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00:00Who was your most exciting, weirdest, craziest celebrity collab?
00:04You know, I think it is this girl named Haley. Have you met her?
00:06No, she's horrible.
00:07She's got red hair.
00:08She's awful.
00:09She's got a big window.
00:10She lives in the West Village.
00:11Yeah, she always is like making an egg for me.
00:22What's up, Haley?
00:23Hi, what's up?
00:24Nice to see you again.
00:25Hi, I know you. I'm Haley.
00:26I'm Caleb.
00:27Nice to meet you, Caleb.
00:28Pleasure.
00:30So how did you get into your content journey?
00:32How did I get into my content journey?
00:34Yes.
00:36I picked up a camera when I moved to New York City about nine years ago.
00:39Started making YouTube videos, helping Instagrammers.
00:42I guess there was no TikTokers at that time.
00:44Okay.
00:45There was music clears. Maybe there was Facebookers, right?
00:48There's probably, there's still Facebookers, right?
00:50Yeah, yeah, there's still Facebookers. Guilty.
00:52Oh, you're a Facebooker now.
00:54I need to get out my Facebook game. Oops.
00:56Yeah, and I just helped a lot of people.
00:58Ran around the city doing photos.
01:00And I worked in the music industry for a bit.
01:02Okay.
01:03Kind of like Max.
01:04Are we allowed to mention Max right now?
01:06You mean my friend Max?
01:07Yeah, yeah, your friend Max.
01:08We're not allowed to mention Max.
01:10He'd be really happy about that shout out.
01:11Okay, shout out to Max.
01:13Music industry, you know, and then TikTok rolled around and that's all she wrote.
01:17Well, then wait, when did you get into touring people's apartments?
01:20Oh my God.
01:21You know, when I tracked you down and I was like,
01:23Haley, can I go into your home?
01:25Yes.
01:25It was around that time.
01:27So you started around the time I started.
01:29Exactly.
01:30So we started together because you almost started my channel.
01:34I know, I know. Double high five. Yes.
01:37Wait, is this why they paired us for this together?
01:39I think so.
01:39I think so.
01:40I think so.
01:41Because I got started with your apartment tour.
01:46So I was already doing TikTok, but I wasn't doing YouTube.
01:49I wasn't really doing Instagram.
01:50I was working as a model.
01:51I had had enough.
01:52It was bad for my mental health.
01:54And I was going to move home to Minnesota to go back to medicine.
01:57And then you found me and were like,
01:59Hey, can I tour your apartment?
02:01And I said, yeah, let's do this.
02:03I hope he doesn't murder me.
02:04And then you toured my apartment.
02:06I think we got, what, 60 million in the first day on that video?
02:09Yeah, it was absurd.
02:10It was like two hours in, it said 40 million views.
02:12And I was like, what's happening?
02:13I remember watching the numbers because I never, I watched TikTok,
02:16but I didn't really like look at numbers.
02:19I didn't know what was good.
02:19Like I thought 20,000 views was insane.
02:22So then when I saw yours hit 40 million, I was like, wait a second.
02:27That means 40 million people might be looking at my page.
02:30And then that's when I started posting comedy videos.
02:32And then that is literally the day that I started my YouTube channel.
02:35Yeah, I remember.
02:37That's crazy.
02:38Yeah, I know.
02:38And that was like a year and a half ago.
02:40Do I need to give you 10% of my career?
02:42No, not at all.
02:43Oh, thank God.
02:43Beautiful.
02:44Let's shake on that.
02:45Did the cameras get that?
02:46Amazing.
02:46Yeah.
02:46I'll use that in court if you ever ask me.
02:48You know what I was thinking, actually?
02:50Right before I started the apartment tour series, I got fired from my job.
02:55And you did?
02:56And I had like basically like a month's worth of severance.
03:00And I was like, I have to make this work in 30 days or I'm going to be fucked.
03:04Wait, when?
03:04Okay.
03:05You were working in what industry before you started doing the apartment tour?
03:10I was building a startup in the media space.
03:12And I was doing like all the photography, videography, all that stuff,
03:16all their social media stuff.
03:17Then they let me go.
03:18And I was like, oh man.
03:20I had like 4 million followers on TikTok at that time.
03:22Okay.
03:23Okay.
03:24But I had a niche.
03:26I didn't have like my thing though.
03:28So you were just floating?
03:29I was floating in the ether.
03:30I was like just around, you know, like.
03:33What made you think of it?
03:34Like, were you like, dang, I really wish I could see the inside of people's apartments.
03:40Yeah.
03:40It's like, you know, when you're in New York, you always look up and think that question.
03:43And then I did a bunch of research.
03:45I was thinking, oh, who's doing this?
03:47I was like looking at Architectural Digest.
03:49MTV Cribs isn't there anymore.
03:50And no one was doing it on YouTube.
03:52I was like, wait, this might be a great idea.
03:54Which is crazy to me because when you started doing it,
03:57I remember following you on TikTok and thinking, this is genius.
04:00Like, how has nobody done this yet?
04:02I've seen you make some videos with some very notable people.
04:06What? Me? No, no.
04:07Yeah.
04:08Who's some of the, well, what's the one of the wildest experience you've had?
04:11Oh man.
04:12With some of them.
04:13Wildest?
04:14I don't know because I'm usually the one being wild in the videos.
04:17I'm running up on them on like a carpet somewhere asking them some crazy question.
04:22So many celebrities are really wonderful, truly.
04:24Like people come up to me all the time and ask, are there any mean people?
04:28Is there anyone who didn't treat you well?
04:30I have been so lucky.
04:31Every celebrity that I've worked with has been nothing but wonderful.
04:34I love Michael Buble so much.
04:36He is like one of the funniest people I've ever met.
04:39Came out of left field for me because like I've always liked Michael Buble.
04:42But I had no idea how like unhinged and funny.
04:45He's like a stand-up comedian.
04:46When he came over with Jason Derulo, he was just cracking jokes the entire time.
04:49And I was like, this man in another life was definitely a comedian.
04:53Who was your most exciting, weirdest, craziest celebrity collab?
04:57Because I know you do just as many, if not more than I do.
05:00It always has to go back to Barbara Corcoran.
05:02Because when I was first starting this series,
05:04like two months in, she DM'd me and told me to come over.
05:07And I was like, what is going on?
05:09And that was like a cosign.
05:10It was like the tipping point for everything.
05:12So from that moment on, it was like so many other people that I got to make videos with.
05:17So you think that that...
05:18Because it is true.
05:19In content, there's almost like somebody that opens the door for celebrity collaborations.
05:24Because celebrities need to know that you're somebody they can trust.
05:26Or that they can feel safe with your concepts.
05:29Or that you're not going to post anything that makes them look bad.
05:31Totally.
05:32Do you think Barbara was that for you?
05:33Totally.
05:34Totally the tipping point.
05:35You know, a more funny one.
05:37I went to Dwight Howard's house, the NBA player.
05:39That is so cool.
05:40And I was editing his video.
05:42And I took an edible that I thought was just mushrooms.
05:46But there was a weed in it.
05:47Yeah.
05:48Wait, wait, wait.
05:49But I have something.
05:50I have something here.
05:51And I'm like editing the video.
05:52And I start like freaking out.
05:54And I'm thinking, why do these people trust me with their brand image?
05:58This is insane.
05:59Like he didn't even want me to send it to him.
06:02He just is like, yeah, just post it.
06:04And I was like, why do these celebs just...
06:06Why are they okay with this?
06:06Yeah, I wouldn't trust you either.
06:07And then the amount of, you know, just like trust they give us.
06:10Because I want to make everyone look as good as possible.
06:12Oh, of course.
06:13Yeah.
06:13As you do too.
06:14So I think we just built that reputation up, you know.
06:17I think for me, Courtney Cox was like my first big celebrity collab
06:22that was able to get me Jared Leto.
06:25So I worked with Courtney in LA.
06:27And then once that video was posted,
06:28because she hasn't worked with a lot of content creators or influencers,
06:31celebrities just kind of started reaching out.
06:34I think because she's such a like staple in Hollywood of like
06:38this comedic presence because of friends,
06:40that people are like, oh, if Courtney signs off,
06:42then I trust her.
06:43And then Jared Leto was next with the Met Gala costume.
06:46Yep.
06:46And then it was just craziness from there.
06:49I know.
06:50I feel so lucky.
06:51It is.
06:51Me too.
06:52Go us.
06:53You have been in the creator space or playing around in the creator space for,
06:58I think, as long as you've lived in New York, maybe?
07:01Or...
07:01Yeah.
07:02Nine-ish years?
07:04What is the one thing that you wish you would have known prior to starting?
07:08You have to do everything.
07:10Yeah.
07:10You really, and you have to know everything,
07:12like every piece of the puzzle, which you know,
07:14like each and every platform, the nuances of them,
07:18how to, I don't know, just play in all the realms.
07:22And it's not, it's not just like, I'm a YouTuber, you know?
07:26There's so many like nuances and details that everyone thinks you just go
07:30and you just make a video and that's kind of it.
07:32And it's honestly, that's the best part.
07:35The best part is being able to like play for 30 minutes
07:37and then the rest of it's like this intense amount of work.
07:40I wish I knew that in our career,
07:44you are a normal person creating for normal people.
07:46And there's something really inspiring about that.
07:49Like I love watching movies.
07:50I love watching TV shows.
07:51But there's something that hits different about like a person that directs,
07:55produces, writes like their own little comedy sketch,
07:57films it on their phone, in their house,
07:59and then puts it out on a platform just to reach other people
08:02chilling in their house or like chilling at work.
08:04And it's just really, really fun like to create for people
08:07that are like your friends or your family,
08:09or just like the people that live by you in New York,
08:12the people's apartments you walk into.
08:14I wish I wouldn't have thought of it in such a serious way
08:17and I would have had more fun with it in the beginning.
08:19You have switched mediums within content creation,
08:23I think multiple times.
08:25Like you said, you were working at a startup,
08:26but in media, taking photos and website.
08:30What did you do before that?
08:31And how did you transition through like all of these periods of your life?
08:34I taught tennis.
08:36You taught tennis?
08:37That's how it started?
08:38I was a tennis instructor, yeah.
08:40Really?
08:40And I was like making little comedy videos here in New York,
08:43just like when I was waiting on clients.
08:44Yeah.
08:46I've done so many different things.
08:48Like I did photography...
08:51Words.
08:53Words.
08:54Photography tutorials, you know.
08:56Photography tutorials.
08:58I've seen a couple.
08:58I was teaching people how to, I don't know, work a camera.
09:02And did some sketch comedy.
09:04I was just trying to figure it out.
09:05I've reinvented myself a lot of times.
09:07Testing the waters.
09:08Yeah, I mean, I really think the new mediums is the most exciting part
09:13because you're always wanting to reinvent yourself and challenge yourself
09:15and see how you can get better and improve.
09:17Right now, it's more of improv.
09:19I've been doing a ton of improv.
09:21Congratulations.
09:22Yeah, yeah.
09:22The comedy world likes hearing those things.
09:24Totally, totally.
09:26And that's just like a new medium I'm not even sharing online,
09:29but I'm like going to all these classes and doing shows.
09:32I might rope you into doing some improv with me.
09:34Oh, there we go.
09:35She's never going to come over and do improv, but I'm going to try.
09:38When I go by your house, I always call you.
09:40You do, but I'm never home.
09:42I know.
09:42You are never home.
09:43Or I'm wrapped up like a baby in my bed.
09:45But I think the key with the new mediums is you shouldn't be afraid to go and try it
09:50and just fail, just fail, fail, fail, fail, fail,
09:52and just fall on your face and look dumb and then have a laugh.
09:56And then reinvent yourself, get back up and try all over again.
09:58Yeah, because in two years, like whatever we're making right now will not be working.
10:02Will not be cool.
10:02Yeah, it won't be cool and it won't be working.
10:04So it's like we got to stay on it.
10:06We're both going to look back at our content and be like, wow, we were so cringe.
10:09Totally.
10:10Especially you.
10:11Especially me.
10:11No, I do that now.
10:13I'll film a video and be like, this is cringe.
10:15Post, perfect.
10:17Once I was done with modeling, I experienced all the different sides of modeling.
10:22And some of it is very negative about the way you look or your self-worth.
10:26And so I think that experiencing that during my modeling career actually helped when I
10:31transitioned to social media.
10:32Because it didn't feel as scary having all of these people comment on the way I looked
10:37or what I posted or what I wore.
10:39Because I was already used to that coming from modeling.
10:43But it's always scary to start something new.
10:45I was going to move home to Minnesota and go back to medicine.
10:48And then I decided, you know what?
10:49I'm going to risk it all.
10:50I've always wanted to be on Saturday Night Live.
10:53And there's all of these views on my page because of you and the apartment tour.
10:58Let's risk it and just start posting comedy.
11:00And I've been posting every single day since that apartment tour.
11:03I haven't had a day off and I would not have it any other way.
11:06Yeah.
11:06I love it.
11:07You know what I always say about you, though?
11:09Because a lot of creators, they talk to me.
11:12And I'm sure they talk to you and they ask advice and stuff.
11:14And I'm like, you know, out of everyone I made a video with, there's only one person
11:17who just worked super fucking hard.
11:19And that's you.
11:21And I always tell everybody that I'm like, she works super hard.
11:24And like, yeah, it looks like she's having a fun time.
11:26But she knocks out like three videos a day.
11:28And that's not easy at all.
11:30So if you want to have a career like Haley has or like I have, you really got to put
11:35in the work.
11:36Yeah, that was good.
11:36No, I don't do anything.
11:37I just sit at home all day.
11:38I know.
11:39So you're lying to people.
11:40No, I work really hard.
11:44That means a lot.
11:44You work just as hard, if not harder.
11:46I watch you crank out content like crazy.
11:48But it's always good content.
11:50Who has been somebody that you really look up to, whether you've met them, worked with
11:54them, or just really enjoy their content?
11:56Call out some names.
11:57I'm actually curious.
11:58I'll call out some names.
11:59You know Recess Therapy?
12:01Love them.
12:01Oh, he's fabulous.
12:02Julian.
12:03Yeah.
12:05I love meeting someone and then like hearing their whole backstory.
12:08Because he's just like worked super hard in entertainment.
12:12He's like really good at improv.
12:14He's been doing stand-up comedy.
12:15And then you just kind of see this one moment of someone's life.
12:18And you think like, oh, they've been doing 10 years of work before this like magical
12:22thing that's happening in their life.
12:25I mean, then there's just all the classics who have just been out there just killing
12:28it, like Zach King.
12:29Oh, he's so good.
12:30Yeah, so good.
12:31He's the nicest guy ever too.
12:32I know.
12:33Deserves all the success in the world.
12:35Benny Blanco.
12:36So funny.
12:36Yeah, so funny.
12:37And it's really cool to watch him just jump mediums.
12:40Like he's just like, I'm just going for it.
12:41Let's just make something.
12:42He does everything so well.
12:44And I'm like, how does he do it?
12:45He goes from like comedy to cooking to something just completely random with a celebrity back
12:50to like a collab with an influencer.
12:51Yeah, back to a collab with an influencer.
12:53And then he's just walking down the street and someone's screaming out the window.
12:56Hey, what's your favorite meal?
12:58And then he's on like the Tonight Show.
13:01And then he's like back.
13:02And I'm just like, that's the way I would like to play.
13:04Whoever is playing the best, like the ways that I think are fun, that's who I like hanging
13:08out with and like learning from.
13:10Because they jump mediums so well because they're just trying to play.
13:13Yeah, they're just having fun with it.
13:14Yeah, they're just having fun.
13:15It's almost like they're not trying too hard.
13:17They're just there enjoying it.
13:18And all of the content that they post is wonderfully incredible.
13:21Totally.
13:21And if it's not, they're like, well, I had fun.
13:23Yes, exactly.
13:24They're like, who cares?
13:25I'm leaving it up because I enjoyed shooting this video or making it or posting it.
13:29Totally.
13:29Who are some of your favorite creators?
13:31Oh man, I have so many.
13:34I love, I'm going to shout her out because she's like the coolest person ever.
13:37And I think she's going to be super famous one day.
13:39I'm calling it now.
13:40Her name is Leah Denham on TikTok.
13:42And she is a small creator.
13:44She has less than a million.
13:46Writes original comedy sketches that are just unbelievably funny.
13:51Like her comedic timing, her satire, the way that she scripts, the way that she captures
13:56is just so good.
13:59Like she is going to be huge.
14:01I'm calling it now.
14:02I'm calling it right now.
14:03I'm making my bet.
14:03Leah Denham is going to be absolutely huge.
14:06I love Cole Wallister.
14:07He's like the sweetest guy.
14:09What you were talking about, about like not seeing the journey before they enter TikTok,
14:14but knowing that there's a really long journey there.
14:16Cole is one of those guys who worked really, really, really hard, was always good at his
14:20job and then ended up getting that spot with E and then making it his own and creating
14:25this entire glam bot.
14:27And he's just become one of my really close friends.
14:29Meeting him on the carpet.
14:30I have so much respect for him.
14:32He's awesome.
14:33Zach King's another one that I would call out.
14:34He's incredible, really talented, works really hard.
14:39I think there's so many good creators out there.
14:40It's hard to pick people.
14:41I'm going to shout out Max Goodrich too.
14:43Oh yeah, I love Max.
14:44He's my best friend.
14:45So he's also a creator and he's just really, really good editing, lighting, script writing,
14:51the whole nine.
14:52What's something that you have wanted to do with an entertainment that you're really
14:56excited that's going to happen in the future?
14:58Manifesting.
14:59Yeah, yeah.
15:00Manifestation.
15:01Manifestation.
15:02I did so many videos on my For You page about manifestation.
15:05Same.
15:06And I was like, it's so weird.
15:08I didn't used to believe in manifestation.
15:10I was like, you can't manifest things like that.
15:12No.
15:13But then I realized because I'm such a logical brain, I'm like a science brain.
15:16I was like, no, no, no.
15:17Manifesting is just telling yourself that you can do it, which then makes you get out
15:21of bed to then start doing it.
15:23So really, it's just like you're doing it.
15:25But you're forcing yourself mentally to do it, right?
15:28So probably being the lead in a romantic comedy.
15:33Whoa.
15:34I would love that more than anything.
15:36That's insane that you're saying that.
15:38That'd be sick.
15:39That's the same for me.
15:40No, it's not.
15:40I'm not even joking.
15:41Are you trolling me right now?
15:42I'm not trolling you at all.
15:43Are you trying to like get in a movie with me?
15:46No, I'm just saying like being a lead in a romantic comedy is like something.
15:49You want to be in a romantic movie with me, Caleb?
15:51I see what's up.
15:52They told us to act like we're on a second date, you know?
15:54I'm telling William.
15:55My middle name's William, remember?
15:59Is it actually though?
16:01Yes.
16:02Wait, why?
16:02Tell me.
16:03I'm like very curious about your reasoning.
16:04Wait, why is my middle name William?
16:06Or why do I want to be in a romantic comedy?
16:09Yeah.
16:10Oh, I just I grew up on them.
16:12They're like so funny and fun.
16:14And I always pictured like love stories of my own life to be like that.
16:18And I've had like romantic comedy moments, like crazy ones happen.
16:22For example, I'm going to tell you a story.
16:24I was on a date with a girl in Dumbo and she brought her roller skates.
16:27And she's like, let's go roller skating.
16:29And I brought my skateboard.
16:31And there was a ladder with a rope right here.
16:33And I'm skating by.
16:35I'm going to go under the ladder.
16:36And I look at her.
16:37I'm saying, do you believe in bad luck?
16:38The second I say that, I get clothes lined at the neck.
16:40Boom, hit the ground.
16:42And she just comes over to me.
16:43She's like, did you plan that?
16:45And I was like, no, like look at my neck right now.
16:47And there's a like a rope mark on my neck.
16:51Like this shit happens to me in real life.
16:53Wait, did you get a second date though?
16:54Or did this end in a first date?
16:56Oh, no, it ended on a first date.
16:57Well, then I don't think.
16:58OK, then, you know, maybe it's a comedy, but it might not be romantic.
17:02Well, I mean, I'm just saying those romantic comedy moments happen in IRL.
17:06No, it's true.
17:06I mean, that was like the bread and butter of the movies that I watched when I was little.
17:09And I think that that's part of the reason why I wanted to be a comedian,
17:12is like finding comedy in heartbreak, which happens to me too often.
17:16Yay, loving a girl, living in New York City.
17:20No, it'd just be fun to like be in a romantic comedy.
17:23Yeah, agreed, agreed.
17:24Let's be in one together.
17:25OK, boom.
17:27Lock it in.
17:28Locked in.
17:30Manifesting.
17:30What do you think are the hardest parts of collabing with another creator?
17:34And what do you think are the easiest parts?
17:36The easiest part is if it's somebody you want to collaborate with,
17:39you just know it's going to mesh well because you're already a fan.
17:42So you already know what they kind of make and you already have an up.
17:45You're picturing how you're going to fit in together in a way.
17:50The hardest part, I would say, is like if somebody wants to collaborate
17:53and you just like don't see how it's going to fit or work.
17:56And then you kind of have to just be like, no, like the turning.
18:01Yeah, it's the turning down.
18:02It's like, no, I don't think this is the right fit,
18:04which doesn't always sit well with me because I might be a fan of somebody
18:07or I appreciate them asking.
18:09But I'm like, it doesn't really make sense.
18:10Well, what yours is also very much one type of thing, right?
18:14So like if there's somebody that doesn't fit with that video narrative.
18:19Totally.
18:20Like within the realm of the few different series I do.
18:23Yeah, it's not like you can just grab somebody randomly
18:26and make a video that isn't part of it.
18:28You could, but it might turn your audience for a spin.
18:31They'd be like, wait a second, what is this?
18:33Where are these extras coming from?
18:35Exactly.
18:35What about for you?
18:37What's some of the easiest and hardest things of working with other creators?
18:40I love collabs.
18:42Like collabs are my bread and butter, I swear.
18:45I think collabing makes you so much quicker and better at creating content
18:49because you get to see how somebody else does it,
18:51somebody else who you respect and look up to.
18:54The hardest part is always when you get another creator who is really good at ideas
19:00because there are too many good ones and then it's hard to just like pick one.
19:03So you almost get like ADHD stuck in this loop of like,
19:06oh, let's do this, but then this, but then this.
19:08And it's hard to drill down one idea.
19:11The most fun part, I think, of collabing with other creators
19:15is the challenge of working their type of content into the type of content you do.
19:20Like I think I could collab with almost any creator and make something work.
19:25Or like I can take a fashion creator and have them do fashion, but through comedy.
19:30Totally.
19:30Or like I can take an athlete and have them do that type of thing,
19:34but through the veil of comedy.
19:36It's more fun that way.
19:38I love collabs.
19:39I mean, it started my career, right?
19:40Same.
19:40I mean, my whole career is collabing, you know?
19:43True.
19:44I collab with everybody.
19:45So it's just like if someone doesn't want to let me into their home, I'm like, bruh.
19:49You're like...
19:50What else do you want to do here?
19:51Bruh.
19:52I should be like the poster child for you should let Caleb Simpson into your home.
19:55It could change your life.
19:56But I also don't want to give my legal signature of that, you know?
20:00What if you steal something?
20:02What if there's a cool spoon?
20:03And you're like, that's coming home with me.
20:05And then they sue me because I said, let Caleb Simpson into your home.
20:07True.
20:08I actually, I've never stolen anything from someone's house.
20:10Good.
20:11I hope not.
20:11Oh my gosh.
20:12It would be kind of funny though.
20:14Only if they let you.
20:15Yeah.
20:15If it was like an agreed upon stealing.
20:17Like a trolling type of collab.
20:19Totally.
20:19Those are my favorite.
20:20Yeah.
20:20Trolling is the best.
20:21Trolling is the best.
20:22Oh, it's so much fun.