Name: Caleb Pressley on Leaving Barstool, and How They Make "Sundae Conversations"
Uploaded: 2025-05-20T17:44:24.000Z
Description: Watch the stand-up comedy video 'Caleb Pressley on Leaving Barstool, and How They Make "Sundae Conversations"' from Theo Von Clips on Comedy Buff. Published 2025-05-20. Transcript available.

Watch the stand-up comedy video 'Caleb Pressley on Leaving Barstool, and How They Make "Sundae Conversations"' from Theo Von Clips on Comedy Buff. Published 2025-05-20. Transcript available.

Caleb Presley what's going on man Sunday conversation we just got to do it dude
thank you for having me back
It's your own show now so you guys are free from Barstool
Yep my contract ran out the end of last year so January 1 me Glenny Balls came
with me
And then I have a producer Kelsey and then
Editor and shooter Tom so that's they're my little company
And then we have like the same freelance people that we always work with
So we really have like a team of seven that's kind of like our little our
little squad
Yeah it was good man I felt like it was the same everything was felt exactly
kind of the same
We did an exact same location in chairs oh that's true yeah it was good
Yeah that was fun dude and you guys just did who else have you done recently
Did you have some episodes you've done that aren't going to come out haven't
come out yet
We just did Morgan Wallen I don't know when this comes out but we did Morgan
yesterday
That'll come out this weekend so I don't know if this is coming out
So that'll already be out then because it's coming out I think next week maybe
We just did Luca
Oh Luca huh
Yeah bounce from the playoffs right after
Oh he did huh
Yeah
What do you feel like how they did Luca
Bad
But dude he's still making I mean it's hard to feel bad for someone who's
making
Whatever 97 million dollars the next two years but I think he lost out like 116
million
And in his country or whatever
That's crazy I think it's like
You could buy every you could buy a mountain or something
Yeah you'd never have to go back with that amount
You'd never have to see Slovenia again with 116 million bucks
Free at last
Free at last
Oh yeah dude that's what's up bro
No it's been good
I've enjoyed
It's kind of the same thing I was doing when I was at Barstle I mean it's
pretty much exactly the same thing
Just doing Sunday Conversation plus I'm like
I did Drewski's show which was fun
Just like one-off kind of collaboration
Oh yeah
Just running this company is not I wouldn't say it's hard and I do enjoy it
I wouldn't say it's easy or hard but it's time consuming
Yeah
So I've been working I wouldn't say really hard I would say really often
Really often
Really often
Figuring out how to like just organize like basic stuff that I just have no
clue what I'm doing
Yeah
And probably making a lot of mistakes and stuff like that but
Oh
Do you I mean do you handle that kind of stuff for your business?
I mean you have a you run a business
Yeah I mean a lot of stuff you have to do yourself I think because you are you
want it a certain way
It's like Drewski it's like you kind of know how things need to be
So it's like
Which is tough because I do that for Sunday but by Sunday it's like three
minutes long
Yeah
This is two hours
Yeah I just want to and I like to be reminded of what goes on
I like to sometimes I'll look back and feel like how could I maybe have done
things a little bit different
I think you always just want to do a little bit better I think right
And then you're like well how are things evolving like in podcasting or
whatever job you're in
So you want to try to be like on the future of it a little bit
A hundred percent
So but yeah I think you have yeah it's like I think when you work for yourself
or work with people in a small group you
You have to you have to stay pretty hands-on like if you started letting
somebody else edit your episodes
It's impossible
It's impossible
I have an editor Tom who's great but we've worked together for so many years
now and we correspond
I mean we go through notes and notes and it's a huge process and even he if he
was left to his own devices
He would do a great job on the episode it would be great
Maybe people wouldn't even know but I would to me
It's like I would there's certain things I just like him the way I like him
And he's great because he's like
He doesn't have an ego I feel like a lot of
Everyone has egos I mean he's just like a nice
Gym of a person but
When you're corresponding in on some creative and I'm giving notes do this do
this
It would be really easy to be offended if you're he's a very creative guy
Right you know so it's like if you're a creative person you have your own ideas
of how you want things done
And he has his own ideas he can provide those but then he also doesn't get butthurt
if I'm saying
I don't think that's good
Yeah
Which is I think it's such a rare find
Oh I think you're right and I think also a big thing is that editors I mean let's
give a round of applause for editors
Yes
They are
Because people are just yelling at them
Yep
No one appreciates like the long snappers of media
Oh yeah
Oh if you saw an editor across the street and you were walking by
He'd be like oh look at this desperate
Then you just get into your car and go home to your husband
No as they are they are
They're the icebergs of our planet really
They're out there by themselves
And yeah they're involved with cold water but nobody thinks about them like
that
Everybody thinks like they're about to sink a ship
Think about that being iceberg
The only thing they're known for basically is every now and then like
Somebody sees a polar bear on one of them
But really the thing they're known for most is sinking that boat
Isn't that crazy?
The one thing that can be your whole life can get into one thing one moment
Could you cut together a bonus episode of Sunday out of this you think?
Yeah easily
Not easily it'd be fucking really hard
But that's what's amazing about your show
You go in there, you sit in there
A couple things come up, you accuse people of something
You make a face or two
You don't know if you have Bell's palsy or if you're asking a question
And then you send me home
You send somebody home
I know
Every time you wrap up everyone's like
Yeah
Because I don't shoot it like this
I don't shoot it like a free-flowing conversation
Because I know how it's going to edit
So I just like that's a waste of time to even do all those
Segways and middlemen parts of the conversation
I skip right to the meat
Yeah
It's a very awkward conversation
Oh it's a good point
You do skip right to the meat dude
Because now that you're doing your own thing
Do you feel like you're more capable to do something new?
Like tell me about something like branching out on your own
Like the fears of it and stuff like that
And did you think it would be okay?
Did you think it would fail?
Like do you have any real fears about it?
Because I think a lot of people work with somebody
Or under an umbrella
And then they go out and do their own thing
Yeah
I think
Well the thing that was how Barstool was set up
Was Dave is very hands-off
So he doesn't tell you what you should be doing
When you start doing what you're doing
He doesn't talk to you
You really just go complete non-communication with him
100% of the time
What that culture breeds I think
Is like a kind of entrepreneurial spirit I guess
The people who are successful there at Barstool
Because you have to be
And they have the resources
Obviously they're taking the risk on you
By paying your salary
Because they're going to pay you if your content sucks
Or if your brand loses the brand deal
Or whatever
Like every two weeks you're getting paid
So they're taking that chance
And obviously if you do well
They have the upside
Facts
But it's really
It's a place where I was able to
They gave me the resources
But I was able to kind of build out
I started working with Tom
Who's my editor
And we worked together for years
Developed a camaraderie
Of my producer Kelsey
Who you've met
Like we started working together
Developed camaraderie
So we had to make my own little business
Inside of Barstool
So going out and doing my own thing
Really was pretty much exactly the same
Because I already had my business
Inside of Barstool
Inside of the bigger business
Oh yeah
But I would like to do some other stuff
Outside of Sunday conversation
I don't know what
I mean how was your movie experience
I've heard that
It's kind of boring shooting a movie
Oh yeah
It's boring
I like the revolutions I can do on Sunday
I can put out one Sunday a week
It's a lot of work to get out once a week
But we can do it
And then it's like
You move on to the next thing
If you had a stinker
You can still move on
And have a good one the next week
Yeah
And things happen so fast now too
Yeah
How I even consume
How everyone consumes content
Is like
It's so fast
It's like
You know in the first couple seconds
Do I want to keep watching this or not
And sometimes it's interesting
It's like
Something will just pique your interest
And sometimes
It can be the same thing on the next day
And it will not pique your interest
But then two days later
It'll pique your interest again
Yeah
I think it's very fascinating
And I'm sure there's a lot of like coding
As to how they're figuring that out
And they just keep hooking you
Or finding different ways to hook you