, didn't he, Tom?

Chris Black

[laughs]

Tom Freston

[laughs] They, they did. Yeah, Hindu Kush had a whole new name.

Jason Stewart

Yeah.

Tom Freston

But, you know, it, it was very relaxing.

Chris Black

[laughs]

Tom Freston

And, you know, they would sell it... When I checked in at immigration going across the border they said, "You know, you gotta stay here at our hotel because, uh, it's too dangerous to leave." And they'd, they, and then the guy at the ho- government hotel, I changed some money, and then he said, "You want hashish?" And he holds up all these little disks.

Jason Stewart

Mm-hmm.

Tom Freston

He says, "You know, we have the world's finest hashish." And I said, "Isn't this duty-free?" He's going, "Duty-free."

Jason Stewart

[laughs]

Tom Freston

I go, "You know..."

Jason Stewart

"Yeah, is this a fucking trick? We're at a government building, you're selling me hash?"

Tom Freston

It, it was everywhere, yeah.

Jason Stewart

Okay.

Tom Freston

That was the good part.

Jason Stewart

So that sound, that sounds like when I go to San Francisco, they say, "Here, welcome to the hotel. Don't go outside, though, it's not safe."

Tom Freston

Yes.

Chris Black

Keep you in- "We'll keep you indoors but occupied."

Jason Stewart

Okay. So you, so you, you... Final verdict, the ha- the hash is quite relaxing, but you don't really partake anymore, I'm assuming, or, or who knows?

Tom Freston

No, I do, I do.

Jason Stewart

Okay. My man.

Tom Freston

You know, whenever I find the time.

Chris Black

You're a, you're a real lifer. I appreciate that.

Tom Freston

Yeah. [laughs]

Chris Black

That's commitment.

Jason Stewart

Yeah. And inspiration to me, 'cause you'll, you look great and professional and successful. And if you're still smoking some pot, what an inspiration.

Tom Freston

Well, a little, a little, a little here and there is, uh, good for, you know, s- s- is good for you.

Jason Stewart

Mm-hmm. For your mind, brother.

Chris Black

I, I...

Jason Stewart

[laughs]

Chris Black

Yeah, it feels like it informed your approach to life a little bit, but you didn't let it, uh, let's say, take over like some people might.

Tom Freston

No. I've seen that, I've seen that, I've seen that. I was a, I was a light user.

Jason Stewart

Sure. Good, good, good. Half a joint max. Well, as, as somebody who came from the advertising world, knew how to sell one or two things, when you touch down and you see all this going on over there, were, were the, the alarms ticking in your head of, of opportunities of how you could sell this stuff back to Americans?

Tom Freston

Yeah. Well, first of all, I, I met this woman in Greece, and she, she would, uh, show up at these beach cafes, and she had trunks of clothes. And she lived in Kathmandu, in Nepal, and she said, "Well, I've been there for four years." She was an American. And she would make her own and design clothes, and then ferry them to Greece and Italy and sell 'em. And, and I, I saw that and I said, "Wow, that's interesting. I could do that. What about if I could do that on a grander level? Make, you know, sell to stores?" And it would be... What I was really looking to do was find a way to support myself over there so I could live there and travel, 'cause I was just totally engaged with what... It was crazy over there in those days. It was really-

Jason Stewart

Mm-hmm

Tom Freston

... you know, you're really living life on the edge.

Chris Black

Would, would you, would you call it lawless? Is that fair to say?

Tom Freston

Well, yeah, no, I wouldn't say it was lawless, no. I mean, Afghani-

Chris Black

[laughs]

Tom Freston

... Afghanistan, a m- my main business was in India.

Chris Black

Okay.

Tom Freston

Which was then, you know, sort of the greatest show on Earth, crowded and crazy and s- sort of in a socialist incarnation. But it was, it was the hardest work I ever did in my life. But I, I bought a, I got a house in Delhi and I wanted to live there, so I started this business, and it became quite lucrative, you know?

Chris Black

You rented it. So how, was it easy as an American to come in there and just rent a house if you had cash, or buy a house if you had cash?

Tom Freston

No. [laughs]

Chris Black

[laughs]

Jason Stewart

[laughs]

Tom Freston

They were very, very paranoid of foreigners. And today if you're American you can go work there, but in those days, uh, the Indians were, you know, newly independent, paranoid about foreigners-

Jason Stewart

Mm-hmm

Tom Freston

... getting out of colonialism and all that.

Jason Stewart

Yeah.

Tom Freston

But I, my agent, I, I found a partner in India, so he would rent the house for me. We would live there. And, uh, you know, you could live a, quite a nice life. It wasn't that expensive. It was really, you could live like a pasha.

Jason Stewart

Yeah.

Tom Freston

But, uh, built the business, and it grew and grew, and it was a lot of fun, and I got to travel everywhere.

Jason Stewart

And you, one of your first account or, like, big scores was, was getting the Bloomingdale's account, and we had Gene Pressman from the Barneys family on, um, a month or two ago.

Tom Freston

I listen, I listened to that, I listened to that podcast.

Jason Stewart

Oh, nice.

Tom Freston

Yeah.

Jason Stewart

Nice, nice. So where's, where's-

Tom Freston

He was in Palm Beach

Jason Stewart

... yeah, he's down in Palm Beach. He, he gave up.You're still, you're still fighting the good fight

Tom Freston

Yeah, he's on the bench down there

Chris Black

He's on the bench [laughs]

Jason Stewart

He n- he needs a little bench time, but I g- I guess my question was, was there ever a desire to be into Barneys, or did you want Bloomingdale's more than Barneys? Was there a bidding war, or, or do you, do you know Gene?

Tom Freston

In, in, in those days, Barney... Well, yeah, we, we were in, uh, like most of the Macy's, Bonwit Teller, which is now the Trump building. Uh, B- Macy's, uh, Barneys then was largely on 7th Avenue. He probably explained that to you, in its early incarnation selling discount suits.

Jason Stewart

Yeah.

Tom Freston

So it wasn't really the player that Gene made it to be-

Jason Stewart

Yeah, yeah, yeah

Tom Freston

... at that point.

Jason Stewart

Okay.

Chris Black

Do you have a relationship to Palm Beach? I feel like you really said it with some, uh, pizzazz in your voice.

Tom Freston

No.

Jason Stewart

[laughs]

Tom Freston

I don't have any.

Chris Black

[laughs]

Tom Freston

It's, I'd ra- I'd much prefer California than, than to be a Florida man.

Jason Stewart

Oh, okay.

Chris Black

Yeah, I would have to agree with you.

Tom Freston

Smart.

Chris Black

So you're saying if you need a little R&R, you would rather go to California, or are you like a Hamptons guy?

Tom Freston

I'd go to California. I mean, I've been out in the Hamptons, but, uh, you know, I like a good beach. They have lovely beaches. Little, little traffic jam out there, you know?

Jason Stewart

Sure. Well, yeah, Chris, Chris just flew in from JFK. He's at the Chateau Marmont right now. Is that where you stay, or do you stay somewhere else in LA?

Tom Freston

Uh, well, I had a house there for a lot of years, and I sold it. Before that, I used to stay at the, uh, Sunset Marquis, and then when I was on expense account, I used to go to the Hotel Bel-Air in the olden days.

Jason Stewart

Mm-hmm. [laughs]

Tom Freston

And now I'm sort of in, in between hotels. When I go out there, I don't know where to stay. I generally stay with a couple of friends.

Chris Black

Yeah.

Tom Freston

Uh, you know?

Chris Black

I feel like your friends have houses bigger than my friends, so there's, you know, you kinda have your own entrance maybe. You know, there's, it's a little-

Tom Freston

[laughs]

Chris Black

... it's a little easier to bunk up with the homies.

Jason Stewart

If you feel like going all the way over to Malibu, yeah.

Chris Black

[laughs]

Tom Freston

I, uh, I, I, I have some friends who have some money, but I also-

Chris Black

[laughs]

Tom Freston

... have some living closer-

Chris Black

Share some

Tom Freston

... to the ground like you guys.

Jason Stewart

Uh-huh. [laughs]

Chris Black

Thank you for noticing within 15 minutes that we're living closer to the ground. [laughs]

Jason Stewart

You got a moonvez on the top.

Chris Black

[laughs]

Jason Stewart

You got a Graydon Carter down below.

Tom Freston

Well, you're at the Chateau out there. You know, that's pretty cool. I've stayed there a bunch of times. I love the Chateau.

Chris Black

It is cool. It is, it is, uh... It's also an expense account hotel in its own way, but I... The Bel Air is a very special. That feels like its own planet. I've never stayed there, actually. I've only been for, like, lunch, but it feels very removed.

Tom Freston

It, it used to be nicer. They closed it for t- three years to renovate it and modernize it, so I would find a trend. Whenever a hotel that was nice, and kind of unique, and had wooden floors, and then they redo it and everything has a marble floor, it's generally-

Jason Stewart

Mm-hmm

Tom Freston

... loses the vibe.

Chris Black

Yeah. The charm is gone, for sure.

Tom Freston

Yeah.

Chris Black

They can charge more somehow. They f- always find a way to charge more.

Tom Freston

Yes. That's not a problem.

Jason Stewart

[laughs] Okay. Well, you, you said you were coming back here on, on the expense accounts way back in the olden days, and, uh, you're obviously exaggerating a little bit, but what... In, in your mind, it seems like you were in that perfect time where the getting was good, the last great moment of, of the media, entertainment world. If you could put a year, like around what year did the, the media landscape kinda stop being a fun place that was ascending versus the, the-

Tom Freston

No

Jason Stewart

... you know, the whatever it is now?

Tom Freston

The '80s and '90s were ch- totally key. I mean, the '80s, you had the beginning of the cable TV revolution, and that kinda carried through big time, right on through to the '90s. So MTV, Comedy Central, all the cable networks were really like cash machines. And then we began to see the decimation of that as the digital revolution began in the early 2000s, and I'd say I left in 2006, and that's when, you know, YouTube had launched in 2005. Facebook was just getting going. And, uh, from there it was just a question of, uh, down- how do you manage your, your business going downhill as cable homes dropped off. More people, particularly younger people, were moving their, you know, their time on, in media to the internet, and various websites and so forth. And then social media came along, and it's been, it's been tough sledding.

Jason Stewart

Mm-hmm.

Tom Freston

You know?

Chris Black

I, you know, I wanna ask you a question about Nielsen, uh, the ratings system.

Tom Freston

Mm-hmm.

Chris Black

Because I, I want... I feel like that was accurate, and now everything we get is not accurate. Is that fair to say?

Tom Freston

I, I think so. I mean, I, I don't know what their methodology is anymore. I don't know how they can keep track of... Everybody's on phones, and they're, uh, you know, they're, uh-

Jason Stewart

Mm.

Tom Freston

Y- you know, you just don't know where... It used to be easy when you had three networks to meter, and then you had 35 cable networks.

Jason Stewart

[laughs]

Tom Freston

They thought that was complicated. Now it's like infinite fragmentation.

Jason Stewart

Mm-hmm.

Tom Freston

And, um, you know, there's smart people there, and they're trying to figure it out, and I haven't kept that close a track t- of it anymore, but I would imagine it's not as accurate as it used to be. You know, they can add up the traffic on websites and so forth-

Jason Stewart

Mm-hmm

Tom Freston

... and aggregate it, but-

Jason Stewart

And on podcasts.

Tom Freston

Podcasts are easy.

Jason Stewart

Yeah.

Tom Freston

Like you guys. You guys know exactly how many people download you and how long they listen, right?

Chris Black

Yeah. I can't count that high thankfully, but yeah, it's... Yeah.

Tom Freston

Yeah. Those are box car, box car numbers.

Chris Black

Exactly. [laughs]

Jason Stewart

Mm-hmm.

Chris Black

Exactly, yeah. Exactly. Some I can't really get-

Jason Stewart

We got their genders. We got their pronouns. We got it all, Tom.

Chris Black

[laughs]

Tom Freston

[laughs]

Chris Black

I, I would say the data we get is maybe too much. Like, there's data I don't need. Like, I just want a n- a... I don't like data. I don't care about it, but I want one number that feels successful.

Jason Stewart

Like, like we sh- like podcasts should have one, like, FICO credit score to show the overall health and quality.

Chris Black

Yeah, exactly. Exactly.

Tom Freston

That would be good. Yeah. I mean, even if you're like a, like a guy with 600 Instagram followers like me, you get all this data. I mean, and what am I gonna do? This is more data than I used to get running a cable network.

Jason Stewart

[laughs]

Chris Black

Well, Tom-

Tom Freston

You know?

Chris Black

... luck- luckily for you, the trend now with g- it, it's a, it's considered hot for a guy to have low followers.

Tom Freston

Oh.

Chris Black

So you're kind of, you're at the forefront.

Tom Freston

Mine, you know, they're probably dying off of old age, and, uh, it's dwindling.

Jason Stewart

[laughs]

Tom Freston

I need, I need new users.

Chris Black

[laughs]

Tom Freston

But maybe it's good they're-

Chris Black

New users

Tom Freston

... I get down to one or two people.

Chris Black

Yeah, you get all the way. Let's see it as low as you can go.

Tom Freston

I'll be, like, totally analog.

Chris Black

Yeah, just one, one person is all you got left. One person.

Tom Freston

[laughs]

Chris Black

Yeah. The nu- the nu... I mean, podcasting is... What is your podcast digestion? Do you, do you listen a lot or no?

Tom Freston

I, I don't listen as much as I'd like to, because I don't really have these moments where, like, I'm driving a carOr, um, you know.

Chris Black

Yeah.

Tom Freston

But I, I, I do SmartLess, I've listened to a bunch of yours, I do Walter Isaacson, I do some science stuff, I do stuff to The Daily and things like that. But I don't, I don't-

Chris Black

Sure

Tom Freston

... I don't listen to podcasts or l- audiobooks as much as most other people do.

Jason Stewart

So you're not walking the dogs, you're not w-

Tom Freston

I don't have a dog to walk. Or I'm not s- smoking a dog walker.

Jason Stewart

[laughs]

Tom Freston

Or however that goes.

Jason Stewart

And you're not, you m- not a, not a ton of dish doing every night, and, you know, taking the trash out, things like that?

Tom Freston

No.

Jason Stewart

Gonna clean out the garage, not a lot of that?

Tom Freston

I live by myself, I don't have that much trash.

Jason Stewart

[laughs]

Chris Black

Damn, bro.

Jason Stewart

Really?

Chris Black

Tom, you're living the dream, man. All right, you live alone, you got no dog, you don't do dishes.

Tom Freston

Oh, no, I don't do dishes.

Jason Stewart

Your doorman listens to your podcasts for you, probably.

Chris Black

[laughs]

Tom Freston

[laughs] I don't know if it makes me a bad person, but, uh, you know.

Jason Stewart

No.

Chris Black

I think that all of our media consumption, uh, really is dependent on sort of age and habit, and w- how willing you are to break those. You know? Or, or modify those after years and years of doing it a way that works for you.

Tom Freston

Yeah. I've been surprised, you know, I talked to my publisher, I, this is my first book I had out, so, so e-books and audiobooks are anywhere from 30 to 75% of the amount of books they sell these days. Which is, you know, the hardcover books are like a dwindling species.

Chris Black

Mm-hmm.

Tom Freston

I said, "Where the hell do people have time to spend 13 hours listening to somebody's book?" You know? It's hard to just whiz through it.

Chris Black

I, I... Look-

Tom Freston

But they do. I don't, I don't have a car, so.

Chris Black

I tried an audiobook one time, and I just was like, yeah, you know, th- I totally understand it and I think it's efficient, but it just didn't feel the same.

Tom Freston

Yeah.

Jason Stewart

I l- I like a biography or a memoir for the audiobook-

Chris Black

Yeah

Jason Stewart

... while I'm, while I'm working out. That's what I like.

Chris Black

It's also r- if it's read by the author, it's kinda interest- you know, that makes it nice, I feel like. If it was-

Tom Freston

Well-

Chris Black

You know.

Tom Freston

Well, you gotta get mine, then. You know? Kinda, r- 11 hours of me. You know, you're only getting one hour.

Jason Stewart

Yeah. I can knock that out in a weekend with the kettle bells, Tom.

Tom Freston

[laughs]

Jason Stewart

No problemo.

Chris Black

[laughs]

Tom Freston

You don't listen to mu- you know, I, I mean, I work out, you gotta, like, listen to some upbeat music, so I guess, uh-

Jason Stewart

I, no, no, I'm already upbeat. And, and once we get to the SmartLess level, we'll be able to get the, the copy of the book and we can read it-

Chris Black

[laughs]

Jason Stewart

... before we have you on, so we can talk about your rich life and history. But it is an honor to be talking to somebody who was on SmartLess the same week, which means that we've, you know, closed the gap between our sworn enemies.

Chris Black

We consider, Tom, we consider SmartLess the enemy because they're doing exactly what we do, but they're rich from it. Um, and that's, it's sort of a, you know-

Jason Stewart

Just a few guys talking about some bullshit, and they happen to be very rich.

Tom Freston

[laughs] They, I, they, they... I'm thinking this is the greatest job in America. They're getting $100 million deals.

Jason Stewart

Yep.

Tom Freston

No set, no hair, no makeup, just-

Jason Stewart

No jokes. It's all there.

Tom Freston

Yeah, they [laughs] like you guys. Yeah. Now, you say they're working in their underwear, and I can see you guys are, too.

Jason Stewart

[laughs]

Chris Black

[laughs] Well, look, when we get, when we get two different $100 million deals, my underwear's gonna change, too. It's gonna be a whole different me.

Tom Freston

[laughs]

Jason Stewart

Yeah. But, but when they finish their, their Vuori underwear podcast, they go out and play golf and get lunch. I'm in the trenches. I have the episode fired up. He's doing the booking, I'm doing the post-production. We're m- we're promoting it ourselves, so, you know.

Chris Black

We're in the trenches, Tom.

Jason Stewart

Root for the little guy.

Chris Black

You know?

Jason Stewart

Mm-hmm.

Chris Black

We're like you selling clothes in India d- for year one.

Tom Freston

Yeah. You're in the trench at the chateau.

Jason Stewart

[laughs]

Chris Black

[laughs] Look, hey, look, I'm saying there are some perks. I'm saying there are some perks. But we don't fly private. I just wanna put that out there. I, you know, this is-

Tom Freston

I got that feeling.

Jason Stewart

[laughs]

Chris Black

[chime] Every time I go to the doctor, I walk out of that bitch feeling dumb. I got no real info. This guy in a white coat just say, "You're fine," you know? "Drink more water."

Jason Stewart

He knows how to charge my copay.

Chris Black

Exactly.

Jason Stewart

That's about it.

Chris Black

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Jason Stewart

[laughs]

Chris Black

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Jason Stewart

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Chris Black

What is Revolve, man, Jason? It's, oh, funny you ask.

Jason Stewart

What's a Revolve, man?

Chris Black

It's a r- a place where guys who care about how they look go to shop. Revolve, man, is stocked with only the elevated essentials and trend-forward styles from brands like Polo, Ralph Lauren, Solomon, Fear of God Essentials for our hoopers out there, and more. It's not fast fashion and it's not stuffy. It's the sweet spot between looking intentional and not looking like you tried too hard. That's what we're all trying to accomplish out here, Jason. New arrivals drop twice a week, with free two-day shipping and next-day options. Plus, returns are genuinely easy.

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Genuinely, yeah. It's one of those things. We're all busy. Let's say we got an important dinner coming up at the end of the week. It's Tuesday. You're working every single day. You don't have time to go shopping and try clothes on and blah, blah, blah, or even just browse. You know, Revolve, it's all there. It's all curated for what you want, and then you click buy, you go to bed. Couple days later, that shows up in packaging that's a little nicer than y- the other places you're buying clothes from, and you've got a nice look for the big night out. And then you're like, "Wait a minute, I don't even have to return this because I enjoy this clothing and I wanna wear it again another time," versus all those dumb other websites. So whether it's a big night out, a wedding, a trip, or you just need something last-minute that actually works, Revolve, man, always has it. Go to revolveman.com/howlong to shop, and use code HOWLONG for 15% off your order. Free two-day shipping, easy returns. It just makes everything easier. That is revolve.com/howlong, and use the promo code HOWLONG to get 15% off your entire order. Offer ends soon. Don't sleep on it. And you don't need clothes, too. You can get just, you know, a cool candle or an incense gift for a baby shower. Whatever it is, revolve.com/howlongUm, okay, so we've got a lot of weird government shutdowns and things happening in the world. A lot of things that you used to do and be able to get away with, you know, tariffs, and international importing and exporting, and so a lot of gray areas and legal loopholes and things like that, that you've been able to sort of skirt around and take advantage of in your lifetime. After seeing all of that go down, what do you think the next kind of gray area or, like, little fuzzy loophole area is gonna be the next to crumble in our surveillance state?

Tom Freston

You mean a loophole for what?

Jason Stewart

Just anyth- anything legal, you know? Just, like, how we used to be able to do all kinds of stuff, and now we can't at all, you know?

Tom Freston

I don't know. It's kind of a dark time.

Jason Stewart

That's right.

Tom Freston

You know-

Chris Black

You know, people keep-

Tom Freston

... saying this. I went to JFK this morning. I had no problems at all. Fully staffed. And I feel like I keep hearing these horror stories on the internet, but no one-- I haven't heard one from a human being, human being's mouth. Well, you know, I look at the news. They got, like, these lines going out the door and around the corner of some of these airports. It looks like it's a nightmare. I haven't been fly-- I'm supposed to fly next week, so I'm a little terrified that, uh-

Jason Stewart

Mm

Tom Freston

... I'm gonna be in one of those lines outside.

Chris Black

I think it's over. I feel like it's over to some extent. What is your... Did you build with Trump back in the day? I feel like you guys are probably crossing paths.

Jason Stewart

Trump's in the news today, right? [laughs]

Chris Black

Not, not in a business sense, just in a nightclub sense, you know?

Jason Stewart

Not in a business sense, just in a party, an Epstein party-

Chris Black

Yeah

Jason Stewart

... you know, just to chill.

Tom Freston

You know, I, I, I, I didn't really know Trump. I don't really know Trump, uh, very well. I u- he used to always call up and want tickets to the Video Music Awards or the VH1 Fashion Awards, and we'd take care of him. And he, sometimes he would send me a note with that, you know, you'd see that signature.

Chris Black

Look, the guy's got a-

Tom Freston

I had no idea

Chris Black

... the guy's done a lot of bad, but the signatures are amazing.

Jason Stewart

For all of his faults-

Chris Black

That's maybe his be-

Jason Stewart

... strong signature

Chris Black

... maybe his best work.

Jason Stewart

[laughs]

Chris Black

Yeah, the be- the signatures are amazing.

Tom Freston

That's his best work.

Jason Stewart

[laughs] Like a Japanese calligraphy master.

Chris Black

I just feel like the idea of calling you to get tickets to an award show that you have nothing to do with is such a, it's such a ego move. It really says a lot about someone.

Tom Freston

Well, you know, i- it was the MTV Music Awards. He figured I was sort of Mr. MTV, and you know, why mess around? Go to me. So yeah, give Donald Trump tickets. He, he was sort of a, you know, quasi-celebrity, uh-

Chris Black

Yeah

Tom Freston

... he wasn't a real favorite in New York City, you know?

Chris Black

No, no, no. Still, still isn't, uh, you know, from what I can tell.

Tom Freston

No, I mean, he, he, I think he got 20% of the vote the first time around.

Chris Black

From what I can tell. But the MTV-

Tom Freston

Mm-hmm

Chris Black

... I, I've been to, I've been lucky enough to attend the MTV Video... Maybe, when did you say you stopped?

Tom Freston

20- 2006.

Chris Black

Honestly, I think I went the year after for the first time. I, I think. I think.

Tom Freston

Yeah.

Chris Black

But, but I remember, I, I used to manage a band-

Tom Freston

Mm

Chris Black

... and, and I remember you looming large, uh, i- you know, o- our TRL success was very important to the Epic Records family. And, uh, I, I always found that TRL was such a magic time that can never be replicated.

Tom Freston

Yeah. I mean, it, we had more of a, a monoculture. Now, what was the band?

Chris Black

They were called Cartel.

Tom Freston

As in Mexi- as in Mexican? [laughs]

Chris Black

As in, uh, white guys from Conyers, Georgia. But yeah, it, the word is-

Jason Stewart

As in Venezuelan drug cartel. That's right, Tom

Chris Black

... the, the word is spelled the same, yes. The word is spelled the same. But that was the first time I ever... You know, we were in, like, the green room at TRL, and it was, like, uh, you know, us and Soulja Boy and, you know, and ac- and, like, Natalie Port-

Jason Stewart

Melissa Joan Hart.

Chris Black

Yeah, it was just, like, such a strange mix of people that you could get in the same room. And a- you're right, though. It, like, the audiences were all, there was one audience, so it worked.

Tom Freston

Well, it was, you know, 'cause you'd have all three or four different music genres kinda locked together, whi- which I always liked. That's how radio was in the '60s, you know? AM radio, Top 40 radio was all kinds of different mus- the Rolling Stones, The Supremes. Now everything is-

Jason Stewart

Mm-hmm

Tom Freston

... algorithmized, how you might say it.

Jason Stewart

Mm-hmm.

Chris Black

How were your relationships-

Jason Stewart

Yeah

Chris Black

... with the, like what, what relationships were you managing the most during those MTV days? Was it with record labels mainly, or was it with just your team, or did you have to interface outside of the building a lot?

Tom Freston

Well, I, you know, we had to, I had to deal with the cable operators and satellite guys. They were our distributors.

Chris Black

Sure.

Tom Freston

Then there was the advertisers who brought the money in. Those two groups brought the money in. And then there was the music industry, who gave us our programming. And I kinda always gravitated towards the music guys, 'cause they were, they love music and I love music, and we could kinda talk the same language. They were fun, they were clever, and, uh, we needed to have good relations with them, 'cause they were giving us these videos. So, you know, my default was sort of hang out with the people who were more fun. But I, I, I had exposure to-

Chris Black

Sure, sure. [laughs] Me too. Me too.

Tom Freston

You know how that goes, right?

Chris Black

Yeah, I do.

Jason Stewart

If you gotta choose a side.

Chris Black

Yeah, I do. I'm trying not to kick it with the cable programmers quite as much as the A&R guys.

Tom Freston

[laughs]

Jason Stewart

It does seem, you said the word clever, and the word clever struck out at me as we are, we, we could use a few more clever folks in, in this, in this whole world and industry.

Tom Freston

You know, the, the, a lot of the creativity's been sucked out of the entertainment business at large in a way as companies consolidated and costs became paramount, and, uh, as these entertainment... You know, when we started MTV, there was 40 record companies. A lot of them were run by, like, entrepreneurs and who based o- on their taste.

Chris Black

Yeah.

Tom Freston

And you love that, you know? The Ir- Ahmet Erteguns of the world and so forth.

Jason Stewart

Mm-hmm.

Tom Freston

Chris Blackwell. Now, it's two and a half record companies really, you know, big ones.

Jason Stewart

Yeah.

Tom Freston

They're all consolidated, so they, you know, they run more efficiently. But, you know, on one level you could say maybe music isn't as vibrant. I don't know if that's true. But the, a lot of the outsized characters that used to exist that made the business more interesting don't seem to exist anymore.

Chris Black

Mm.

Tom Freston

And part of that is the woke, the woke thing kinda came along, and, uh, I don't know what happened to those characters. But it is, it is an, it, it, it seems not to be as much fun, and people that I talk to in that business seem to tell me the same. But I don't, you know, I don't know.

Chris Black

That's because they're looking at s- streaming numbers instead of out, you know-

Tom Freston

Yeah

Chris Black

... discovering a band play, you know? It's a different thing. I, I think it's a different-

Tom Freston

Yeah

Chris Black

... I think the job has changed. But you're right. I also think that that, the behavior that we're talking about and sort of the lifestyle is not rewarded in the same way that it was then.

Tom Freston

That's true.

Jason Stewart

And I, I al- I think that, um-Back in the day, it was like the creative people were approached by the, by the nerdy people, the brands, the whatever, the money people, and they say, "You guys are awesome. Here's a bunch of money. Do whatever you want with whatever this is." And I feel like now the, the nerds are drunk with power, and they have the ability to call the shots. And now, you know, I feel like we need to get the creative people back to doing the creative work versus doing the bidding of the brands because it's the only money left.

Tom Freston

Yeah, I mean, when the money got sucked out, I mean, in, in the '90s, say, it was raining money for a lot of places, so you could afford to make mistakes and take risks, and you weren't held under such a-

Jason Stewart

Mm

Tom Freston

... a microscope about everything had to work and work really efficiently. And so it allows some sort of more creative, larger than life, interesting people to fit in there and survive and prosper.

Jason Stewart

We can't afford a mistake nowadays.

Tom Freston

It's not raining money anymore. [laughs]

Chris Black

Yeah, I know. You're telling me. I would love to need an umbrella right now.

Jason Stewart

[laughs]

Chris Black

Um, I just wanted to ask about MTV News, because I think that i- if you're our age, Jason and I are both in our, like, early 40s, MTV News was... I mean, I remember, like, you know, life-changing events, hearing about them from-

Jason Stewart

Kurt Loder

Chris Black

... Gideon, Kurt Loder, Tabitha Soren. Like, those people were, like, sorta like, that's where... You know, they'd break in.

Jason Stewart

Michael Jackson died, you put on MTV, not CNN.

Chris Black

Yeah, when Kurt Cobain died, they'd break in and they'd, they'd give you the news, and I think that was pretty... I feel like you guys did a good job of delivering that in a way that resonated with your audience, but still got the, the meat of the story across without having to sorta put it on training wheels.

Tom Freston

Yeah, the, the... People love the news, and we built up a formidable news operation. And, uh-

Chris Black

Mm

Tom Freston

... there's a formidable news library going back to 1980 that still exists. And, you know, MTV now become kind of a repository for, uh, reality shows. 16 and Pregnant, whatever you wanna, you know-

Jason Stewart

[laughs]

Tom Freston

... you wanna do.

Jason Stewart

Yeah, and speaking of, my con- ... Our condolences for your loss of Ridiculousness.

Chris Black

[laughs]

Tom Freston

They even sawed the, they sawed the words Music Television off the bottom of the logo, 'cause they, the, all the music people who were there, there were great people there like Judy McGrath, and there's... I could list a whole, but they all kinda left, and kind of traditional TV people came in. So there's been no music equity really pumped into it. The news thing got marginalized. It was all about reality shows and ratings. And, you know, so now, uh, there's not much of a future for running music videos on traditional cable networks. The new owners there, the Ellisons-

Chris Black

Mm

Tom Freston

... you know, they got a chance to reimagine what MTV could be as a music brand, 'cause I do believe, you know, people, you could get some corner of the music fan audience to go for some place where people are having cl- intelligent conversations about music.

Chris Black

I agree 100%. I mean, I, I say I c- you could bring back Unplugged, and that would be enough, honestly-

Tom Freston

Yeah

Chris Black

... to some extent. I think that, like, that concept would resonate with an older audience, but also really capture a new one that hasn't experienced that before. You know, you can get all the, you can get Sabrina Carpenter to, to do-

Tom Freston

Totally

Chris Black

... that. You, you-

Tom Freston

Yeah

Chris Black

... you know, you can get these people that are really popular to do that stuff. But I think that the opportunity feels... I mean, everybody still makes music videos, which I always find interesting, because-

Tom Freston

They make more. I looked it up. They're making more now than ever. I mean, they make 'em more cheaply, but there's still some-

Chris Black

Mm-hmm

Tom Freston

... some great ones, you know?

Chris Black

No, no, but it's, it's, it's because YouTube is just a music discovery sur- It's, like, not about the video. It's about a place to discover the song.

Jason Stewart

Or the podcast.

Chris Black

Right.

Jason Stewart

Or the anything.

Chris Black

Yeah, yeah. It's a different thing, but it's like it, at least the video still gets made, I guess, but it's surprising how many, how many there are, and they pump 'em out.

Tom Freston

And, but there's no context or conversation around it, or even about the music so much anymore. Uh, maybe in some places, but, uh-

Jason Stewart

Yeah, I've no- I've noticed when I go to Europe, they still play music videos on television, so-

Tom Freston

Yeah

Jason Stewart

... it seems like it's a, the American attention span is particularly fucked.

Chris Black

I, I feel like the, the news and the video, like, those two things seem very different in a lot of ways, you know, as far as programming goes. But I, I feel like, was that, like, a struggle to make that work, or did it make a lot of sense based on the audience and sort of the, the, the way that the world felt at the time?

Tom Freston

Well, you know, when we started, we used to run music videos pretty much back to back, then we realized we could-

Chris Black

Yeah, yeah

Tom Freston

... be a bigger place if we were also about some of the things that the music was about, which, one of which was news-

Chris Black

Oh, I see

Tom Freston

... and fashion, and things like that.

Chris Black

Yeah.

Tom Freston

So we integrated that into the programming, and people were interested in that. And in the beginning, we found out, like, we did The Real World, which was firstly, like, the first reality show.

Chris Black

Show changed my life, Tom. That's one of the greatest s- it's... [laughs] Real World San Francisco is one of the greatest TV shows ever made.

Tom Freston

Young people at that age, they like to look at their peers, and they get a lot of signals for how they're acting and what they're doing, and they're fascinated by it.

Chris Black

Mm-hmm.

Tom Freston

And, uh, but problem was, uh, it sort of became contagious. Then you had celebrity reality shows. We had The Osbournes, and then the networks realized that, hey, these reality shows are popular, and we can make 'em cheaper than scripted comedies or dramas.

Chris Black

Mm.

Tom Freston

So the airwaves get... You know, now we're into The Bachelor and all these competitive shows, and I don't know, The Apprentice would be a good example. Wasn't, uh, didn't necessarily lead to-

Chris Black

[laughs]

Jason Stewart

Mm-hmm

Tom Freston

... great things.

Chris Black

I mean-

Jason Stewart

It l- led to success for him.

Chris Black

Don't talk about Omarosa like that, one of our greatest, greatest ex-

Tom Freston

[laughs]

Jason Stewart

One of, one of the interesting parts about, uh, MTV's growth that I heard you mentioning in some other interviews was that it grew first, and correct me if I'm wrong, in, in the Midwest, in the middle of the country, and then it took some time to eventually get LA and New York on board and s- and spread the, the good gospel about it, which seems like a thing that doesn't, it's the opposite of how almost everything works.

Tom Freston

Yeah, there was one simple fact for that, which was that was early days of cable, so the cable really existed really in rural areas where people needed to get distant signals in.

Jason Stewart

Mm.

Tom Freston

And they had wires-

Chris Black

Ah

Tom Freston

... that allowed them to get the reception. So, you know, like a place like Tulsa or Wichita or Ja- Des Moines in the middle of America, they had large cable systems, and they needed programming when the-

Jason Stewart

Mm-hmm

Tom Freston

... cable things started up, so we would get carried there. But no one in New York or LA who worked for us got us at home. There was no... You know, when we launched it, we had to find, there was, like, one bar in, uh-New Jersey that had a satellite dish. There was nobody had it. No one who worked there ever saw it.

Jason Stewart

[laughs]

Tom Freston

So, uh, it gradually moved from the Midwest.

Jason Stewart

What a concept.

Tom Freston

Moved from the Widwe- Midwest, and then, you know, if you were in the Midwest, MTV was, like, revolutionary in those days. It was, in a way, you know, hard to, hard to think now, you know? It was, uh, it wasn't like a flying car or something, but it had a new visual style and format that no one had ever seen before.

Jason Stewart

Might as well be an alien transmission of what's going on in the world-

Tom Freston

Yeah

Jason Stewart

... back when there was truly nothing else like that ever-

Tom Freston

Yeah

Jason Stewart

... ever.

Tom Freston

Those were the golden days.

Chris Black

Yeah, I mean, it all goes back to technology, which is sorta crazy. You know, I always take that out of it, 'cause I don't care or don't, like, romanticize that, but that's, like, kind of what it comes down to. Like, the satellite is what [laughs] kinda made it all work.

Tom Freston

But cable and then the satellite, I thought if, if, if in 1985 they had all the choices that we have today with the internet and satellite and all, you know, thousands of choices on every device, people would've loved it then. It wasn't like they suddenly got acclimated to this. It was it wasn't available.

Chris Black

Mm-hmm.

Tom Freston

This is what people always wanted, to have control over what they wanted to see-

Chris Black

Mm

Tom Freston

... wherever they wanted to see it, whenever they wanted to see it. So, you know, with technology, you're right, really, uh, as it evolved, people cheered for it.

Jason Stewart

Well, m- since we have a, a large brain in this space on the pod today, a lot of people talk about, like, the reverse engineering of cable into streaming, and now there's so many streaming services. You might as well go back to cable, and there's bundles and rundles and all these things going on. There's a new acquisition of a new network every day, and it doesn't make any sense. What do you... How, how do you think the next step should be to, like, get us back to a place that we can find some more financial success?

Tom Freston

A first thing would be to, to be, uh, people be able to tell how many streaming service they have. It's like Substack. How many, you know, I, I... You have to... But it's like the old days of cable. You, there's so many of these streaming services.

Chris Black

I don't wanna see your, I don't wanna see your MX bill. I bet you got them all. You got Disney Plus, you got Paramount Plus, you got-

Tom Freston

Well, and then you realize that you get Criterion and some of these niche ones, which are really good, but then you realize you don't watch them much. But, you know, it'd be nice if someone could put them all together in a bundle like the old cable system, right?

Jason Stewart

[laughs] Yeah. No, I, yeah.

Tom Freston

This l- this the new boss, same as the old boss. And, uh, and then, you know, there's more choices within it. Some kind of packaging would be helpful to the consumer.

Jason Stewart

Okay. Do you, do you... I think, I think people are working on that, but using AI to potentially do that, figure out what your tastes are based on them monitoring every single thing that you've looked at on your phone in your entire life, and they know you more than you know yourself. And then every day, you open your TV or your screen or whatever, and there's 11 Criterion movies that you have never seen being recommended to you that are about to change your life, and a Bravo show, and a new record or whatever. Do you, do you feel like that's good even though it's AI based?

Tom Freston

No. I, I, I-

Jason Stewart

[laughs]

Tom Freston

... I, I don't like that because you never, you never... You're in a silo, and you never bump into any- something you don't know about. I heard someone say the other day, "Hey, you're on Instagram." You know, when they, all that stuff. "Press on something that you don't even care about and see where that leads you."

Chris Black

Be not interested.

Tom Freston

And maybe-

Chris Black

Yeah, yeah, yeah

Tom Freston

... you know, shift, shifts your, shift your algorithm and maybe-

Jason Stewart

Okay. That's what, that's what the random button is for.

Tom Freston

Oh.

Jason Stewart

Shuffle mode, you know what I mean?

Tom Freston

I don't have... I gotta find that. Man.

Jason Stewart

Oh, yeah, on that phone.

Chris Black

[laughs] Uh, you know, so you wrote this book, and I feel like there's been a, a handful of books from, you know, your contemporaries in, in other indust- you know, there's the Barry Diller, uh, there's the Graydon Carter, there's the Keith McNally. Have you read your competition? How do you think you stack up?

Tom Freston

Well, I got a... Mine's a bit different. Sure. I mean, I, I, they, everyone would probably say that, but I mean, I try to make mine more an adventure story with a business story wrapped inside, and I had a different kind of career path.

Chris Black

You've done a lot of fu- you've done a lot of fucked up shit. Graydon Carter, you know, like, Graydon Carter had some magazines. [laughs]

Tom Freston

Yeah. I mean, I took a lot of left-hand turns early on, and what I found that, you know, life off the mainstream was, could be a lot more interesting, and I would pursue those things and quit jobs and do different things and go live in different countries. And what I found out was that a lot of what I'd picked up in those years, which was, you know, living in Asia, for example. You know, you learn about humility, you learn about empathy, you learn about being, uh, you know, able to move, you know, with, and deal with eccentric people and deal with craziness.

Chris Black

Mm.

Tom Freston

All of it sort of prepared me for... It was a perfect fit, in a way, to run an en- enterprise like MTV Networks was in its prime, which was sort of a creative-focused thing, always trying to push boundaries, and dealing with a lot of young people and, uh, being tolerant. That it, uh, that my background was different than, uh, your traditional television executive, and, uh-

Chris Black

Yeah

Tom Freston

... it worked for me in that particular company. You know, if I was running a CBS, which really required more mainstream kinda perspective, I might not have been nearly as successful. But we, we attracted-

Chris Black

Mm

Tom Freston

... you know, like, in our business, we, I put creative people in charge of all the networks, Doug Herzog, Judy McGrath, a wh- you know, and... 'Cause to me, that would send a signal to the employees that creativity was our main attribute, our main aptitude. That's what we focused, and we weren't looking so much for the financial results, we were looking for creative results. Wanted to encourage risk-taking and so forth, and it worked for a long time.

Chris Black

Mm.

Tom Freston

And so I would say that if you l- look at my book, I mean, about two-thirds of it is about stuff outside the media business.

Chris Black

Mm-hmm. I know what you mean, but I think that there's, like... That was your experience, you know? With some of these, with some of these... But, like, some people wanna write 100 pages about their childhood. I don't give a fuck about that. Like, let's get to the good stuff. You had a lot of good stuff that wasn't necessarily, like, work-related in the, in the senses, uh, of the MTV sense.

Tom Freston

Exactly. So-

Chris Black

That's a blessing

Tom Freston

... so that would differ- that would be different for... And that's not to say these guys didn't have... You know, Keith McNally's book is great. You know, it's a great story about triumphing in New York with, uh, those restaurants, and, and Barry Diller, you s- and, and Graydon. I mean, they were very successful. But-Mine has a more of an element of adventure to it, and, uh, so-

Jason Stewart

Mm-hmm.

Chris Black

I would love to drop Graydon in Mumbai, see how he does, but that's a different, that's a different conversation.

Jason Stewart

[laughs]

Chris Black

That's a different conversation.

Tom Freston

You know, I took him to, I, I took him to Cuba once, Graydon.

Jason Stewart

Wait, didn't you guys all meet Fidel?

Tom Freston

We all had lunch with Fidel. Yeah, I wanted to go down there just to chase down the music scene.

Jason Stewart

Mm-hmm.

Tom Freston

And then I told, uh, uh, Brian Grazer about it, and he said, "Oh, man, I wanna go." But he told somebody who told somebody, and then next thing I know, I got a, a plane load of, um, moguls flying to a communist-

Jason Stewart

[laughs]

Tom Freston

... flying to a communist country I knew nothing about.

Jason Stewart

[laughs]

Tom Freston

And when we get there, you know, i- i- it was 2001. You know, the, the, at the hotel, you know, there you had the Lucky Luciano Suite. The suites were all named after gangsters-

Jason Stewart

Mm

Tom Freston

... at the hotel.

Jason Stewart

[laughs]

Tom Freston

It was a crazy time in Cuba. Then they said, "Well, Fidel would like to meet you." 'Cause I had made some appointments at the Ministry of Culture to try and drill into the music scene there. They said, "Fidel wants to meet us. Come on." So we had lunch at the palace, and he wined and dined us. And he said at one point they had us in the, uh, Hall of Heroes or something, the Hall of Ferns, which is at the Presidential Pal- Palace. Well, when we met, we came, we had these rented convertibles, and we came up the stairs to the palace, and he's standing on the wa- to greet us, Fidel Castro.

Jason Stewart

Damn.

Tom Freston

You know, a man from history.

Jason Stewart

[laughs]

Tom Freston

And I'm thinking, "Jesus Christ, it's him. What's he gonna say to us?"

Jason Stewart

[laughs]

Tom Freston

And he got, so he looks at us, the first thing out of his mouth is, "Which one of you guys made The Sopranos?"

Jason Stewart

Wow.

Chris Black

So that's what got, that's what got you in the door-

Jason Stewart

Man

Chris Black

... over there, I guess.

Tom Freston

He said he's, like, the only subscriber of HBO in all of Cuba.

Jason Stewart

[laughs]

Tom Freston

And Brad Grey raises his hand and he says, "That was me." So maybe they're gonna shoot me, you know? I mean-

Jason Stewart

[laughs]

Tom Freston

... Castro had a bad re- uh, relationship with gangsters.

Jason Stewart

Guy hasn't been, been seen since.

Chris Black

That's, that's a g- that's a... So at that point, going to Cuba, you just had, you had to get, like, a travel visa. It was, like, some paperwork, but you could still go.

Tom Freston

Oh, you had to get special visas.

Chris Black

Yeah.

Tom Freston

And, uh, you know, I, so I found this guy, uh, Jonathan Brandstein from LA. He's a comedy manager. He would go there all the time, so he kinda wired me up. It was just gonna be me going-

Chris Black

Sure

Tom Freston

... and before these other people came. And he said, "You can get a cultural exchange visa, and I could tell you how to do it," blah, blah, blah. So this guy knew all the tricks of how to do it, 'cause it wasn't as easy as it might have been, like, during the Obama era. And then, uh, when it came out that we had lunch with Fidel Castro for five hours and people got ahold of that, they called the, the, the Bush White House and Cheney White House, and I got a letter saying, uh, "You went to Cuba, you had lunch with Fidel Castro. We're fining you $55,000."

Jason Stewart

Wow.

Tom Freston

I go, "Whoa, whoa. Man, that's, that's, uh, ruined my day." And then, you know, we had the, I had got, we got Ry Cooder. You remember Ry Cooder? He did the Buena Vista Social Club.

Jason Stewart

Yeah, of course. [laughs]

Tom Freston

He had the same problem. And he got a lawyer, and I said, "So we got a lawyer." And there's a lawyer who used to work at the Treasury Department fining people for doing exactly this.

Jason Stewart

Wow.

Chris Black

He went to the, he, he went to the dark side. He crossed over.

Tom Freston

He, he crossed over, and now he's representing people like this who he used to prosecute. So he said he'd get the fine down. So we all hired him and, you know, we still had to pay a lot of money 'cause his fees were high.

Chris Black

So you're telling me that all of you guys got hit with a fine for going?

Tom Freston

Yeah. Except Graydon Carter, because, uh-

Chris Black

He's Canadian?

Tom Freston

He was a, he was Canadian [laughs] and he was a journalist.

Jason Stewart

Wow.

Chris Black

Oh, I see. They were making-

Tom Freston

And journalists, journalists were exce- exempt. So yeah, we all got hit with $55,000 fines, and we had to, you know, hire this guy.

Jason Stewart

I would've sent that invoice over to the desk of Fidel Castro.

Tom Freston

[laughs]

Jason Stewart

You gotta pay for that one, daddy.

Tom Freston

Yeah. Fi- Fidel, call Cheney and work this out. I don't, I don't have time for this.

Jason Stewart

Okay. That actually, Tom, that reminds me of a question I wanted to ask you. Who's the last person you had dinner with where you did not pick up the check?

Tom Freston

Where I did not pick up the check?

Jason Stewart

Yeah.

Chris Black

[laughs] Yes, yes.

Tom Freston

I had dinner last night with a guy, Oz Whelushen, who's got a company called Kaleidoscope. He's a podcaster.

Chris Black

Yeah, yeah.

Tom Freston

He picked up the check.

Chris Black

Wow.

Tom Freston

God bless him.

Jason Stewart

[laughs]

Chris Black

Okay. Just-

Jason Stewart

Where'd you guys go eat?

Tom Freston

I, I... Look, I grab as many free checks as I can. I'm, you know-

Jason Stewart

Okay

Tom Freston

... few and far between, I'm sure, so you gotta take them when they come. Well, you know, it's not like I'm running around with an expense account anymore.

Chris Black

This is coming out of Tom's pocket, so you gotta sort of protect the-

Tom Freston

Right.

Chris Black

Sure, of course.

Tom Freston

Right. Mm-hmm.

Chris Black

What, where do you eat in New York? Where, where are your s- where are your favorite spots? I live in New York, by the way. I, I didn't, I, I'm, I'm just here visiting. But I live-

Tom Freston

Oh, do you?

Chris Black

... I live downtown. I live, um, right near the courthouse, like, sort of between Chinatown and Tribeca, so I, I'm in your general old, your former area.

Tom Freston

Yeah. Well, I go down there. Where was I the other night? Uh, the Bowery Hotel, in that area. And I went to, uh, they have an LA branch they just opened down there, Gelina.

Chris Black

Oh, yeah, yeah, yeah. The, yeah, yeah.

Jason Stewart

Mm.

Tom Freston

There's a new Gelina. It took a while to open it, and that's good.

Chris Black

Well, it opened-

Tom Freston

It was just there

Chris Black

... and then it had a f- a questionable fire.

Tom Freston

Had a flood or-

Chris Black

And then-

Tom Freston

Yeah.

Jason Stewart

[laughs]

Tom Freston

Special kind of fire.

Chris Black

A special kind of fire.

Jason Stewart

[laughs]

Chris Black

But it, honestly, Gelina in New York is a very different experience, and it's pretty good. And it, the, the room, it, they did a really good job on the build out. It's very nice. Like, the, the actual space is very nice.

Tom Freston

So I like going there. And, you know, a, a whole b- whole host of downtown spots and uptown spots. I'll go to, like, uh, there's a place called Lilio's, kinda old-school Italian up on the East Side.

Chris Black

Mm-hmm.

Tom Freston

Or, uh, The Modern, which is connected to MoMA. That's kinda fun to go to if you're going to a show or something. Uh, the, the, I still go to The Waverly over on, uh, Jane Street.

Chris Black

Love The Waverly.

Tom Freston

Over by, it's on Waverly, yeah. Corner of Waverly.

Chris Black

No, the, I, I lo- I hadn't been there in a long time, and I went recently and I forgot how fun it is. It feels like a real, uh, relic, in a good way.

Tom Freston

Yeah. It's a nice spot. Yeah.

Chris Black

Dark. [laughs]

Tom Freston

So you're in New York, are you?

Chris Black

Yes, sir. Yeah, yeah. I've lived in New York for, at this point, I don't know, 16 years maybe. So I feel naturalized to, to some extent. Um, you might agree with me, but I think if New York works for you, there's kinda nowhere else to live. And if you like it, then it's ki- everything else is sort of boring.

Tom Freston

Yeah. I, I went to school here, and then I just kinda always kept a place. And, uh, after the pan- you know, during the pandemic, a lot of people I knew, they all moved out to California, Hudson Valley-

Chris Black

Right

Tom Freston

... Long Island, wherever.Florida. And a lot of them didn't come back, but I see them now starting to come back 'cause they miss the action.

Chris Black

Yeah.

Tom Freston

I mean, I w- I've been here all fall, and it's really been fun. There's so- there's a lot, so much going on. I mean, it's hard to, you know, even we got a new mayor coming in now. I mean, the city's sort of electric, particularly you go to south of 14th Street, you really got a, a good, uh, vibe that things are going up. Mm-hmm.

Chris Black

Yeah, up, up where you are, things are always the same I think, and that's the point. It's b- it's just serene, and I, uh, at least you can come down a little bit and get the action. It's not hard. It's not far.

Tom Freston

No.

Chris Black

Do, so you never lived, you, did you ever move the whole operation to LA, or were you always in New York?

Tom Freston

Uh, no, I was, New York was my base, but I would spend four to six a months, four to six months a year there.

Chris Black

Okay.

Tom Freston

You know, 'cause we did a lot of business there. We had offices in Santa Monica. We had a, a animation studio in Burbank. And, uh, I love being in LA, particularly in the winter, particularly right around now when it's getting cold, you know? [laughs]

Chris Black

Sure, sure, sure. No, last night, yesterday I was like, "Oh, shit, it's happening." It's like I had to put on a real jacket yesterday-

Tom Freston

Exactly-

Chris Black

... for the first time

Tom Freston

... what I thought. That cold wind comes around off the river, and you go, "Oh."

Chris Black

I was, I was like, "I gotta put up a goddamn hat on now. This is not what I bargained for." I also wanted to ask you about the, the Vice stuff 'cause I was very close to that, and that chapter, uh, is funny. And I think that, um, you captured Shane and that whole thing as a guy coming in as sort of like a successful adult. [laughs] I think you really captured it, uh, in the right way as far as, like, the temp check on it. But I feel like you've seen a lot of fumbles in your, in your career. I feel like that's one of the be- the worst fumbles of all time.

Tom Freston

Yeah, they made some big fumbles, and it's too bad because for a long year they had a great run, you know? I mean, I was involved with, uh, you know, I helped get them, uh, the, as HBO show, which really-

Chris Black

Yeah

Tom Freston

... elevated their whole game and, and made them better at it, and they were great at it. And Shane was great at sniffing out a cool story that was sort of on the edges and putting it together. He loved doing that. And in his heart, he really wanted to, you know, not just entertain, but to like inform young people and take them to different corners where, you know, mainstream media wasn't covering it. And then, you know, they would spend too much on it. And, uh, you know, he, there was a thing where we're always gonna get bigger and bigger. We're gonna grow this thing to the sky, and a lot of times the organization didn't keep up with that. But they had attracted this cadre of young journalists who really wanted to do good work there.

Chris Black

Mm-hmm.

Tom Freston

And they did. And then, you know, because the finances were out of whack, the thing kind of imploded. And, uh, you know, they bring in a private equity company, and, uh, you know, there's certain, like certain handcuffs on the business, and-

Chris Black

Mm-hmm

Tom Freston

... it didn't end well. [laughs]

Chris Black

I just know a lot of guys that I think were told very convincingly they were gonna be very rich, and then, uh, they aren't. It did not work out that way, uh, after it was all done.

Tom Freston

Options, look, I, uh, you know, you're looking at one. [laughs]

Chris Black

[laughs]

Jason Stewart

You had a better, bigger chunk coming for you than, uh, than Eddie did?

Tom Freston

I had a ch- I had a chunk, yeah. You know, the o- the, all the options were worth zero.

Chris Black

[laughs] Oh, man.

Jason Stewart

So you're saying that you ... Wait, did you invest or were you just on the board?

Tom Freston

I invested some money. I mean, wasn't, I brought in to help bring in investors, uh-

Chris Black

Yeah

Tom Freston

... initially. Then I c- then they did that very well on their own. You know, they, it was a continual process. [laughs]

Chris Black

Hmm.

Tom Freston

But I, I got options in the company, and I helped, uh, connect them to other people. I was on the board. I was a consultant. I would spend a lot of time with them. I enjoyed going, uh, to Williamsburg and seeing it, and I would see Shane all around. Travel, he used to travel around. I'd see him in Afghanistan. I'd see him all over the place, and his people, Ben Anderson. I knew a lot of the reporters there, Michael Moynihan. Yeah, but all, and a lot of them, uh, who started at the very beginning had big equity positions-

Chris Black

Mm

Tom Freston

... that they were counting on, and everything was just wiped out.

Jason Stewart

Hmm.

Tom Freston

And then there was the investor class, you know, the, the, the Disneys and the CVCs-

Chris Black

Yeah

Tom Freston

... and all these other people who had invested, the Murdoch. They all got wiped out, too.

Jason Stewart

And Shane had, Shane left with how much money?

Tom Freston

Uh, that, you'd have to ask him.

Jason Stewart

Mm-hmm.

Chris Black

That's how much it is, Jason. That's how much it is.

Jason Stewart

[laughs]

Tom Freston

I mean, uh, he's never disclosed it. I don't know. I mean, uh, you know, people would take out, some of these guys would take out money every year. Some of them would borrow money against their equity, and like box cars of money. And then when, when the thing began to implode, they had to pay it back.

Jason Stewart

Hmm.

Chris Black

Geez, I don't like that.

Tom Freston

So it wasn't like you're not gonna get anything. It's like the stuff you've got, you gotta sell your houses and boats and everything.

Chris Black

[laughs] Gotta pay back? Yeah, you gotta sell your boat.

Jason Stewart

God.

Chris Black

That, that is-

Jason Stewart

Yeah, I mean, he probably got a, you know, at least 100, 100 million.

Chris Black

When he got that, he bought that crazy house that you me- you mentioned the house. Like, that was, like, a big, when he did the Wall Street Journal picture of the house, people were like, "All right, go fuck yourself. This is a little much. This castle is, like, a bit much." Um-

Jason Stewart

Yeah

Chris Black

... well, a- as far as investing goes, have you had a real hit th- or have you had something that you really thought was gonna go and it flopped besides Vice?

Tom Freston

Yeah. I mean, I, I'm, I'm kind of a conservative, but I've invested in a bunch of stuff that hasn't worked.

Chris Black

Sure.

Tom Freston

You know? Uh-

Chris Black

And the, and, but do you go outside of your interest areas, or you kind of like to stay in stuff that you-

Jason Stewart

Oh, wait, wasn't there a little, there was a little MySpace at some point, right?

Tom Freston

Well, we looked at MySpace when I was at, uh, when I was a CEO of, uh, Viacom and, uh, I got promoted up to that level. And, uh, we looked at it, and we didn't, never made a bid, and then Rupert Murdoch came in and bought it.

Jason Stewart

Mm-hmm.

Tom Freston

But we were interested in the social media space because we kind of saw what was coming, the idea that you're gonna be a gatekeeper network. But now we had something where people could connect per, peer to peer. They could com- you know, YouTube was really, to me, the game changer of all. You know, you could upload your own video. You could share it and you could comment on it and all, and, and, and, you know, it, it, it's now worth, uh, you know, $550 billion. It's become so much more than what any of us ever imagined was possible. They took that simple little model and built an infrastructure around it and kept innovating, and it's like, I wouldn't say it's a monster 'cause that's a bad term. I mean, it's, it's, it, it's-

Chris Black

Yeah

Tom Freston

It's a pheno- it's a phenomena.

Chris Black

Yeah. I think it's bigger than it ever has been, and like you said, in ways that maybe people didn't expect it to be. Or, like, the use is different than people expected it to be.

Tom Freston

Yeah, you watch YouTube TV, for example. That which, you know-

Chris Black

Yeah

Tom Freston

... like, what, that's the greatest interface television's ever had.

Chris Black

That shit costs me $80 a month. Yeah, it kills me.

Tom Freston

Yeah.

Chris Black

Kills me.

Tom Freston

And now we can't get ABC.

Chris Black

See? I got, I got, I got a Disney, I think I got a $20 Disney credit 'cause they had a blackout-

Tom Freston

[laughs]

Chris Black

... recently with YouTube T- I got all these emails, class action lawsuits. I don't, I don't keep up.

Jason Stewart

It's tough, guys.

Chris Black

What is, so what is your relationship with Rupert Murdoch over the years, and how does it stand now?

Tom Freston

I haven't seen him in a while. I mean, we were competitors, but I was friend- I was friendly with him.

Chris Black

Of course.

Tom Freston

You know, I c- I had issues of course with Fox News, but I was friendly with him. And then this guy, Saad Mohseni from Afghanistan, came to see me, and he's the guy who enlisted me and invited me to come back and start this media company there after the fall of the Taliban, which I was, like, eager to do when I left Viacom. I said, "That sounds fun. I go back and do something kinda purposeful, and I could be back in this country," that still remained a fascination to me.

Chris Black

Yeah.

Tom Freston

And then he was described to me initially as the Rupert Murdoch of Afghanistan, which, you know-

Jason Stewart

What a title

Tom Freston

... I spit up my Pellegrino when I heard that.

Jason Stewart

[laughs] You're like, "Is, is that good or bad?"

Tom Freston

But then he, he came, and, uh, because then I said, "You know what, Saad? I'm gonna introduce you to the real Rupert Murdoch."

Jason Stewart

[laughs]

Tom Freston

And, and Saad had been, uh, his father was a diplomat in Afghanistan, and they were in Japan when the communist coup came. And, uh, they g- they, they, they became refugees, and they found their way to Australia. So he's Australian like Rupert.

Chris Black

Ah.

Tom Freston

So he, he and Rupert really hit it off, and Rupert and News Corp became an investor in his company-

Chris Black

Wow

Tom Freston

... on successive rounds, and that was a great thing. And then, uh, you know, he became buddies with James, and, uh, but, and Rupert was, um, I, my ex-wife was very friendly with his, uh, his wife, Wendi.

Chris Black

Sure.

Tom Freston

One of his ex-wives. He's had a-

Chris Black

Yeah, he's had a few.

Jason Stewart

Old Rupe's had a couple.

Tom Freston

He's had a run of them. [laughs]

Chris Black

He's had to ta- he's had to, he's had to peel off some duckets in court. But the, so did-

Jason Stewart

[laughs]

Chris Black

Are we talking, like, double date friends, or are we talking, like, friendly when we see him at a charity event?

Tom Freston

Yeah, that, and then there, there were times when I would double date, you know, I mean, way back.

Chris Black

Sure, I love that.

Tom Freston

I wouldn't call it, we, we'd never call it a double date. "Hey, I'll pick you up in my car."

Jason Stewart

"Hey, Rupert Murdoch, do you wanna go on a double date this weekend?"

Chris Black

[laughs]

Tom Freston

[laughs]

Jason Stewart

[laughs]

Tom Freston

"No, no, I'll bring my wife."

Jason Stewart

"You and ice skating."

Chris Black

"It's not, it's not weird if we're both gonna bring our wives."

Jason Stewart

[laughs] With the wives this time.

Chris Black

No, I think that, well, wives will bring you together with people maybe you wouldn't, you know, maybe you'd sit across the table from in different scenarios, let's say.

Tom Freston

Well, yeah, look, no matter what you say about him, he's an interesting character.

Chris Black

Totally. No, I mean, that's what I've taken away from you in general, too, is, and I, I feel like this myself. I'm attracted to the, the business is, like, secondary to the characters and, like, the personalities.

Tom Freston

Yes.

Chris Black

That's the most-

Tom Freston

Yes

Chris Black

... interesting part of anything, really.

Jason Stewart

Yeah.

Chris Black

You know?

Jason Stewart

A, a freak is a freak.

Tom Freston

Sometimes I think that's what's being taken out of the business in these last few years.

Jason Stewart

Mm.

Tom Freston

You know, the personal relationships.

Chris Black

No, I mean, it's, that's like Jason s- like Jason said earlier, it's, it's the nerds and the numbers, and I think the personality stuff has been sort of, you know, put to the backseat. And, and hopefully we can get there. You know, it, it doesn't seem to be trending in that direction by any means, but hopefully we can get there because I think that-

Jason Stewart

We need to make bullying great again.

Chris Black

Exactly. [laughs]

Jason Stewart

The first step in our initiative.

Chris Black

Exactly.

Tom Freston

Yeah. Well, maybe it's a pendulum and it swings back. I hope so.

Jason Stewart

Let's hope so.

Chris Black

I think, I think there's probably some, there's a possibility. Uh, uh, yeah, I think that that always happens to some degree.

Tom Freston

I mean, there still are, there still are companies around the edges. Like, you know, look at A24 and some of these young movie studio-

Chris Black

Yeah, yeah

Tom Freston

... m- movie companies that are pretty interesting, and they still rely on gut and instinct, and they take chances. And, uh, you wanna root for them.

Jason Stewart

Mm.

Chris Black

But I think that, I think A24 is a pretty good example, a- and film in general is, like, I think that a lot of that stuff, you, you can miss a lot and hit a lot, and it kinda evens out. Like, you can miss a lot and hit a lot less, and it evens out, I guess, is what I'm trying to say.

Tom Freston

Yeah.

Chris Black

'Cause I think the budgets are so, the budgets vary so much depending on what the project is.

Tom Freston

And if it's an independent company and it isn't wedged into a public company, it's not trapped into having to grow to the sky-

Chris Black

Yeah

Tom Freston

... every year, you know?

Chris Black

Yeah, yeah.

Tom Freston

You can have a bad year, but, you know, I'm not gonna-

Jason Stewart

Right

Tom Freston

... I'm not gonna fire everybody.

Jason Stewart

You're s- you're still rich.

Chris Black

We're not turning the lights off.

Jason Stewart

It's, you, you don't have to go-

Tom Freston

You, yeah

Jason Stewart

... exponential hockey stick year over year until you die.

Tom Freston

That's right.

Chris Black

That will ruin something. All right.

Jason Stewart

Um, I gu- I guess speaking of the cy- cyclical really quick as we end, the book called Unplugged, obviously a reference to the MTV Unplugged series. Maybe not a, a complete inspiration for it, but of all, uh, of all the Unpluggeds over time, what has been your favorite episode?

Tom Freston

Oh, there was a few. Uh, LL Cool J was a, he did a great one.

Jason Stewart

Yeah? [laughs]

Tom Freston

You know?

Chris Black

Wow, that, that-

Jason Stewart

Yeah

Chris Black

... I gotta say, it's an unexpected answer.

Tom Freston

Mama Gonna Knock You Out. I mean, yeah, he was really-

Jason Stewart

People talk about it 'cause that was an early one

Tom Freston

... fucking playing with a band. You know, we did an early-

Chris Black

Yeah

Tom Freston

... one with Paul McCartney to kick butt. Nirvana, of course, was the big one 'cause I remem- I'll remember that so clearly. We did them with Dylan. We did them with, like, uh, you know, a whole run of people. REM did a great one. There were some-

Chris Black

REM's my favorite. Uh-

Jason Stewart

I'm partial to the Alice in Chains. Little more dirt under my nails than you guys.

Tom Freston

Mm-hmm.

Jason Stewart

You know, a little more working class. It's fun.

Chris Black

Well, uh, my, mine are painted like Michael Stipe, so, uh... [laughs]

Tom Freston

[laughs]

Chris Black

What, what is the, w- Tom, can we watch those any, 'cause they're not on YouTube, right? Is it on one of the-

Tom Freston

Yeah, yeah. I think if you go onto Paramount Plus, I believe they're all there. There's a big library of those. There's a big library of another show I really love, which was on VH1 called Behind the Music.

Chris Black

Storytellers? Oh, Behind the Music, yeah, yeah.

Tom Freston

And Storytellers too.

Jason Stewart

Oh, yeah.

Tom Freston

But Behind the Music is sort of the predecessor for all these music docs we see today-

Jason Stewart

Yeah

Tom Freston

... which are also, I, I, I love them. You know, I'll watch almost any one, whether it's good or bad.

Jason Stewart

Yeah, I, I love it when there's a, a, an old guy behind a mixing board and he's pulling up the old, you know, he's got the Neve console, and we're gonna bring the hi-hats in, and then everyone's like, "Oh, that's that stuff. That's that magic."

Tom Freston

[laughs] Yeah.

Jason Stewart

It doesn't even matter if it's a band I don't like.

Chris Black

Yeah, it's true.

Jason Stewart

I'm still watching every episode.

Chris Black

No, I'm with you. I'm with you on that.

Tom Freston

And you're right. They, they could be bringing them back now with, like, Sabrina Carpenter and people like that, but they, there's no, there's no infrastructure. They need to hire some music people.

Jason Stewart

Absolutely.

Tom Freston

That would be what, that would be a start.

Chris Black

Yeah. I think it's gonna, I think it's unfortunately gonna happen probably somewhere else, you know? I think that, that concept will have-

Tom Freston

Could be.

Jason Stewart

It's happening now at NPR.

Chris Black

Yeah, I mean, yeah.

Jason Stewart

Like I said, the nerds have taken over.

Chris Black

Exac- yeah. Uh, all right, Tom.

Tom Freston

[laughs]

Chris Black

Thank you for joining us. Uh, the book is, when's the book out?

Tom Freston

The book comes out next, uh, Tuesday, the 18th of November.

Chris Black

Next Tuesday-

Jason Stewart

18th

Chris Black

... the 18th of November. Get it wherever you get books.

Jason Stewart

Bob Lefsetzglazing review this morning on the email. He really loved it

Tom Freston

I saw Lefsetz and I, well, that warmed my heart. I was at dinner last night getting that free dinner.

Jason Stewart

Yep. That's right.

Tom Freston

And my, and my, my phone started blowing up-

Jason Stewart

[laughs]

Tom Freston

... you know, with all these emails about Lefsetz. And I, you know, I read that 'cause he's a, he's, he can be harsh. I mean, he, he cranks out so much stuff, it's remarkable. But he, that was a very nice one, yeah.

Jason Stewart

Yeah, we, we had him on-

Tom Freston

He got the book

Jason Stewart

... a couple years ago. He was a goddamn bulldog talking to him, good Lord.

Chris Black

He did not, he did not like us. He did not.

Tom Freston

Oh, no?

Chris Black

Well, I think, I think he just didn't get what we were doing.

Jason Stewart

He was just like, "What is this? What is this operation-

Chris Black

Yeah, it was a very weird-

Jason Stewart

... you're trying to run here?"

Chris Black

But I've been, I mean, I've been reading Bob Lefsetz, like, since 2006. Like, that was the first newsletter I may have ever subscribed to, honestly.

Tom Freston

Remember, it used to come out in paper.

Chris Black

Yeah, yeah, yeah. No, I mean, that and Hitz Daily Double were the bo- that, that was it. Like, that was-

Tom Freston

Yeah

Chris Black

... sort of the music business news that wasn't, you know, from a major source. But anyway, all right, the book is out the 18th. Tom, thank you for joining us. We appreciate it. And, um-

Tom Freston

Okay

Chris Black

... we'll see you soon. All right.

Tom Freston

Thanks. Thanks Jason. Thanks Chris.

Chris Black

Of course.

Tom Freston

Okay.

Chris Black

Our pleasure.

Tom Freston

Take care.

Chris Black

Later.

Jason Stewart

A pleasure, Tom.

Tom Freston

Enjoyed talking to you guys. Bye-bye.

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