Gabe Dunn

September 27, 2023

[Ep. 374] Breaking Bad Money Habits with Gabe Dunn

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Hello!
I’m Jessica and I’m a money expert, speaker, Accredited Financial Counsellor Canada®, host of the More Money Podcast, and am currently writing my first book with HarperCollins Canada (2025).
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Welcome back to the More Money Podcast and the premiere of Season 17 of the show! To kick things off, I’ve got New York Times best-selling author, podcast host, actor and filmmaker Gabe Dunn on the podcast, who you may already be familiar with from their popular book and podcast Bad with Money.

In this episode, Gabe shares their personal finance journey from navigating private school as a lower-income kid, to studying at an elite college accruing mountains of student debt, to working an unpaid internship that got them further into debt to afford food and rent, to eventually becoming one of the most honest and vulnerable voices in the personal finance space today. Not only does Gabe openly share the mistakes they’ve made and lessons they’ve learned along the way (so you don’t have to repeat them), but they also share the raw truth about managing money with bipolar disorder and the real costs of transitioning especially in the midst of losing health insurance due to the WGA strikes.

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Transcript

Jessica 

Welcome Gabe to the more money Podcast. I’m so excited to have you on.

Gabe 

Thank you for having me. Nice to see you again.

Jessica 

Yeah, nice to see you again. It was such a treat to be on your podcast talking about the difference between the US and Canada and finance so I’m thrilled to have you on the show to talk more about you your amazing book bad with money and just what’s going on what’s what’s been going on since you really Use the book a lot has happened. I also just like listened to your like, love you just dropped podcast episode about what you’re dealing? Oh yeah. You know you’re what I think is so great about you is you just you’re very honest and real and unfiltered and I think that’s not what you see often in personal finance it’s all through a filter lens of Look at me I’m perfect. Well, fans really just not the reality.

Gabe 

Thank you. I feel I feel horrible. I felt I’ve been like so stressed out since it dropped like so stressed.

Jessica 

I’m so sorry. I literally almost like how can I help? Do I know someone who’s a lawyer that will work pro bono? I don’t Oh, my God. We’ll get into that in a little bit. But yeah, I hear you. It’s that’s not a fun. That’s not fun. But I know. But so what I absolutely love right in the get go of your book was you trying to get I don’t see this a lot in lots of books, you talked about your kind of family background and how, you know, growing up in a certain way with your parents and how they managed money and talked about money and thought about money, how that had a huge impact on you then managing money as an adult. And probably still today, I’m very influenced by my parents. Everyone’s very influenced by the environment that they grew up in. And it is hard to sometimes learn and unlearn things. So I wanted to kind of start there, because I know your book is bad with money, which sounds, which sounds like you’re so you need to be nicer to yourself. But I think part of it is like that is a common saying that I hear people saying like, Oh, I’m just bad with money. So do you want to kind of share when you had to start making some financial decisions for yourself? And I guess that really started when you were planning on going to college? You know, what was kind of the reality of the situation like, oh, there’s some costs involved? And you know, should I which college should I go to and all that kind of stuff.

Gabe 

I didn’t know anything, I didn’t know anything about money. I didn’t know any like that loans would have to be taken out that they would be X amount of loans, that there was a chance you wouldn’t be able to pay them back right away. I very much I was so I was like gay in Florida, which now everyone sees is bad. But the time nobody really

Jessica 

Florida’s had a yeah. I mean, it wasn’t great back then.

Gabe 

So this was like, the 2006 is when I graduated high school. And it wasn’t like great for gay stuff. I wasn’t like out or anything. And, and so I knew that I wanted to leave Florida and I wanted to go to like a city in the Northeast. And I also wanted to study journalism. And there was a program in Florida called Bright Futures where I could have gone to, like University of Florida for essentially free. But I was so nervous about being gay in Florida and not being able to come out. And I was so nervous about like the prestige of where I was going, that I really wanted to go to like a good quote unquote, school. And I got a scholarship to Emerson. And so I decided to go there are also because I didn’t get into North Western, which was my first choice. But like, that would have been so expensive. Emerson was expensive, but it was it was like still half tuition, which was good. But I had no concept like nobody sat me down and said, Oh, the loans are going to be X amount. And here’s how you could possibly pay them off. And here’s what happens if you don’t pay them off. And all these things like I talked about in my book, that my little sister when she was 18, she went to go get a neck tattoo, not not irresponsibly, like was in honor of a friend who died. But you know, sort of, she was like, I want to get neck tattoo. And the guy at the tattoo parlor was like if it’s your first tattoo, and you’re also 18, I’m not tattooing your neck, and that person showed more care for an 18 year olds future than any loan person ever did. And so I think about that a lot in terms of like, what we normalize and what we have allowed, like young people to do. And I think like, I think that, at least for me, my parents really believe in me, really wanted me to succeed. They we don’t come from like a wealthy background. So to them, they were like, well, you’ll be an investment, we’ll push you forward, we’ll have you like, you know, go to this good school or whatever. Because I had always done really well academically, and I think they they just want they don’t want to have negative feelings, I think is what I’m realizing like, they love a good time. They love like being able to do stuff they don’t, they never sort of let they never let us know about money and then they never sort of let money be an impediment to like, things that they wanted to do. So my parents would be very confusing because they would somedays be like hey, let’s go out let’s do this. Let’s get this you know, like, be very spendy and then the next day they would be Like, what have we done? We can’t buy anything. This isn’t this is a disaster. And then when I, as a kid would remember, I would say, hey, remember yesterday, when when we spent all that money? That might be why there’s problems now, they would be like your kid Mind your business.

Jessica 

Wow. Yeah, it was very confusing.

Jessica 

I guess were you then did you adopt some of those habits when you were an adult? And sometimes you would just splurge and then sometimes you’d really regret and it’d be really hard on yourself. And then it was kind of just a back and forth of, you know, guilt, shame, but then oh, treat yourself or, like, yeah, yeah, cuz it’s interesting, as I’ve talked to a lot of people over the past year researching for my book, I’ve heard a lot of similar stories. And it’s just, if you have mixed messages, the lesson you’re going to learn is, you know, just mixed, you’re not going to have a straightforward path.

Gabe 

Yeah, I mean, I think, you know, I grew up in an addict and an alcoholic home. And I think that that also leads to impulsive behavior. You know, I have bipolar disorder. I think that there was a lot of I still grapple with this, like, life is short, who cares? Like, everything, none of this is fair, or makes any sense. Or like, I don’t want to sit here and doing like, be doing paperwork my whole life, like, you know, all of this stuff that would then lead to sort of carelessness. Like, with my first job, I didn’t check the box for tax deductions, or, you know, which like, is that fair? That that’s a thing that’s allowed to happen?

Jessica 

No, I feel like you have, at least for any job I’ve ever had, it was automatic. That was ever a choice. And that should not be someone’s choice, especially when you’re like in your early 20s. No idea what that checkbox means.

Gabe 

And I think like I just, I still do deal with wanting to say fuck it and do whatever I want. I think you know, when you when you have someone in your life, who’s an addict, the highs are high and the lows are low. And I I thought maybe that I was imagining some stuff. And when I went back to write my book, I went and read my journal from eighth grade. And I didn’t really even notice how much in that journal I wrote about money, even though it didn’t seem like I was, like, I had entries where I would be like, my mom just took my sister to the mall, they came back with all these bags. I don’t know how we’re going to afford this. Like, they asked me if I wanted to come. I was like, No. And then it became this running joke in my family. Oh, gave like a worrywart gave, never wants to go shopping, gave never wants to spend anything like we would go out with like my aunt and my mom, and my sister would buy like five things. And they’d be like, Do you want anything? And I would always be like, no, no, no, no, because I knew that she was getting stuff. Or like, even now I grapple with, or, like, taking any sort of gifts or money from them. Because I, you know, my sister did and my oldest brother did. And I want to be the one who, you know, I’m like, calculating in my head. Well, they don’t have any left for me. So my sister now has a she got promoted. So her job I think, is much better. She’s a much better place. But yeah, like, I think there was a feeling of like, okay, I I’m doing the math here. And I think that I should just kind of bow out of this situation. But that didn’t. Yeah, but that didn’t really happen with with school, I justified it because I was like, Okay, I’m going to school. But I just never I made that decision myself to not engage with it. Because I don’t I just I just suspected something was wrong.

Jessica 

And I know there’s a part of your book, you talk about having you being part of a improv troupe and having a boyfriend, he was the one who said, Why do you still have a bank account that’s connected to your parents? And I think a lot of people probably have systems that are set up like that, actually, my younger sister used to, and I’m like, why is mom still have access to your bank account? She never took money out. She would just put money in. But I’m just like, that’s kind of weird. We’re almost 30 Why is that happening? You should be independent. Yeah, I thought that was so interesting. Because, you know, having that connection kind of still kind of ties you to that place, maybe making it difficult for you to move forward and be more independent. I don’t know, what was your experience, like? And then you obviously did, you know, get your own bank account.

Gabe 

I think stuff comes with ties, like my sister is much closer to my parents than I am, I think because she, like we’re different in the sense that like, if there was a leak at her apartment, she would call my dad. Whereas like, I always am like, what is he going to do? from miles away? Call your landlord. Yeah, like what? But like for a lot of people my age, I see them even you know, I’m 35 I still see people be like, Oh, I got a form in the mail. I’m gonna call my mom. And I’m like, it’s weird. What? But it’s not weird. I guess you have like a good relationship with your your parents. And like, that’s fine. I have a good relationship with my parents, but like, I just don’t, I just don’t call them when I get something in the mail. And my sister you know, still does it. And so and my co host, I think my co host of my podcast, who’s my age a little younger, was still like, gets a form and calls her dad like interest. Yeah, no. And my mom is a lawyer. So there have been like legal things that I’ve run by her, but not just on the on the premise of being my mother.

Jessica 

It’s like, she’s a lawyer, the lawyer, she probably knows this. Yeah.

Gabe 

But, um, but yeah, so I think I just, I started realizing that I needed independence. And they didn’t really like that at first. And it was a real uphill battle. Because when I got my own bank account, they were they were furious. And they’ll probably say they weren’t, but they were. And then when I wanted to what was the other thing I did, oh, I got my own, I went on my own phone plan, I removed myself from the family plans, logical, you know, they were mad. And then it started to be when I would go home to visit, I started staying at Airbnb or hotels instead of staying with them. And that was like, a whole rigmarole like a real problem. And I think sometimes for a lot of people, parents are like, well, as long as we have access to the money, we can control you in some way. As long as we’re giving you money or taking money, or whatever it is. But then it’s like, it’s a process because it’s like, okay, it’s part of me is like, if your parents can give you money, just take the money, like, I get frustrated with friends of mine, who but like, I get frustrated with friends of mine, who I’m like, you’re rich, like your parents could just give it to you. But then I’m also like, but I understand some times that like, especially with friends of mine who are queer or trans, it comes with a lot of strings. It comes with, you know, my, my parents gave me like a little something to pay off a credit card, which I’ve just I used to really worry about where the money was coming from. I’ve just stopped asking, like, if they’re doing crimes or doing crimes, it’s not my business, but not your problems. It’s not my problem, but or whatever they’re up to, I don’t know, I used to really worry about what they were up to. And now I’m like, it’s, it’s none of my business, but they’re not doing crimes, but you know, something’s weird. But anyway, so they, so but, you know, they did say on the phone, they were like, Okay, our caveat is when we text you, you have to write back. And I was like, right, and that’s fine.

Jessica 

Like for that, not unreasonable. But still, like, it’s not, it’s not a gift at that point. Then you’re like, well, it’s we’re doing this so we get something too? Yeah.

Gabe 

And that makes total sense. I mean, I had a, I always think about in Gilmore Girls where she has to go have dinner with her grandparents in order to go to that school. Like, that happens to a lot of people and like, I get that and like, of course, like how do I know if I was a grandparent? I wouldn’t be like, well, I want to see the kid I’m paying for you know, like, I get that. So I don’t know it. It was really hard to disentangle. I think too. And I mentioned this a little bit in the book, I think, is like we’re Jewish family. And I think with ethnic families, there’s a bit of a difference in the idea of the collective and like, we are a family this is the family. And so if you like leave, you know, the family plan or you move away or you whatever it’s very like, but this is the family.

Jessica 

Why are you leaving the family? It’s like, I’m gonna leave and family just leaving the phone plant. Yeah.

Gabe 

Or everything is, is everybody’s or like, why, you know, we talk about everything we do every you know, it’s very, it was seen, when I started to pull away and do my own thing. It was very, it was seen as like another me sort of being difficult.

Jessica 

And you’re like, I just want to grow and do my own thing and explore. And

Gabe 

I mean, definitely, like things have changed. But in the very beginning in in early 20s, it was very much like games, a worrywart games, like doing all this stuff, and trying to be independent from us for no reason and wise gave difficult and that kind of thing, which I think a lot of people have come up against.

Jessica 

I think that’s, that’s a really common and another thing too, it’s, I mean, I really enjoyed it, it really brought me back to some of the things that, you know, I experienced in my 20s especially was, you know, when you did that, you know, free internship and that is, it’s becoming less I think of a thing now, but back when, yeah, you know, I’m only two years older than you and like, that was a big thing, free internships. And for me, I’m like, I was telling my husband listen, I’m like, I can never, I was never able to do a free internship I have to pay for school. So my parents let me stay at home for free, but I had to pay for school and pay for everything else myself. I couldn’t afford to do a free internship that was you know, kind of a luxury and privilege and you kind of vase with that. You’re like, Well, I really want to do this. And it seemed very financially difficult and the things that you had to do to make it work just you know, sell clothes and all this kind of stuff. You realize this really is not fair. This is just like getting into college. A lot of the people that you went to school with super smart couldn’t go to college because of the ridiculous cause. Yeah. Well, I thought that was a really important thing that you mentioned in your book is just like it isn’t the same playing field for everybody and their systems that are keeping the rich, rich and the poor where they need To be,

Gabe 

There’s, um, with the internship, it’s now illegal. So I think with, with Viacom where I was working, they ended up getting sued years later. And they were for not paying interns. And that became there were laws that got instance, that got instituted that changed a lot of that. So like, the programs and stuff that I went through, would not, I think are not the same today. And some people sued and got like back pay, I think. So. It was, yeah, it was like peak. What like 2008. So it was like, peak, like, You should be grateful to be in New York, you should be grateful to be doing this internship. It was like peak, like media being seen as like, really cool. Or whatever. Girls was on HBO, you know, it was like, or whenever girls came out afterwards, it was very, when did girls come out? It was like, like, I remember, I feel like I just find out oh, and 2012. Okay, so 20 jobs. So I was I was living in New York, solidly. And like there was this idea of like, the glamour of being an intern or being an assistant or working your way up living in a shitty apartment. But then they weren’t really shitty, because on TV, they’re not but gorgeous. Yeah. But it was very, it was like, shameful if you couldn’t do those things. And so I really wanted to do, I really wanted to do all of that. And I thought that that was the key to succeeding. And I also was a very, it was the height of the Daily Show, which is where I did my internship, I was extremely obsessed with it. I had written like an essay in high school about how I wanted to have my own daily show type show that gotten into like, best teen writers of 22,006, or whatever it was, you can have called authors of tomorrow, you can find it still. It’s very embarrassing. And, and I, and so I this was like a dream job. But they were not going to pay anything. And so I went to New York, and I just blew through everything I had made that year. And I just wasn’t prepared for it at all. And I ended up Yeah. I like.

Jessica 

Do you regret doing it? Like, are you glad that you went through it? Or because I know part of you talking about the book, you don’t know if it it could have helped your career? Or maybe it wasn’t even an element? It’s you’ll never know.

Gabe 

I will never know. But I do think people saw the Daily Show on my resume and got excited. I think so. I mean, I think you know, it’s interesting now, like I worked on a show for Netflix. And I’ve done a bunch of other things. But a lot of times when people are like, What have you done, and I list stuff, when I list that show, people are like, whoa. And that’s like something I did for like eight months in 2018. You know what I mean? Like not, like, that’s not even a blip in my career. So I think like, it’s unfortunate that these big name, things sort of do latch on, you know, people latch on to them, and then they give you credibility, even though it’s like, not necessarily my biggest job. So that was the lawyer, right? Is that they could say that and I could, I could work I could be like, Well, I have to work here. I have to work here for free. I have to. And I was like I mean, I talked about in the book, I had like no clothes for the job, really. I was like got shoplifted from Urban Outfitters, which I guess I still stand by. But yeah, that was, that was not great. And like, just had a bunch of I tried to sell a bunch of stuff. And I think I like Pong, some stuff that I really wish I hadn’t. But I like go through that every few. I mean, I don’t know if it’s bipolar disorder, or if it’s scarcity mindset, or trauma or what but every so often I I think, I don’t know if it’s a manic episode, but I do sell everything I own every periodically.

Jessica 

Am I like, I don’t know if I’ve ever done that before.

Gabe 

I get really nervous about not having enough money. And it does happen obviously. Like we alluded to my situation now my quote unquote divorce which is fucked me up heavily financially. And so, yeah, like, I’ll go I would like go through phases where I would sell all my books, or I would sell I would like sell all my like, I’d be like, What do I need this table for sell it or so like there was, you know, things in New York and then there’s the scene that I write about where I’m trying to sell my I was like, a thing that they an alarm clock, but it was also an iPod. Yeah. And I was like walking through New York and it’s really hot. And I was walking to the pawn shop, and the bag broke and the speakers fell on the sidewalk and broke and I just that like broke me.

Jessica 

Oh, yeah, that sounds like it’s like an episode of it.

Gabe 

I just, I just like cried because yeah, I mean, still to this day, the thing I cry about most is money for sure. Number one.

Jessica 

So even now, like you, and I know you kind of touched on this in the book too. And this is I think a big problem we see is, you see the outward facing, like looking at your resume and just like you have a Wikipedia page, for God’s sakes, it has all these amazing things. And so from the outside, you’re like, Oh, I know, you have like all these followers and stuff like that. And you’re like, yeah, it doesn’t necessarily equate to wealth, having all of these things listed. And I think a lot of people, especially when you’re on like social media stuff, you see someone Oh, someone has a, you know, a lot of followers. Like, I feel like I was watching something and yeah, I was talking about that. It’s like, oh, you assume this person has 200,000 followers on Instagram, they were they have a lot of money. And they’re like, no, no. And that’s kind of the problem, because then it’s harder for you to talk about. Yeah, you talked about in the book where, you know, you can get you were doing what was it? One where we don’t have that in Canada, but it’s like you you deliver people’s Oh, post eight or something, post mates and we don’t have posters here. But you were doing that to make some extra money. And then the fan saw you on the street, they’re like, Hey, can I get a photo? And you’re like, Oh, my God, I may not make money from post mates if I’m late. And that’s the reality. I think people get this idea that if you’re, you got some fame that you’re doing okay. And you’re like, No, we all got, you know, shit going.

Gabe 

And people come from different financial situations, my co host who I did a lot of stuff with. She’s very transparent about her family being wealthy, which I do appreciate. And she, we would get paid the exact same thing. Let’s say we both get 50k for something. Mine would pay off a student loan, and she would get to keep hers.

Jessica 

And you’re like, so this is how you are easy. You know, it’s easier for you to build your own wealth compared to me, because I’m starting under 50k. Like I’m in debt. And you are starting in the black, which is fine. I want to talk. Yeah, which is fine. It’s a reality. That’s the prop. That’s the reality. And that’s also why it frustrates when people were like, just work harder, or just do this XYZ. And you’re like, we’re not starting in the same place. But I want to talk about that. 50k, because you mentioned in your book that that was life changing money. And I think a lot of us, especially you know, if you’re a bit older, I’m reaching FUBU. There’s been a couple of times in my life where it’s like, that changed, that changed everything, like I always earned very little at all my corporate jobs. But then I got this one job. And it was like $15,000, more than I was earning. And literally, I remember calling my husband and be like, you won’t believe my salary was $56,000 in this new job, like, you’ll never believe how much I’m earning. And he’s like, we’re rich. Remember that? That was life changing. Because before that I was earning like 30 or $40,000. And just really, really just having a rough time of it. And for you, you were able to sell a pilot of the show, which is so cool. And you got $50,000 And you’re like that changed things. You want to kind of talk about what that experience was like?

Gabe 

I mean, we Allison, I sold a show. It’s funny, because it’s like, oh, you sold a show. You sold a book, but the money gets doled out over a year. So it actually kind of ends up being like a 50k. Yeah, actually. So like it gets doled out over the course of like, you know, the time or whatever. But, yeah, it was huge. I paid off my student loans. And I think I started a little retirement at that time, maybe. And that was like, you know, I think getting out of debt was like a huge, huge thing. Not that it’s been like smooth sailing or whatever. Like, you know, obviously things go back and forth. But that was like a start to being able to have more than just like 50 bucks in my bank account at a time. And I didn’t really have guidance around it. So I think I would have i What happened was like lifestyle creep, where I moved. I like went to I like went fucking Great Gatsby. Like, I moved, I started throwing parties like, it was so like, what, like, I just felt like, I don’t know, I felt like I wanted to like, I was like, now I can have a better life. I want to have a better life. But like, I didn’t think about saving, or I didn’t even know what investing was. I really never even thought about it. Yeah, I just kind of wanted, I wanted the things that other people had.

Jessica 

That’s literally everybody. Like we look at people all the time, and we’re comparing ourselves and we just want better.

Gabe 

Social media is hard because I think things are not real. And as you said, like, there was that guy who was talking about how he was on the red carpet for being in the bear that showed the bear and he was saying that he was on the red carpet for being in the bear And he didn’t have like 20 bucks. Which Which character was I can’t remember it was a it was a it was a thing where he was talking about the strike the bear actor, no money. Was that what I would do?

Jessica 

That makes me sad that that’s a Google I know. Yeah.

Gabe 

Oh, writer for The Bear SORRY, right.

Jessica 

I feel like I, I saw that. I think it was, yeah, I read that or he saw that online or something about it’s like you think that the successful show and I think that is an incredible show. I love it so much, right? And you think everyone would profit off it and do well?

Gabe 

It’s a writer Alex O’Keefe, who wrote for the bear. He was like, on the red carpet for the bear. And he didn’t have any he was living below the poverty line. And so I think there’s like a lot of stuff where like, you can see these photos. I’m seeing it now. It’s kind of interesting. I’m my feed is almost entirely people who are at New York Fashion Week. And I’m wondering if they if any of them have money. Does that make sense? Like I keep looking? Yeah.

Jessica 

And being like influencers, or whoever’s going to New York Fashion Week, and like that, it’s gotta be expensive, especially you have to dress up and all that stuff.

Gabe 

I’m like, maybe I could go like, is it better? Here’s my thing, Jessica. Yeah. Is it better for me to have pretended, and not done the podcast episode where I talked about what’s going on with me financially? Is it better for me to pretend and to get some clothes and go to New York Fashion Week and take the photos and be an influencer? And show those and be and then people think I’m successful? And then they give me more jobs? Or is it better for me to be honest, not do that, and quote, unquote, fake it till you make it, which I did a lot in my beginning of my career, as it is better to not do that. And to just like, be honest about what’s going on? Because I’m mostly embarrassed. I would rather be posting from New York Fashion Week.

Jessica 

Sure, who wouldn’t? But no, I think there’s, there’s a couple of things there. It’s like, on the one side, it’s like, you’re like, well, financially, maybe it would be better, like maybe this is an investment if I you know, fake a go to New York Fashion Week and stuff, and I can get more jobs. And then then maybe I can bridge that gap with that money. So it’s true, but I feel like in the grand scheme of things, the best thing you could do, especially for your audience who follow you and are like looking to you, as someone that they can really trust. It’s always better to be honest, even if it means leaving money on the table. Like, I know, well, I don’t know this, but I believe part of the reason that I’m probably not as wealthy or as successful, you know, outward facing as it could be, is because I say no to a lot of things that ethically just do not jive. Yeah. And part of that is like, I don’t talk about how much, you know, I’m honest. But I also keep certain things private. And part of that, too, is just like respecting my partner who’s like, I work in music. I work with a lot of people that do not earn a lot of income. And it just is awkward. If you talk about our financial situation, no matter what it is, I just don’t want people to know our business because he wants to also, you know, be just have control over how he sounds respond. Yeah, yeah, exactly. Just as a want people to know, all of our details, and I totally respect that. But I tried to be as honest as possible and say no to a lot of things. And I think it was really, like I don’t think you should be embarrassed. I think it’s really brave for you to be that honest about your situation. Because for me, I mean, I’m like, Oh my gosh, this is amazing. This is we don’t hear enough of this. All I see on my feet is people being like, I made $100,000 this month and I’m like, so that makes me feel like crap. Whereas yours I’m like, I feel seen and I feel like so many other people feel seen and that is how you can start to make change in your life. If you feel like oh, I have a similar situation. Well, I’m gonna follow you would see where you go and I’m sure it’s going to end up in some situation, you know, maybe not how exactly you want it, but it’s going to end okay, and you’re going to thrive after it because you’ve proven so many times you’ve faced so many difficulties and you always come out on the other side.

Gabe 

I think sometimes i You’re just going through it right now so it’s hard to see it. I think sometimes I look at stuff and I go well the bad guys when you know like life isn’t life isn’t fair like a lot of people monetarily you know they do everything right and they still end up in a car accident they still end up you know, something anything addiction, anything like stuff that people go well, that’s your fault. Like, you know, any anything that like it’s not fair, like life happens to people in a way that is just exceedingly unfair.

Jessica 

Absolutely. It’s not about just making choices and doing the right thing and working hard. It’s not It’s like some people will just always have a tougher time and never be able to reach some of those heights that other people are a lot more easily because of circumstance because of generational wealth and all these things that are you know, you can’t control and it’s an it sucks. I mean it bugs me that was it. You know the Amazon guy or whatever he has like a $500 million yacht and like, if this person had more of a moral compass it maybe you’d realize instead he could donate $500 million and change the world but you want so yeah, well, and there’s nothing.

Gabe 

In the US things are not set up. Well, for example, we had a woman episode that came out today with a debt lawyer. And she was talking about how, like, they have to, like negotiate to get things forgiven and stuff. And she was like, Well, you know, I have, it’s up to the creditors, and we don’t know how they make their decisions. And I have people that are like, like, she was like, I have a client that both kids have cancer. And, and the creditors are like, too bad. So sad. Like there’s like not really hardship. Like there’s not the same sort of like hardship, forgiveness as you would think.

Jessica 

No, yeah, it’s I mean, I guess that’s the big problem of in a capitalist society. It’s all about money first, everything else second.

Gabe 

What do these companies need their money for?

Jessica 

Shareholders, shareholders dividends, which always drives me crazy when I see all these like dividend investor be like, This is great. Like, there’s it’s a lot more complex. And then and this is how, anyways, that’s a whole other Yeah, sorry. One other thing I really wanted. Or two other things I really, really want to talk about. Where, number one, you did mention your bipolar disorder, this is something that also is not talked about enough in the personal finance space as if you have some mental health issue or even like a chronic illness or anything that is going to make things more difficult for you. And it is never talked about people just assume oh, no, everyone’s you know, fine. And like, Well, I’ve been doing a lot of research for a book, everyone has something that’s got something. But how is that affected you? And what have you been able to do? Once you were diagnosed to recognize, oh, maybe I’m acting in a certain way. And this is not going to help me if I make this financial decision.

Gabe 

That’s my favorite chapter in the book. Because I talk about the breakdowns that I’ve had and flying to Paris, which I guess is a thing that people with bipolar disorder, love to do is fly to Paris. Just Paris. Yes. If there’s something about Paris, where like, so many people with bipolar disorder are like, I flew to Paris, like, I don’t know what it is. People with mental illness love Paris. So I it’s romantic, romantic. It’s beautiful. Yeah, I got it. And so like, I think getting diagnosed helps me look at whether behaviors are based in reality or not? Like, do I actually need this? Can I slow down? Can I, you know, am I going to really do this? But it’s scary. Because sometimes I do have ambitions and things that I want to do. And I go, am I am I? Is this real? Which is really hard to grapple with? Is this, is this real? Is this something that is going to be a problem in the long run? Like, you know, I’m trying to make this I’m trying to get this movie made? And it’s like, Is that is that? Am I being crazy? Am I being delusional? Is that real?

Jessica 

Are some of the risks you took to succeed in your career? The real one the real question, or was it your bite? Yeah. What made like, yeah, you can do them?

Gabe 

And like, does it matter? And where are they if they came, if they didn’t shake out financially, were they worth it? Because of getting me to somewhere like, I’m not very good at I mean, I always say this. And people say, that’s not true that I’m not very good at being strategic. Like I just have never had whatever people have where they can move through the world in a non emotional way to sort of get things.

Jessica 

But sometimes that doesn’t work. You know, I’m very strategic. And I’m like, I wish I took more risks. I wish I did. You know, I wasn’t too analytical. Because then when you analyze too much, then you don’t do anything.

Gabe 

Yeah, that’s true. But sometimes it’s like, I needed to stop and do things in a more methodical way. Like, every day, I want to go on tick tock and just like start problems. And I have the just not. And that’s hard, and like, I’ve made bad decisions, because I’ve had poor impulse control. And that sucks. And there’s not really any way to like, get that back or come come back from that in some ways, like you just have.

Jessica 

So how do you how do you manage that on a day to day basis? Is it just like something like an act of, you know, practice, you have to do? Yeah, just to be mindful.

Gabe 

It sucks. It’s hard. It’s like not just that it’s not fun. It’s not great. Like, I’m medicated. But like, you know, it’s not like I talked, I’ve talked about this a lot. But people think that if you’re medicated for something, then you’ve like, you just have to stop having the problems. But yeah, like it’s a cure. You know, it’s not a cure for bipolar disorder. I describe it as like a train and the train is barreling and it wants to go down one track, and normally if I wasn’t medicated, it would just go but what the medication does is give me the five seconds to pull the lever and it’s not as though I’m not having the thoughts. It’s not as though I don’t want the train to go. It’s not as though. Like, I’m not like living a blissful, whatever I’m like, just have the ability to pull the lever. And that’s like gives, you know, that gives me time to like, live life, productively or live life, whatever in a way that isn’t distressing to me. Do I always get do I always get to lever in time? No. and is like, so it’s still fighting with your own head. It’s not like, oh, that everything goes away, which I found interesting. Like when I spoke to people with schizoaffective disorder, or schizophrenia, that I assumed I even assumed I was like, Well, if you’re medicated, you don’t see things anymore. And my friend was like, No, you still see things you just know. They’re not real. And I was like, Cool for everyone. Cool.

Jessica 

Gosh, that’s yeah, I mean, I think that’s, that’s it? I mean, yeah. Again, like that is not something anyone talks about, because a lot of I mean, as we becoming a society more aware of mental health. Yeah, no one talks about how that could affect your bottom line. Of course, it can, of course, every decision that we make, you know, has some semblance of some some effect on your financial life. And so how could that not affect that? Yeah,

Gabe 

I mean, I got I got started seeing a therapist for autism. Couple years, last year, a couple years, a year and a half ago, what his time. And yeah, and that I think, is factored into a lot of stuff, too. Because I think with my current situation with my breakup, I think I was very trusting in a lot of ways, because I’ve had a lot of problems in my life surrounding the idea that, well, I’m a good person, and I don’t have bad intentions.

Jessica 

So so why would anyone else which has been a problem, which is sad that that’s a problem, because that’s how we should look at our fellow human. It’s like, I’m good. I’m going to make the assumption off the bat that you were good unless you show me otherwise, but sometimes it’s too far down. You’re too far down, you know, the road to find out, Oh, maybe maybe I go,

Gabe 

Well, why would I like if? If I was to do that to someone, why would they do that to me, but someone else? But it’s like, it just leads to being taken advantage of?

Jessica 

Yeah, yeah. It’s yeah, it’s a cruel world. It’s a cruel world. The last thing I really wanted to touch on, I think this is, you know, something I’ve definitely never talked about on the podcast, I think is important. As you know, you have transitioned your game, when you came out with a book originally, you were, Gabby. And that, again, is something that, you know, I actually have a cousin who’s trans. And something that I always kind of thought about was like, the financial side of things. No one really talks about that, like, obviously, it’s a whole big conversation, but just talking about the financial side of things, if that’s something that you’re like, This is what I want to do, there’s not a lot of support, whether you’re in Canada or the US, not a lot of financial support, if that’s something that you want to move forward with. And so did you want to kind of talk about did a little research on the Canadian side to be like, what is covered? And it isn’t most things even though we have technically universal health care? In the US, what’s it look like?

Gabe 

It’s interesting, because my top surgery was covered. For health insurance, I had to go and get like, diagnosed with like, gender dysphoria, but like, it’s interesting, because I’ve been keeping track a lot more of like, DIY transition stuff. So like, so like, people who have been saying, like, hey, you know, if you’re not going to be able to get hormones in your state, you can order them here. And then it’s like, you know, I’m not saying you should, but this is an information or like, you know, and it’s kind of harkening back to like, early days of, or like people transitioning in times before trans people really visible where it’s this like helping each other sort of underground railroad type thing of like, Hey, this is the doctor that’ll let you do this, Hey, this doctor does top surgery for this, you know, thing or like, people really like coming together and sort of taking care of each other helping each other or if somebody gets a surgery, helping them or, like, so you don’t have to pay for as much, you know, care or whatever. I mean, I went to the store I bought like $300 worth of like bandages and stuff, which I did, like ended up needing, but it was like, other people came through and said, Oh, I actually when I had top surgery I have I used this thing for my seatbelt. That was really helpful gave me that or, you know, so there’s been a lot more of like a community coming together that I think was always there, but now it’s like more visible from so for media. And so, you know, my top surgery was, it was like 10k, it was covered by health insurance, maybe a little more, I don’t know. And then, you know, I’m dealing with losing my insurance through WGA because of the strike. And so when I lose that, that one of the considerations was, well, I want to be able to stay with my gender affirming care, doctor, but Is that does that mean that I’m gonna have a higher, you know, payment per month? Could I go see a doctor who’s a little further away for gender affirming care? But would that how would that timeout with gas versus paying just, you know, so it’s like, like, you know, it kind of dovetails with health care being very unfair and untenable in the US. But yeah, I mean, it depends on what you want to do. Like, my testosterone is covered. For I get it for like 12 bucks. But there was a thing where it was like, I had to wait like seven weeks for it to get approved. And it was a whole rigmarole. And they were like, we can give it to you now for $700. And I was like, very tempted. Yeah. And then I was like, no, and then I, I made a series of TiC TOCs crying about it. But yeah, it was just like, you know, and I was sort of, like, baffled where I was, like, you could just give this to me. Why just give it to me, but like they can’t and then you know, there’s different doctors at different pharmacies are different pharmacists, like, you know, my, I needed a certain type of needle. And it was like, wasn’t prescribed or blah, blah, blah. And this one pharmacist was, like, just handed them to me and was like, go. And like, it’s just, you know, like, depends on who you’re talking to. With name change stuff. That was like some paperwork. I cost me about, like, 625, I think to change my name, like $625. Yeah, and to get the end to get the three certified copies. So it was like for something to change the name and then 150 For the certified copies 50 each. And then I had to go to the bank to get the change. Bank of America did it no problem super easy. There’s certain things that are funny, like Bank of America did it no problem, Marriott bonvoy is giving me a hard time. Like, it’s, you know what I mean?

Jessica 

Like, it’s free, you’re like, bon voyage through.

Gabe 

lt’s like a whole thing. So it’s super funny, like who you are. And then also, it really depends on who you get, like, I went to the Social Security office to get to get a new social security card. And I was in line. And I knew that if it timed out that I got the young woman, I would be okay. Versus I didn’t know about these other people. So I ended up, it timed out that I did end up getting the woman at the young woman at her window. And I knew as soon as she looked at the paperwork and looked up and was like, she was like, hey, congratulations. I was like, Alright, this is going to be smooth sailing. But it’s, it’s you never know.

Jessica 

That’s something to worry about. It’s like, who am I going to get on the phone or at the checkout.

Gabe 

I went to the DMV to get all of that changed. The day after, there was that shooting where the shooter was a trans guy, allegedly. And I went to the DMV. And I was like in line. And it occurred to me like, oh, I should have gone a different day. Because I don’t know what these people are thinking. I don’t know what news they’ve taken in, I don’t know. And ended up being fine, because I got a really nice, well, I got the first time I got someone who turned me away. And I had to go to the Social Security office first, which was fine. And then I came back that and those are the rules. But also like, there could have been someone who would have been like, whatever. And then when I got back there was I had another woman and she was very much like, Oh, this is so exciting. And like was like positive.

Jessica 

So that’s gonna be really difficult, not knowing what you’re gonna get in terms of someone being like, Oh, this is great. Or someone being like, I’m gonna make this really difficult for you. Yeah. And you’re like, it’s already difficult.

Gabe 

Yeah, we don’t know. You don’t know. And they don’t, they might not understand initially what’s happening. Like, they’re, they’re like, Oh, you’re changing your Oh. And then they like, don’t really know. But I did change my gender marker, too. So I think most people understood what was happening. But yeah, it’s just a lot of, you know, little things.

Jessica 

Yeah. Do you think about how I especially, you know, being a woman transitioning to a man, is that you ever worry about is this going to impact my financial future? My earning potential? Absolutely. To look at me differently.

Gabe 

Of course, it absolutely has, of course, there’s tons of I mean, it you get, I mean, I don’t even know where to start, like, hey, best finance books by Women list on Forbes or whatever, right? I’m not on that list anymore. Or brands that I’ve worked with in the past. I see them still working with other people. For like female empowerment financial, which like I totally understand, even like a sex toy company that when worked with me is like, hasn’t reached out. And I’m like, That’s interesting. Like, it’s, it’s, and it’s like, great, but like, it’s funny because there’s never gonna be a list that’s like, best trans books.

Jessica 

Or best personal finance books by trans authors. You’re like, we’re not at that stage yet.

Gabe 

That’s exactly it. And you know, there’s people who I think there was like, a jarring situation with my following which they really, you know, they felt very, some of them. Were going through a similar thing or felt seen other people were like, you were this feminist voice. And now you’re, you know, and now

Jessica 

But you could still be a feminist. Well, yeah, it’s just yeah, they had this idea of you. And they’re like, I’m confused. Yeah.

Gabe 

The brand is not consistent. So it was not, I would say, it was not a people think like, I remember someone saying, like, Oh, now you’re gonna get so many jobs. And I was like, That is not, that is a falsehood that you have been sold? Because you’re becoming a man. No, because you want diversity? And I was like, Oh, that’s gross. I was like, gross thing to say, that’s not that has not been the case at all. Like, it’s not gonna I mean, some movies don’t play in certain countries, because there’s a transactor in them. Yeah. So it’s not it’s not it was not a good business decision.

Jessica 

But it’s, I mean, hopefully, this, I mean, I hope the, you know, the stuff we’re talking about won’t be much of an issue in the future. But it’s, it’s yeah, that’s just even Yeah, you mentioned it, like, when they list books, they are gendered like best. Maybe you don’t really see any list about best books by men anymore. Like see them about women. It’s funny, too, because it’s like even being a woman, I hate how things are so gendered. Because I’ve just been fighting as a feminist. I’ve been fighting my whole life. Like, I’m more than a woman. I’m actually like, just good at fight. Like, like, whenever I meet someone new, they’re like, Oh, so you teach women about money? And like, No, I just happened to be one, right? It drives me crazy. Like, why can I only teach women about money? Because I’m a woman. And I teach, like, I teach pink finance, like. What are you thinking?

Gabe 

Yeah, it’s that.

Jessica 

Yeah, we’re not there yet. But I hope you do, because you still have an amazing voice. And it’s, it’s, it’s insane to me that, you know, people would have a problem with that.

Gabe 

Yeah, I don’t want to discourage anyone from transitioning, but it is. Yeah, it is definitely an interesting new world.

Jessica 

Yeah, I mean, I worried about that with my cousin. I mean, she’s, she’s young, so she’s just, you know, many years, but I was just like, I was really worried. Like, is she gonna have a difficult time finding work now? Yeah. Has, you know.

Gabe 

Could be still I mean, they’re not like allowed to discriminate, but they still kind of are.

Jessica 

They still do! I mean, yeah, they say they’re not supposed to do that on race. And they do so. Right.

Gabe 

Exactly. Exactly. Yeah.

Jessica 

Gosh, yeah. Well, I appreciate you being so candid and honest about that. Because I think, again, people listening, they don’t hear this often, you know, podcasts, but especially personal finance podcast. And I think it’s really, really important for us to talk about some of these things. So I don’t want to keep you much longer. But again, I know you have the book bad with money. You have another book that we have a couple books, you’re also a New York Times bestseller, which is like you have again, the craziest resume Do you want to kind of share anything else that you have that people can check out? And then also where can people find you? You have an amazing YouTube channel? Amazing podcast.

Gabe 

Yeah, I have a podcast with my friend Allison. We do just between us. Then we have I have bad with money, which is my finance show. And I also have a trans guy podcast called the new guys K debut with my friend, a lover. Thank you. And yeah, the second book that came out was called stimulus wreck. And it was through Scribd. And that was super fun. It was like an update to bad with money based on what the pandemic. Yeah, and so yeah, I mean, I’m kind of all over the place. I’m on Instagram at Gabe s done. That’s like where you can find everything and of course, your tick tock. Oh, the place of Gabby Khan. Yeah. Which I not allowed to change because they’ll lose my blue check. So I figured out what to do about that, too.

Jessica 

There’s gotta be someone you know, that’s the frustrating thing is like, there’s gotta be somebody you can talk to you. Yeah,

Gabe 

Like it’s right, though. I know.

Jessica 

Right? Yeah. Well, thanks again for joining me on the podcast. It was such a treat having you on so thank you.

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