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Jared Freid is a stand-up comedian based in New York City whom you’ve most likely heard on one of his two highly popular podcasts — U Up?, a dating and relationship series he co-hosts with Jordan Abraham of Betches; and The JTrain Podcast, where he welcomes fellow comedians to help him answer questions and give advice to listeners on all sorts of topics. Since appearing as a New Face at Montreal’s Just For Laughs festival in 2017, Jared has performed on The Tonight Show Starring Jimmy Fallon, hosted shows on both Snapchat and Spotify, released a stand-up album in 2019, as well as a half-hour stand-up special on his own YouTube page in 2021. His debut Netflix special, 37 & Single, premieres in August 2023. But first, he spoke with me over Zoom about how he carved his own path in comedy through writing columns, what it’s like hosting live-streaming shows from The Comedy Cellar, and how he’s already living his comedy dreams.

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If you’re not already subscribed to my podcast, please seek it out and subscribe to Last Things First on the podcast platform of your choice! Among them: Apple Podcasts; Spotify; Stitcher; Amazon Music/Audible; iHeartRadio; Player.FM; and my original hosting platform, Libsyn.

Last Things First on Apple Podcasts

This transcript has been edited and condensed only slightly for your convenience.

Last Things First: How old is too old to be called J Train?

Never. Never too old. It's a self-given nickname. So it's already a douchey crazy, self-aware joke, I think. I mean, if someone doesn't know, I remember one time I was at the Comedy Cellar. I was filling in for someone, so they crossed out someone's name and wrote J Train. And it was Mike Lawrence sitting down, and he looks at me, he's like, you going by J Train now? He was so disappointed. Is this your thing? Is this your marketing thing? He was so upset. I was like, No, we’er fucking around. Everyone who says J Train is like smiling and laughing at me while they do it, which I love.

I thought for sure it was a nickname you’d picked up in Needham or at Penn State, but learning that it’s self-given somehow makes it worse.

It was self-given. I didn't have a nickname and you know, I was like, OK, when I am my most cockiest, douchiest, understanding the joke of being that, I would be like, ‘Bring it in for Papa JT,’ you know, Uncle J Train’s here. My whole life, I was like there's no nickname for Jared. It always left me upset, and then bring it back to the Comedy Cellar. I'm at the Village Underground and they have the band. They have the piano player and the drummer on stage with you. And the piano player is Red. And Red is fantastic and has become a friend over the years. Red comes up to me and goes ‘you know, I'm Jared, too,’ and I'm like, what? and he's like, ‘Jared that's why they call me Red.’ It was in plain sight the whole time?! I could have been a musician? I could have been cool! And now I'm stupid J Train so

It makes sense 11 years ago, in 2012, when you're with BroBible doing Dudes Being Dudes With J-Train.

I mean, I was never with them. When I wanted to do stuff on the internet, I would always look to: I'm a comedian who’s looking to put his funnies out to the world and the internet is like, anyone can find you and you know, I'm doing stuff that I would do to make my friends laugh and then all of a sudden you know like people find you, and then BroBible and Total Frat Move and Betches — which you know, again, all of these names, people would like roll their eyes at but it's also stuff that when you’re in their mid 20s, you are eating lunch at work. What are you going to read online? Something to clear my head. Something to put my brain on the shelf, you know?

I guess my only point was J Train makes sense when you're associating with brands like BroBible or Total Frat Move. But the last time I saw you in person, you were co-hosting U Up? live at a packed house at the Palladium Times Square. It somehow seems less fitting there.

I saw you on a podcast five years ago where they were asking you what your dreams in comedy were. And you said you didn't really have any. Mostly that you just wanted to make money doing comedy. So five years later, how much of this is stuff you couldn’t possibly dreamed of happening?

I guess, you know, make money doing comedy. I understand what it sounds like but the goal is doing it, working as a comedian. I think we forget that, as comics, that like you're doing the dream. You get to go on stage every night you make a living doing it. These are not low aspirations but pretty simple, and make something that can feel so complicated and so hard just a little bit more simple. It lets you go, Oh my God, like I'm doing it! Like I get to go and do the new hour in Raleigh this weekend and people are going to come out and I'm feeling fulfilled from being able to put out stuff and people laugh and, again make a living doing that. I think you always have to keep that in mind. Because this is a fun thing. And sometimes I think the people that end up progressing and doing more, they keep in mind: Was this fun? It is a career you want to have forever. Like I want to do this forever. So like with the Netflix special coming out, it's a dream come true to be able to extend my career and keep the ball in the air. And do the next special. You have to do the first one to do the next one. You know, Tom Brady, when they asked him what's his favorite championship, he says the next one. And I think that with stand up. What's my favorite joke? The next one I get to do. The next one I write. That all sounds hokey and cheesy but it is really the way I try to keep my head straight with comedy and stay on task and keep excited about the next thing, and the next show and the next step.

But if you were to go back in time and be able to say something to young Jared in Happy Valley at Penn State and tell him that someday he's going to have a stand-up comedy special that's on a platform that was delivering you DVDs in the mail. And that this coming weekend, you're gonna be hosting a show at the Comedy Cellar, but it's going to be live-streamed into 48 movie theaters across the country. What would Penn State Jared think of this?

I would think it was it goes crazy? In college, I didn't know what I wanted to do. I was having fun with my friends and enjoying college in the way that privileged people get to enjoy college. I'm very privileged. I'm very lucky. That version of Millennial that was told you go to college for the experience, which feels stupid now. You know, but you would say I'm going for the life experience, getting away from home, and I wanted to go to a Big 10 school because I liked football. These all sound as an adult — you go, were you even thinking?! I look back on that and I'm like that was it? But you know, if I was to say like, oh my God, you have a Netflix special. I'd be like well, are they going to mail you a Netflix special? I’d have so many questions, but I guess I'd be proud of myself. If I look ahead, look back, I’d be like really? That’s your job? Like you get to go and travel the country and make jokes? Because I wasn't that person who growing up — actually, my dad and I went and saw George Carlin late in his life. We went and saw Seinfeld together, but it was never like, Oh, my God. You know, I love Seinfeld. I love, this is George Carlin, and you go see him live and you knew this was a big moment. But I wasn't the person who knew this is what they wanted to do this every day since they've been born. My thing was I love being funny for my friends and I love ballbusting with my friends and making them laugh and I was like, alright. How do I do that and make a living doing that?

I was telling you before I hit record about my own family's connections with Massachusetts with Penn State and with the insurance business. Those are three things that most people don't choose naturally. I mean, you obviously don't choose where you're born. You told me why you chose Penn State: party school, Big 10 football. Why was insurance the thought out of the gate? And why New York? You can sell insurance anywhere.

I just wanted to be in New York City, again for the same stupid reasons I went to Penn State. Like, that feels stupid now. I was like, young successful people go to New York. That was my thought.

That’s not what Massholes think. What, Boston’s not good enough for you?

Right. You think you're better than us? It's not good enough for you? I’m from Needham, which is a small town. I wanted to be around other 20-somethings doing stuff. Also my family was always in family businesses. So like I think there was a lot of like, my dad being like, go away, get out of here, you know, get away from family stuff and make your own way. And, you know, I'm very close to my family. I don't know if that's, some comics. I think there's a comic for every background to tell you the truth. I think it's definitely the most first workplace of all, every type does stand-up it seems. I was always close to my family and always liked hanging around them. And I remember telling my dad and mom, I was like, I gotta do this comedy thing. I’ve got to do something. And they were both more supportive than I think I could be. I'm a judgy asshole, and my dad, he was like, and this goes back to like, sounding like someone who's like, I just want to make money doing comedy. I don't really look at it that way. I hope it didn't sound that way. But you know, I think my dad was like, Oh, you're starting a business. And I kind of felt like it was going to grad school at that point. I was selling life insurance. I really wasn't happy. It wasn't for me. I was jealous of the people who liked it, because there are people like doing that job. And then I was like, I'm gonna go create my own curriculum. I went and took sketch writing and improv and I reached out to DC Benny, who is hilarious and a wonderful comic, and I was like, Hey, can we give me some insights, tips? How do I even write a joke? And so that's kind of how it all began. But you know, when I was doing insurance, it was just more of a New York thing. I wanted to be in New York.

Was DC Benny the first person to really kind of mentor you or who really stepped in in the beginning?

DC was coaching me. I was paying him.

Like a personal trainer for comedy

A little bit. You can go take a stand-up class, and I was coming from selling life insurance. I was in a big group of people that were like, go cold call, and all that stuff. I just wanted someone to tell me what the truth was. And I think DC was great for telling me — he always taught me as far as like, do people that sell tickets on the street, do they get taken seriously? What about like a bringer, like what's a bringer? You know, like, when you bring five people and you can do five minutes. So this was like a nice thing — he was like, Yeah, don't do that. Don't do the bringer. They're not going to take you seriously at the club when you eventually want to be at the club and I'm like, oh, OK, that cut through the bullshit a little bit. And you know, Lenny Marcus was always someone that was so nice to me. DC is still a friend. Lenny Marcus has always been a good friend. And then you have the people that you're around. I love the community of comedy.I love hanging out being around other comics and just seeing people who started with me doing great things, too, that's the coolest thing in the world.

Who were some of those people when you started out, who were your first friends?

I met Nimesh Patel at my first ever open mic. That first ever open mic I met Nimesh Patel, which was like crazy to think of, and then and he seemed to like in my mind, Nimesh knew everything. He was like a year in and I'm like, oh, this guy knows at all. I met Michael Che at like The PIT open mic. I met Michelle Wolf really early on at the open mics and, you know, these are people I still bullshit and text with and have fun busting balls with today like I mean Michelle, I ended up opening up for her like 100 dates on the road before she taped her Netflix special and she has been like, Michelle is a friend but also someone I confide in and you know, care about and she you know, there's no one better in stand-up than Michelle. So like, it's cool to be around those people.

What's interesting to me about your journey is you mentioned having mentors like DC Benny to tell you skip the bringer part of the of the growth experience. So that way you're not wasting yours time on that. You also, through Bro Bible and these other brands, you were writing columns, doing podcasts, or finding other avenues for expressing your point of view, expressing your comedy, but you didn't have to compete with like 50 or 500 other open micers for those same three spots at Gotham on a Tuesday.

Yeah, to me, no one was hiring. No one was hitting me on the shoulder, because I think my comedy is broad. I think my comedy is meant to have fun. I'm not looking to go on stage and tell you about my traumatic story because I don't have a traumatic story to tell. And I think those stand-ups stick out earlier, and I think you know, I was building. When you're not getting cast on stuff and you're doing auditions but your packets aren’t getting to the top of the pile for whatever writing job. To me the internet was like the great opportunity. I can go be funny on a stage on the internet and people can come to my little corner and join me there. So again, I don't know if I would have done all that stuff if someone had hired me to do something else. I wouldn't have had the time. But like I loved Bill Simmons, the writer for ESPN. I loved Bill Simmons and he used to come out with columns every Thursday and I would look forward to them. So I was like, OK, I'll copy that. I’ll do an every Thursday thing that maybe someone out there could hypothetically look forward to and then, like I was listening to podcasts. I love talk radio. You know the Boston area Connecticut area, and I listened to WEEI my whole life growing up. I love talk radio. And I started listening to podcasts. I was downloading 15-minute segments of podcasts onto my iPod Nano. So I was like, why don’t I do that? There might be someone like me that wants to listen to me talk about stuff. I saw the internet as an opportunity. Now you see it with the clips and all that stuff, like I've been doing versions of that since day one. It turned into like me yelling at The Bachelor Monday nights. I yell at The Bachelor on my Instagram stories every Monday night and it's my own show. There was a time where it's like, when do you get a show? Well, you gotta get cast as the friend on the sitcom. That wasn't happening for me. I kind of saw that that was going away like to me, being on a sitcom right now to be on, Abbott Elementary? That's as much of the chance of winning the lottery. So I was like, I don't have the confidence to believe I'll be cast on one of those things. So I started doing other stuff. And I was like, you know, the money will come if it's funny, you know? So I started the podcast over a decade ago and then I started, I was always doing that type of stuff and I was lucky enough to kind of do it during the day and do stand-up at night and I think when you do stuff on the internet it can get looked at — the stand-up community a little bit, we're a judging community. They see you doing something on the internet and they're like, you're internet guy. So like that was always tough because I was in the same open mics as everyone else. I was doing the same stand-up rooms as everyone else. You don't want to get a reputation of like internet guy because thata has its own negativity that goes with it, but you can't worry about that. I was just worried about the people who like me, they'll come to shows one day when I'm ready.

When you were starting out doing your version of Bill Simmons, though. Were you able to make money off of that? Or was it more for the exposure to just have people from these other websites being able to tap in to see what you were all about?

I was always like 50 bucks a column or 25 bucks to like freelance because I didn't want to work for them. I wanted to do stand-up. I wanted to do my own thing, so I would barter retweets and Instagram posts. We live in the follower economy and that's more apparent now than it was I was always living in the follower economy when it came to like, and again, and that's why like so I'll have people respond to my Instagram stories: This is so funny. And then they don't follow me I'm like personally offended I'm like, I see it as like, you know, like I do see a little bit of an economy there. So I’ve been doing that since minute one. And then you know, podcasts are getting ads and things like that and those things come along, which is nice.

Looking back, how important was it to be flexible and adapt because you were taking your columns to all these different sites. But also the podcast was evolving. J Train is such a different thing from Dudes Being Dudes, which is such a different thing from U Up? But if you follow it all the way through, you can see a progression.

You can see a human being maturing a little bit.

You didn't start off thinking I'm going to be a dating advice guy and then suddenly that's the thing you might be best known for.

When the dating advice started happening, I was getting emails. In the beginning I gave out my email I was like hey if you have any questions — because I loved the Tony Kornheiser podcast, or radio show back when it was, and he’d take emails at the end. I was like OK, let me copy that. I thought people would write in with funny emails, and they started asking questions. It was because I was going through the same part of life that they might have been going through, and I could speak kind of into this void. You don’t have to look anyone in the eye when you're doing a podcast except the person you're talking to — we can turn off our screens and not have to deal with the judgment of someone. So I think a lot of people started writing in. They heard me speak honestly about things and in a way that wasn't judgmental, and men started writing in. It was always men in the beginning. And they were asked about dating because they were dating, too. And the male emails weren't very interesting. It was like ‘I met a girl in a bar. How do we fuck?’ Like, you know, that was generally the vibe. But then when women started listening to podcasts, I was already like, kind of preparing in the gym of some sort to be a podcaster and then also like taking these questions from men and hearing how they're thinking and then women started listening to podcasts when like the murder genre came up like when Serial started, that's when women started listening to podcasts more and more. And I also introduced the Betches to podcast people to help them get their podcast off the ground. So then they’d be guests on my show. And when women started writing in, the questions were so depthy, so interesting. And then also, I'm who they're asking about. So I had an interesting take because I'm like, Oh, I know exactly what this guy you're dealing with is doing saying feeling. And then over time you get better at saying it in a way that's edible and fun. I'm straight guy talking about dating, like it can be not fun very quickly. You go down a road and wasn't aware not to say I've never said the wrong thing…but again, it's all from an honest place. It's not a gotcha thing. You know, I'm not looking to get anybody I'm not looking to like embarrass someone. Because we're looking at talking about dating in really frank and open way. So over time you kind of evolve and you learn how to do it and honestly, like, I wouldn't have it another way. I love the relationship I have with the audience like it's very familiar you saw it that show. People are there to like, Let's talk this out.

Did Betches reach out to you before or after you had done New Faces?

After New Faces. I did New Faces in Montreal. I’ll never forget it. Betches and I had a relationship before that. But then they were like, we want to start a new podcast about dating from the male female perspective. And then what should we call it? And then we discussed we kind of brainstormed and U Up? became the name and then like November, next year, almost six years ago, this coming November will be the six-year anniversary. So that show. I always knew — I always knew that what I was doing on J Train was for a female audience and an enjoyable show. I knew that the name J Train wasn't exactly inviting to a female audience. And I knew if I could just get in front of an audience that wanted to talk dating that it would do well, and then U Up? comes along and now you're the center of the bullseye. Betches audience, who helped co-produce my special. I thought and when I remember we taped the first episode I'm thinking they’re gonna think I'm the biggest asshole on Earth. Like, I don't want to be. I'm not trying to be me. The response was unbelievable. Minute one. Because they were like, oh, this is an honest conversation about dating in the social media era. You know, this is a real discussion that's going on

It's not like morning radio discussion.

No, this isn't like, gotcha. And men do this, women do this. Even though it's a male female show. It's more like I'll tell you how I emotionally feel about these subjects.

You mentioned how it magically started happening just a few months after you did for Montreal New Faces. I also can't forget it because that was that was not only a stacked lineup, but I went back and looked at what I wrote. And I remember you went up first. It was kind of a rough start of that showcase, which is pressure packed to begin with. You're up first. The opening is rough. The crowds still not warmed up. Your intro was botched.

I remember it like it was yesterday. I'll tell you, I get a little emotional talking about it, because I you know — I never shut the fuck up… So I did New Faces Montreal. Here's my opportunity at first time in the be on stage and shown as a stand-up. Then they're like your first on the lineup. And I'm like, fuck, you know, you don't want to go first but I go it's OK. That's the least of my issues. The host of that night didn't seem to care about it being New Faces in my opinion. Like I think because they were Canadian. And I think when it's an American stand-up who's hosting the new faces, who has done new faces. They know what the new faces are hoping for. That's my opinion of what happened is that it was someone who didn't really care about the show. But when you’re a host. I’ve hosted over 1000s of shows at the Comedy Cellar. Good hosts care about the show going well. And I genuinely, if the show wasn't going well, I felt it was my fault. I think if you host New Faces you have to care that New Faces goes well for these people. You have to give yourself to that. It didn't feel like that was happening. And so then the host, that happens. He brings me up as Jordan Fried or whatever he botches my intro. And I'm like, God damnit, you have six minutes! I don't know if I would have done it differently today as a more seasoned comic, but then like, do your act, you know, be respectful. I'm not gonna like call out the host. Maybe I would have had a different plan today and I wore a suit, because I was just like, I'll wear a suit. Why not?

I'll get on Letterman. I have a suit on.

I don't know! I put on a suit. Looking back, I wouldn't have done that. I would hav been more myself.

Did you have reps?

Yes. So I did have reps, an agent and manager at that time. So I go on stage and I do my thing. I’d say the first two minutes were trying to get people to like not thinki I'm a douchebag I guess I don't know, and then it did OK. In my head, I thought I did OK, but I remember getting off stage and going, that ain't gonna change my life. That set is not going to be it, and I remember going into a stairwell, sitting in the stairwell. Having like a little bit of a moment to breathe. I didn't want to be around the other comics. I’m a realist, you know, I'm not delusional. I don't think every set I do is good. I also knew that nobody was gonna watch that and be like, get im on NBC or get him on Netflix. I just knew it, and I took a few deep breaths and I was like, I do believe in being a mensch. You can't be Mr. Miserable the whole rest of the weekend. I put on a happy face and enjoy the rest of the weekend and had a better second set, which didn't matter. The only one that matters is that first one in the theater.

Just in terms of like who's in the audience, yeah.

Like the second one is like the fun one, and I ended up having a great set that and that doesn't matter. Tree falls in the woods. But I remember, that's a very pivotal moment where I'm like, What am I going to do now? I'm gonna go back to the internet. That was my thinking like, go back to the internet and do your thing that you've been doing and keep growing your audience and you'll get another shot someday and Betches a few months later, was like, let's do U Up? and I didn't think of it as the opportunity it became, because that helped build the audience. And you know, I'm sitting here with a Netflix special coming out and I'm like, I wouldn't do it any other way.

Most New Faces come to Montreal hoping to get a six or seven-figure development deal with a network. Try to base a sitcom around themselves or get that big supporting role. Or at least get Fallon or something or get a writing job on SNL. I know there's people from that class with you who did those things. You had that rough first set. The fun second set that you think didn't count. Yet the year that followed, you started U Up? You did Comics Come Home, the big annual show at Boston Garden that Denis Leary does. And then you did have a Snapchat game show.

Right. So things did happen. It's just everyone has their own road and journey. All I remember is just that feeling after that set of like, you're gonna have to keep going and this isn't gonna be the thing. It's funny you remember like, how rough that beginning was. I was like, damn it. I wanted to walk away just feel like I did everything I could and I was like, maybe I missed an opportunity to have an opportunity. The Tonight Show ended up coming years later, you know. But I will say this about New Faces. Everyone says it isn't what it was, to the point where I don't think it ever what it was.

Right? It's always five years down the road, oh, it's not what it was five years ago.

People have been saying that since the first New Faces, they're like, no, you should have been here before.

When they weren’t even faces.

Right. Right. Right. Pre-Faces, man. Everyone took home a million dollars, you know? But you know what it is? What I've learned and again, with doing a special on Netflix, it takes away will have they done this? It's more of a rubber stamp. So there's no promotions in stand-up comedy, and we have to kind of invent our own. Like getting New Faces, that's a promotion. The way people view you. The way you view yourself. Doing the Comedy Cellar, that’s a promotion. Doing The Tonight Show, promotion. Netflix: promotion. And it's all about, again, to come back to it, I want this to be the rest of my life career, you know?

So are you truly kind of living the dream now, or still?

I’m having the best weeks of my life, pre-special comes out. I get to live here dreaming about what maybe audience can come from it and how people are gonna like it. You know, reality hasn't hit yet. What's better than this, right? This is the week before the trip. Oh, the trip is gonna be amazing! You know, and I'm trying to enjoy that, you know?

Are you going do anything special for the Regal Cinema live stream shows? Your family could go to the movie theater and watch you. This will be your first movie credit, technically.

August 11, 2023

Right. This is technically my first movie credit. Liz at the Cellar sent me a picture what it looks like. It looks unbelievable. It's very cool. I have new material from the special that I've been doing at the Cellar in the last couple of weeks. So I'm happy to have a new set. I'm happy that I can do some new material and I my my big wish for it, and I think the cool part about going to the Comedy Cellar and if you're gonna make people feel like they're in the Comedy Cellar. I hope it's just loose. I hope the audience is loose. I really hope it's this like loose fun thing because that's when the Cellar is at its best when you feel like you're at the ground level of a new bit or the the first few times the comic has said it or something happens in the audience. Because I've done a bunch of those Mint shows and I’ve have had friends text me afterwards and people that follow me text me, DM me and be like, Oh, that was great. You get the DMs about like ah that thing with the audience. And that new thing that you were kind of stumbling through was cool. And people do appreciate it. So I hope we can be loose and fun.

That spontaneity where you realize, oh, this is really just happening at this show.

Right? This is the only place on Earth at this time. That's the fun part of a live show is let's watch the tight-wire act.

Jared, I really appreciate you taking some time with me in this calm before the storm and keeping it loose. I really appreciate it.

This was a blast. It's nice to finally meet you in Zoom world. This is great. I really appreciate you having me on.

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