Hey there...
What if we told you it was possible to 🚀 boost your revenue, ⏰ gain free time, and 🎉 have more fun in your business?
We can help! 💪
FREE QUIZ! What's Your Business Bottleneck?
7 quick questions to identify the ONE area holding your business back from financial freedom.
TAKE THE QUIZ
Don’t show this again, thanks!
Carol Interviews Jason!

Wandering Aimfully Through Our Podcast: What is it all for?

Carol Interviews Jason!

This week, Caroline grabs the mic and asks Jason some hard-hitting questions about childhood, the beginning of his entrepreneurial journey, and more!
Jason ZookJason Zook Jason ZookJason Zook

Written by

Jason Zook

Listen to our full episode where Carol Interviews Jason! below (with full transcript) or find our podcast by searching What is it all for? in your favorite podcast player.



Five Key Takeaways from Jason’s Interview

1. Growing up with a single parent made me super independent

Obviously, everybody needs human interaction, but I think I need a lot less human interaction than most people because I probably had less human interaction while my mom was working and I was figuring out how to entertain myself as a kid.

2. Building self-confidence through sports

Attending four different high schools, sports became my way in socially. I didn’t feel like I was in the money crowd and so when I ended up at an affluent high school, it didn’t feel like money was a way for me to relate to other kids. I was goofy and awkward and independent, but I liked sports, and I ran into some people who were also into that.

3. Trying to fit in didn’t work

I definitely know that it’s in my DNA because I remember my mom telling stories of me being a child and doing things just differently. In hindsight, rejecting convention since I was young helped in my creativity as an adult, especially in business.

4. Going above and beyond

Flipping cellphones on eBay when I was in college helped me learn how to take good photos (photography), write good headlines, and go above and beyond what’s expected, which is what we apply in our current business, Wandering Aimfully.

5. People pleasing is a losing game (to me)

I think my ability to not care what people think about me stems from my IWearYourShirt days when I would get negative comments on YouTube, Twitter, and Digg.com. The sooner I realized none of the bad comments mattered (it was ultimately about the other person), the sooner I saw how little I needed to worry about what other people thought of me.

Bonus: You don’t get what you don’t ask for!

I don’t have blind confidence. I have earned confidence. At the beginning of my IWearYourShirt business, I asked for basically nothing in the beginning ($1, $2, $12, etc) until I acquired the skills and experience to ask for more.


Show Notes for Episode 168: Carol Interviews Jason!

If you’ve been listening to our podcast for a while, you know we don’t ever have guests. However, we thought it would be fun to pretend we were a guest on our own podcast and interview one another.

This week Caroline is interviewing Jason (Part 1). Next week, Jason grabs the interview microphone and will ask Caroline a bunch of questions (Part 2).


Full Transcript of Episode 168: Carol Interviews Jason!

⬇️ You can also download the .TXT file of the transcript

Caroline: Welcome to What Is It All For? A podcast designed to help you grow your online business and pursue a spacious, satisfying life at the same time. We are your hosts, Jason and Caroline Zook, and we run Wandering Aimfully, an unboring business coaching program. Every week, we bring you advice and conversations to return you to your most intentional self and to help you examine every aspect of your life and business by asking, What is it all for? Thanks for listening. And now let’s get into the show.

Jason: And I’m here, too.

Caroline: Hi.

Jason: Welcome to an interesting twist on our podcast.

Caroline: Who saw this coming? No one.

Jason: Okay, so for 160 plus episodes of this podcast.

Caroline: Sure.

Jason: We’ve recorded just together. We’ve not had a single guest on the show.

Caroline: No.

Jason: We’ve gotten emails all the time from these dumb PR companies that are like, Dr. Swanson is a leading metaphysicist in the kneecap urology system and would love to be a guest on your show. And when we get those emails, I just get like, I die a little bit inside because I’m like, first of all, we’ve never had a guest on our show, so just a little bit of research would be great. Second of all, Dr. Swanson and the kneecap urology is going to be the first guest we have? Come on.

Caroline: My favorite is when the cold emails lead with, “Big fan of your show, blah, blah, blah, blah.” Then…

Jason: Big fan of your show, comma, What is it all for?, colon, Wandering Aimfully. They just copy and paste the show name.

Caroline: An intentional creative business podcast. And it’s like, no one says that.

Jason: No one says that.

Caroline: And then they go into pitching their…

Jason: Dr. Swanson.

Caroline: Their client. Again, just a quick cursory glance to show you not a single guest.

Jason: Not a single… I used to actually write back just when I was like, more spiteful. Now I just block them.

Caroline: Wow, babe, you’ve really evolved.

Jason: I think so. Speaking of evolved, let’s see how this goes.

Caroline: Okay, so just to set the stage for this, about a week and a half ago…

Jason: This is the preamble, by the way, we’re going to skip kind of Portugal stuff because we just want to get into this. It might take longer than we think.

Caroline: About a week and a half ago, you and I… Well, I would say, like, almost… I would say 75% of the time, we sit down and we have lunch together.

Jason: Yeah. Oh, more than that.

Caroline: More than that?

Jason: Lunch is pretty solid together these days, yeah.

Caroline: You’re probably right.

Jason: You know what helps? Having a dining room table.

Caroline: Yeah.

Jason: Haven’t had a dining room table in our home for years.

Caroline: Haven’t had a dining room table in our home for years. Now we have one, and also, it’s perfectly in the middle of the day, so we need a break from our laptop. So we sit down and we eat lunch together. And about a week and a half ago, we somehow got usually it’s just like shooting the shit, talking about business, like, whatever. We went on this tangent where we had a very deep conversation where I learned new things about you, and I just was like, wow, we should do this more often, like, interview each other and actually learn about each other. Because for those of you who don’t know, we’ve been together 13 years.

Jason: Good job, babe.

Caroline: Thank you. And so then later that day, I thought this would be kind of fun to do on the podcast because we don’t say yes to a lot of interview requests anymore. Not because we think we’re too cool for it, just because it’s…

Jason: Well, you’re busy and I’m cool.

Caroline: Right.

Jason: That’s the problem. So in so many emails…

Caroline: I’m doing stuff, and Jason’s way too cool.

Jason: Sorry.

Caroline: Right.

Jason: Now, if one of us was just cool and the other was available, we’d say yes. It’s the perfect combo. Yeah.

Caroline: And so I thought, what if we on the pod, did one episode where I get to interview you and one episode where you get to interview me? So that’s what we’re doing.

Jason: That’s what we’re doing.

Caroline: It’s the interviews.

Jason: No one is having any fraughty feelings about the questions that they’re going to ask anybody. No one is worried that…

Caroline: Yeah. Also, we didn’t share the questions, obviously, with each other. And so we’re both feeling a little unsure because we also were very aware that we’re different people. Our questions are probably going to be very different. And so both of us are feeling a little insecure about how those questions…

Jason: Like I want to ask you all your numbers. I want to know how much money do you make? How much money do you spend? And you want to ask me like, What are your feelings?

Caroline: Like if you could be a butterfly…

Jason: I know the answer to the questions that I would ask you. It’s like, how many website visitors does the website get every month?

Caroline: Yeah. And I’m just dying for you to ask me the questions I ask myself.

Jason: Exactly.

Caroline: Not going to happen.

Jason: What we should have done is this.

Caroline: What?

Jason: We should have done is written the questions out we were going to ask the other person and then swapped them. That’s what we should have done.

Caroline: There’s still time, babe.

Jason: There’s still time.

Caroline: No. This is the beautiful thing about this is we’re different people.

Jason: Yeah. So you’re going to start. You’re going to interview me. So if you’re wondering, listener, why I’m maybe not asking questions back, it’s because…

Caroline: It’s because imagine I had a solo podcast and I asked Jason on.

Jason: Exactly.

Caroline: Okay.

Jason: Now I might ask some questions back. I mean, you just never know.

Caroline: Sure.

Jason: Could be some things.

Caroline: I’m also a little nervous because I’ve only done maybe one or two audio interviews where I was the interviewer in my life.

Jason: But you’ve never intervieweed or interviewered.

Caroline: That’s what I’m saying.

Jason: Yeah.

Caroline: I did… Remember, I did those bonus interviews for my Connecting With Your Core way back in the day?

Jason: And I’ve only ever done interviews with a course as well, which is kind of funny. That’s the only time either of us have done interviews is with a product.

Caroline: This is not going to be that.

Jason: All right. So we’re going to get into it. If you hear, like, a hard stop and then it seems like we just took a left turn.

Caroline: We got in a big fight.

Jason: Someone asked a question that the other person didn’t want to answer, and we cut it out.

Caroline: Real talk.

Jason: So you get to just, like a little inside of the old baseball.

Caroline: We decided that this was a fun idea and it probably shouldn’t wreck our marriage.

Jason: All right. Are you going to intro me real quick? Are we going to do, like…?

Caroline: Oh, God, no.

Jason: The full thing?

Caroline: This is Jason.

Jason: Okay.

Caroline: Last name Zook. He’s had many last names.

Jason: Cool.

Caroline: He is very tall. Taller than you think. Think about how tall you think he is, and when you meet him in person, he’s even taller than that.

Jason: But not like, uncomfortably tall. No. We don’t want to start this rumor where I walk up and people are like…

Caroline: Yeah, no, not uncomfortably tall.

Jason: Yeah.

Caroline: But, like…

Jason: Just taller than most.

Caroline: The first time I met you was like, Whoa, taller.

Jason: Living in Portugal, I am the tallest person almost everywhere we go.

Caroline: True.

Jason: Not in, like a… again, scary. No one’s like…

Caroline: You’re not in the bell curve where you’re just like, way…

Jason: Lurch. I’m not lurch…

Caroline: You’re not lurching. But you’re almost…

Jason: All right. I’m so sorry I derailed your beginning of this podcast interview.

Caroline: I’m not going to do an intro.

Jason: Okay.

Caroline: Google him.

Jason: He does have a Wikipedia page. Me, speaking of the third person.

Caroline: Yeah, that’s actually my…

Jason: Did you cite some Wikipedia…?

Caroline: That’s actually my 13th question is, how does it feel to have a Wikipedia page?

Jason: Did you do any citations on my Wikipedia page? I read it here on Wikipedia.

Caroline: I just realized in order to do this interview, I probably should have read your books.

Jason: Oh, nice.

Caroline: I did read your books when I edited them.

Jason: I was once on a podcast about a book, and the interviewer was like, I didn’t even read this book, but I’ll ask you some questions about it.

Caroline: I hate that.

Jason: Cool. That’s cool.

Caroline: It’s like, you don’t need to read the book, but definitely don’t say that.

Jason: Just don’t tell me. Yeah. Just don’t tell me.

Caroline: Yeah. That’s rude. Yeah, just pretend.

Jason: All right.

Caroline: Okay. So here’s where we’re going to start.

Jason: Wonderful.

Caroline: It’s a little bit of a left field question, but we’re going to start here. Where do you think your sense of humor comes from?

Jason: I think I know.

Caroline: Well, then, what’s the answer?

Jason: I think it’s a coping mechanism to make my mom feel good in growing up together as a single parent.

Caroline: Okay. We went there.

Jason: Yeah, yeah, yeah.

Caroline: Okay. I thought this was going to be a softball, but okay. Great. Let’s dig in.

Jason: No, I just think if we’re just being 100% totally honest.

Caroline: Let’s cut to the core of it.

Jason: If a therapist was sitting here, we could pramble on that is the answer. I grew up with a single mom until I was eight years old, and my dad was out of the picture immediately when I was born, basically. And so I think just as a child, to make my mom as happy as I could and to make her laugh and smile and to get through some of the tough times, because, again, we talked about this in a previous episode. We didn’t grow up poor, quote unquote, by the definition of society that we know that it is poor, but we grew up with less than most. And so I think that was just a way for me as a kid to make my mom happy.

Caroline: Do you have any early memories of like…?

Jason: I have no early memories. You could just stop there.

Caroline: Let’s talk about that. This is something people would not know about you. I don’t think we’ve mentioned it really. Maybe a few times offhandedly, but this is something that I learned about you when we first started dating. You have very few childhood memories.

Jason: I’m a compartmentalizer.

Caroline: Tell me more about that.

Jason: I got a lot of black boxes.

Caroline: Tell me more about that. When you think about your childhood or do you just never think about your childhood?

Jason: I never think about my childhood.

Caroline: You never think about it?

Jason: Never. Yeah, I mean, I try and think back to early times, like, when you’re like, oh, when I was four. Like, I remember being a kid and, like, running around and I’m like I remember like I can remember a couple of things. I remember living in some type of apartment complex townhouse thing where I remember the covered doorway that we would go in. And I also remember that house had cockroaches that came out of the drains.

Caroline: Oh, I hate that.

Jason: Which I’ll just never forget. But also we lived in Florida, and they did that…

Caroline: Oh, of course.

Jason: In a perfectly nice house.

Caroline: It’s just a Florida thing.

Jason: That wasn’t like a we lived in a…

Caroline: Squalor.

Jason: Terrible place. Yeah, it was just like no, they just like, I have some memory. It probably happened twice…

Caroline: I have some forged cockroach memories as well.

Jason: In, like, seven years, but as a child, it’s, like, traumatic.

Caroline: It sticks. Yeah.

Jason: So I remember some of that. I remember going to the movies with my biological father’s mother, so my grandmother, and I remember walking down, like, a tunnel in a movie theater and just thinking it was like, bright lights, and I thought I was going to a new world. I’m sure you go to an AMC 24 now, and it’s just literally the entrance. It’s nothing at all.

Caroline: But in your mind, it’s like Willy Wonka tunnel.

Jason: Exactly. Totally. It’s like 300ft long. It was like just a foot. That’s all it was.

Caroline: Now, do you think that your love of movies comes from those early formative memories, or do you think you always loved movies and that’s why it’s a core memory?

Jason: I think I always loved movies. I remember… So, again, like, a couple of memories that do pop up. Like, I remember my mom making me Gordon’s fish sticks. So the yellow box.

Caroline: Could sing the song in my head.

Jason: Yeah, with the frozen fish sticks. That’s not food, by the way. And that’s not a criticism of my mom. That’s just like, in general, that time in society, like Pop Tarts, fish sticks, Hot Pockets, Totino’s pizza rolls.

Caroline: Chicken tenders.

Jason: None of those things are food. It’s processed amalgamation. But yeah, I remember watching movies on Saturday morning or like Saturday morning cartoons. But then I also remember Teenage Mutant Ninja Turtles came out on VHS or the Godzilla movies, like the old ones, like the super old ones. I had those on VHS as a kid. I had like four movies on VHS and I’m sure my mom got them at the Dollar Bin. And so that’s why it ended up being movies I watched. But I do think it was probably pretty formative that I went with my grandmother and that was an outing that we did. Honestly, and I’m sure it happened, but again, this is just a memory thing. I cannot remember going to a movie with my mom as a kid, and I just attribute that to like, she always had to work to provide for us. But I’m sure we did. When I think of as like a kid going to movies, it was my grandmother, or then I was a teenager and I was going by myself and driving myself to movies with friends or whatever.

Caroline: I think that is so interesting that you and I, very early on, on our first date, connected over movies and loving movies. And I think about some of the overlaps in the ways that we grew up. And I just think it’s interesting that we now still to this day we’ve mentioned it. We do Saturday movie nights and things like that. And it’s like this… I don’t know if it’s a coping mechanism.

Jason: Probably. Escapism.

Caroline: Yeah, escapism. But it’s interesting to me that there’s overlaps in our story in that regard. You mentioned growing up with your mom. Would you say basically a single parent?

Jason: Oh, for sure.

Caroline: Right.

Jason: That’s not really basically like she was a single parent, for sure.

Caroline: And what do you think growing up with basically a single parent, what impact did that have on you growing up?

Jason: Yeah, I think it makes you super independent. I think that’s why I can be alone by myself forever. Obviously, everybody needs human interaction, but I think I need a lot less human interaction than most people because I probably had less human interaction while mom was working and I was figuring out how to entertain myself. Which again, probably why I like movies and things because it was stuff I could do by myself. But yeah, I didn’t have a father basically until I was eight. And then my mom remarried, had my sister. That was an abusive father relationship and mix of psychological and physical. And it’s not terrible. We just watched an interview with Logic, and that’s like a whole different world. The rapper, Logic. And again, I’m not trying to belittle the trauma that I had, but also comparatively, it was not much. But even having that father at the time, you look at him as a father figure because he’s there. But I’m also old. I can look back now and be like, that wasn’t a good situation for me. And so moving… I still had to be independent, I guess, my point. And so even from there and then when my mom remarried again, that was a much better father situation for me. But I think by that point, I was, like, starting to get into my teenage years. And then you’re already trying to become independent by nature, so carrying all that independence through.

Caroline: Do you think that you were subconsciously searching for male role models since, like, positive male role models, since you didn’t have that? Or do you think that your mom sort of had to play both roles and be kind of like the mom and the dad? I think of your mom as a very strong woman, and I just wonder, do you almost think of her as…?

Jason: Oh, for sure. Yeah, yeah.

Caroline: That she occupies that traditional space of, like…

Jason: Yeah, I think of mom as, like, everything.

Caroline: Right.

Jason: Yeah, there’s no void in me that’s also like, oh, man, I really wish I had a dad. I had a mom who did all of it. And so even if I’m saying she wasn’t there, she was working a lot. Like, she was she was there. It’s just I’m just saying, like, I can remember being independent and, like, working through that, and and so, yeah, I think of her that way. And we joke all the time, like, when movies have, like, a happy dad moment. Like, the actually, the only movie with a dad moment that gets me all the time is Chef, the movie Chef. And it’s because it’s like, I see my mom in that role of that dad, John Favreau’s character trying to succeed and trying to make it and trying to be there. And it’s obviously not that similar.

Caroline: Only to kind of realize that it’s the time, it’s the quality time together. And I do think I’ve always thought it’s interesting that Chef the movie has a very redemptive father arc to it. And I think maybe that’s why you resonate with it because it kind of speaks to that healing that I think, deep down, maybe you wish you had. And it’s also joyful and playful and creative.

Jason: I think about, like, my mom, definitely. She helped me get into sports. Like, I played every sport as a kid. I was a rock star football, now that we live on this side of the world, but soccer player. We have a VHS tape to prove it. But I was, like, nine years old and just, like, running circles around other kids. It really wasn’t that great. I was just better than all the kids who were, like, picking their nose.

Caroline: That’s so interesting. Do you think that…? I’ve thought about this recently. Do you think that being good at something or feeling like you’re good at something early on in your childhood positively propels you forward, like, builds confidence?

Jason: Oh, for sure. Like, how couldn’t it? You know what I mean? But I think it’s dangerous because if that’s where you get all of your self worth…

Caroline: Right.

Jason: Then you see all these stories of child athletes who then struggle to kind of cope in the world because they’re always trying to one up and feel that way. I was just good enough that I was on a team that won regionals or something like that for Pop Warner football. But like, I didn’t play. Like, I just like I was kind of like, too small at the time, so, like, I didn’t really feel like I earned much of the success.

Caroline: Well, you didn’t.

Jason: I really didn’t. I remember they called to play for me. This is like, I don’t know, I’m like ten or eleven maybe. And I was, I think, a tight end. When you’re that age, you play like, all the positions. You just run out there and just, like, smack into another child. But I remember it was like the one player where they’re like, all right, Jason, they’re going to hit the ball. You just run straight and they’re going to throw you the ball. And I’ll just never forget, I just took off and I never looked back for the ball. And I could just remember hearing my mom screaming in the background, like, look for the ball. Never looked back. I just ran. Like it was my one time to shine, and I did not know what to do. Anyway, sorry.

Caroline: Well, I wanted to ask about sports, actually, because I didn’t know until a little bit into our relationship that I knew that you loved basketball. I knew that you were very good at basketball. I knew that you were a college basketball player. You played for a D1 team?

Jason: I didn’t fully get to play, but I was supposed to.

Caroline: You didn’t get to play, but you made the team, okay. And was on scholarship, if I recall correctly. But I remember finding out that you didn’t actually get into basketball until like, pretty late in your high school years?

Jason: Yeah, when I was a sophomore in high school was the first time I picked up a basketball. When I was a junior in high school, was the first time I played in a game, like, at all with other people.

Caroline: What was the catalyst for that? Was it just that you got tall?

Jason: So we moved from California to Virginia when I was like twelve. Somewhere around there.

Caroline: We can’t trust any of your…

Jason: Can’t trust any of these timelines.

Caroline: Timelines.

Jason: Also, I don’t really know the difference in children between like 5 and 15. So it could have been anywhere in there. It’s somewhere around there. And so that stopped. For some reason, I didn’t go into continue playing football. Probably because I wasn’t very good.

Caroline: Probably because you never looked back for the ball.

Jason: Never looked back for the ball. Could have played a lot of different positions where I didn’t have to track the ball.

Caroline: You should’ve gone track and field, babe.

Jason: What’s really ironic about that is, when I became good at basketball, my hand eye coordination went through the roof, and so I would play flag football, and I was, tooting my own horn, very good at flag football.

Caroline: Interesting.

Jason: Because I could jump, because I could catch, and because I could track the ball really well.

Caroline: You learned how to look for it.

Jason: But it was way too late. I firmly believe if there’s, like, one humble brag thing that I could say about myself athletically, I think, had in a different life, had I started with football, I could have played in the NFL. If I had started with football from the very beginning because my size, my hand eye coordination.

Caroline: Again, we established you’re large.

Jason: My athleticism. Yeah, I was given the gifts to do that. I just never went down that path. So, anyway, getting back to the basketball thing, when I moved to Virginia, for some reason, I didn’t get in. I thought I was probably too slow to play soccer anymore or just, like, fell out of love with it, hated baseball, worst sport in the world. And then I think basketball was just kind of like the next thing. But I didn’t play it in Virginia, to my recollection, because I was only there for a short period of time. And then we moved to New Jersey. It was, I think, a way to like again, I was an independent kid, and I didn’t know anybody, and so I’m guessing my mom probably was like, let’s get him a basketball hoop, and then he can be outside and play. And we had, like, a big driveway. And so I think that’s, like, where it started.

Caroline: Here’s what’s interesting to me is the way…

Jason: How am I doing, by the way?

Caroline: You’re doing great. I’m loving this.

Jason: How are you doing?

Caroline: I’m learning new things about you.

Jason: How are you doing?

Caroline: Oh, I’m killing it.

Jason: Got it.

Caroline: What’s interesting to me is the way that you speak about yourself in the realm of athletics is with such confidence and pride that I only hear you really talk about yourself in that way when it probably comes to business. But it made me think, going back to my question about early on, you having this memory of being good at soccer, and it made me wonder if… because I know you, and I know how hard socially it was for you growing up because you were moving all the time. And I’m curious about what you think maybe the role that sports played in building up your own self confidence because in these more social realms, you were feeling more insecure. I mean, you were bullied, if I got that right. So I don’t know. Tell me about the difference in feeling that you got between I’m just a kid walking into a cafeteria and trying to make new friends for the first time versus I’m joining the basketball team and I’m actually good at this.

Jason: Well, joining the basketball team, I was terrible.

Caroline: So same. They feel the same. Maybe fast forward to your senior year. You’re playing, you’re actually pretty good.

Jason: But I’m not. That’s the thing. I was decent my senior year, but I really didn’t get good until the summer between, which is why it was really weird. Like, I came and did like, a walk on tryout for college, and that’s where I was actually given part of an athletic scholarship was because it was like, oh, wow, if we looked at… I don’t even think I had a tape for high school just because I didn’t have anything really to put on tape. It was like, oh, you in the tryout is good enough. That was the thing. But anyway.

Caroline: But when you think of yourself as an athlete, you think of yourself as a good athlete.

Jason: But after high school.

Caroline: Okay.

Jason: Yeah, yeah, yeah. So moving around a ton, I went to four different high schools, as you learned in our lunch conversation the other day. Started out in Virginia at the first high school as a freshman, I was literally only there for, I think like a month or two. Again, my timing is all off on this, but I’m pretty sure it wasn’t that long. Maybe it was six months, I don’t know. Mom would have the actual receipts here for this. But then moved to New Jersey because Mom’s job and then stepdad at the time, he was already working out of New York.

Caroline: Different stepdad.

Jason: Different stepdad. And then she got a job in New York. So we lived in New Jersey, as people do, and they commute in and out. So I ended up we were renting a house and I went to a school. But then come to find out like a couple of months into going that school, I was in the wrong… Like, the house that we were renting was half in one district, half in the other, and so it was more in the half that I had to go to another school. So I transferred right away. So now I’m at three high schools within like, one year, which, if anybody ever remembers anything about high school, the first time you go to a school sucks. The second time is really hard. The third time really sucks. And my third high school was in a very affluent… Actually, I got that wrong. I went to New Jersey.

Caroline: We’re opening a couple of black boxes here.

Jason: I was in the house that was dual zoned. I went to the closer one, the one that the address was in, and they said, no, you’re in the county even though your address is in this town, you’re in the county of this other school.

Caroline: You have to go to the other school.

Jason: So I went to this… It’s Mountain Lakes, just because this is quantified easier with the name. Mountain Lakes was the school that I was in the town of that the address was in. I went there for, like, two months, and they’re like, no, you have to go the other school. I go to the other school. So now I’m at my third high school, Virginia, Mountain Lakes, and this other school. And then I’m there. Then my mom and stepdad buy a house literally down the street. But then now that’s fully in the county of the first high school in Mountain Lakes. So then I have to leave and go back to that school. Yeah. So anyway, that tells you a lot about my high school experience. And I did not fit in in any of them. All four of them.

Caroline: Did you have any friends? Did you feel like a loner? Like, what was your…?

Jason: No, I mean… I think, fortunately, like, all of my humor tools that I had built up… I was, again, independent as a kid, and I kind of at that point in my life was just like, I mean, you’re a teenager, so you still care what people think. But I was, like, already bleaching my hair blonde out of just, like, rebellion and just, like, not caring. So that did attract a certain type of group of people. And so I really don’t remember any people from except for the kid that I became good friends with in Virginia, but that was more in middle school than in high school. And I got my initials on my back tattooed in Korean because he was Korean, his name was Wes, and we were just, like, best buds and watched Dragon Ball Z.

Caroline: Okay, so you didn’t get the tattoo in middle school?

Jason: No, not in middle school. When I was 17.

Caroline: Wes made such an impact on you. Now, just to be clear, they’re not Wes’s initials on your back.

Jason: I don’t know because I don’t speak Korean.

Caroline: It could be…

Jason: This is one of those “ragrets.” Anyway, yeah. So at the first time going to Mountain Lakes, I didn’t really have enough time to meet anybody. I remember being in the cafeteria, eating by myself, like, getting made fun of.

Caroline: Hate that.

Jason: All those things. And this was a very affluent school, so people are already assholes by nature.

Caroline: Not only are you the new kid, but you’re like, comparatively you’re kind of like the…

Jason: It’s tiny. Like, the whole four year high school, total amount of people in that school was, like, 200.

Caroline: It’s like an OC vibe.

Jason: So small.

Caroline: Yeah.

Jason: With no ocean or a beautiful views.

Caroline: Right, but I just meant, like, the whole premise of the show, The OC, is like, it’s just like, rich kids and then you’re kind of the new bad boy in town.

Jason: But at the other school…

Caroline: With your bleached hair.

Jason: I did end up meeting a couple of people, Alan, who you knew and met a bunch of times, and he and I became good friends, and we stayed friends long after I left that school, and so we hung out. But then getting back to the sports question, I don’t know what led me. I think it was just because I was like playing basketball in my driveway and then in “recess times” or break times in high school, I would just go into the gym and just shoot hoops by myself and run around and be dumb. And I think I probably ran into a couple of people there that were also doing the same thing and then they were going to try out for the team and they’re like, oh.

Caroline: So sports is kind of like your way in socially?

Jason: Totally.

Caroline: In a way.

Jason: Yeah, because I wasn’t going to… I didn’t really think that the whole money thing when my mom got a better job and then married this other stepdad and he had money and so I didn’t feel like I was in the money crowd. So when I got to that school, that didn’t feel like a way for me to relate to other kids.

Caroline: Pay your way into social circles.

Jason: It was more of like, oh, well, I’m kind of goofy and awkward and independent, but I like sports. And then I ran into some people who were kind of also in that little bit outliers.

Caroline: You mentioned this word rebellious that I want to dig into a little bit because when I think of you and the core person that you are, obviously humor was one of the first things that came to my mind, which is why I started with that question. But also I don’t know what the word is for it, but you are perhaps of anybody I’ve ever met personally, the most like rebellious isn’t quite the right word for it, but I wrote down rejecting convention. You’re allergic to convention. Whatever is the normal thing, whatever is the expected thing, you look for boundaries and you sort of are allergic to them and run the opposite direction. And I’m interested about whether you think you were always that way or do you think that it was parts of your environment and your upbringing that cultivated that.

Jason: Yeah, I definitely know that it’s in my DNA because I remember my mom telling stories of me being a child and doing things just differently. And there’s this classic story of I think it was like 6th grade math or something like that where, you know, I got all the questions right on an algebra test. But the teacher was like, oh, but he didn’t show his work. And it was like, yeah, but he got them right. Like, why does he have to show his work? And she’s like, well, that’s how you have to do it. And I was like, well, you’re barking up the wrong tree with that because he’s just not going to do it that way. And so clearly it was there. And I’m sure there are even other examples when I was younger, but yeah, I think it’s always, A, been part of me. But then I think as I changed schools and changed friend groups and changed things and changed different authority figures throughout my life and parents and other things, it got worn into me of just falling in line and doing things the way they’re supposed to be done. Just felt incongruent to living a life that felt good to me, I guess.

Caroline: Well, yeah. And I imagine if you’re having to withstand so much change and be so adaptable, why would your brain tell you that it’s a good strategy to follow the rules because the rules are always changing on you? You know what I mean? So it’s like, if you go to this school and you’re like, hey, we do it this way here, and your brain’s like, okay, I’ll do it this way, and then you’re just going to go to a different school two months later. So I wonder if it was almost this developed personality trait that said, listen, I’ve tried to play by the rules, and they keep changing on me, so I’m just going to write my own because it’s like such a losing game.

Jason: Yeah.

Caroline: Does that resonate at all?

Jason: Yeah, totally. And then also trying to fit in didn’t work. So it was like, the more I tried to fit in, the more I got made fun of or I got bullied or whatever. So I was like, Well, I’m not going to do that. I’m just going to do things my own way because at least that won’t be painful, that won’t be difficult to deal with.

Caroline: I wonder what role your mom played in that because I think one of the most amazing things that she did, raising you, was exactly what you described. I remember her telling me that story where she really sort of… I think a lot of parents would tamper that down within their kids and say, like, no, the best way to life is to try to fit in. And she just sort of always allowed your rejection of convention to flourish.

Jason: Totally. Yeah. I think as a parent, she did a fantastic job of understanding who I was as a child and being okay with the fact that I was rebellious or different or didn’t fit in these boxes. And then also creatively, I think she allowed for a ton of creativity and probably because it was a way for me to just be independent and do my own thing. So it’s like playing with toys and making up worlds for them and drawing and all these different things that allowed for me to be able to entertain myself. And so she just embraced that and was very happy for me to be a creative kid, which is incredibly formative for me as an adult getting into business stuff because creativity has led the way to all the things we’ve been doing.

Caroline: What role do you think that learned adaptability that you had to learn, changing schools and all these environments, what impact do you think that had on becoming an entrepreneur?

Jason: Oh, yeah, I think it’s enormous but the funny thing is that I didn’t really do anything with it until multiple normal jobs and then a normal nine to five job. And it wasn’t until I sat at a desk every day realized, like, oh, I don’t like the way this feels. Probably because my entire existence up until that point, I’m always changing and doing things and feeling the rush of something new, whether it’s good or bad, like, it’s still a different rush I’m feeling, but like the monotony of showing up to a beige desk in a beige chair and a beige monitor and beige walls. And even though I was a graphic designer, it was the most mundane and boring thing that I could think of to do. And that’s not to belittle people who do that. It was just like, for me, I just all of a sudden realize, like, oh, my gosh, I’m going to do this for the next 30 years of my life. This will kill me. And I don’t mean that in a terrible way. I mean, I will die inside.

Caroline: Crush your soul.

Jason: Yeah.

Caroline: Yeah. Well, now that we’ve dug into your past, it does kind of surprise me that you even tried to go towards normal path.

Jason: And I wouldn’t say pressure because I definitely don’t remember getting any pressure from my mom about it. But I do think that was probably do this thing for my parents because they want me to go to college. They want me to get a degree because also, in their defense, it’s the year 2000. Like, the Internet barely exists, so what other options are there? I’m not going to flip real estate as an 18 year old. I don’t know what I’m doing. But it’s more of like at that time we had a gateway computer. I’m bopping around in HTML and being in chat rooms and starting websites like GeoCities and things like that are starting to come up.

Caroline: But you don’t really see how it could be a business.

Jason: We all laugh about that, but what is the path? And the only path that I had was I told you this when we were having this deep and meaningful– was like a Nintendo internship had popped up that was for a programmer. But I think at the time it was literally just like writing HTML. It wasn’t for coding games, it was for building a website and doing things like that. That actually seemed really interesting to me, but I think it was probably in my full defense of my mom, she was like, what? I don’t know what this is. You need to go to college so you can get a degree that you could do something with your talents, which, looking back, that’s the logical thing to do. Sorry, I was going to say, it’s so easy to look back and be like, should have chased the entrepreneurship thing, but into what? The Internet wasn’t formed enough to really know what that could have been at that time.

Caroline: Right. It’s like the opportunities were not only much less, but they were also hidden. So it’s like twofold. It’s like the opportunities are less and you don’t know they exist what little opportunities there are.

Jason: Also in that time, if you think about, like, this is like when PayPal is being built. Like I’m not building PayPal. I’m like coding Dragon Ball Z websites. It’s a whole different world that I was existing in.

Caroline: It does amaze me because I think of your history and I think, god, all of these factors come together to… there is… it’s such a quintessential past of an entrepreneur, right? Creative, rebellious, entrepreneurial thinker, whatever. But you think of you existing 40 years ago, and maybe you don’t have any…

Jason: Outlet for it.

Caroline: Outlet, whatsoever.

Jason: Totally. I’m just getting soul crushed at a job like that’s it. My first…

Caroline: I said 40. I always think it’s the year 2000, so I meant, like, really 7 years ago.

Jason: I think back to… I was having these part time jobs while I was in college, and none of them were really satisfying enough in a creative way at all. But I remember eBay started to come around, and I also remember this is where the technology bugs started to hit me. And this is where I bought cell phones on eBay that were literally from China, Korea, Japan, Vietnam. But this evolution of technology and cell phones had just started, which was like the SIM card that you could then take out and put in other phones. So I could buy these phones that literally some of them weren’t even in English, but they were so unique. Like, a phone was so tiny. Like the Will Ferrell joke in Saturday Night Live where he flips up on the phone, I had a phone like that that was like, it truly existed. And I just remember buying these phones. I would use them for, like, three weeks. It would be a funny thing that I would show my friends as, like, the goof that… I’m class clowning with, like, a cell phone that I can barely use, and then I would just turn around and sell them on eBay. And I just made this tiny career. But that was, like, really my first…

Caroline: Okay, so when is that? When are you doing that?

Jason: That’s my…

Caroline: Are you in college?

Jason: Oh, yeah, that’s my sophomore or junior year of college.

Caroline: Jason.

Jason: So, like, freshman year of college, I was supposed to play basketball. I got injured just playing in, like, a five on five pickup game and didn’t play. And so I was at Jacksonville University in Florida, and I hated that school because it was yet another small school that was just, like, tiny and clique-y and also super expensive because it was a private school. So I’m like, I’m going to leave here and I’m going to go to UNF, which is the neighboring school, but it’s more of a public school. It’s a bigger school. It’s a commutiny school. So that made a lot of sense to me because then I made good friends at…

Caroline: So you can keep your friends?

Jason: My first college. So we actually got an apartment together, and half of us went to one school and half of us went to another school. And then it was so my sophomore year. That was just like I just had like part time jobs and things. That was my Athlete’s Foot time, selling shoes. For those who don’t know what Athlete’s Foot is, it’s a shoe company that may not exist anymore because terrible name, but still going to classes. And then that was like the year after that I moved in with Travis, who we actually just met up with here, if you listen to the pramble many episodes ago, who lives in Berlin. He was my original freshman year roommate at Jacksonville University. But I was terrible to him and he moved out, and then we moved back in together in an apartment. And that is when I started the eBay because I was already dabbling a little bit out of the dorm room, or out of our first apartment, too. But I didn’t really do too much. But for some reason, getting into that apartment, I’ll never forget that was the start of all of everything.

Caroline: So would you say that’s your first entrepreneurial venture because you’re selling cell phones at that point?

Jason: I think so. I definitely made like a couple websites here and there for money.

Caroline: For money.

Jason: But it wasn’t enough that… and I don’t even remember what they were for.

Caroline: Did you learn any tips from your cell phone flipping?

Jason: Oh, photography.

Caroline: Okay.

Jason: Like how to take good photos.

Caroline: Interesting.

Jason: Because this even translates to now, right?

Caroline: Totally.

Jason: When we sold all of our stuff to leave in 2022, it sounds silly. Everybody knows it today when you’re taking photos to sell things online. But I’m still doing the same thing I did back then. I’m taking more photos than most people do. I’m cleaning up a background. It sounds so straightforward now, but 22 years ago, when you’re selling something on eBay, someone’s like, why would I take more than one photo? You can see it. And I was like, Well, I’ll just take eight photos because there’s other parts of this that look good. So it’s like that and then also writing headlines. I remember putting asterisks in things in headlines…

Caroline: Just to catch someone’s eye?

Jason: Yeah, literally, just to like, I would pay for the bold. Like you could pay like twenty five cents to bold the headline because I’m like, it’s an investment. It’s going to stand out.

Caroline: That’s so interesting. Yeah. This idea of going above and beyond what a normal person would do that I feel like shows up in… You have brought that to our businesses.

Jason: Never had a cell phone go unsold.

Caroline: Never. Jason’s eBay Store. Never had a cell phone go unsold.

Jason: I still have my same eBay username from back then.

Caroline: What was it?

Jason: It’s like a Dragon Ball Z reference.

Caroline: Of course it is. I wish we had more time to cover Dragon Ball Z.

Jason: Oh, I’m so sorry. Maybe part two if people like this.

Caroline: Maybe part two.

Jason: I have a whole collection. That’s like one of the one things that I kept from our multiple moves. I didn’t keep it. Mom kept it, my Dragon Ball Z collection.

Caroline: Well, collections are hot, man.

Jason: I know. Well, I probably should have taken better care of it and wrapped things nicely because it could actually be worth something in like 50 years. But that’s all right. It’s more of his keepsake. Anyway.

Caroline: Blazing right ahead in time. I want to shift gears into the I Wear Your Shirt years.

Jason: Okay.

Caroline: And I don’t want you to touch too much on like the origins of I Wear Your Shirt because there’s plenty…

Jason: Keep asking this. I’m just going to pop up and shut the door because there’s hammering going on. But go ahead.

Caroline: Okay. There’s plenty of interviews on the internet out there where you can find the story of how I Wear Your Shirt was started. And I’m less interested in that, and I’m more interested in digging into what the experience was like, kind of being behind a business that kind of rose to visibility. Well, first, for anyone who doesn’t actually have any context, can you give us a short description of what I Wear Your Shirt was so that someone at least has a little bit of background?

Jason: Absolutely. So in 2008, I’m standing in my closet and I’m looking at shirts that all have different brands on them. And at the same time I’m running a design company. I had left my nine to five job and started a design boutique, as I liked to call it, with a friend. And we were building websites for different companies and apps and things at that time, and it was going pretty well. But I kind of had this urge and also was hearing from our clients of these social media apps like Twitter and Facebook. What are these things? Again, it’s 2008. So Facebook is still closed to college. Twitter, basically no one is using it. Like YouTube is nothing. There’s a panda rolling around video. That’s it. And I remember walking into my closet, seeing all these shirts and being like, why am I wearing all these companies and not… like I’m paying for the shirt that I’m wearing these companies names around? And so it just hit me. I was like, oh, this could be interesting. I could wear a shirt with a company’s name on it. I could promote them on these social media platforms where people are starting to put their attention, and I could create things, photos, videos, tweets, messages around those things and get paid for it. And so, essentially, through a bunch of different chats with friends and mentors and random people on Twitter, I came up with this idea of iwearyourshirt.com, and I was going to wear a different shirt every single day in 2009, starting with the price of $1 on the first day, $2 on the second day, $3 on the third day. So you’d pay face value for the day of the year. And the whole idea was I would wear your shirt on the Internet and promote it on social media.

Caroline: And this is before influencer marketing is even…

Jason: Doesn’t exist.

Caroline: Years before it’s even thought of. But what I think is so interesting when I look back at the timeline of everything, is, like you said, this is 2009, 2008, really. So at the time, the only thing that you’re starting to see is maybe a few businesses starting, like, a Facebook page or a Twitter account as the brand.

Jason: I remember…

Caroline: You don’t have normal people talking about brands and getting paid.

Jason: Oh, no, I remember iJustine and Jenna Marbles. And these were people that were starting to get on YouTube, or maybe they were on YouTube at that time, but they had no idea what they were doing either. They were just like, I like technology. I’m kind of a goofball. Like, I’m just going to share some things.

Caroline: And they’re certainly not doing paid…

Jason: No.

Caroline: Brand integrations.

Jason: Not at all.

Caroline: It’s just creating content.

Jason: And I think it’d be really funny to like… I don’t know if I justine has ever done an interview. For those of you who don’t know iJustine, she’s like a very famous YouTube personality who lives in the technology space, and she’s been around forever. Like, literally started before I did, and I feel like I started super early. But I really wonder when she made her first dollar on YouTube and what was it for? Was it for a paid kind of, like, integration/ brand deal? Or was it like when AdSense started and she started to make money because there were ads in front of her videos?

Caroline: I would have to imagine it was ads first.

Jason: I think so, too, but also as I started to do what I did.

Caroline: That’S like a totally different model, right? That’s not the I Wear Your Shirt model of like, I’m a brand and I’m paying to be associated with this regular content creator. It’s more of like, oh, it’s more of an ad placement than a sort of integration.

Jason: Now that I think back about it, I’m like, was anybody literally getting paid on YouTube for anything other than AdSense?

Caroline: So you’re wondering if you were the first brand sponsorship, basically?

Jason: Right.

Caroline: Maybe.

Jason: I mean, I’m not saying that to toot my own horn. I already had my one humble brag of this interview.

Caroline: It’s more of like a, Oh, maybe I was.

Jason: More of a curiosity.

Caroline: Anyway, we could do some research. We’ll have our producer research that.

Jason: Dr. Swanson.

Caroline: And to fact check.

Jason: Dr. Swanson’s got us.

Caroline: What I’m more…

Jason: What was your question, though?

Caroline: I just wanted you to give context so people now know what I Wear Your Shirt was. But by the time you and I met in 2010, like Spring of 2010, so I Wear Your Shirt had been… really, you’d been doing it for a year and a half at that point,

Jason: I was famous at that point.

Caroline: I am interested in this idea because you were many famous, I would say.

Jason: Right. Yeah.

Caroline: By that point, by the time we met, you had been on CBS Evening News. They had done a spot on you.

Jason: Yeah, that’s when I’ve been on everything.

Caroline: You had been on New York Times. You had been on everything. And we had a couple of interactions where you would get recognized, literally, and that felt kind of weird. But I’m curious from your perspective, we don’t talk a lot about what that felt like, the visibility of it, the acknowledgment of it. And I’m curious about at the peak of I Wear Your Shirt, when you tasted this little dose of an E list celebrity…

Jason: Yeah, I used to say Z list celebrity. So you’re giving me way more credit.

Caroline: Yeah, I don’t think you were E.

Jason: Twenty more letters.

Caroline: I think that was generous. I would call you an L list celebrity.

Jason: Okay. I got dropped pretty far there from E to L.

Caroline: I’m just being honest.

Jason: All right. Can I be H? How about J? Is J lower than L? Great. Now I don’t even know the alphabet.

Caroline: J is the two spots before L. So I’ll give you J. For your name.

Jason: I’ll be a J list. Yeah, exactly.

Caroline: Jason. You’re a J level celebrity.

Jason: Better than Z for Zook.

Caroline: I’m curious, what were some of the… for people who will never experience that, what were some of the good parts about that? And then what were some of the shitty parts about that?

Jason: Yeah, so I got enough notoriety that sometimes I would be walking around and someone would recognize who I was. Like, if you remember when we were in Durham, North Carolina, we were walking through Tobacco Road, which is like a very outdoor dining space thing, and we literally walked by a restaurant and someone yelled, like, T-Shirt guy. And said hello.

Caroline: It happened to us another time in Durham when we were eating sushi. Do you remember that?

Jason: I do, yeah.

Caroline: I think it was like the person came up after. They were like, Didn’t want to bother you during your meal. I’m like, I’m not Brad Pitt.

Jason: But also, thank you. When you hear of celebrities that get hounded, so I had just the right amount of that that really tickles your ego because it’s just like it makes you feel so good that someone recognize you for a thing…

Caroline: A stranger.

Jason: That you did. So that was definitely a very fun part of it because it’s like…

Caroline: You feel important, right?

Jason: Yeah, for sure. It’s like everybody grows up wanting to be rich and famous and, like, all of these…

Caroline: Certainly of our age.

Jason: Yeah, for sure.

Caroline: Now, I think there’s enough.

Jason: A little bit of like, oh, yeah, that’s not…

Caroline: But I think still, probably, because I think you’ve seen people throw it on that statistics of, like, 80% of kids now want to be YouTubers, and I think that’s what they want is, like, fame, right?

Jason: Yeah. So I think, honestly, looking back, I think I had just like the perfect amount of quote unquote celebrity. Just enough where some random people would see me. And I’ll tell you, one of the funniest things that happened at that time that made the biggest jump was I was on an interview for maybe it was like MSNBC. And they syndicated that interview through Jiffy Lube and like, this network that’s in, like, if you’re ever sitting in a waiting room of a place where you’re waiting for your car fix or your dental office or whatever, and there was, like, a looping. Like, they don’t do it anymore because now they just like, with streaming services, it’s easy to set up. But that wasn’t a thing back then. Literally, the amount of people that would say, like, I saw you in… it was a Jiffy Lube waiting for my oil to get changed because it ran on loop constantly there, I guess. And it was probably like an interesting story that they just… So I’ll never forget when it hit Jiffy Lube was like… it was like a whole other level. It was like, I would get more emails, I would get more notoriety. And the good thing was it never got to a place where I couldn’t go out without… We could still go to the movies or whatever and no one would know.

Caroline: You never felt like your privacy was invaded?

Jason: Never. So that was probably like one of the best things because it just made you feel good. Like it really did. Am I glad that it’s over? And do I love anonymity now? Absolutely. I don’t want to be recognized by anybody.

Caroline: Well, that’s what was going to be my next question is, do you feel like having a taste of that, though, makes being more anonymous that much sweeter? Because you never hit this place where you can’t go back. I think of this now of some celebrities who kind of not… I know overnight success is a very rare thing, but someone who had like a viral song or something like that, and then they just got propelled and we watched the Lewis Capaldi documentary, and I’m like, Lewis can never go back, right? There is no more anonymity, ever. And I imagine for a celebrity, that would actually really freak me out psychologically because you can never undo it. And so you’re in the rare position where you only made it to J level, and so you went back. And so what were some of the crappier parts about it that now maybe give you more gratitude for being anonymous?

Jason: And again, I only had a small taste of it, but just like some of the negative commentary and DMs or messages or emails or that type of stuff of people feeling like they have some type of say or opinion in your life. The funny thing is, now everybody deals with that. If you’re on Instagram, you don’t have a private account, you’re getting those messages.

Caroline: Everyone’s a mini-celebrity.

Jason: You have probably gotten some type of form of that in some way. But ten years ago, that was only happening to a small handful of people or, like, actual celebrities, A, B, C, D and other list celebrities.

Caroline: Tell me about that experience of, like, do you remember the first time you got a negative comment, or do you remember the early days of that?

Jason: Oh, yeah, Digg.com.

Caroline: Okay.

Jason: So I had a story. This was actually the very beginning of I Wear Your Shirt, but Digg.com is basically what Reddit has become, but early on. And it was just a different version of that that Kevin Rose started and then ended up getting sold and moved on. And there was a bunch of other things too, but there was a big kind of the face of the Internet, like, what’s going on?

Caroline: Right. It’s like, what’s popular on the Internet today?

Jason: Exactly. And so someone posted I Wear Your Shirt there. And a bunch of people just were like, this is the stupidest idea. This guy looks stupid. Why would anybody pay this loser?

Caroline: They always go to the looks.

Jason: Always. Yeah, that’s what people do. People who are hurt inside, especially from superficial commentary in their lives, then project that on other people. So at the time, I did not have the foresight to understand why that was happening. I was very angry about it. But I also, weirdly, was too busy to worry about it.

Caroline: Interesting.

Jason: Because I had to film a video every day for YouTube, which I had never done before. So I had to operate a camera. I had to edit it, I had to upload it. I had to record a live video show for an hour. I had to engage on Twitter and Facebook. I had to take photos on Flickr.

Caroline: This is every day without a break.

Jason: Every single day. Every single day, 889 days straight without a single day off. 889 days.

Caroline: Filming and editing a video, plus doing a live show every day.

Jason: There’s a reason why we can’t stay consistent on YouTube, and it’s probably because I just had PTSD from filming 1,600 videos. And I don’t mean to belittle PTSD in any way whatsoever. I understand that it is a true trauma response. But when we go to edit a video, I feel a certain negative way toward that process. That will probably never go away because I did it 1,600 times in five years. You do anything that takes a certain amount of stress that much, that fast…

Caroline: Well, I definitely do want to dig into the toll that that eventually took on you. But let’s get back into the comments for a second because I’m really interested in this. This is something about your personality that I actually want to learn from. So I’m glad I brought you to this interview today because you, now fast forward to current day, you do have this ability to sort of not care what people think about you. And as someone who really does struggle with that, I’ve gotten better over time, but it’s not my nature. I am just curious about maybe some lessons I could learn from you. So there was a time where you did care.

Jason: I think I cared, but not to a point where it derailed me for too long.

Caroline: Do you think this also even goes way back to the high school thing, where, yeah, that hurt in the moment, but that was your sort of ground for thickening up your skin, because, again, going back to the ways that your brain adapted in order to protect you, it goes, yeah, kids are going to make fun of me. Kids are going to say X, Y and Z about me, but if I let that take me down, I’m not going to survive this. So I got to come up with ways to thicken up my skin. Do you think it goes as far back as that?

Jason: I think so. I think it goes back even further to being an independent kid and having to entertain myself. I’m not trying to please anybody else.

Caroline: Interesting, you don’t have this feedback loop.

Jason: I have no dynamics that I’m trying to juggle. I have my own dynamics that I’m trying to entertain and to do something with. That’s it. So it’s like I think, and I heard this on a recent podcast. I think it was our friend Michelle Rohr’s podcast, where she was talking about people pleasing stems from as a child. You were trying to make everybody happy and you were… all this family dynamic stuff. I didn’t really have that.

Caroline: Interesting.

Jason: I mean, I did have a tiny bit of it, but I really rebelled against it when it got to like, beyond eight years old.

Caroline: You have this unstable, I mean, family unit, right?

Jason: Yeah, for sure.

Caroline: It’s changing all the time. So it’s not like you are falling into these well worn grooves of making everybody happy. And that’s so interesting. I never thought of that. Of kind of your independence and kind of loner thing where it’s like, you’re not getting into this feedback loop in a social circumstance where you’re going, oh, the way that I succeed is by forming myself because it could have gone that way for sure because you’re adapting. It could have gone like, oh, I’ll people-please because this is the only way I can survive.

Jason: Right.

Caroline: But you went the other direction, which was like, my only way of survival is to actually not play this game.

Jason: It’s to entertain myself and to know that I can work through this on my own.

Caroline: Which is very similar to what we discovered about your brain’s reaction to conforming and norms and stuff. It’s like it could have gone the way of like, okay, the rules are always changing, but let me adapt myself, let me be a chameleon, let me fit in. And your brain just was like, this is a losing game. Maybe it’s like your efficiency brain in you where it’s just like, this is actually a very inefficient way to fit in because it’s going to always change. So why not just establish that foundation right out of the gate and validate yourself?

Jason: Yeah, and I mean, truthfully, anybody who has published anything on the Internet that has commentary on it, it has had any type of growth or actual numbers to it. And let me quantify that. So let’s say you make a YouTube video and it gets 100 comments on the YouTube video. I mean, even probably like 20 comments is enough. Probably 19 of the comments are like, this is great, great job. I love what you did. But you have that one comment that’s like, your head looks stupid and you’re like, great, cool. Can’t fix the shape of my head, but thanks so much for saying that. But then you can’t stop thinking about that one comment, right? And I think what happened for me over time, especially with I Wear Your Shirt because I’d never done anything publicly up until that point. The only public thing I’d ever done was play sports with other people. You’re in a group, it doesn’t really matter. But I remember getting enough of those comments, of the Digg.com commentary, like YouTube comments, people randomly messaging me on Twitter, whatever. All these things would happen. And it’s just like one after the other, you just go like, none of this matters because you know what? I have 100 other people who are super happy with what I’m doing. And honestly, I think doing the live show every single day, that’s literally one of the best things anybody could do to sharpen their skills in dealing with people, especially people on the Internet, because a lot of days it’s not fun. Like you did a lot of those live shows with me after joining my life and being a part of the I Wear Your Shirt thing, and you probably remember what it was like. Some days it was just, like, so amazing and there’s so many fun people who are there that you’re chatting with, but some days it’s like you get a couple of trolls in there and it really derails you. But you got to figure out how to deal with it. And so I just constantly figured out how to deal with it. So fast forward all the way to today. If we get a negative comment or a negative email, it bothers me for literally a fraction of a second. And I’m just like, I don’t care.

Caroline: Well, it’s going back to what you were saying about your brain just goes, I have work to do. I’m not going to let this derail me. Like, I got to get back to work. And I think that is an incredible quality because I struggle with that a little bit. Like I said, I’ve gotten better. But I watch the way that you can just handle things, and I think it comes from being so sure of yourself. And when I do feel that way, when I feel like it gets to me too much, I remind myself to just be more like you in the sense of to validate myself.

Jason: Right.

Caroline: It’s like if someone said something and it made me feel like, oh, I said the wrong thing or I’m not a good person or whatever because that’s my soft spot. It’s like saying the wrong thing or hurting someone’s feelings or something and being a quote unquote bad person. But I just go to myself. Like, how do I see myself? What do I think about myself? Do I know that I try? Do I know that I care about people? Do I know that I’m compassionate? Like, yes. And so then I just go, okay, then I just have to chalk it up to a misunderstanding. If there’s something to learn and do better next time, I’ll do that. But a lot of times people just want to be angry at you and that’s okay.

Jason: Oh, for sure. And honestly, one of the things that I learned early on was like… and that’s what I said about the Digg.com commentary is like, it’s 99% of the time, it’s always about them. And what I found, too, is I would just start to write back to some of these people.

Caroline: I remember you used to do this in the YouTube days of when we were still doing I Wear Your Shirt.

Jason: It would be email YouTube, whatever. I just write back, I’m sorry for whatever’s going on in your life that you felt you needed to say this. That would be my go to response. And when people would write back, because most of the times they didn’t, they would say, like, I’m so sorry that I wrote this. My sister was having a really bad day. We got some bad news and I just took it out on you. And it’s like, yeah, see, it wasn’t about me. This is totally not something that I can control. And so I’m just not going to let it wear me down and get to me. And again, that is easier said than done. And for people who I think grow up in a family dynamic where they have to be people-pleasers and keep the family together, quote unquote, that’s going to be much harder forever because it’s just ingrained in you to do that. Whereas for me, it’s like, I just need to figure out a new game to play with my Battle Beasts, which is just like, as a kid, you just move on. Like you just do it.

Caroline: It’s going back to what I was saying, it’s a losing game. So it’s like if you take the practical route, you almost are like, yeah, you’re better off figuring out who you are and deciding that’s enough because the other way, the people pleasing way, is it is a losing game.

Jason: Also, I should have said Micro Machines or Lego because that would have really like… more people would have understood that. Battle Beasts was this, like, tiny little figurines. They were like little characters. I mean, I do love them, but literally no one knows what they are.

Caroline: Before we move on from I Wear Your Shirt, that era, let’s talk about the downfall, if you will. I don’t want to dig in too much because, again, there’s lots of commentary about that. But do you think at the heart of it, it was trying to grow too fast?

Jason: I think it’s a couple of things. I wouldn’t change any of it because it’s shaped who we are today and we have the life we have today because of those decisions.

Caroline: Absolutely.

Jason: But I think in an alternate reality, I wish I would have done I Wear Your Shirt as, like, a vlog channel, but no one knew what vlogging was. What’s funny is I made fun of vlogging in some of my videos because it was a thing that no one was doing yet.

Caroline: So give people context to how you think your content was different than just a vlog.

Jason: On I Wear Your Shirt, I was making skits and commercials. So I was, like, trying to tell a story of, like, Good Life Granola is the one I always go back to because I can always remember it.

Caroline: Yeah, you’re basically making these low budget commercials.

Jason: Totally.

Caroline: It’s all about the brand.

Jason: Exactly.

Caroline: Not really about you. It’s just you’re kind of the actor in the thing.

Jason: I would do, like, a blind taste test of, like, five granolas and, like, could I pick out the Good Life granola there? I would go to the grocery store and I would secretly put Good Life Granola on the shelf even though there’s no skew for it and it couldn’t be sold. So I just think it’d be funny. It’s the thing to do. You know, it’s just like that or, like, going into the kitchen. Like, I visited Michigan where it was made, and, like, I watched them make it, and, like, that would actually be kind of vlog style.

Caroline: Do you know what’s kind of funny, though? All of these ideas. Now that I think about it, all the videos are actually what are now usually the 15 to 30 second…

Jason: Pre rolls.

Caroline: Not pre rolls, like, brand integrations.

Jason: Oh, yeah. For sure.

Caroline: So if you watch, like, our friend Matt D’Avella, if you watch his videos, he’s doing a video about something else that he wants to do, and then there’s 15 to 20 or 30 seconds about Squarespace, right?

Jason: Exactly.

Caroline: And he’s thinking, how can I highlight Squarespace in, like, a unique way?

Jason: Making a website for his biceps.

Caroline: Yeah, exactly. But you’re taking the 30-second ad and you’re doing the whole video that and so nobody is falling in love with what your actual content is.

Jason: Exactly. And so, looking back, I wish I would have just done more day in the life, but no one was doing that. So it was, like, impossible for me. All I thought of at the time when I was doing this was like commercials. Commercials are on TV, they feature brands. Now I’m going to make commercials on YouTube because that didn’t exist.

Caroline: Well, but here’s where I do think you only… I do think you ultimately did make the right decision for the business because, again, at the time, one of the only value propositions that you had for people to pay $300 or when it got more expensive, $600 for a day of advertising was, Okay, but at the end of it…

Jason: You’re going to have a commercial.

Caroline: You get a commercial, you get a video asset that you can use.

Jason: For sure.

Caroline: And at the time, people’s video presences weren’t getting big enough where you could sell the value of that.

Jason: 100%.

Caroline: But maybe there came a point where maybe you could have pivoted, right?

Jason: Yeah. And I think it’s like the companies wouldn’t have understood why a day in the life video would matter, but I think what they would have seen over time is my viewership would have gone up. I think all time viewership of all videos on the I Wear Your Shirt YouTube channel was like 15 million views last time I looked, which is nothing to sneeze at, but with 3,000 total videos on the channel, I made 1,600. And then I had hired people that made videos. That’s not a ton. There are channels that have like 20 views.

Caroline: Who wants to go watch…?

Jason: A bunch of commercials.

Caroline: A bunch of commercials.

Jason: Yeah. And at the time, though, people did.

Caroline: They did because it was new and it was different.

Jason: But it’s like, looking back, I wish I would have gone the day in the life thing because I think more people would have been more attached to that. And what’s funny is when we got towards the end of I Wear Your Shirt, I saw that coming. And I remember when we were at like a team retreat, I was like, guys, we need to feature your day in the life, whatever. But I didn’t really know how to do that myself in a compelling way, so I didn’t know how to teach them how to do it either. So we just never kind of got there. But yeah, the real thing that happened with I Wear Your Shirt was I think all of the video commercials kind of ran their course. I think I got really tired and burnt out from just working every single day forever and ever and ever. And so I just was running out of energy to manage things. I definitely tried to grow the business. So it was just me the first year, two people, the second year, five people the third year. But by the third year, I also needed an operations person to help manage the other people, to help make sure all the T-shirts were arriving at our different houses, to deal with all the inbound information and requests and sales opportunities and sponsorship deals that were getting done.

Caroline: You had a girlfriend that was mooching on your money.

Jason: I was wondering where you were going to go there. Mooching on my what?

Caroline: On my what?

Jason: What am I mooching on? But I think it was the perfect storm of all those things and just not a sound business model, to be honest. Like, the calendar pricing mechanism of being small at the beginning of the year and growing throughout the year, that’s great in theory, but when you have to pay people’s salaries, their salaries don’t get paid like that. Their salaries get paid. Hey, I get $3,000 every month in January. But as a business, the business only made $1,000, but I had to pay $15,000.

Caroline: Which could have worked had you maybe had someone who had an eye more on the cash flow.

Jason: Totally, 100%.

Caroline: But it was so early in your business career that you don’t know those things.

Jason: Yeah.

Caroline: So I Wear Your Shirt ends. You decide to shut down the business because it’s just not making enough money. At that point, you’re in debt, which we talked a little bit about on…

Jason: The last episode.

Caroline: The last episode about money. What was the hardest part about the ending? Was it…?

Jason: Ego.

Caroline: It was the ego.

Jason: 100%.

Caroline: The hit to your ego.

Jason: You go from being on every Jiffy Lube TV out there.

Caroline: It was really just the demise of the Jiffy Lube celebrity.

Jason: The Jiffy Lube celebrity. The J List.

Caroline: Oh, the J List.

Jason: Oh. Perfect. There are already people who will listen to this…

Caroline: Your next memoir is going to just be called the J List.

Jason: Yeah, it was ego. I mean, it was 100% like, I went from a person who was getting featured on all these news outlets, and hilariously enough, in 2013, I had then done the Buy My Last Name project for the first time. So that had its own notoriety of me auctioning off my last name. And that getting talked about everywhere again. But it was this idea that I was the T-shirt guy. For five years, I had built up this persona, and people knew me for this. And all the stories that were being written about it were the guy makes half a million dollars a year from wearing T-shirts. Yes, the business on paper brought in $500,000, but we were upside down. We were in the red every year because expenses were too high, and I didn’t know how to manage money, and I didn’t know what I was doing. So it’s like it looked good on the surface from the outside, but it was all crumbling from the inside. And so yeah, when it ended in 2013, it’s funny because I think you were telling me that someone talked about this idea of the last. I had no concept of what my last video would be. I didn’t even say… There was no goodbye video. There’s no goodbye video on the channel. I thought about that the other day. I think my last uploaded video was a question for Gary Vee. And like an Ask Gary Vee thing. This is 2013. This is ten years ago, though. This is like pre Gary Vee getting super famous.

Caroline: That’s so funny.

Jason: And it’s like, I think about it now, I’m like, man, I didn’t even get to say goodbye. It all crumbled. And it got to a place where we had $124,000 in total debt and I just felt so overwhelmed by all of it. I had let employees go. I had borrowed money from family. I felt like I was letting you down. I felt like I was letting our best friend Sean down, who literally moved to Florida to work for my company. And at that point, I was just like, this sucks. I just feel like a complete loser who couldn’t hack it at this. And now I look back and I have a completely different outlook. I tried the thing and I nailed it for a while, but I also didn’t know what I was doing. And I learned a ton of lessons. They were expensive to learn, but they taught me so much about what we do today. And I think that’s why I say I don’t regret that. I wouldn’t change that. It’s who I am. But I do wish that I would have tweaked it in a couple of different ways just to see if I was way early on the whole influencer thing and social media marketing thing. And there probably would have been a big business there with like a big exit opportunity and all that, but that doesn’t really matter.

Caroline: Yeah, after… you said after kind of the Buy My Last Name, because that came after the end of I Wear Your Shirt. But you still have these little projects… not little, but you still have these projects that are kind of keeping the ego alive. But there comes a point where money is not coming in. Tell me about that time period. Did you ever actually have this real fear of like, oh, how are we going to pay bills?

Jason: Oh, yeah, all the time.

Caroline: You did? All the time.

Jason: Yeah, especially when all the credit cards were maxed out when I was like, oh, I literally don’t… at least, when I Wear Your Shirt…

Caroline: How do you move forward in that? When you’re in that place?

Jason: You just do whatever you can. You take a speaking gig here or there because it’s like, when you hear this, you think like, oh, well, who’s going to pay this entrepreneur to come do anything? Like his business failed. But from the outside looking in, everyone still saw all the greatness of this. They still saw the story. Maybe they see the fall of it ending. But again, there was no big goodbye. There was no big send off. It just kind of like trailed off, which is maybe a good thing because that’s how we were able to scrape by for the next two years.

Caroline: And you think that everyone knows exactly the ins and outs of your failures, but people are busy with their own thing. Even half the people that probably hired you didn’t even know it ended.

Jason: Even in 2015, people are like, oh, you’re still wearing shirts? I’m like, I haven’t worn shirts for two years. That’s a whole different… that’s dead to me. I’ve sold three different weird things since then. So I think it was just being scrappy. It was just doing anything that I could. And honestly, that’s where the online course stuff started. So it was 2013 when I cobbled together the Sponsorships course, and it was 2014 when I was still doing speaking stuff. And then that’s also when I wrote Creativity for Sale and did the Sponsor My Book project, which brought in $75,000, which was enough to keep us going, plus the sale of the last name. So it’s funny, it’s like on the surface, I Wear Your Shirt shuts down. I have no opportunities, but I sold my last name for $45,000. That was a good chunk of money. Then I did the Sponsor My Book Project, where I did a different sponsor in every page of the book. That was $75,000 in that year. So it’s like we still made $100,000 from my ideas in that year, not including speaking gigs, not including some course sales.

Caroline: Okay, here’s what I want to…

Jason: Here’s what I was just going to say. We both know how shitty it was at the time, but when you look back, you’re like, but hey, you’re still making over $100,000 a year. It’s just like it didn’t seem super positive at the time, I think.

Caroline: Totally. And none of it was sustainable, right? It was these one off ideas that really just came through at the last right second. And so it felt like we were clawing our way through it all. But yeah, in hindsight, you look back and you’re like, okay, you were making it happen. But I just want to dig into this for a second because I do think it is valuable. One of the most valuable things you ever taught me and I think changed my life in terms of… is just this idea of there’s money out there. If you have to make money, it exists out there and it’s up to you to go out and figure out how to get it. And I know that sounds really like hustle-y bro stuff, but I just mean from the sense of, if you’re struggling and you don’t know how you’re going to pay bills, you really open my mind to this idea of you don’t get what you don’t ask for. So you have to be able to get out there and withstand rejection in order to have those opportunities come to you. And so I wanted to ask you if there’s any advice that you could give people about coming up with Sponsor My Book or speaking gigs for… You would be asking people to pay you $15,000 for speaking gigs and I’m like…

Jason: You’re a failure. I’m kidding.

Caroline: How are you sending this email? I don’t understand. So if there’s any tips about… or like your first course, like this Sponsorships course for $500, it’s like you’ve never had that voice in your head that says, this is too much money to ask for, where I think a lot of us do. And so what helps you in those situations where you go, oh, I’ll ask for this?

Jason: I think it starts with, I sold a thing for $1 on a day. Then I sold a thing for $2. Then I sold a thing for $3. I asked for nothing in the beginning for my work, and eventually… I didn’t start out going, pay me $15,000 to do this Buzz Time Beers and Trivia tour that we did, where we had a branded car and we drove around eight cities and we showed up at these sports bars and we got paid like, 30 grand for this integration, basically. That was the fourth year of doing this. In the first year, I got paid a dollar. Then I got paid $2.

Caroline: That’s so interesting.

Jason: And I think what happens for anybody listening to this who’s trying to build their own thing is they go, Well, I got to make $5,000 this month. It’s like, okay, well, good luck. I literally don’t know when you’re just getting started. You can if you’re super scrappy, you can figure it out, but it’s really hard. What’s not so hard is to make $50. You can make $50 pretty easily. Then you can make $100. Then you can make 250. Then you can make 500, and it can go up from there, and that can take time. But also, in my public speaking trajectory, and I think anybody who’s done paid public speaking has seen this trajectory as well, you start out by making zero. Then you get your first time of someone being like, oh, do you do charge for public speaking? You’re like, Do I ever. $500. And someone’s like, okay. And you’re like, oh, my God, I just got paid $500. That’s amazing. And then years go by, and you’re like, okay, well, I want to do this less, but someone’s still asking me for it. So I’m like, well, the number that I would want is $5,000, and there are people that get paid so much more. But I’m like this person’s asking for my time. I don’t necessarily really want to do this anymore, but I have a track record of being good at it. I’ll charge this amount for it.

Caroline: You have leverage at that point.

Jason: Exactly. Totally.

Caroline: That’s such an interesting answer.

Jason: Which is why, when we were walking to that movie theater that one day, and we got that phone call, and I told that person it’ll be $18,000 because that was the price that I was willing to do it for, and I did not want to do it. I didn’t want to go.

Caroline: It was a long flight.

Jason: Like, I Wear Your Shirt was literally coming to an end. We were at the worst of the worst of the time for that business. And I was like, this is the number that I would do it for also because we need money and I just don’t want to do it. And so they were like, yeah, sure. I’m like, great. I probably should have doubled that. And then to come to find out, like, I go there and Anderson Cooper is the keynote speaker. They clearly had a ton of money to spend on speakers.

Caroline: Anyway, I’m so glad we’re doing this because that’s an answer I never would have expected from you. I always think of you as this guy who… I always thought the answer was like, you just have something I don’t have, which is that…

Jason: Like, the confidence.

Caroline: The confidence to ask for it. But your answer is so true, and it’s just that you’ve sold more things from the beginning, from zero.

Jason: You know what I don’t have? I don’t have blind confidence. I have earned confidence.

Caroline: Yeah.

Jason: There’s a huge difference. There’s a huge difference to…

Caroline: I’ll throw out a number.

Jason: What’s up, bro? $20,000. Pay me. There’s a difference to that. It’ll be like, Why? Where’s that coming from? As opposed to me, where it’s like, I made a dollar, I made $2. I made $3.

Caroline: And because of the experience, because of you doing every step of that journey, $1, $10, $50. Then it’s a speaking gig for 1,000. Then it’s a speaking gig for 5,000 because you’ve put in the hours of experience, you also know that it’s possible because you’ve done it. And so then you can ask for $18,000 because you know you’ve had a speaking gig for 15, so why wouldn’t they do 18? Whereas people want to come in and they want the shortcut to asking for the money, but they don’t even have the real earned confidence or the earned data or the skills to be able to go all signs point to, I have this value. This person even has the money to pay me that, and I have the courage to even ask for it because I’ve practiced the courage 10,000 times by now.

Jason: Yeah, I mean, this is what we talk about all the time. If someone’s listening to this podcast, and they’re like, I’m pivoting my career, or I’m starting over, and I want to design Squarespace websites. It’s like, great. Design as many as you can for $250 a site. $100 a site, whatever you can do. And your answer to that, if you’re the person listening this is like, oh, well, that’s not enough. I can’t pay my bills. You’re not going to get paid more. We live in a time now where good graphic, Squarespace designers get paid 15, $20,000 to design a site because they’ve made 500 sites, and they started out at $200 per site five years ago or ten years ago.

Caroline: Right.

Jason: So it’s like everybody, nearly everybody, has to earn that confidence and has to earn their price value.

Caroline: Right. Now, I have some random questions.

Jason: Okay.

Caroline: This one’s kind of selfish.

Jason: Sure.

Caroline: Because it’s about me.

Jason: Yeah. Okay.

Caroline: So you and I met in 2010, and we started working together basically at the end of 2011. But really…

Jason: Are you talking about when you were doing my lion makeup?

Caroline: No, that was for free. That was just pro bono.

Jason: That was mooching.

Caroline: You were mooching on my makeup skills.

Jason: This was true.

Caroline: But I’m curious, as I’ve never asked you this before, if there was ever, like, a moment where you suddenly realized that I liked business as much as you did, or, like, creativity or, like…

Jason: Oh.

Caroline: Was there a moment where you were like, oh, she actually likes this like I do?

Jason: Yeah, for sure. So when we met, you were working, or you were in college, and you were running the Advertising society, and you were helping with this nonprofit idea that I had. That’s how we kind of got together. That nonprofit idea was a bad idea, fizzled out, and then we just kind of kept talking as friends. Then we started to date, and we met. I saw a spark in you, like a creative spark, and you wanted to go in advertising and everything, and I think we had… You were savvy in social media, for what you knew.

Caroline: I DM’ed you, so you knew I was on Twitter.

Jason: You… all lowercase text, which…

Caroline: Just to be young and flirty.

Jason: Different, better than uppers and lowers that’s hard to read.

Caroline: I’m just, like, not super serious.

Jason: Yeah. FoxyGal16.

Caroline: HazelFox, thank you so much.

Jason: HazelFox, HazelBaby. It wasn’t until I think you worked in Durham at the ad agency, and we would talk about I Wear Your Shirt and whatever. Then you moved back to Jacksonville, and you worked at the agency downtown. And then I think because every day we were together working on I Wear Your Shirt together, you were helping me come up with ideas. And that’s where the creative spark that I saw that first meal at Cruisers where we shared fries and you wanted to pour ranch on the fries, and I said, Absolutely not. Keep your ranch on your side.

Caroline: I still dream about that ranch.

Jason: That I think is where I really saw, like, oh, wow, you have a whole set of skills strategically, creatively, that this is awesome. I knew there was a spark there, but that, I think, was the real turning point was when you were putting on my lion makeup, but you were so much more than that.

Caroline: For a video.

Jason: You were like, well, what if you did this? Or, what if you did this? Or what if with this company, you thought about this? And I’m like, oh, this is amazing. This is so helpful to have a person who can support me. And it’s why having a co-founder is so great when you’re starting a business because you have someone to bounce those ideas off of. So does that answer your question?

Caroline: Yeah, I like that. That was just selfish. I was just like, I don’t know.

Jason: And then it just went downhill from there.

Caroline: Right.

Jason: No good ideas.

Caroline: No good ideas. I really thought you had something there, but…

Jason: We just had three business ideas in the last week.

Caroline: And I really want to do that one. You know which one I’m talking about, but I really want to do that.

Jason: Can you pull your mic down a little bit or sit up?

Caroline: You know I…

Jason: I know you drift. You’re a drifter. You melt.

Caroline: We talked about it on a podcast. I melt.

Jason: You melt into the couch.

Caroline: I have poor posture. It’s fine. I’ve made peace with it. I have some random questions.

Jason: Yeah, that’s fine. We’re rounding down here where this is like the rapid fire round.

Caroline: Why do you think…?

Jason: You do this every interview, right? What do you call this? Every interview, you do this.

Caroline: The round down.

Jason: This is the round down.

Caroline: Yeah.

Jason: The round down round?

Caroline: The round down round.

Jason: Round down round.

Caroline: Okay.

Jason: Yeah.

Caroline: I do it every episode. My loyal listeners will recognize this as the round down round.

Jason: The Cinnamon Rollers?

Caroline: Yeah. I call them the Cinnamon LOLers, actually, on my podcast.

Jason: There you go. I was wondering if you were going to remember that.

Caroline: So why are you so good at remembering details about people? How do you do that? You remember people’s names. You remember like, this is why you’re the community manager in our business because I love people, but your superpower is so much better than mine in terms of my brain cares so deeply about people that it won’t almost let me make that many connections because I will just care too much. But you’re really good at knowing a good amount about a lot of people.

Jason: Yeah, I don’t think I have a good answer to this.

Caroline: It’s just a superpower.

Jason: I think it’s just a thing that I’m very fortunate to be wired in a way where I can do that because doing the live video stream shows with I Wear Your Shirt, it just came naturally to me to be like, oh, Frank, you live in Arizona and you live with your girlfriend and whatever. And then like, oh, Digi, like, you live in Atlanta…

Caroline: Do you think that the live show helped cultivate that skill?

Jason: 100%.

Caroline: Do you think it’s there to begin with?

Jason: Yeah, it’s both. So it’s like there’s a tinge of it that’s there to begin with and I have the ability but then that superpower kind of got honed over time where every day I’m in a live stream and it’s like I’m building neural pathways to remember things about people.

Caroline: Do you think that you have so much more room in your brain for other people because you…?

Jason: Compartmentalize all this other crap? Sure. Probably. Black boxes.

Caroline: Black boxes for the win. We talk a lot about, like, we mentioned it on the podcast sometimes and our WAIMers in our community will know that we lovingly refer to you as a robot just because you are so… compartmentalization.

Jason: Childhood trauma.

Caroline: Childhood trauma. And you have this ability to just like you’re not at the whim of your emotions the way that maybe I am.

Jason: I’m not at the whim of my emotions, period.

Caroline: Period. But I wanted to ask you, what do you think you would say is your greatest challenge that you face now on a daily basis?

Jason: My greatest challenge that I face now?

Caroline: Do you feel like you encounter any obstacles throughout your day? Emotionally, psychologically? It’s okay if the answer is no. I’m not trying to lead you here. I’m just genuinely curious about what your inner world is like.

Jason: Yeah, for sure. I mean, I think our having kids is a challenge, and that’s mostly just because I just have this real push and pull of giving up this life that we made for ourselves.

Caroline: Yeah. Losing your freedom and flexibility.

Jason: I get it. Kids are amazing. Love them. Like a whole new set of experiences you’re going to have. I get it. But I really have this difficult time letting go of this version of my life that feels like we have worked so hard to, if we’re just being honest, live a dream life. I get it. I am fully aware that we live a dream life by our standards, by other people’s standards. And to see that that’s going to change when we have kids, genuinely, it keeps me up at night. Not because it’s like, I don’t want this to happen. It’s just because it’s like a loop that my brain has created where it’s like, you can do anything you want in a day. All the things are great. You can do anything you want in a day. All the things are great. It just keeps going around forever.

Caroline: I feel like you’re, like, focusing because you know that it’s going to change. It’s like your brain can’t help focus on the fact that it’s almost, like, ending.

Jason: Yeah, it’s that it’s almost ending. And it’s also that like and we’ve talked about this. I don’t have a lot of great examples because I don’t seek out this content. So it’s hard for me to even know where to find it, of like…

Caroline: Positive parenting examples.

Jason: Positive parenting and parents who… Listen. I know that a lot of people listening to the show are like, I live a good life with my kids and I love it. Yeah, but you don’t have a YouTube channel. I can’t watch you do that. And I don’t want to watch celebrities with kids because that’s not going to be us. So it’s hard for me to find the examples. And again, this is just where my brain works. This is the way my brain works, where it’s like it just wants the examples to rebel against them, but also to be able to see, like, I don’t know anything about this and I’m perfect… I’m not scared at all about being a dad. I’ve had a bunch of father issues growing up. I know I’ll be a good dad because I know what not to do. I know… maybe don’t leave.

Caroline: For starters, stay.

Jason: Just stay. Be loving, don’t be abusive. All these different things.

Caroline: Wow, babe. You’re like…

Jason: I’m nailing it.

Caroline: You’re starting off on this thing…

Jason: Dad of the Year. Give me the mug ahead of time. But anyway, I like to see how things are done so that I can see, like, okay, great. I want to pull this from that, or I don’t want to pull that from that.

Caroline: And there’s this trend now happening, which I think is overall a good thing, which is people are now talking about the hard parts of being a parent. Right. But now it’s like…

Jason: It’s, like, too much, though.

Caroline: It’s like, swing to the other direction, where those of us who are yet to embark on that chapter, we’re like, okay, but there’s some of it’s good, right? But I think…

Jason: Besides just the photos you post on Instagram.

Caroline: Yeah, I’ve told you this before, which is I think there’s a couple of things happening, which is, first of all, from my perspective, I think all of the cons of being a parent, like, all the hard parts, are very easy to talk about. It’s like the sleep deprivation and, like, the way that you can’t just pick up on in a moment’s… Like, these are all things that are very tangible things to talk about, but it’s all the positives are completely intangible. It’s like experiencing a love like you’ve never known, having the joy, being able to see you and your partner in another person. All of these things are so almost transcendent beyond this human experience that it’s hard to make a YouTube video about the depth of my joy because my kids came along. And so it’s a little bit of a lopsided kind of…

Jason: Scale.

Caroline: Scale in that way, but I totally understand that, and I think it’s interesting that you said that as your answer because I didn’t know you thought about it on a daily basis in that way.

Jason: I mean, every day I’m making coffee in the morning. I’m like…

Caroline: Really?

Jason: Yeah.

Caroline: Babe.

Jason: Because I’m like, this is going to be different. Right now, it’s uninterrupted pure enjoyment of a craft. I’m measuring it out. I’m swirling the water, doing whatever. But there’s going to be a time where there’s, like, crying happening while I’m doing that.

Caroline: And it makes it less peaceful.

Jason: And I’m like, this needs to go faster. I can no longer take eight minutes to make my coffee every morning. And again, I’m not trying to say it’s all doom and gloom. I’m just answering the question honestly that this is something that I think about. I know it’ll be fine. I know the transcendentness of children and their ability to become D1 athletes and get huge signing bonuses will really make me happy.

Caroline: At the point where they can go get you something from the fridge, that’s cool.

Jason: Get dad a Bud Light. All right.

Caroline: But do you think that?

Jason: We need to do a lot more episodes on kids.

Caroline: Oh, no. This feels very vulnerable for me. But I do think it is valuable to talk about because you don’t get a lot of people who are in our position, which is we’ve waited longer to have kids, and I don’t think people are honest about what the journey is to come to that decision as a couple. And so I appreciate you for sharing that and being vulnerable in that way of letting people into what those fears are. But my last question about that is, instead of kind of dreading when that chapter is over, when you can no longer…

Jason: Do whatever I want?

Caroline: Do whatever you want. Do you think that there is something about the finite nature of the chapter? Like, oh, I know that there’s only going to be this amount of time in my life where I’m fully free, that makes it more sweet, that makes you able to appreciate it more. I know this is a weird kind of comparison, but it’s like us knowing that we’re going to die one day makes life that much sweeter because we know it will end and so we value it while we’re here.

Jason: Yeah, I think there’s definitely someone to that.

Caroline: And I just wonder… I wonder if there’s a way for you to reframe it in your mind where you go, Yeah. It’ll be different in the future, but for right now, that’s what makes me appreciate…

Jason: Yeah. And that’s what I’m trying to do for sure.

Caroline: Yeah. Is just use it as like lens for gratitude.

Jason: Yeah.

Caroline: My final question that I would like to ask you, sir, for joining on my podcast is would you consider yourself someone who plans for the future?

Jason: Would I consider myself someone who plans for the future? Yeah, I think so. I think a few years ago, I wasn’t, but I think now definitely more than I was.

Caroline: Like, how far out?

Jason: Think like five to ten years.

Caroline: You know what our lives are going to look like in ten years?

Jason: Well, really because what this boils down to is like we’ve talked about this. We didn’t talk about it in our Money episode, but this was like another part of the Money episode that I was going to kind of go on a longer thing about is like, I see Teachery as our retirement fund.

Caroline: Right.

Jason: And we’ve talked about this, so maybe you see it the same way as well now, where it’s like the next couple of years we want to focus on growing Teachery because it is a product that has the potential to be sold to another business. WAIM really doesn’t. I mean, as much as we could get creative and maybe and whatever, it just feels so tied to us that it just feels difficult to do that.

Caroline: As it should be, right? I wouldn’t want to just…

Jason: Right. Teachery is… Like I could see maybe there’s like a WAIMer who really loves WAIM and there’s an opportunity for them to they also do some type of business coaching or I don’t know. We haven’t even really ever thought about that. It’s just kind of been WAIM’s going to be what it is for as long as it is. But Teachery is really the thing that we invest time and effort into, we really start to put focus into and selling that becomes our retirement fund so that in that sale, that’s kind of like, we never have to work again.

Caroline: Right.

Jason: And so I’ve been thinking about what that timeline looks like, and if that timeline is ten years, I think that’s the conservative timeline. I think five years would be the aggressive timeline. And I don’t even think it’s really realistic in five years, but I’ve just been kind of thinking that.

Caroline:: Lot can happen in five years.

Jason: Exactly. And also, now that we’ve moved to Portugal, I have thought a little bit further out because it takes five years to earn citizenship here, and that’s not even a guaranteed thing that could happen. But now that we’re here and we love it, I’m like, yeah, I could see myself living here for five years and learning the language fully and completely and being able to go anywhere and feel super comfortable being able to talk with anybody in Portuguese, and then also just being able to take more trips around Europe. There’s so much more of Europe that we haven’t seen yet that I want to see. And then obviously having kids, starting to think about what does that look like? And I also, trying to take care of ourselves a little bit more as we start to get older and investing in decisions now that will hopefully make us more well abled 60, 70, 80 year olds.

Caroline: See the episode on us talking about getting older.

Jason: Yeah, exactly. Right. I think that’s it.

Caroline: Yeah. I just was curious because I think in the past, you and I have had conversations about how the way that your brain works. It’s often like, I can only focus on kind of what’s in front of me. But I think as you get older, your lens has widened a bit, and you’re like, okay.

Jason: And also I think a little bit of is just like having predictable income creates space to be able to think about the future.

Caroline: True.

Jason: Whereas from the 2000…

Caroline: You’re just thinking about next month.

Jason: 2009 to 2016 years, it’s like, I don’t even know how I’m going to make money next year.

Caroline: It’s all so unpredictable.

Jason: Yeah.

Caroline: That’s a good insight as well. Well, thank you for coming on this podcast.

Jason: That’s the round down round.

Caroline: That’s the round down round. And learned some new things about you.

Jason: Wow.

Caroline: I put some pieces together.

Jason: Do you think anyone’s going to like this, or do you think they’re just going to be like, wow. This guy.

Caroline: Well, Jason, I learned that I don’t need the validation.

Jason: Oh, nice.

Caroline: I don’t care.

Jason: Okay, great.

Caroline: Let me just try to say the words. I don’t care what anyone thinks about this episode. Just kidding.

Jason: Well, it’s not you getting asked questions, so it’s probably a lot less.

Caroline: It’s true. No, but I am still self conscious about my interviewing ability.

Jason: I think you did a great job.

Caroline: Oh, thanks.

Jason: As people who watch lots of interviews and podcasts and things, like it’s one of the main pieces of content we consume.

Caroline: You would watch this episode?

Jason: Yeah.

Caroline: And listen to it?

Jason: I think you did a great… Well, not for the guest, but for the interviewer, I’d be like, I want to see that interviewer maybe chat to Childish Gambino. If you get Donald Glover to sit down with you.

Caroline: It’s just my interviewing roster is you and Donald Glover. That’s my dream.

Jason: That’s it. Then that’s over. That’s the end.

Caroline: That’s it. I just retire.

Jason: Who would be your final interview?

Caroline: Who do I actually want to interview? Who would be my final interview? Taylor Swift.

Jason: Yeah, that’s what I thought.

Caroline: And I’m embarrassed to say it.

Jason: I think it’s probably…

Caroline: Because I know people are judging me but if I’m answering authentically, who I would like to interview, it’s Taylor Swift.

Jason: Okay, great. All right. Thanks for coming out, man.

Caroline: Thank you so much for coming on the show. And thanks to our sponsor, we don’t have one yet.

Jason: Tune in next week for my side of the interview table.

Caroline: Are you going to do a round down round?

Jason: That’s your show. I got my own show.

Caroline: Okay, cool.

Jason: Okay. Bye.

Caroline: Bye.

Carol Interviews Jason!

(Big Fat Takeaway)

In this interview, we talk about Jason's early life and career. We share how rejecting convention can lead to more creativity and freedom.

IT IT

This article written by

Jason Zook

(he/him) Co-head-hancho of this WAIM thing. I used to wear t-shirts for a living, now I just wear them because I'm not a nudist. You can usually find me baking things, watching JCVD movies, and dreaming of living on an island.

Continue the conversation:

Now What?

Join “Wandering Weekly,” a newsletter to help you live, work and create with more intention.

Each Monday we’ll visit your inbox and share a lesson we’ve learned on our own entrepreneurial journeys. We keep it real and aren’t afraid to be vulnerable, honest, and 100% transparent when it comes to working for yourself.

Wandering Aimfully Through Our Podcast: What is it all for?

Pros and Cons of An “Invisible” Business

Listen to our full episode on Pros and Cons of An “Invisible” Business below (with full transcript) or find our podcast by searching What is it all for? in your favorite podcast player. Five Key Takeaways for Pros and Cons of An “Invisible” Business 1. Have a “Core Content Stack” Our articles, email newsletters, two […]

Wandering Aimfully Through Our Podcast: What is it all for?

Jason Interviews Caroline!

Listen to our full episode where Jason Interviews Caroline! below (with full transcript) or find our podcast by searching What is it all for? in your favorite podcast player. Five Key Takeaways from Caroline’s Interview 1. Working for myself is my greatest accomplishment When I hear the word accomplishment, I tie it directly to a […]