From Cold Calling to a Hit Netflix Special

How do you go from cold-calling life insurance leads to selling out theaters and landing top-charting Netflix specials? In this episode of Uncorked, comedian and podcaster Jared Freid reveals the relentless hustle behind building his direct-to-consumer entertainment empire. Listeners will learn exactly how to bypass traditional industry gatekeepers, leverage digital media, and turn a risky creative passion into a highly profitable, multifaceted business.

Jared breaks down his unique "mutual fund" approach to his career, explaining how he used early podcasting and viral internet writing to build a massive, loyal audience without ever waiting to be "discovered." He shares the behind-the-scenes reality of self-funding his own stand-up specials, his journey to becoming a leading voice in modern dating with the U Up? podcast, and the hilarious challenges of writing his upcoming book, Walking Red Flag. But what does a successful touring comedian actually do to stay sharp when the cameras are off, and why is he still willingly crashing local, five-person open mics? You'll have to listen to uncover the gritty, unglamorous reality of playing the long game in the comedy industry.

If you enjoyed this highly entertaining masterclass in creative entrepreneurship, be sure to subscribe to Uncorked and leave us a review. Don't forget to check the show notes for links to stream Jared's Netflix specials and to pre-order his highly anticipated new book!

Introduction: From Life Insurance to Comedy Powerhouse

Bill Green:

Welcome to another episode of Uncorked: Wine, Business, and Life with Bill Green. I'm your host, Bill Green, and today we're sitting down with someone who understands the hustle better than almost anyone in business. 

Before he was selling out theaters and landing Netflix specials, he was in the trenches of the New York financial world, spending his days as a life insurance agent making hundreds of cold calls a day. But while he was crunching numbers, he was also building a brand, one funny email at a time. 

Today, he is a comedic powerhouse. From his hit Netflix special, Jared Freid: 37 & Single, to his massive podcast empire with the J-Train podcast and U Up?, he has become the leading voice on the business of modern dating. 

He just wrapped up his global Table for One tour, starred in the 2025 hit 31 Candles, and is gearing up for the release of his highly anticipated first book, Walking Red Flag. He's a very talented comedian, actor, writer, and podcaster. I am proud to introduce today's guest, a savvy entrepreneur who turned his safe career path into a comedic empire. Please welcome Jared Freid.

Jared Freid:

Bill, what an intro. It is so hard. It's great to be here. Thank you for having me. There's nothing more difficult than hearing your own bio. It makes me want to scrunch into a ball and disappear off the planet.

Bill Green:

But it all is true, right?

The Evolution of the Podcast Industry

Jared Freid:

It's all true. It's all there. Other than the life insurance—I made a few cold calls. I didn't do it long enough to feel like I did annuities, the whole deal. I did that when I got out of college, but I've been doing comedy now for 16 years this April.

It's been fun, but I love this. I love seeing people doing podcasting. I've been doing podcasting for 13 years. When I started, it was because I listened to podcasts and I loved them. My dad and I would be in the car listening to talk radio, W.E.E.I., local Boston sports radio. That's what we grew up on. 

I was downloading podcasts a segment at a time between commercials. They were putting out podcasts in 15-minute increments on the podcast part of your iPod Nano. Before I left for work, I'd download the podcast. 

When I started doing comedy, I wanted to start a podcast. As far as entrepreneurship is concerned, it's my direct line to my fans. You can speak directly to them. There is nothing more intimate than podcasting because you are literally inside of someone's body while it's happening. 

Unless you sing during sex, that is the only art form where you are in someone's body physically. It is a pleasure to be here. 13 years in, it's weird to feel like the old dog in the business.

Bill Green:

You started in the early years of podcasting.

Jared Freid:

I thought I was late at the time, too. Honestly, when I did it, people were already saying everyone's got a podcast. People say it now, and you believe it even more because you've been hearing it for a decade. 

What I've learned is that good ideas and doing it right—the way you're doing it, like being prepared—is truly underrated in podcasts. I do a lot of podcasts where I'm hosting their show, which is the worst.

The Path to New York City

Bill Green:

No, this is all good. So you go to Penn State, which—good blue and white. We're Philly guys, so we love Penn State. You get this entry-level job selling insurance in New York.

Jared Freid:

I would say with selling life insurance, the thing I didn't know and you learn is low barriers to entry. I don't even think you need a college degree. I think if you have the licenses, you're pretty good.

Bill Green:

So you one-upped me because I don't have a college degree. But you had this job, and you could see the path down the road. If I close X amount of deals, I'm going to make it. At what point did you say you had no clue, you didn't want to do this, and you just wanted to do stand-up?

Jared Freid:

I've thought about this a lot. It wasn't exactly like that to me. I moved to New York after Penn State. I'm from outside of Boston, a town called Needham. A lot of it sounds stupid now—I hear myself saying it and I'm like, "You idiot." 

I went to Penn State because I wanted a college experience. It was very millennial, very of the times. I wasn't thinking of the degree. I was thinking of a big football school, something I've never seen. I wanted the rah-rah, stupidity in the streets, cheering for a team, and wearing the jersey. 

My parents both went to BU-ish. They weren't college fraternity or sorority people. They were like, "Yeah, go see what that's like." My parents were very encouraging of that mentality. They weren't telling me about the education first; it was go for the experience. 

I was an econ major because it was the only one that didn't need a GPA to get into the business school. It had no GPA requirements so I could get a business degree and be an econ major. That worked out. 

I graduated and wondered where I wanted to go. Well, New York has motivated people and women, so that's where I wanted to be. My dad is the number one guy to push that. He told me, "Don't come to Boston. Get out of here."

Bill Green:

Living through you.

Transitioning from Sales to Stand-Up

Jared Freid:

Living through me for sure. My dad hates New York. He goes there and says, "This place sucks." But he said, "Go, women and motivated people, you'll figure it out." That was the idea. 

I parked myself at this job because of those low barriers to entry. Everywhere I interviewed, I felt stupid. I didn't really have an idea of what that meant. I graduated in '07 and I was sitting at this job figuring it out. 

At first, I thought I'd do this, and some people love selling insurance. There is no shame in that career. It's a valuable career, but it never felt right to me. I felt like I was doing something I wasn't ever going to be good at. 

During the day, I was writing funny emails to friends. Every time someone would email me individually to say, "That was funny, I'm dying at my desk," it felt great. When my dad and I talked on the phone in the morning, it would be about TV from the night before. It wasn't about the markets. 

I just wanted to inject into my veins this feeling I get from someone telling me what I said was funny. I was in New York, and New York is the place to start. Part of the reason I have been successful is I started wide. I just wanted to be funny for money. I told my parents if it's writing greeting cards, that's totally fine. I just wanted to do something. 

I care very much about being good at comedy, which means I formed my own grad school. I signed up for improv at Chicago City Limits and sketch writing at Upright Citizens Brigade. I went to a comedy club, found a comedian, and hired him for personal coaching to teach me about stand-up. 

I took a storytelling class which became very handy. I took a few sessions to figure this out. I had never written a script. I was doing bits with my buddy in my fraternity house. I had no background in this and no one in my life was telling me to be creative.

Family Expectations and Emotional Support

Bill Green:

Where were they? What were they saying?

Jared Freid:

My mom didn't get it. Moms specifically care if they did a good job, and the fastest way to prove that is saying what your kids are doing to another mom. "My son's a doctor." Check. Mom did good. 

My mom was like, "I don't know how to sell this." It wasn't that she was negative, it was more like, "Why would you do this to yourself?" My dad was like, "You have no kids, some savings, and no wife. Do what you want as long as you're motivated." 

I thank them every day for that type of encouragement. They weren't telling me I was hilarious, which is what you should say to someone going into the arts. They have to really want to live it. My dad saw it as now or never. Along the way, my parents saw that I was working hard at something. 

There were small milestones, like being on a bill or working something out. I was always coming back saying, "This has happened and this has happened." Nowadays, 16 years later, if I was coming home with those wins, I'd probably sound a little crazier than I did at 25. 

I'm very lucky. My parents aren't the smartest—Kim, sorry about that one. Bill can't say it because he knows you. He has to see you at Lakeside. But they understood how to push me and what to look for. They looked for motivation, and I feel lucky for that.

The Reality of Being "Discovered"

Bill Green:

Was there a point where you said, "I'm really good at coming up with jokes"?

Jared Freid:

I still don't.

Bill Green:

You could be a comedy writer and not be a stand-up.

Jared Freid:

It's a hard one to explain because everyone says to you, "Would you want to do SNL?" Are you kidding me? My life would be 10 times easier just writing on a show with health insurance and a 401k. 

I'm more realistic than most comedians. That would be the easiest job in the world where someone tells me if I do a good job and I get a raise. There are promotions and recurring income from residuals. But the writer stuff is a little bit of a club. 

My parents are my biggest investors from an entrepreneurial sense. I mean that emotionally and as far as belief is concerned. My cell phone plan? They pay it. That leaves me more time to do work or fewer things to worry about. 

No one really invested in me. There are very few people I can think of that were like, "Jared's the guy." There was no potential seen here. I was never cast in anything. I've been given a lot in life, but in comedy, there's never been a moment where someone said, "I see something in you."

Bill Green:

I've always heard "discovered." No way?

Jared Freid:

If this is being discovered, I'm working too hard. It makes me so angry because I've seen it happen for other people in their own way. Everyone has their lot in life. But for me, I have a very normal story. 

I have no horrific backstory, which a lot of comedians lean on because it makes you immediately interesting. The more different you are, the more interesting you are because you don't have to try to tell people a different story than they've already heard. I'm telling the same story. A lot of people in the audience are just like me.

Bill Green:

A month or so ago, I was walking with my son-in-law, who is in insurance. Very successful. We're walking and he says, "Have you heard about this new comedian? He's really hot right now. He's got a Netflix special. He talks about his parents from Boca." And I go, "No kidding." Tell me how—at what point did you walk out of the office to be a comedian? You probably did some stand-up while you were still working.

Investing in Himself

Jared Freid:

No, just day one. I just gave up. I said, "This is grad school." No one says anything bad about someone going to law school full-time. I understand that this is less guaranteed, but there was no doubt to me this was going to work out. 

I had a guy who was my manager for selling life insurance. He said, "I've got a cousin who does this in New Jersey and he does both." I'm like, I don't want to be your cousin from New Jersey. I want to be the biggest of lives. I'm here to win. I'll take the loss if it's all on me.

Bill Green:

So, Uncorked: Wine, Business, and Life with Bill Green started about wine and quickly pivoted to entrepreneurship and life. I'm sitting here with a glass of wine and Jared tells me he doesn't drink.

Jared Freid:

I haven't drank in a bit.

Bill Green:

So this is the new wine business in a nutshell. The younger folks don't drink. I don't know what's going to happen in my business. We have to get the old people to drink twice as much. Cheers to Jerry and Kim.

Jared Freid:

Cheers. I wish I could share a glass with you. I took a month off and then started seeing how that feels, and that was it. But I go to the Sail Inn down the street. It's the best-looking dive bar right by the bridge.

Bill Green:

It is. I had a company Christmas party there.

Jared Freid:

How great is that place? There's something about the dive bar. I drove by there on the way here. It was 3:30 and the place was packed.

Bill Green:

It's interesting when the younger generation isn't drinking as much, but you guys are all judging us now. Like, the old people are just sitting there drinking and the bar is packed with old people.

Jared Freid:

Not me. I would love nothing better than that first sip when you're sitting in a nice place and having that buzz. That's a fun thing. But for me, I wanted to take a minute and take a breath. The sleep has been the one thing.

Building an Audience Through Digital Content

Bill Green:

So you were writing for Total Frat Move and BroBible.

Jared Freid:

I realized pretty quickly that no one was casting me. So I decided to go direct to consumer. I wanted to build a following on Twitter and Instagram so I didn't have to deal with someone asking for my story. 

I went to these websites that had their own following. I would offer to write an article every Thursday if they promoted it on their socials. I wanted to be promoted as a comedian. 

They would offer $25 to be a contributing writer, but I didn't want their $25. I wanted extra tweets and Instagram posts. There are people today who have been following me since Total Frat Move 15 years ago, which is the greatest thing in the world. 

When I started the J-Train podcast, it was originally the TFM podcast. They were sharing videos I made, and I DM'd them through Twitter. I went to Austin, Texas, for a bachelor party and went to the offices of Total Frat Move to meet their two founders. 

They recognized me from the videos. I told them I wanted to write for them and start a podcast. They asked what a podcast was, and I said, "Perfect." I went back to New York and worked with Stand Up NY comedy club, which was starting a podcast studio. 

They took care of production, I hosted, and TFM promoted it. Over time, podcasts got more popular and they wanted their name back. I took the RSS feed and we went amicably in different directions. That was how my podcasting days started.

Bill Green:

How do you think about the business of Jared Freid? Is it more podcast or is stand-up driving the audience?

Jared Freid:

It all holds hands. I'm a mutual fund. When the pandemic hit, I realized how true that was. A live stand-up show wasn't happening. I had a lot of friends that didn't perform for a year, but I decided to do more internet, more podcasts, and more Instagram. 

I yell at *The Bachelor* on my Instagram stories. That is like my own show every Monday. I went to daily with my podcast instead of once or twice a week. I wanted to be there for people when there was no other entertainment. It's always been about pivoting and figuring it out.

Comedic Influences

Bill Green:

Of all the awesome comedians out there—I love Sebastian Maniscalco. Who inspires you?

Jared Freid:

It's funny because now I get to know some of them. I've opened for some big people and it's always amazing. I didn't grow up with a George Carlin pillow, but my dad and I saw him together. He was more poet than comedian at that point. 

We saw Seinfeld together. I was more a fan of the show. I loved Kevin James: Sweat the Small Stuff. That was one that was physical and funny; the bits still work today. Dave Attell is the best comedian alive. He's the reason New York City comedians are better than anywhere else because he still gets on stage and writes every day. You can't think that highly of yourself if you see him perform. He's the king.

Bill Green:

Take us back to the stand-up. It’s not about money now; it’s about getting out there.

Jared Freid:

You hope to make money, but you have to stay realistic. With any passion pursuit, you have to think about what you spend monthly. I always joked that I'm the fullest starving artist you've ever met. 

Over time, I connected with Betches and introduced them to podcasts. They are a female-owned media company. I was sending them stuff to post to get people to come to "Jared Island." 

I had them on my podcast and they loved it. They asked me to do a dating show from the male-female perspective. I'm the guy and Jordana Abraham is the female side. Now, the U Up? podcast has become its own business.

Experience on a Movie Set

Bill Green:

Let’s talk about 31 Candles.

Jared Freid:

It’s a Jewish rom-com movie. You have to put yourself out there because comedy is embarrassing all the time. You have to try jokes and get feedback. 

A friend of mine invested in the movie and they were looking for a brother-in-law character named Greg. I had never been on a movie set. They pay you very little because it’s an indie movie, but I wanted to see what it was like. 

I went to the premiere with my parents and they didn't shut up the whole time. They were screaming in their seats, talking to everyone. They’re like John Madden and Pat Summerall. 

My mom was narrating every person who went to the bathroom. You can buy it right now—31 Candles. Jonah Feingold wrote and directed it. It’s cool to do it. You have to be curious.

Navigating the Netflix Ecosystem

Bill Green:

Let’s talk about Netflix. That is as entrepreneurial as it gets.

Jared Freid:

I made it myself. I paid to make my own special. I have an agent and a manager, but you have to go out to all the players. Netflix started getting popular and stand-up specials became cheap content for them. 

Early on, they did specials with Iliza Shlesinger, Tom Segura, and Bert Kreischer. I was opening for Michelle Wolf on the road for about 100 shows and I saw how her career went. I wanted the special too. 

I had to tape the material so I could walk away from it and grow as a stand-up. You have to pay to make it good enough that Netflix will put it on their platform. I made it with friends, including Mike Lavin, and people really pushed for me. 

Netflix rented it for two years. Jared Freid: 37 & Single was number one in the U.S. and in Canada for almost a week. I thought that would be enough to get them on board for the next one, but it didn't get where I needed it to go. 

That was a disappointment. I was ready to tape the next one. I had to accept that they weren't going to just buy it, so I paid to make this next one called The Family Plan. 

I taped it in December, and finally, Netflix signed on to put it out. When you see it come out, just turn it on. Turn it on for your dog and let it run so the father algorithm looks kindly upon me. 

I've done this material all over the country, Canada, Europe, and Australia. There are no holes in it. It's about my family and going to the beach. To me, it's like an episode of *Seinfeld*. I'm really proud of it.

Bill Green:

You make fun of life, and that's the kind of comedy I love.

Jared Freid:

I’ve been trying to sell it as "Jewish Sebastian." Italians always say they're just like Jews, but Jews never say that. Same corporation, different division. 

Larry David and Jerry Seinfeld are pretty funny. The Italians always try to latch on to us. We're okay. You've got good food, but how about a good lawyer?

Bill Green:

I’m hearing that this is a different business. You’re an entrepreneur selling your words and your talent. The minute you let down, it’s done.

The Long Game of Comedy

Jared Freid:

Stand-up comics get a bad rap, but people don't understand how much hard work goes into it. The prize is to go on stage. Everything else I do is so I can get to a hot show. 

I just went to Seattle and had a sold-out show for a thousand people. People across the country show up and know your stuff. That's the win. But every day is a puzzle. I can see the end and I know where it’s going, but I don't know how long it will take me to finish the puzzle.

Bill Green:

When do you say you "made it"? Is it a Netflix special? Millions of dollars in the bank?

Jared Freid:

I don't know. I want to be able to go on stage anywhere, anytime. I want to be able to walk into the Comedy Cellar in New York and have them welcome me. 

If you go to New York, go to the McDougal Street Room. Make a reservation. You don't even need a lineup because whoever shows up will be great. My dream is to get on a flight, go to New York, and just go do some new bits for fun. 

I’m going to an open mic here in Delray tonight. People think open mics are for beginners, but I need a place to say stuff out loud to practice. No one cares that I have a Netflix special there. 

I audio record every set. I have to sit through the guy who brought his 10 friends because it's his bucket list item. I’ll show up and do it. Last time, I went second to last and there were only five people left. 

That's more comfortable to me than you would think. When I started, I was doing three open mics a night. You just know when something works for the first time. It's like skydiving. 

Ray Romano is the best. There’s a scene at the end of his special where he’s having pizza with his family after the show. That’s my goal. I want this to be a career that never feels like it's going to be taken away from me. It feels like one false step could lose everything, and I want to be in a position where I’m just having that pizza.

Publishing and Future Goals

Bill Green:

Tell me about the book, Walking Red Flag.

Jared Freid:

Pre-order Walking Red Flag. It’s a dating advice book with funny stories about my dating life. It will make you laugh if you're single and make you reminiscent if you're married. 

It was the hardest thing to do because you have to be so personal. My editor said I didn't need a ghostwriter because I'm a comedian. I spent all night writing the first page, and 20 minutes after I sent it, she told me we needed a ghostwriter. 

I hired Taylor Phillips, who writes for John Oliver. She is an unbelievable writer. I would send her answers to questions over email and tell her stories, and she made it legible. 

Even my mom said it was funny. It comes out in June, but you can pre-order it now. If it does well in pre-order, I might be on the New York Times bestseller list. When I told my dad that, he just scoffed.

Bill Green:

Wasn't that motivational?

Jared Freid:

Well, now I'm telling you the story! I had a book come out in 2017 and I sold a thousand on pre-order. I’m working on a second book now and it’s hard. Are you doing the Audible, too?

Jared Freid:

I'll read the Audible. With a podcast, people are used to my voice.

Bill Green:

I made a mistake with my business book and hired someone else to do the Audible. It has to be your voice.

Jared Freid:

It’s a piece of you.

Bill Green:

If you go out tonight and those new jokes at the open mic land well, how do you celebrate if you don't drink?

Jared Freid:

I started having non-alcoholic beer. But usually, I just go home. I’ll leave a show and wonder if a joke did okay. I'm a boring loser.

Bill Green:

You’re awesome.

Jared Freid:

Thank you. This is awesome. My dad is definitely watching on YouTube and he’ll come back with notes. He argues with me after listening to the podcast. I’ll definitely get a review from him for this show.

Bill Green:

Folks, this has been awesome having Jared Freid. Till next time, Uncorked: Wine, Business, and Life with Bill Green. Have a great day.