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Becoming A Top 100 Comedy Podcaster With Jared Freid

Performing alongside Jim Gaffigan and Dennis Leary at The Boston Garden would be a massive accomplishment for any comedian. For Jared Freid, it felt like a bar mitzvah. It was clearly a new milestone in his life, but it was also just one night – a fleeting moment that would mean nothing without continued focus and dedication to his craft.

Since leaving his job in insurance to pursue comedy full time Jared has treated his career like a business, constantly putting out new content while building relationships and forging partnerships that would lead to new opportunities like his iTunes Top 100 JTrain Podcast, a show about modern dating called U Up, a SnapChat show called How Low Will You Go that lets him travel the country attending college football games, massive sold out live performances and more.

In our live recording event (full video below) we breakdown the process that has lead to Jared being featured on NBC’s The Today Show, MTV, his live recordings at the Comedy Cellar and more. We also discuss how Jared first started his career as a comic writing weekly columns for major online publications, and how he continues to stay motivated by focusing on small realistic goals.

You can find Jared on Instagram at @JaredFreid, and on Twitter @JTrain56. He releases new episodes of the JTrain podcast every Tuesday and Friday and his tour dates can be found on jaredfreid.com

Show Notes

2:30 Jared starts off saying how he’s not sure about giving advice since he’s not yet where he wants to be with his career.

3:00 We think Jared has a lot to share, given the success of his podcast with over 400k monthly downloads, and the ascent of his comedy career having performed alongside Jimmy Fallon, Jim Gaffigan and other top names in comedy.

4:40 Jared is also from Massachusetts. Went to Needham high then Penn State. He moved to New York to just get a job. Didn’t know what he wanted to do at that point. Just wanted to live and have fun in the city.

5:00 Was selling life insurance, and best part of his day was writing funny emails to his friends.

5:20 Would get people to reply saying it’s funny and think, oh that’s a drug I want more of

5:36 Telling people you want to do comedy is kind of offensive to people. Like you think you’re funnier than me.

6:00 It’s like starting with any business, everyone’s going to think you’re stupid until you’re not

6:34 Started doing everything he could. Take classes at UCB, Chicago City Limits. Went to comedy clubs and reached out to established comedians to get advice. Was looking for his own mentors because he had never had that before.

6:55 Wanted to learn from successful comics, not take classes from people who weren’t comics.

7:24 Clubs have a concept called “bringers.” If you bring 5 people you can do a 5 minute set. He didn’t want to do that because then he wouldn’t actually know if he’s improving as a comic. People can be bringers for their whole career and not get anywhere.

7:43 Sergei: You did something many entrepreneurs do which is reach out to people who have done it before instead to learn from them, instead of just learning from your own mistakes. That ability to reach out, where did come from?

8:00 Jared was selling life insurance making 100 calls a day to make 5 appointments, so that wasn’t hard for him. He was used to failure.

8:30 What helped is he went into it knowing nothing, and being open to learning. And not telling people what he was going to do. Just doing it.

9:30 He started just wanting to be better at it and had short term goals.

10:48 Performing alongside Jim Gaffigan etc. was like my bar mitzvah

10:52 Vadim: How did you get to perform alongside Jimmy Fallon and the like.

10:52 Jared knew the organizers of the show. Comics Come Home.

11:29 With social media you have to share the message that you’re performing with these people, but the reality is that Jared doesn’t know Jimmy Fallon personally. But you have to talk yourself up to convince people you can do the job.

12:08 What do you say to someone who is not comfortable being self promotional in this way? Because after all you do have to be self promotional to get anywhere.

12:12 Jared: You can either get over it or just have nothing.

12:30 For Jared, if he’s being self promotional he also has to be funny or else people will hate him.

13:03 Even when he puts out screenshots of tweets on Insta, he gets hate for it, but they do the best. He gets 500 new followers per week from that. That’s more people who could like the podcast.

14:00 Everyone embellishes their successes. You kind of have to do it.

14:03 Jared thinks you can be upfront sometimes about the fact that you’re being self promotional. That way your audience trusts you. He admits that he makes things look better online to his fans.

14:50 Jared focuses on short term goals because he has learned that from others. Bill Burr says a new minute of material per week is a 52 minute special by the end of the year.

15:43 He mentions another podcast, Betches, where he learned a video posting strategy they use and started implementing it for himself.

16:53 Jared started writing for Total Frat Move, an online publication, to get his name out there. He chose websites that had audiences he thought would like his comedy, and wrote for them in exchange for retweets and mentions on social media.

17:50 He would use “click baitey” articles and then be honest with his readers whether something would work or not.

18:40 We ask Jared how he got his writing gigs.

19:00 He did it by asking to meet with people over coffee for advice.

19:56 He then made a video at Comic Con acting like a frat bro, which got picked up by BroBible blog. He then asked them to do a column every Thursday in exchange for a certain amount of Retweets.

20:34 Through his work at BroBible he was noticed by Total Frat Move and actually reached out to them when he was in Austin and asked to write for them.

21:11 His main goal was to get in front of these audiences through writing.

21:22 After working with Total Frat Move for a while he asked them if he could host a podcast for them. They didn’t even really know what a podcast was at that point, and they agreed to promote it if he hosted and produced it.

22:00 He found a producer in New York called Stand Up NY Labs and they all split it three ways.

23:00 He had tried doing a podcast with Bro Bible before that but no one was truly behind it so it didn’t get anywhere.

23:49 A few years later Total Frat Move decided they wanted to have their own podcast and go in a new direction. They agreed to keep the name and let Jared take the audience that he worked to build up over the years. That’s how he went off on his own and changed it to the JTrain podcast.

24:40 The format of the show evolved overtime where they started asking people to send in emails and listeners started organically asking for advice. Pretty soon Jared was getting 50 questions per week that he could answer on the podcast.

25:30 Sergei asks what Jared did in the beginning to make sure that Total Frat Move would actually promote the podcast.

25:48 Jared was up front with them. He said if they were going to put out a podcast we need to push it to your Twitter audience. He had to constantly push, which is probably why eventually they decided to do their own show.

26:36 When Jared was in sales he learned how to be “Pleasantly Persistent”

27:00 Vadim mentions how we always recommend people get a job in sales even for a year or two just to build up the persistence skill, and learn to face rejection.

27:44 Vadim acknowledges that Jared isn’t simply having fun performing. He’s doing a ton of work writing, and constantly marketing his work.

27:58 Jared says that the tough part is that as a standup comedian you’re not making any money for a long time, if ever.

28:21 So many comics have podcasts now.

29:12 Jared also started a dating podcast with Betches, which has a big Instagram following, a year ago called You Up. That has taken off even faster than JTrain.

30:40 While JTrain grew quickly it first, it plateaued because guys don’t really want dating advice. But once Jared started going on female focused podcasts, he grew his audience even more.

31:47 Jared learned that the best way to grow your podcast audience is by going on other podcasts because you have to go where the listeners are. It’s not easy to get in front of people via any other medium.

31:58 He also thinks that once it becomes very easy to listen to podcasts in your car, we’ll see an even bigger wave of adoption.

32:39 Sergei asks what Jared’s process was to actually get on other people’s shows.

32:42 Jared would offer for people to go on his show first and show them a really good time before he asked to be on their show.

34:06 Jared also took a personal approach to this. He found that it’s really relationship based. Getting referrals, meeting people in person etc. Sending emails wouldn’t really work. That’s how we got Jared on our podcast, by first meeting him and getting to know him and then asking him to go on.

35:19 Jared now has publicists reaching out him to book comedians on his show, but he never puts people on this way. On the other hand, if he gets referred to someone who he really finds funny, he’ll invite them to be on his show himself, unprompted. He also often gets past guests recommend new people.

38:00 Jared says that podcasts are one of the most intimate forms of entertainment. The podcasts that do well give you exactly what you expect they’ll give you in terms of value.

38:59 The Mentors ask Jared how he quit his job and financed his comedy and podcast career.

39:01 He started off with savings and now he makes money through the podcast and through ticket sales.

39:50 Live podcasting seems to be blowing up now. Pod Save America just sold out Radio City Hall.

40:37 Jared has been doing live podcast recordings at the Comedy Cellar for a few years. Initially he started off just doing his show live and saw that it wasn’t great, so he changed formats.

40:47 They now do stuff like Bumble, Tinder makeovers in online dating live on screen in front of the audience, and bring people on stage to discuss. That seems to add a lot of energy to the show.

41:20 They do other bits like showing people’s text conversations to show what happened.

42:04 Jared is also doing a game show on SnapChat called How Low Will You Go where he travels to college football games all over the country.

42:47 Comedy is a million jobs that makes up one job

43:11 Vadim mentions that what Jared does to try new shows and to adapt content to work for different formats is part of the creative process. It’s why he keeps growing his audience, because he’s constantly improving.

43:20 You have to be brutally honest with yourself about the quality of your work. You also have to be consistent with a podcast. Your audience will start depending on your show to come out on a regular basis.

44:00 The show also has to move in a consistent way every time. The audience needs to know what to expect from you.

45:28 Jared talks about how the concept for #FeatherNation came about. Listen to hear what feathering is.

47:44 Jared says that you have a space to be creative and try new things, and it’s ok if you fail. But you have to keep trying.

48:36 The Mentors ask Jared at what point this started to feel like a real career to him.

48:42 Jared wants more. He wants to do more standup and the podcast to be bigger. It weighs on you when new people come into your space every day. But he thinks it’s good if you have a little fear motivating you.

49:49 The Mentors ask what keeps Jared pushing through, since he’s been doing comedy now for 8 years. He keeps pushing. What would he tell someone in their first year of comedy or podcasting?

50:13 Jared thinks you have to have small goals that maybe other people would find unimpressive, but that you can achieve.

51:01 Jared’s goal for the first two years is just to have one live show he did and make it the best show it could be that his friends at least would love.

51:45 Little things lead to big things. But you also have to be a little delusional. Jared probably wouldn’t do some of the things he did before to get noticed, like drive somewhere to do free show, but he did go through it early on.

52:16 Sergei mentioned that Jared must have seen positive reinforcement from his audience to keep going.

52:21 Small wins have been big for Jared. No one is going to push him to do more standup. “We don’t need another white dude doing standup”

53:35 Jared sees comedy as a selfish pursuit. He does it because he loves it.

54:33 Sergei asks what the next big goal is that he’s trying to achieve?

54:45 He doesn’t really know. He takes it one day at a time. Jared wants to just continue living off of doing comedy. If it gets bigger than that, that’s great.

56:00 Garrett asks how someone just starting off in their career can offer value to others when they have nothing to offer yet?

56:54 Jared says for a podcast, if you have a well thought out and well produced show, having them go on your show can be enough value in and of itself.

58:24 In comedy, if you’re hustling people think you’re not funny. You just need to hang out in the community and try to be funny.

59:27 Sergei adds that everyone has something to offer. Jared started off writing as a way to add value, you could offer to make an introduction to someone useful to them in your network, you can offer some industry insight that’s valuable to someone by doing some research for someone. There’s always some way to add value.

1:00 FYI You can find Jared on Instagram at @JaredFried, and on Twitter @JTrain56. He releases new episodes of the JTrain podcast every Tuesday and Friday.

1:00:40 Cho Cho asks if Jared has any bigger dreams.

1:00:50 Jared thinks the You Up podcast could make a great TV show and he would love something like a Netflix special. He would love for that to happen, but he doesn’t get hung up on these materialistic dreams that will never satisfy him.

1:01:27 Jared mentions that he has given a lot of his life to stand up and he’s not going to stop. While his friends were getting girlfriends he was doing open mics. Some comics get famous overnight, but he’s not banking on that.

1:04:00 Barry asks for people starting a podcast how to engage people when you’re just starting off, in particular in early childhood education.

1:05:49 Jared says that segments worked really well for him to get people engaged.

1:06:28 With that topic you could also partner with online groups like Mom blogs to get the show out there.

1:07:32 Jared also makes time stamps of every episode so people can scan it and go where they want to in the podcasts.

1:08:26 Your audience needs to see your podcast and think, oh that’s my life. That’s relevant to me.

1:09:40 Emily asks how do you strike the balance of being off the cuff and properly planned.

1:10:10 Jared says that making sure the topics that he’s bringing up at least interest him. If he is bored by a topic and not enthusiastic about it, that shows.

1:10:40 If you’re going to start a podcast, it has to be something that interests you because you’re going to be talking about this topic every week.

1:11:40 Jared’s parting words of wisdom are that it’s ok to not know what you love right away. It can take time to figure it out. It took Jared years to figure out that he loved comedy.

1:13:19 Go to JaredFreid.com and subscribe to JTrain Podcast and You Up Podcast.

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