How to Get Financially Smart Without the Shame ft. Mrs Dow Jones (Haley Sachs) - CHIT CHAT WEDNESDAY

Summary

The JTrain Podcast: "How to Get Financially Smart Without the Shame"

Guest: Haley Sachs (Mrs. Dow Jones)
Host: Jared Freid
Date: May 20, 2026

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Episode Overview

In this lively "Chit Chat Wednesday" episode, Jared Freid sits down with comedian, financial educator, and creator of Mrs. Dow Jones, Haley Sachs. They discuss breaking cycles of financial shame, approachable money strategies, her new book “Future Rich Person,” and how comedy and finance intertwine. The episode is peppered with personal anecdotes, candid lessons from their New York experiences, and a fun, irreverent tone highlighting the importance of finding your own path to financial security without guilt or jargon.

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Main Discussion Points & Insights

1. Haley’s Journey: Comedy to Finance Guru

• Backstory: Haley recalls her pivot from comedy (doing stand-up, improv, working at Letterman and Above Average) to establishing Mrs. Dow Jones, blending financial literacy with humor for a broader, younger audience.
  • “I was always digital first and then I started in stand up. My first job was for David Letterman ... but then I had my ‘Aha’ money moment.” (09:21)
• Revelation: Her first “real” job forced her to confront finances (health insurance, 401ks), sparking the need to create accessible, shame-free financial content.
  • “I went home that night and tried to learn. And it was either the most depressing financial content ... or jargon-heavy stuff that didn’t hit for me.” (21:19)

2. The Power and Downside of Financial “Shame”

• Traditional Advice: Both reflect on outdated financial advice, especially targeting women, that relies on deprivation and shame—advice like “never get a manicure” or “rewash your paper towels.”
  • “The financial advice from their era was like, all just so based in shame … we only have so much, like, chutzpah towards our finances. To waste that on small fry moves—we're never going to get rich.” (22:38, 23:10)
• Modern Reframing: Haley advocates for focusing energy on impactful financial strategies (tax optimization, building wealth) instead of penny-pinching.
  • “You’re so much better off penny-wise, dollar-foolish, right?” (23:10, 23:13)

3. Accessible Money Talk: Making Finance Fun

• Approach: By combining celebrity culture and humor, she makes financial topics less intimidating and more digestible.
  • “No one really cares about money. Everyone loves celebrities. What if I combine the two and start by teaching myself—and seeing if anyone else likes it?” (23:19)
• Immediate Audience: Her content quickly found an audience, validating her playful, meme-driven teaching style.

4. The “Future Rich Person” Book: New Rules for Wealth

• Book Structure: The book starts with facing your money, mindset work, and continues through practical steps for financial growth tailored to a younger, digital-savvy generation.
  • “The first part is about facing your money. We do a lot of mindset work … then these proprietary methods from years of helping people.” (28:44, 29:08)
• Defining ‘Rich’: Haley stresses that “rich” isn’t one-size-fits-all—it’s independent, secure, and unburdened by shame.
  • “Rich is different for each person. Your rich life could be more time, less stress, or something else.” (30:12, 32:55)
• Wealth Strategies: Focus on playing by “new rules” the system favors without losing perspective or values:
  • “The rules were written by the people that they serve. … Even if you’re not one of those people, you need to learn how to play the game.” (33:56)

5. Shame, Insecurity & Social Pressure

• Cultural Expectations: Jared and Haley discuss how social circles—and traditional definitions of success—influence financial decisions and the shame of diverging from parental or peer expectations.
  • “The insecurity gets talked about ... you think you have to do it exactly how your parents did it, because it will be embarrassing to do it any other way.” (31:59)
• Moving for Money: Jared’s move from NYC to Florida illustrates breaking free from expensive status symbols and maximizing "arbitrage" for a better quality of life.
  • “The minute you get rid of those insecurities ... you start realizing oh, this is how people made money.” (32:01, 32:55)

6. Personal Finances and Relationships

• Dating & Money: Haley shares her criteria for partners as a financially independent woman, emphasizing partnership and support over income.
  • “I'm not a gold digger at all. I always say I’m a gold digger with her own gold.” (35:00)
• Taboo Topics: Both note that money is deeply honest—and often reveals compatibility or deep values in relationships.
  • “People think the amount of money they have is what gives them value. But it couldn’t be less true.” (37:32)
• Debt & Honesty: Redefining debt as a learning moment instead of a character flaw.
  • “If you have debt ... you think that’s a reflection on who you are—whereas it's maybe just not having the literacy before.” (37:32)

7. Financial Nihilism & Keeping Up Appearances

• Social Media Illusions: Discussion of people prioritizing the image of being rich—via luxury, social signaling—over the reality of stability.
  • “There is this obsession with looking rich instead of being rich, that comes from what I call in the book ‘financial nihilism.’” (39:03)
• Reframing: Haley’s book urges readers to move past nihilism, focus on real opportunities, and build their own definitions of security and wealth.

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Notable Quotes & Memorable Moments

• On Financial Energy:
  “We only have so much, like, chutzpah towards our finances … to waste that on small fry moves—we're never going to get rich.” (23:10) — Haley
• On Combining Comedy and Finance:
  “No one really cares about money. Everyone loves celebrities. What if I combine the two?” (23:19) — Haley
• On Redefining Rich:
  “Rich is different for each person.” (30:12) — Haley “Future rich person doesn’t mean everyone gets a private plane or twelve houses ... some just want a life where they’re not so stressed about money.” (32:55) — Haley
• On Partnership and Money:
  “I'm not a gold digger at all. I always say I’m a gold digger with her own gold.” (35:00) — Haley
• Comedy Highlight:
  “Every text I’ve ever gotten from you was weird. Me, looking at the sky wondering if I was on a hidden camera prank show.” (04:54) — Jared

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Timestamps for Key Segments

• 00:00–02:07 — Intros, banter, and Florida as a financial move
• 03:05–06:48 — Personal chemistry and texting quirks between Jared and Haley
• 07:03–14:28 — Haley’s comedy beginnings, working at Letterman, and breaking into television
• 15:11–17:23 — Early NYC life, odd jobs, and growing up with family support
• 21:19–24:21 — Haley’s “Aha money moment” and why old-school financial advice doesn’t work now
• 28:44–30:12 — Book overview: method, mindset, and actionable steps
• 31:53–32:55 — Jared on life “arbitrage” and moving for finance/quality of life
• 34:06–35:00 — Haley on relationships, dating, and what “rich” means as a woman today
• 37:32–39:03 — Financial honesty, shame, debt, and “financial nihilism”
• 40:01–43:34 — Fun rapid-fire game: “How Rich Are You?” touching on privilege, NYC/wealthy family quirks, and luxury

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Tone & Style

The episode balances light-hearted humor and vulnerable reflections. Both Jared and Haley use self-deprecating stories and candid conversations to illustrate big points, making the topic of money approachable, relatable, and free of shame. Haley’s energy is upbeat, direct, and nerdy-chic, while Jared grounds the discussion with wit and practical skepticism.

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Takeaways

• Face Your Finances: Start by looking directly at your money—don’t let shame delay your journey.
• Redefine Wealth: Your "rich" is personal—don’t let society or outdated advice set your goals.
• Avoid Energy Sinks: Save effort for big financial moves, not penny-pinching.
• Play the System: Learn the new rules, even if you didn’t write them.
• Use Humor: Lighten the load—finance doesn’t have to be intimidating!

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Listen if:
You want to laugh, demystify money, and learn how to be smarter with your finances in a world that rarely teaches you how. Learn from someone who made the leap from confused newbie to successful financial educator—while keeping it fun.

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Find Haley Sachs at:

• Mrs. Dow Jones
• “Future Rich Person” (book & audio)
• The Financial Tea podcast

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Memorable Quote:
“I’m a gold digger with her own gold.” (35:00) — Haley Sachs

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Transcript

[A]

Chit Chat Wednesday for you to listen to. I have a guess who will be your new boo. You're gonna love them too. Chit Chat Wednesday. I hope you're having a good day today. I hope it's gonna be a perfect week too. I hope you have a nice poo. It's a chit Chat Wednesday too. Hello and welcome to the J Train Podcast. This is J Train Jared Freed coming to you live from Delray Beach, Florida. That's right, every Wednesday is a Chit Chat Wednesday where I sit with a comedian, a friend, an expert. Today we have all three. Friend, old friend. Known her a long time comedian, expert in finance. That's right, the woman behind Mrs. Dow Jones, Haley Sachs. Thank you for coming on the show.

[B]

Thank you for having me. Jared, my old neighbor.

[A]

I know, we used to live in the same building.

[B]

Those were the days.

[A]

The days. What's going on? How are you? You have a new book that is out right now called Future Future Rich Person. You can buy it, you can audio buy it, you can kindle it, all those good things. We have done the book speech before. We want people to go get it. It's called Future Rich Person. You also have the Financial Tea podcast. What's going. Lots going on. That's great.

[B]

Yeah, a lot is going on. You know, I've just been like hustling getting the book out. I'm jealous of your tax evasion status in Florida. I think that that should be my next move after this chapter. I do need to, I think, take that a little bit to the next level.

[A]

Is that a. Is a state? Is a. Is, is that something that people should do financially? Is, is finding a tax haven state? Is that good financial advice?

[B]

Oh my gosh. I think that's excellent financial advice. I feel like any way that you. I talk a lot in the book about optimizing on taxes because I feel like people, every year that taxes happen, people act like it's the first time that it's happened to them. Like they like, are so offended by the fact that like they're paying taxes as though this is not something that happens every year. So, you know, if you can get past that and start looking for actual strategies, then you're leveling up.

[A]

Have you ever done your own taxes?

[B]

I did my own taxes before I had Mrs. Dow Jones. Yes. Like using like a turbo tax. But now I have to have you have an accountant.

[A]

Right, I'm sure, of course. But when did you do your own taxes? So, so what did you do before Mrs. Dow Jo? Because I remember you being around. Were you in finance?

[B]

No, I was never actually in finance. I was in comedy. So I was definitely like, probably like at your shows being like, you know, trying to get you to like put me up or something. But I started message me but the

[A]

messages were always odd. You. Yeah, I will say for someone that's so with it. Your messages to me were very not with it. They were always interested. Singular. I can, I can read them. Should we bring them up?

[B]

Like, I would weird.

[A]

But I'm just saying as someone in person, never matched who I would get messages from. If I'm to be honest with you.

[B]

Interesting. Like, sort. Like maybe I thought I was being funny or like it would be like,

[A]

I don't know, hello, King.

[B]

Hello. No, I still do that. Is that weird to say hello King. I say hello Queen. Hello, King. Like that's still sort of the vernacular.

[A]

Like, I would wouldn't answer that. I, I would. Honestly, it comes off as like a little bit like what I, I honestly, to me, I don't want to be part of someone's joke that I'm not in on. So I'm always like, I don't know what's going on here. And we don't know each other enough to get a hello, King.

[B]

We got a joke. Okay, so you would have you. I was taking it too far. I thought we were joking.

[A]

Don't you think if I just randomly had a mid, mid conversation level hello to you, you'd be like, what's going on? What don't I know?

[B]

I'm learning a lot right now. Like, sort of like, like about, like how I need to move through the world because I, you know, I mean,

[A]

if you, this is how you move. I'm just wondering.

[B]

No, I am moving in this such a way. I think that I do. I like to, I like to hit people with the hello King, hello, Queen. But you know, you're right. Like it's like if you. There is nothing worse than feeling like you are the butt of the joke and people do, I think sometimes feel like that from me. But I'm always just trying to joke with people and so maybe, but maybe it is a little off putting.

[A]

That was every text I've ever gotten

[B]

from you was weird.

[A]

Me looking at the sky wondering if I was on a hidden camera prank show. I will be totally honest with you. And I've always like. And then when we've hung out in person, I'm always like, she gets it. I don't understand. This isn't an aloof person.

[B]

Okay, well, this is good. This is good for me to, like, bring to my therapist. Like, I think I need. I. Maybe I'll get, like, a diet. I'm gonna get, like, a dialogue coach. No. This could be why I'm single. But you're like, we need something.

[A]

Why. Why are you starting halfway into a conversation with me?

[B]

Like, true. It's true. I need to start. I'm gonna hit you with a. What about a Sir? Hello, sir.

[A]

Even this, I don't think I'm making a crazy request. I think.

[B]

No, hey, Jared.

[A]

How have you been? I know this is coming out of left field. Like, I don't know. I. I get, like, concerned of how people would view me, so I'm always like, hey, I'm sorry. Let me just, you know, I. The reason I'm here today, you know.

[B]

Okay, okay, fair enough. Fair enough. I'm learning a lot today. This is good. This is good. I'm like, you know, I don't think you're learning anything.

[A]

I think you're giving me shit. You know that you do this.

[B]

I know that I do it, but I feel like I get away with it. Maybe, like, for you, though, you're right. Like, it's like, it wasn't the right flavor. You have to think about, like, who you're connecting with. Like, maybe, you know, you. You need to have, like, that boundary a little bit more. But anyways, I used to see you. I remember when you're going through your breakup on the Lower east side.

[A]

That's right. That's when I saw. I think. I think I saw you outside the building, like, the day I was moving, getting a coffee.

[B]

Yeah, we were. That was our closest moment. That was actually a hello, King moment because we did have intimacy emotionally in that moment because we. Well, you needed a friend.

[A]

I. Well, I was looking to you, going, hi. You know, talking to you as a human. You know, I. Every time I talk to you, I was like, is this AI? Before AI even existed. I didn't even know. There was, you know, some thoughtful, you know, some thought behind these texts. But I.

[B]

Sorry, what.

[A]

At what point are you. Because I remember meeting you around, and then all of a sudden, it's financial comedy. So.

[B]

I know. Well, financial. Yeah.

[A]

So what started that?

[B]

Well, so I started in comedy. Like, I always was into making content. Like, I would make videos on Facebook. In middle school, I was, like, famous on Vine. In college, Like, I was always loved, like, doing school. I went to Wesleyan.

[A]

Huh.

[B]

And so where are you from? I'm from the I'm from New York. I'm from New York City, from the Upper east side.

[A]

So from the Upper east side, you go to Wesleyan. You're like, I want to make videos online. Vine is there. You're younger than me and younger than you.

[B]

Were you big on Vine?

[A]

I never did it. I, I never tried it. I think it was, honestly, before I even started putting stuff out there, maybe I had heard of vine and it also.

[B]

Are you comedy first? Like Santa first?

[A]

Yeah.

[B]

And then you're like, oh, I should. I'm doing the digital thing because, like, that's what I have to do with this.

[A]

Right? In the same. Yeah, you have to. It was like, I'm doing stand up and I want to do other things to put my name out there. And so I started a podcast and started doing the stuff that honestly, like, if. As far as financial advice is concerned, you know, I remember I used to sell life insurance and annuities. And one of the big pieces of advice that I got from one of like the managers that was like a hot shot. He thought he was like Wolf of Wall street guy was like, he was like, you should send out mailers every week or month or whatever. And his advice was that you could hire the mailman for the price of a stamp. And I always thought that was like, in nature, good financial, you know, good working advice. Because yes, a stamp is very cheap, but now you have someone who's your messenger and you like. I don't think mail, I don't think snail mail at the time was a, you know, a good long term plan for a business. But I do think it, like, the, the message stuck with me because I was like, okay, how do I work at comedy and get people to know who I am without having to be, you know, moving my feet? I could just do it, you know, online. How could I have something live out

[B]

there that's so smart? I feel like. Didn't Dane Cook start that way too? Like he was the OG with the, with like his email list. I mean, it's so whatever. We all. To get our lives going, you have to be hustling online. I was always digital first and then I started in stand up. So then I. My first job was for David Letterman and so I was working at David Letterman.

[A]

What did you do for Letterman?

[B]

Well, not much. I was like, it couldn't. Didn't get the paid ship with NBC. And so it was like the other paid ship for cbs. And so we were like in Times Square basically trying to get tourists to come to the show like literally like next to the Eminem ma', am, looking for like honeymooners who loved Letterman to like bring to his audience. And then you would put them in like the better dress that they were and sort of the more like polished, the closer that they got to the stage. It was this whole like infrastructure algorithm that they had about like what kind of audience he liked. It was crazy.

[A]

So, I'm sorry to interrupt. I'm. I'm sorry to interrupt, but. So you were. It's. What was that, that. What's that program called?

[B]

Page. Like they just being a page. So you get paid like, you got

[A]

paid like 12 program, right? But the page program is for those at home that don't know if you want to work in, you know, 30 Rock, you want to be a part of NBC or, you know, you want to be a part of David Letterman, a late night show when you're like out of college. There are these programs where like, you're in like you're in the suit. You're Jack from 30 Rock.

[B]

Exactly.

[A]

The guy who's.

[B]

Yeah.

[A]

And it's like a hybrid. For those at home that don't know, it's like a hybrid internship slash job that gets you into the funnel of NBC or David Letterman and cbs basically. Good way to get to know writers if you want to be a writer one day or if you want to be an improviser. The page program is like a well known kind of start for a lot of people. But it's generally a well known start for a lot of people who know people.

[B]

Yes, absolutely. Like Aubrey Plaza was a page randomly. Like, you'll always hear these people in Hollywood who like started as pages and you're correct. Like it was absolutely like bitch work, bottom of the barrel. But you're in the place where it happens. It's so exciting. You also, I got to see every show that he was doing and it was like his final season, which was so cool. And so, I mean, it was amazing.

[A]

What was the hook into the page program? Because those are tough positions to get you, say $12 an hour and you're out in Times Square. But the people who are in the page program generally know someone who knows someone.

[B]

So the NBC page program is like cutthroat. Like it's literally like getting into Harvard. That is like, not only do you need to know someone, but you have to have like, you know, the most insane resume. Like drum through a million hoops. Like they are not messing around. Those are like thoroughbr. I think the CBS pages we were Like a little bit more bootleg. You know, there was like someone who.

[A]

So you just put your resume in and you got the page?

[B]

No, no, no. There was definitely like a Nepo part of it where, you know, my dad's friend was like the announcer and so he got me in. But like my friend Pat who now works at Barstool, went to the show for a taping and was like, oh, I want to work here and like got the job. Like it wasn't okay. So that one was a CBS David Letterman page, was a bit easier, but it was so cool and like a really good foot in. And so it's a great experience.

[A]

Like, you know, like, like, you know, the, the idea that like you have to do all these things but like you're young and able to do them. Like that's like, you know, if I just think if there's someone in the Midwest who's like sitting in Des Moines and is like, I want to go work at David Letterman, like, I think they're going to be surprised to find out these things exist, you know.

[B]

Oh, I think that all of these shows have these programs and like you would be surprised how far you can get with cold emails because like when you are just starting and you do have that hunger, like everyone starts from that same place. Like all of us, I feel like in entertainment are self realized because it's such a like dreamy career that you have to like really push to get wherever you've come, come to wherever you are at. And so it's like, I don't know, I feel like most people want to lift others up and so yeah, I think that like you could, I mean if you trying to think like what late night shows are really out still. But you know, NBC might be a little bit more difficult, but I think any of these shows, I also think that if like you were a big fan of a podcast and you wanted to get like start there, like I'm sure you could like they have programs too, like the bigger shows for young people to start.

[A]

You think they have programs like, I

[B]

don't know if it's like start.

[A]

I don't know if it's. I mean the page thing is a very, like, it was a very, like you said Harvard. Like that, like that thing was like set up, you know, in a way

[B]

I also think that at the beginning of your career it's always good to go for the program that is more established. Like when people ask me for advice and they're like, oh, should I work at this startup or should I go work at, like, you know, this bank that has this like, huge program for, you know, young people who are just starting out. It's like always go and get that refined experience first, so then you can go to like, the more risky job after. But, like, we all sort of have to like, get our training wheels on first, you know.

[A]

So when do you go from comedy with the Letterman to like, the financial stuff? Because, like, I always thought it was a great idea. I was like, oh, this is like palatable financial, like, thoughtful, you know, like, how do I miss frizzle? You know, finance, which is like something people want, you know, people want to be more in the know. It's like wine. You want to know about wine, but you don't want to have to become a sommelier. You want like a couple tips. Like, this is kind of, to me, this is like a great idea, what you're doing. How did you. When did you see that?

[B]

So I saw it. So after Letterman, I was then like hustling in New York, doing improv, doing stand up. I was a nanny for a kid named Winthrop on the Lower east side. I worked at a Pablo studio that like the Olsen twins went to and like all of these sort of odd jobs as I feel like a lot of us do, sort of starting in like the comedy world and then like performing and writing and stuff on the side. Um, and. But I wasn't really, like, finance was not part of it and like, money wasn't really part of it because it was such a, like, such early days in my 20s where, you know, all my friends were sort of broke. We were just like sort of living paycheck to paycheck. I. There was no 4, no 401k option when you're a page. Like, no one was asking me actual, like, adult financial questions. And I think in my head I sort of thought, okay, one day it's just all gonna happen. But, like, I don't have to care about it right now, which, you know, rookie mistake. And then so I was making content online.

[A]

Were you living at home? Were you living at home at the time?

[B]

I was living in a two bedroom apartment on the Lower east side that was like, I think fifteen hundred dollars. And my parents paid for half, which was so nice of them, and obviously like a huge, like, help and so. But like, even now I'm like, that's, you know, there wasn't. I wasn't living like a life of luxury, but I definitely had support, which was. You made it, made it really nice to be Able to go chase my dreams. It's something I don't take for granted. But then I got a job for Lorne Michaels, who started snl, and he.

[A]

Yeah, we're familiar with the name.

[B]

We're familiar with the name. And so sorry, I didn't. I wanted to, you know, warn you. I'm about to name drop Lorne Michaels,

[A]

but we got it. You can check out the documentary now.

[B]

Yeah, you can. Lauren that's sponsoring the pod. Yeah. And he was. It was like the age of college humor and like everyone having those websites, those like comedy websites. And so SNL wanted to start their version of that called Above Average. Above Average was like their production company that did all of their movies. Like, if there was ever a spinoff of a skit on SNL like Coneheads or, you know, like any of, like whatever that Above Average would make that. And then they were also making this like, digital production studio. And so they hired me to. And they hired Ben Marshall, who's now on snl. So it was like his, his first job too. He was a little. He's a little younger than me, but he had just graduated nyu. He was just always like a star. And so we were in charge of, you know, making sketches, pushing out content, all this stuff. But that was what I had my, what I call my Aha. Money moment, which could really happen for people, I feel like, at any time in their life. Like I was Talking to a 58 year old woman last week whose husband had died and like that was her aha. Money moment because he had always handled all the finances. And so in, you know, the moment that he passed away, she had to step into that. And like, that was the moment. She was like, I need to really go to do list. Oh, sorry. Sort of citizen.

[A]

The dog is. I hope the dog is okay.

[B]

He's. He gets really upset when I talk about that woman.

[A]

He's quite a. That dog is having an aha moment itself.

[B]

He is, he is. He's. He's very financially literate. Mystery. I apologize.

[A]

It's okay.

[B]

But so my. So then the first day at that job and there was like so much pressure. Especially like I have like Jewish parents who were like, finally this girl's like getting a real job. Like, oh, wait, I'm so sorry, Jared. I don't know who the hell is here. Give me one second.

[A]

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[B]

Okay, so Jewish parents, they wanted me to obviously they wanted to like tell their friends at the golf club that I was doing something real and not like just like in the basement of a dirty comedy club, like babysitting for a kid named Winthrop. So very exciting. Lots of pressure on the role. And the first day they asked me about 401ks and health insurance and like all these normal questions that you ask people who you're going to hire full time. But I had never had a full time job before. No one had ever explained any of this to me. So I was like very overwhelmed and I went home that night and tried to learn. And it was either like the most depressing financial content for basically women that was like just so much about scarcity. Like rewash your. Literally that night I found a video telling me to rewash my paper towels. Like never get a manicure. Like basically that like, oh, if you want to like be good with money, it means that you're like, couponing and, like, the fun is over.

[A]

Like, right.

[B]

Forget about.

[A]

Don't make your coffee. Make your coffee at home.

[B]

Avocado toast. Yeah.

[A]

You're spending $5 a day on coffee. That equals $20 million. And that could be put in a.

[B]

Yes.

[A]

Mutual fund. That could. That would make you rich. I. That is. That's the going financial advice of a certain era. Yeah, I remember that.

[B]

Yeah, that was our parents. The financial advice from their era was like, all just so based in shame. And it was also, like, for women especially, I feel like it was such a distraction now, especially how much I know. Like, it's such a waste of what I call in the book, your financial energy, because it's like, we only have so much, like, chutzpah towards our finances every day or quarter or year or whatever. And it's like to waste that on such small fry moves is just going, we're never going to get rich. You're so much better off Pennywise.

[A]

Dollar foolish, right? Yes.

[B]

Yes, you. I was going to say yes, King, but I know that's a slur, so I will just say yes, Jerry.

[A]

A little bit. Yeah.

[B]

Yes. I'm learning. Or it was like. Or what I found was like, you know, advice that was. Felt like it was for men, but it was like, just had so much jargon. It was like, guys who look like they've never been through puberty just really didn't hit for me. And so I was just like, okay, let me just read about these things on my own, like, separate from this content and see if I can piece it together. And I started to read it and I was like, whoa, this is actually, like, so interesting. And it's not hard. Like, why is everyone telling me that it's this hard? It's like seventh grade math and just basically a lot of logic. This is not something that's so complicated. And so I was like, well, no one really cares about money. Everyone loves celebrities. What if I combine the two and I'll start just like, by teaching myself this way and then I'll see if anyone else likes it. And, you know, I'd had many shots in the dark in my career up until that point, like, you know, trying different kinds of stand up, different YouTube series, all these things.

[A]

And when did you. I'm sorry to interrupt. When did you start stand up?

[B]

I started stand up in like, 2014. And like, you know, I couldn't. I think also, like, I knew that I wanted to, like, have a voice and that I had Something to say, but I couldn't. You're so good. You always know. You're so strong in your voice. You know exactly, like, what you're here to say as Jared. Like, that's why we all love you so much. But it's like, for me, it took me a little bit longer. I think I was, like, not that into speaking about myself, and I felt a lot better and, like, it was right when I was speaking about a subject, so just clicked in so many ways. And then I also saw the audience sort of grow immediately. And so I was like, okay, I have, like, you know, the data here that shows that there's interest. I'm really interested in this, and it's, like, making my life better and, like, healing this money wound in myself. And, like, you know, at the same time, above average was basically going under. Like, it was really poorly managed. Whenever we would get over a hundred thousand views, they would take us to Benihana, which, like, is a very poor business decision. Like, you know, just. It was just. There was not. There wasn't a real audience for the content. Like, it was just clear sort of that it was a bit of a house of cards. And so it ended up going. We all got laid off six months in. And then I took basically a year of. I wrote for Fuse tv, which was like a music television, like, short videos. So I would, you know, write all these videos for, like, rappers and stuff for the Internet. And that sort of paid the bills. Paid my. I had very low bills at that point. But then it was at the same time building Mrs. Dow Jones. And then at the end of that year in the New York Times, and then it sort of took off.

[A]

I saw it. I was like, this is genius, you know, Like, I. I saw the Mrs. Dow Jones stuff, and I was like, oh, I totally get it. Like, especially, like, you know, with finance stuff. Like, everyone just wants to, like, know it without having to learn it, you know, like, everyone thinks they should know it out of the womb and you shouldn't. Like, it's hard to figure out. It's not so apparent. And if you don't grow up with it, there's a little. You know, there's a little bit of that. Like, if you don't know savings and where to do with it, you get embarrassed, I would think, you know, So I liked. I always liked that there was, like, this, like, insider comedic look that could help people. And, like, I understood why it was huge. Like, right, you see it and, like, the videos are great and do a great job. Of like, telling people specific things and like, what could be done that they, is sitting right in front of them. So I, I always thought it was a definitely, like, it's like, how could this not be done already? You know, I know it's.

[B]

Well, I mean, I think that there's always been this for different generations, like, money especially. I think it's the same way as, like, people like a physical personal trainer or like a therapist. Like, I think emotional health, physical health and financial health are really similar and like, with each of those people sort of like, like a guru or an expert to tell you what to do. And so, you know, I think that there's always, you know, been this space sort of. But yeah, it's been so fulfilling and like, it's. Money is such a deep wound for so many of us. And, you know, I came from money and I still have that wound too. So it's like, I get it. And I think that, you know, being able to help people heal, that even in this time of, like, such economic insecurity, helping them find the opportunity to still level up, because there still is so much opportunity to improve your financial life despite, like, inflation and housing costs and student loans, like, there's still ways for you to become a future rich person, which is really what the book is about. The new rules of building wealth. Like, how to build wealth in 2026 in this modern world.

[A]

So what's the first? So take us from the beginning to the book. Book, it's called How Future Rich Person Go Buy It. Go get involved at Mrs. Dow Jones. You already know and love her. What is like, what, what, how does the book go? What's like the, what's the, how does it start? Where does it go? How does it, someone picks it up. Where, where are they going to be taken?

[B]

Okay, I love that. So, yeah, we start, we definitely go on a journey. The first part is about, like, facing your money. So it's, we do a lot of, like, mindset work because I, in the 10 years that I've been doing Mrs. Dow Jones, I've helped like, tens of thousands of people sort of like in coaching and classes and things like that. And so I've come up with, like, these proprietary methods.

[A]

You're coaching people in their finances?

[B]

Yeah, like, I have a, I had courses, I'll do webinars, things like that. Like, do you.

[A]

With no. With no. I mean, I, I don't, is it. Hi, I worked at Letterman. Please listen to my financial advice. I, I, I, you know, like, I, I, how do You.

[B]

Well, I would say I'm not, I'm not a licensed financial expert, so you have to take the advice at your own, at your own risk. But, like, you know, my advice is so good. People love it.

[A]

I'm not saying, you know, the financial advice is a lot like, you know, to me, is a lot like dating advice and a lot like, you know, working out. It's like diet and exercise. There's like, you know, really, you know, you, you have to do certain things that aren't that sexy, you know, like.

[B]

Yes.

[A]

You know, like, it's like, you know, someone says, that's why future rich person. You look at that and you go, I, I, you know, can you make someone rich? You know, like, you can make someone richer than they would have been. Right.

[B]

Well, I think that rich is like, different for each person, you know, like your rich life, Jared, could be that, like, now you move to Florida, you have, like this great tan. You're, like, closer to your parents. It's probably easier to be in the middle of the country doing all of this travel than it is to be on a coast.

[A]

Like, I'm on a coast, but I,

[B]

you know what I mean? Like, but like, it's my, like, Florida is easier to get to. Going to California from New York is a bitch. You know, probably wouldn't you say Florida

[A]

to California is the same bitch?

[B]

So is it, is it six hours,

[A]

I'm on the Atlantic Ocean, you know, I'm still going coast to go. And there's more flights out of New York. I got one option. 8am Wednesday, I can go to LA.

[B]

Oh, really?

[A]

Correct. Yeah, it's not that bad. It's. I, I, that was like one of the surprises of moving here. Like, I was like, I think, like, financially, you know, what's interesting to me is like, you know, something like my move, I'll make it personal. My move. Moving to Florida, you save with the taxes like that. That's something where you save right away and huge. But you hear about the taxes, but you never have a number to put with it. You, you just hear, taxes, Florida. That's kind of what you hear. And then you put like, oh, okay, well, now, cost of living, like, I was like a coffee in New York and in Delray beach cost the same exact amount. But the gym membership is way cheaper here. Like, the gym membership here is, like, nothing in comparison to, and I'm talking about, like, a nice gym. Like, if you want to be in a nice gym in, in New York and you want to have, like, amenities

[B]

like, you're gonna get that 300amonth.

[A]

It's right. That's $300 a month. It's 120amonth here.

[B]

And you're like, that's crazy, right?

[A]

And it's crazy. And it's like. And I think, you know, when I moved here, I think a lot of us, the insecurity, if you're, if you're doing, you know, if. I think the insecurity gets talked about from both sides, you know, kind of gets glazed over with like, maybe who. Someone who grew up in middle class standings where you're like, well, I have to do it exactly how my parents did it, because it will be embarrassing to do it any other way. Like, if I live in Florida, there's. There's a lot of insecurity of people who move to Florida that they've given up, that they're not as motivated. And it's like, well, you can fly out of here and go to LA from here, and you can do your stuff online, you can work from home and you can go to New York. And it's like the minute you get rid of those insecurities are kind of like, get past them a little bit or enough, you start realizing you're like, oh, this is how people made money. This is how people found arbitrage. You know, like, this is exactly.

[B]

That's the save strategy. Exactly. And that is like, future rich person doesn't mean that, like, you want. Everyone who reads the book is going to get to have a private plane and, like, go to, you know, like, have 12 houses. Like, that's not what every person wants for their. There's going to be some people who. They want that. And it's like, great. Then you have to work really hard and find those earning opportunities and turn those liquidity moments into more wealth. But there's a lot of people who just want a life where they're not so stressed about money and where they're able to, like, have their needs met and where they have, you know, made strategic choices the way that you're talking about so that they're able to, like, enjoy their lives. And that was something that was so important in the book. To sort of get across is like the strategy of the game. Like, that's why it's called the New Rules of Building wealth. Because rich people, the whole game is made for rich people. Like, the rules were written by the people that they serve. And so, but you're, and you're never taught that. So you need to learn. Even if you're not one of those people. You need to learn how to play the game, because those who don't will lose just automatically.

[A]

I think everyone should get the book Future rich Person. Do you get personal in it? Do you talk about.

[B]

Oh, yeah. Oh, yeah. What's the most personal direct we got? We got my whole, like, growing up on the brief side, we've got, you know, dating, like. Like, crazy dates, like, where I went out and dated.

[A]

How does the dating relate?

[B]

Zero credit. Well, you know, money has so. Money comes up in relationships so much because, first of all, like, dates cost money. So even on the first date, there's, like, always that question of, like, oh, is he gonna pay? Am I gonna pay? Like, you know, and then you think about building a life with someone, you're like, am I gonna be carrying them? Do I want them to carry me? Are we equal partners? Do we have the same future rich life in mind?

[A]

Do you have to date someone who has money? Is that something for you that you need?

[B]

That's what's so cool about being a financially independent woman is like, I'm. I'm not solving for money is like, I, of course, love to date people who are successful and who are passionate about their careers. And I dated guys with a lot of money, for sure. But it's like, what I'm really solving for now is, like, who would be a great dad, like, who, like, really supports my career and, like, loves to see me shine, like, who's consistent, like. And that is. That's what I'm looking for. And I think that, yeah, that's what's so cool about having your own money, is you don't have to be like, I'm not a gold digger at all. I'm a. I'm a gold. I always say I'm a gold digger with her own gold. So it's like, I definitely want somebody who has, like, a gold digger. Was her own gold. Yeah. Like, it's like, I definitely want somebody who has a great, like. Like, money mindset. And I'm not looking to, like, support someone fully, but I think that, you know, because I'm in a place in my life where, like, I'm doing. Where I'm doing well. Earring falls out while I say it. Where I'm doing well. Like, it's not. That's not the first thing that I'm solving for, which I feel like, you know, that's sort of awesome. What about you? What are you solving for financially, in a relationship?

[A]

I'm solving for being able to not have to drive Uber and be a former comedian at some point. I'd like to be a current comedian at all times in my life. And that's.

[B]

But like someone like, have you ever dated someone super rich? Have you dated someone where you like, like what is the, like how is money played out in your love life?

[A]

I've been on dates with people who have had a lot of money and not so much money. And it's, it's something that matters to me probably in a way that is not as it, it would. I, I don't think it would work out with someone that I didn't feel was financially independent because I don't know if I have the confidence to do that. I think it takes a lot of confidence to say like, get on my back, we're gonna do the. I'm gonna do this on my own. And also I'm, I'm attracted to, you know, people who are successful. So like that's always been attractive to me. But you know, I think it sounds bad to say you don't want to date outside your socio economic circles and. But that's, that's usually what happens. I think this money is a dirty subject and a very honest subject that you know that like people are the most honest with their money and their time.

[B]

You know, I think what's weird too with money is like, because it is this like value driven thing, like something that we've given so much value to. People think that the amount of money that they have is what gives them money, it gives them value. But like it's couldn't be less true. Like there's, you know, but that's I think where a lot of people get really insecure in relationships. Like if you have debt and you are in a new relationship and you feel really insecure telling the person about your debt, it's because you think that that's like a reflection on like who you are. Whereas it's like, oh, maybe you just didn't have the financial literacy to avoid getting into that trap. And the system is literally set up for you to fail. But like now you have a plan and you're getting out of it. Like to me, someone who's on the up, that's sexy, right?

[A]

Fight. Well, being, you know, the hustle is hard to see, but it's got a hustle while also doing it, you know. You know, you don't want a delusional hustle. You know, there's a lot of delusional hustle.

[B]

Yeah.

[A]

You know, like you can see someone posting Every day about bullshit. Like, you. You look at, like. Did you watch the Manosphere documentary?

[B]

Oh, yeah, I love that.

[A]

That's all paid that. That was all, like, paper money. Like, there's a part in that documentary where he's like, you know, he's. He's like, well, do you rent this place or do you own it? And he's renting a place for 50,000 a year, a month or something. And you're like, this is. That's unattractive. Like, he's got the suit on, and he thinking. He thinks the show of it, but it's a. How you know, to use your term, house of cards.

[B]

You know, house of cards. And there is this obsession with looking rich instead of being rich that I think comes from what I call in the book financial nihilism, which is like, we're fed so much, especially by the media, that the world's over. We're on a floating rock. Climate change. The stock market's gonna crash. AI is ruining everything. We only have a few good years left. And so people are okay. There's no opportunity. So why don't I just, like, I'm gonna ignore my finances. I'm gonna overspend. I'm going to, like, max out on looking rich instead of being rich and planning for my future, because it's like, there's no opportunity for me outside of that. And so much of the book is, like, reframing that mindset, because obviously that's not going to get you anywhere.

[A]

Everyone go buy future rich person. Go, go, go right now. Let's play a quick game before we go. You ready?

[B]

Love it.

[A]

This is called how rich are you? Okay.

[B]

Okay, love.

[A]

Can you do the dinner course called an inter Mezzo?

[B]

Well, I think you cut out a little bit at the beginning. I'm sorry.

[A]

Can you describe the dinner course called Intermezzo?

[B]

I think so. Is it the. Your appetizer?

[A]

No, it is not. Okay, you might not be that rich. It is the sorbet to change your palette in the middle of the meal. It is an Italian. Italian course where they give you the sorbet to cleanse your palette. Okay. Describe your first New York City apartment.

[B]

Tie dye. Couch Avenue. Be a mouse here and there.

[A]

Roommate.

[B]

Roommate. And we were how many bedrooms? Two bedrooms.

[A]

And no fake wall?

[B]

No fake wall, but very small and very bare bones.

[A]

That's rich. Okay, you're not. You're 19 years old. The date is July 14th. Where are you?

[B]

Oh, this is going to. Yeah, I was in Martha's Vineyard.

[A]

That is rich. There is no richer place. Where in Martha's Vineyard? What time?

[B]

Don't ask me this, Jared. Don't ask me what town show Mark

[A]

the richest town on the island. Okay. Did you see Barack Obama there when you were there?

[B]

Michelle goes to the yoga studio. I go to. Yes, yes.

[A]

Okay. Someone says, let's go to the Hamptons. How are you getting there?

[B]

Dream. Unless someone's paying for the Blade.

[A]

Okay. Have you been in a Blade? The helicopter that takes.

[B]

I bit in a blade More than once. Blade has a partnership with Bilt and I work with Bilt, and so I've been in the Blade because of that.

[A]

Okay, so never a blade on your own expense.

[B]

On my own dive. No, no, no. Because honestly, that's where you really get fucked financially. Like the people who start. I mean, you probably see it in comedy all the time. The people who make a little money and then they get all the planes to go from this gig to the next gig. It really messes with your bottom line.

[A]

I mean, if you're spending. To go to the Hamptons, you know, to go on a helicopter. The Hamptons, you must have. I would assume you have generational wealth. That would be the. But you're on. Your money's making money with the built people and. Well, yes. And an anchor. That guy can afford it. So.

[B]

He can. He can.

[A]

Okay, let me do one more. You're on the Hamptons. Do you have your own room?

[B]

Yes.

[A]

It's pretty rich. Okay, everyone go.

[B]

Like, would you have your own room?

[A]

I wouldn't go. I, I. Hotel room. I would be in a hotel room.

[B]

I don't go to the Hamptons.

[A]

I will say that Martha's Vineyard, but I don't.

[B]

Yeah, that.

[A]

Whose house on Martha's Vineyard?

[B]

We're not going there. This is over. The game has ended. Goodbye.

[A]

Okay, we found a clip. Mrs. Dow Jones. Go follow Mrs. Dow Jones. Go buy the book. The book. I'm. I again. I've always thought what you're doing is totally genius and wonderful and can be very helpful for people. It is called Future Rich Person. She has the Financial T podcast. Go follow Mrs. Dow Jones. Haley Sachs, thank you for coming on.

[B]

Thanks, Jared. This is so fun.

[A]

We'll back next week. Boom.