Lindsey Stanberry on Why We Judge Women’s Spending, What We Hide, & What We’re Afraid to Admit

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About This Episode

Today’s guest won’t surprise you if you read the introduction to Rich Girl Nation, which recollected the 2018 event that made me think personal finance might not be solely for people with brown bananas and pocket protectors. Lindsey Stanberry, founding editor of Refinery29’s Money Diaries turned media entrepreneur, joins me for the penultimate episode to talk about:

• ⏰ Why most conversations about money are really about time
• 💬 What she learned about our culture from monitoring the Money Diaries comments section
• 🔐 Leaving a job, even when it means sacrificing financial security for emotional security
• 🔥 What’s really driving our “obsession with FI/RE”
• 👀 The dark side of optimization

Having reviewed thousands of people’s budgets and daily routines, she’s confident about one thing: “People are desperate to talk about money,” she said, “they’re just not talking about it with people they know.” Who are they telling? Lindsey.

This episode was produced by Katie Gatti Tassin. Audio engineering by Nick Torres. Devin Emery is the President of Morning Brew.

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Get your copy of Rich Girl Nation, one of Barnes & Noble’s Best Business Books of 2025 and one of Bookshop’s Top 100 Books of 2025.

Mentioned in this Episode

• Lindsey’s new site, The Purse
• “I Was Refinery29’s First US Money Diarist—Here’s Where I Am 2 Years Later” (2018)

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Transcript

Lindsey Stanberry: [00:00:00] There’s such a interest in the FI/RE movement, which I find to be fascinating. When you dig below the surface there, it’s more that people feel a lot of job insecurity and want to make sure that they have enough money. In the coffers so that if they needed to take a extended career break, they could.

Katie: If you have read the Introduction to Rich Girl Nation, you know that one of my formative financial moments was attending the 2018 Money Diaries Book tour in Dallas, Texas. I had never been to an event about personal finance before, let alone one for women. Aside from the like benefits presentation about our 401(k) plan during onboarding at work, so the happy hour vibe with like free [00:01:00] wine and cheese plates and young women milling about talking about budgeting and saving.

I mean, this was a euphoria that I did not know existed, and it really opened my eyes to my interest in the topic. And it was there that I first watched Lindsey Stanberry, the founding editor of Refinery 29 Money Diaries. So Money Diaries was, if I remember correctly, the first financial media that I ever consumed, and it was the first book about money that I ever read.

So when I was thinking about who I wanted to interview for the penultimate episode of the Money with Katie Show this year, my mind immediately flashed to Lindsey. The woman whose work first made me think, huh, this money stuff’s actually kind of interesting. Like there’s, there’s something here. Lindsey is a writer and a journalist turned media entrepreneur, and the constant in her work from her time at Refinery.

To her next stints at CNBC’s [00:02:00] Make it and Fortune Magazine to starting her own venture. The purse is telling women’s financial stories, so please enjoy this personal and vulnerable and very special conversation with Lindsey Stanberry.

Lindsey, welcome to the show. Thank you so much for being here. This feels like something we should have done a long time ago.

Lindsey Stanberry: I’m so excited to be here, Katie, like I’m really thrilled.

Katie: Oh. Well, I wanna start with something that I heard you say back in an interview in 2018, and that is the origin story of the Money Diary series, which involves cocaine.

Lindsey Stanberry: Does. Can you tell me more about that? Sure. Yeah. I love the Money Diaries origin story. So we had this amazing team at Refinery and their whole. Purpose was to create content that would go viral. And it was led by this amazing editor, Jessica Chow. She’s at the Wall Street [00:03:00] Journal now. She’s so smart and we had both noticed that headlines with dollar signs did really well.

And so she came to me and was like, we should do a money diaries. And I was like, I don’t know. That might be boring. Like it might, you know, like it might not be interesting, but I was like, let’s try it. I always love to experiment. It’s beautiful. The internet, you can always experiment. And she came back about a week later and shared this diary from a friend of hers that was like pretty typical.

It was like, I think she was like a late 20-something living in Williamsburg and she like did the pretty typical late 20 something things. Except that she went on this date and there was a line item at the end of the date and it said, my date, and I did cocaine, but he paid for it and I don’t know what it costs and.

My editor and I both read this and we were like, oh wow, this is something. And so we published [00:04:00] it and it’s really funny if you can like dig it up and find the original one. Somebody in the comments. There must have only been like seven comments and somebody in the comments was like, refinery 29 has jumped the shark, so you’re wondering when Refinery29 jumped the shark, it was when we published that first Money Diary.

Katie: When you read that, were you like, this is gonna work?

Lindsey Stanberry: Yeah. I was like, oh my god, this is gold. It was so good. It was so honest and so real, and. I think that I’m forever grateful. That was the first one. That set the tone.

Katie: Yeah. ’cause I think that there’s like a certain brand of confessional style content now that performs well, but there’s always that undertone of this has been sanitized, right?

They are still presenting a version of themselves to me that they want me to see. I think that as the internet has evolved, that has only gotten more true as comment sections have only gotten more savage. If you’re gonna put yourself out there for consumption, you want to present the best version possible.

And so I still [00:05:00] think it’s kind of shocking when you see somebody admit to something like that. Granted, it was anonymous, but still it’s like very salacious. It was very salacious.

Lindsey Stanberry: None of us, I think had been expecting it to be so salacious going forward. Most of them did not involve drug

Katie: use like that.

So two years after that first one? Yeah. You all published this. I’m gonna read this to you. The initial goal of this project was to show how everyday women spent their everyday salaries, but in the end it actually put on display how our readers, AKA you, felt about women earning and spending money as they please.

It’s been eye-opening. At first, we were struck by how judgmental the commenters were. See what happens when boyfriends pay for things. But we found the community that has sprung up around the series to be as diverse and complicated as the diaries we feature. An OP might be struggling or making mistakes, or absolutely thriving.

[00:06:00] Regardless. The community will have an opinion. They’d cheer them on. Offer advice and call them out when they make mistakes. See the op, who thought avocados rip it in the fridge? (FYI, they don’t.) Who amongst us! The series has raised a lot of questions about what it means to be independent, self-made, and successful, and that is a worthy discussion.

When I read that, that came out in 2018, I was like, whoa, that’s really what it is. Surface level, it’s about are you spending $6 on a green juice? But like the deeper conversation that that inspired and I think the big feelings that we have about, yeah, what women do with their money, and I say we, because I think this is a lot of these commenters are also women.

The New Yorker, for example, jokes that the money diaries comment section was one of the darkest corners of the internet. So, what do you make of that now, in retrospect? Did it change over time? Like how do you [00:07:00] think about that insight now?

Lindsey Stanberry: I don’t know if it’s changed. I think that we still all have really big feelings about how women earn and save money and.

I do think that what I wrote in 2018, I still hold true and that’s why I continue to do this work at the purse, is that I think it’s a really important conversation to be having and really. Just publishing a diary is just the start of it. It really is meant to be, in some ways, provocative and to push the envelope and to get people to really think about, why do I have these feelings?

Why am I so judgmental? Why are we so judgmental of women in general? And I think that for better or worse. The money diary comment section was a place where people could go and sort of vent. They could just kind of relieve some of that pressure [00:08:00] that they felt of not being able to achieve the same level of success as some of the people that we shared, or be lucky to have parents who support them or any kind of number of things or to just feel relieved that like, oh look, I spend like that too. Like I am normal. I’m doing what my peers are doing.

Katie: I come back to the anonymity and the freedom that that grants. I sometimes wonder about, I when you said that it’s a place where people to vent, I think that you’re really hitting on something important there.

Because these stories do stir up feelings in us, and I do wonder to what degree anybody who is feeling those things has the self-awareness or wherewithal to take a step back and be like, what is this telling me about me? But I do think that that is the best case scenario. It reminds me a little bit of the, yeah.

Saying that you should use jealousy as a [00:09:00] guide, like when you feel envy for something that should signal to you that that is something that, oh, okay. I clearly, I really want this. Maybe I didn’t even realize how badly I wanted this. And the blurb that I read to you refers to specific trigger points in the diaries, like a boyfriend paying for something.

Were there any other trends that you noticed, like specific elements of an entry that would always kind of like get people riled up or seem to cause a stir? We

Lindsey Stanberry: had a diary go viral in the summer of 2018 and it was wild and people were very angry because it was a very young woman. She was like 22 or 23, and she was living in New York and she had an internship and I think she was making $20 in an hour at the internship, but her parents were paying her rent, her grandfather was giving her an allowance, and people did not feel like the headline reflected her.[00:10:00]

Financial support that she was receiving and people got so angry. Do you remember what the headline was? The original headline was probably like interning in New York on $20 an hour, and then we revised it to interning in New York on $20 an hour with a thousand dollars monthly allowance.

Katie: Oh, oh, good.

Okay. Okay. I actually think I remember this one.

Lindsey Stanberry: Yeah, it was a big deal. She went out to the Hamptons with her friends and they had like a private chef. Oh God. And it really was like your classic New York City wealthy person summer

Katie: internship. I do remember when that one came out and. I remember at the time actually feeling kind of seen by it.

Not because I ha was in her shoes, but because I had friends whose parents were still giving them money, but I didn’t know how much I just knew from like things that they would tell me or like when they would be like, oh, I’m putting this on this [00:11:00] credit card ’cause this is the one that my mom pays. Like I knew that there was support that was happening despite the fact that we were all working full time.

It was kind of illuminating to really see under the hood and be like, oh wow, this is, this is like how much this is potentially helping these friends and like I really should not be basing any of my financial decisions off them ’cause I don’t have this like extra line of income coming in. Yeah. The other thing that I, I’ve heard you say before is that when you had really high earners do money diaries, that also was oftentimes.

Inflammatory.

Lindsey Stanberry: Yeah. In 2016 when we launched it was anybody making over a hundred K, but people always wanted to read those diaries. They were always without fail, the most popular. And so we would get a lot of blowback that those were the only, the kind that we published. And it was always very important to me that we had diversity of income.

And so that wasn’t true. It wasn’t, it wasn’t a [00:12:00] fair assessment, but they were always the most popular.

Katie: That’s really fascinating actually, that you would get, they would get the most negative feedback and yet you can tell from the numbers of the page views that these are the things that people are actually interested in reading.

Always.

Lindsey Stanberry: And I wouldn’t even say that the most interesting, it’s just, I think that the voyeurism is there. It’s like being, you don’t wanna know what somebody who’s making $50K is making ’cause that’s what you make and like, who cares? But like, you’re like, oh, if you make $200K, like what extra stuff do you get?

How do you get to spend your money in ways that you don’t get at a lower salary?

Katie: There’s an element of projection of like, what would my life look like if I earned that kind of money. Interesting. So if you were gonna ballpark it, how many Women’s Week in a Life spending do you think that you’ve seen since then?

This is going somewhere, I promise.

Lindsey Stanberry: Thousands. We used to get thousands of injuries, so many more than we could ever publish.

Katie: It’s my understanding that you got [00:13:00] more submissions than you really could even count. And that today running the purse, you receive incredibly intimate details about people’s financial lives and by extension their lives.

And this raises a sort of interesting question for me, ’cause I used to do a series on Instagram called Budget Breakdown, and I would put out a call like, tell me what you make. Tell me what you spend, what do you spend on this? What’s your mortgage? What’s your rent? What’s your car payment? What do you spend on food, et cetera.

And we would get hundreds of them within hours. Yeah. And so I know it’s a bit of a truism at this point to say that people are scared to talk about money or they don’t wanna talk about money. I don’t know. Do you think that we might actually be dying to talk about it? Like, do you think that there, there is something to learn from the fact that like we, as anonymous people can ask strangers, tell me everything you spend and like hundreds of them wanna share.

Lindsey Stanberry: People, people are desperate. Desperate to talk about money. I would get these young women on the phone and even still, I get women on the [00:14:00] phone and you tell me everything, but I don’t think that they’re having these same conversations with people that. They know this is really like a cloak of anonymity. We just published an entry in my series on the per home economics this week, and it was a young woman in Idaho who’s a single mom and she’s actually just in a relationship and she’s getting married, but she decided to share her story ’cause she wanted to have a document of how far she’s come by herself as a single mom.

And I get it, like for some people it’s like a victory lap. It’s like, look what I’ve accomplished. And I think that’s pretty cool. I think it’s pretty cool when people feel really good about their finances at a moment in time and wanna share that.

Katie: That’s why I personally enjoy tracking so much. I love to be able to go back and look at a, my spreadsheet from 2019, 2020, and be like, holy smokes.

Like it. It can just be such a source [00:15:00] of internal motivation and inspiration

Lindsey Stanberry: a hundred percent. I always say to people, fill out the home economics form, even if you’re not gonna publish it. Fill out a money diary, even if you don’t want it publish, because it’s so clarifying. It really helps you understand like where your priorities are, what your values are, and um, it can make you feel really good and, you know, it can make you feel bad, but it also can be a motivation to get better.

Katie: You’ve joked before that like at one point with these entries, you had to be like, okay, no more marketing managers. They all make 75 grand no matter where they live. They all spend their money at SoulCycle and juice bars. Like this is getting stale. This isn’t interesting anymore. But when the series began in January 2016, we did live in a different, I think, economic and cultural reality than we do right now.

I think a lot of what has fully come to [00:16:00] fruition today in December, 2025. The seeds were there and the trends were there back then, but I think things have only accelerated. That was almost a decade ago, and obviously you have not been producing these diaries the entire time. That was just the beginning of your journey that we’re talking about today.

But what you’re doing now is thematically consistent in that you are still producing detailed overviews of women’s finances. So have you seen the broader changes in our society? In our economy reflected in these women’s finances that you see?

Lindsey Stanberry: Yes, I think I see women being savvier I in like small things and like investing in their 401(k)s and opening a high yield savings account.

I feel like there is more financial fluency in the last five years to like pat us bow on the back because of the work that you and I do. Right. I do think we do move the needle on that. There’s the obvious [00:17:00] rent or mortgage or electricity. So like those kind of basics are the same. I think what’s interesting is that when you start to dig into like the reasons why people spend money and what they prioritize, that it becomes really interesting.

The stuff to me is less interesting and the dollar amounts are, are not as interesting, but it’s like the feelings behind it and you know. I definitely think I have a self-selecting audience, so I get a lot of primary breadwinners and shocking number of stay-at-home dads. And so like these things are really interesting to me.

And so thinking about how society is changing in those kinds of ways.

Katie: Yeah. When you say it’s more about the feelings and the priorities, can you say more about that part?

Lindsey Stanberry: Yeah. I hear from so many people on the purse that they really are interested in early retirement. There’s such a interest in the FI/RE movement, which I find to be fascinating and, and when you kind of dig below the surface there, it’s more that [00:18:00] people feel a lot of job insecurity and want to make sure that they have enough.

Money in the coffers so that if they needed to take a extended career break, they could, you know, it’s a slightly older audience than Refinery 29 and Money Diaries. So it’s a lot of families. It’s a lot of people spending a huge amount of money on childcare. It’s not unusual for their childcare bills to be bigger than their mortgage payments.

You see stats floating around everywhere. But when I actually publish. These entries, it’s real life people with these experiences. And I think that’s really fascinating is to see, like to take the stats and make them apply to real people.

Katie: I will never forget the first time that a reader told me how much their childcare was in Boston, and it was like a radicalizing moment.

Yeah. I was like, oh my god, that’s more than I make in a month. Like that is actually more than my total take home pay. I actually cannot believe that. So I guess to put some scaffolding around what you’re doing [00:19:00] now. You produce two different franchises for the Purse, which is your media company that you founded.

Home Economics, which is a detailed overview of women’s finances, which the name is Incredible. Chef’s Kiss, play on words, 12 outta 10. Home economics, detailed overview of women’s finances, and then Division of Labor, which is a series that focuses on how families make it work. I’m curious if you had to pick, and I’m gonna ask you to like pick a favorite child here, which of these feels more resonant to you, which tends to get the bigger reader reaction or interest, and why do you think that is?

Lindsey Stanberry: So home economics definitely gets the bigger reader reaction. I think for the same reason that Money Diaries was so popular. ’cause it really does peel back the curtain and allows you to see how people. Earn and spend and save and think about their finances. Personally, I really love division of [00:20:00] Labor because I think we’re all walking around trying to figure out how the hell couples make it work and.

To really like get a sense of what a couple’s day looks like is very fascinating to me. And I often hear from readers, well, it doesn’t necessarily get the biggest readership. I think that the dedicated readers to it get a lot out of it. And I often hear from people who are like, oh, I shared that one with my husband and we talked about it.

Or That one stood out and it was shared in my, like with my. Mom, friends. So I think there’s a lot of like behind the scenes chatter that happens with the division of labor, which I really enjoy. It’s funny because, you know, I’m a Brooklyn mom and so I’m always at these events and everybody wants to talk about, um, Eve Brodsky’s book Fair Play and like, how does Fair Play work?

’cause I think we’re all trying to figure out like, how do you raise children and not wanna murder your partner? Um, and that’s sort of the goal of this series.

Katie: [00:21:00] Okay, so that’s actually a perfect segue. I wanna read you something that someone sent in our diabolical live subscriber chat last night. ’cause I, I just thought of you when I read it.

Any other tired parents in here that want to commiserate or vent? I feel like I can’t juggle any of it. If I focus on my kids and family work suffers. If I focus on work, I feel like I’m not giving enough to my kids. I got a bad review at work yesterday and it just makes me not wanna do anything.

Learning so much about the world, especially capitalism from this podcast, I’m so sorry. Just makes me wanna throw in the towel and find a way to live off the grid. So that was the, the start of the thread and a bunch of people hopped in and quickly commiserated and were sending very long messages, basically getting at this same feeling of just there, there never being enough time or feeling as though they can’t win.

Somebody was like, my best advice is just get comfortable disappointing people because like the idea of balance is not real, but you are gonna have to be making constant [00:22:00] decisions about who you’re gonna disappoint today and what’s gonna be. Take priority. And when I read it I thought, man, this really feels like exactly the struggle that much of the work that you do at the purse speaks to.

’cause this is really like an undeniable element of personal finance. If we scratch the surface a little bit beneath personal finance, this is what you find.

Lindsey Stanberry: Yeah, it’s not money, right? It’s like time. Time is is all of it. That’s the thing. And man, I can relate. I had my own many meltdown this morning about childcare and how much work I have to do, and I haven’t been paying for enough childcare this fall.

And it’s been really tough to then also get all the work done. So it’s a struggle and I would like to believe that the solution is not that we just. That somebody has always let down. Maybe we all like mm-hmm. Lower our expectations a little bit. That comes from me, who’s like a terrible perfectionist and I like to joke.

I’m a really bad boss to myself, like really horrible. Like the [00:23:00] expectations are too high. And so I’ve been trying to reframe things a bit and realize you can’t be everything to everyone, but man, getting a bad review at work, that’s really hard. It is, and

Katie: especially I think if you are already coming at your life or orienting to your life as like, I feel like I’m giving so much and it’s never enough, and it’s like this constant rush where there’s never enough time and like it’s always taking all of me.

I was listening to an interview the other day with Penn Badgley and. The interviewer, uh, asked him basically like, well, do you feel, because I think he has two young children. He was like, you know, do you feel like you get enough rest? And he was like, rest, I dunno about deep rest. He was like, I mean, when you have young children and you’re also.

Working. You sleep as much as you can, and then you use up all that sleep the next day. Yeah. It’s like every night you fill up the tank and then every day you deplete it completely. Yeah. And I thought that was a really good way to put it. [00:24:00] And to that point of like, if you feel like you’re, you’re. In that mode, and then you’re being told by a, someone in a position of authority, or even like your, if your spouse is expressing disappointment in you or you know, your, your kids are expressing disappointment in you.

I think that the amount of resilience that it takes to like keep going when you’re faced with that sort of. What’s the point? Feeling is, I mean, that’s, that’s really, really hard. And I also think kind of universal,

Lindsey Stanberry: right? And I imagine this woman probably needs the paycheck too. So there’s also the, those like compromises that we make just to earn money.

Yeah. Which just makes it all feel worse. And then I feel like on top of it, there’s social media which presents a lot of people who act like they have their shit together. And you know, our offering advice 24 7 on how to optimize your life.

Katie: It’s almost so inapplicable as to be completely irrelevant.

Lindsey Stanberry: Yeah. It’s the [00:25:00] same problem that I have with celebrities who offer advice and I think it’s well-meaning, but you have a different income stream, like you have different resources. The rest of us, you know, are just trying to get by. You know, when your daycare costs as much as your mortgage, there’s not a lot of extra funds around to continue to outsource support.

It would be nice if there was more realistic advice out there, or maybe we just all need to stop listening to the advice altogether and realize that you’ve got a well of knowledge within you and you probably do pretty well just on your own.

Katie: And I think that there, there is a difference too between.

Advice and disclosure, and I think what you offer is disclosure. Yes. It’s like people who are sharing what they are doing, and it’s not necessarily them saying, this is what you should do, or like, I do it this way and that’s better than whatever you’re doing. When I read stuff like that, even if not consciously, I am always kind of looking for like, what could I be [00:26:00] doing differently?

And I think that there is a certain value to that, even just in the variety of. Information, information that is out there.

Lindsey Stanberry: And I’ve written about this before that I really don’t like giving advice because people often come back and say like, doesn’t apply to me for X, Y, Z reasons. And it’s like, okay, that’s fine, but it applies to someone.

So I’ve sort of tried to reframe it more as like you said, disclosure, like let me show you a whole bunch of stories and you can pick and choose how this applies to you and how you want to use it in your own life.

Katie: Well, and I guess in this broader conversation, I keep thinking about what you said about the interest in FI/RE and Retire early movement because I am very, I think, reflective about why that was so appealing to me before I really knew anything about money.

That was the world of finance that I, after reading Money Diaries and after going to your book tour in 2018, like [00:27:00] the world of finance that I ended up getting so enthralled. With was the financial independence movement, and I think it just spoke to a deeper. Fear and insecurity in me. This like deep sense of even at the time not knowing anything, not knowing anything about our economy, not knowing anything about how the US deferred from other countries, not knowing how thin the social safety net was.

I mean, it’s kind of crazy that in retrospect, despite my ignorance, there was still some like felt sense of this is kind of scary. Living paycheck to paycheck on $50,000 a year. In this medium cost of living city, like there’s not a whole lot left over at the end of the month. How am I gonna progress? How am I gonna save for retirement?

How am I going to start a family? How am I gonna buy a house someday? And I think that so quickly after I started working, I started to feel that sense of. Claustrophobia or insecurity and, and it felt like a [00:28:00] way out. It felt like an insurance policy almost. Yeah. Like, okay, well this is a way that I can make sure that I’m never stuck and this is a way that I can make sure that there’s going to be a safety net underneath me if something goes wrong.

Yeah. I’m actually kind of surprised to hear that, like you, you’re, you still hear people excited about FI/RE in your entries.

Lindsey Stanberry: Yeah. So frequently FI/RE drives me crazy. For so many reasons, a big one being that I always felt like it was a really male dominated concept and didn’t take into account having children.

And I almost feel like it could use a reframe, the retire often idea, you know, like take short retirement more frequently. And I, I love the idea of reframing. At the time that women take off around having their children as, as a mini retirement rather than giving up their careers [00:29:00] for their children, totally.

And I think that if you could reframe FI/RE in that way, like this idea that you save a lot in your twenties so that you can have some flexibility in your thirties when you have kids, and then when your kids are old enough, when you’re in your forties, you can turn back to being leaning into your career.

I think that that would be a really interesting way to look at it. I haven’t seen that out there.

Katie: So that is Jillian Johns rude. Her book Retire often. I actually did interview her for the show when her book came out. And that is a concept that I think was met with both excitement and curiosity.

Katie: Mm-hmm.

Katie: And also skepticism and I think some frustration because I think people felt as is often true. Well this isn’t realistic. This is such a departure from the way that society is structured that like. I don’t think I could pull this off, but I, I do think that there is value in thinking about it that way, and I, I think that to your point about how we [00:30:00] talk about when you have young children and you also work full-time.

I think 10 years ago when I was like in the throes of my girl bossitis, I definitely would’ve been like, you never give up a career for your kids. Like, oh my gosh, that’s so whatever. And now I think that I’m, again, don’t have children, but I think now that I have a better understanding of. The economy that we live in and what most people’s work lives look like.

I’m like, I feel a little bit taken for a ride that I ever really kind of bought into that. It’s like, oh yeah, fuck your family. You need to be focused on shareholder value, babe. I’m like, I, not all careers are created equal, right? People get different things from work, but I definitely think that I’ve come to see taking those mini retirements, taking time away.

Having different seasons of your life where you focus on different things is actually like very deeply human and yeah, very healthy.

Lindsey Stanberry: I would think that ultimately in the long run, it would make you a [00:31:00] better worker. Mm-hmm.

Katie: Look at us both we’re like, and it would make you more productive long term. We’re like, yeah.

Take a break, babe. Take a break. Okay. So you were working at Fortune when you left to start your own business, right? Yeah. How long had you been dreaming up this shift by the time you actually left

Lindsey Stanberry: and, and did it? So I never intended to be an entrepreneur that was bottom of Lindsey Gold’s dream job like so far on the bottom.

I had a really wonderful job at a startup before joining Refinery. And, um, I helped shut that company down. And after that I was like, never get like, this is so traumatic. Never, never will I build my own empire. But then at Fortune I found myself having the same conversations. That I had had at Refinery and I was a little bored and I had this idea for the purse, which was called like no name, women’s Site in like a Google Doc [00:32:00] for a while.

And then actually it’s funny, Jacob, who was my boss at the company that I helped shut down, was an amazing mentor through the process and helped me put together a business plan and encouraged me to take the risk. So I would say that the idea stretches all the way back to my time at Refinery and with some things I was trying to hap happen at Refinery that didn’t, and then really the idea of leaving Fortune.

I left in June. I probably, I think I texted my friends in February, 2023 and was like, I’m gonna quit my job. Don’t let me not quit my job.

Katie: Has the experience surprised you at all?

Lindsey Stanberry: Yeah, it’s totally different than anything I ever thought. It’s wonderful and terrible. Equal measures every single day. Like it like, like the highs are so high and the lows are so low, and I second guess myself a thousand times, but the winds are pretty amazing, and having this [00:33:00] creative freedom has been really rewarding.

We’ll get right back to it after a quick break.

Katie: In another recent interview, you said something that jumped out to me and, and this is maybe a little meta, but you said, right now I’m sacrificing financial security for emotional security. What did you mean by that?

Lindsey Stanberry: I had a, like a 20 year career almost by the time that I left Fortune, and I’d always worked for other people and I had good bosses and bad bosses, and I was always very entrepreneurial within organizations.

But it was always very frustrating when people said no, and people were always saying, no. And I could do a lot, and I could still get the feedback that it wasn’t enough. And so it just felt like I had reached a point where it was time to take a chance on myself and to be the person saying no instead of hearing other people say no.

And so I would say in a lot of ways, this is the best job I’ve ever had. Because [00:34:00] I have so much creative freedom and because I’m spending this up on my own and it’s very rewarding. And you know, I hear from readers all the time on how much they like it and it’s growing and that’s fun, but it’s not easy and it’s hard to get used to not getting a paycheck and it’s hard to take that big pay cut.

And going back to talking about FI/RE, my husband and I were such careful savers in our twenties and thirties, and I do have. Safety net, which has allowed me to be able to do this in a way that had I not saved a lot during those first couple of decades of adulthood, but wouldn’t be able to do it. And I also have a husband with health insurance, which is huge.

Which

Katie: is gigantic. Yeah. Preach. Shout out to husbands with health insurance. Yeah, I mean, it’s everything. CC Thomas Toan. Exactly.

Lindsey Stanberry: It’s exciting and it’s creatively satisfying. I’m not getting rich off it right now. Hopefully one day I will, hopefully one day the [00:35:00] paychecks can pull up. That is the goal and mm-hmm.

You know, there’s always that sort of fear that like, oh my God, have I tanked my career? Like, who’s, who’s gonna take me back in corporate media? Should corporate media still exist? You know, when I eventually reached. Know the Apex did this and decide, okay, it’s time to go back to an office.

Katie: Is that on the horizon for you?

Like if it takes off like phenomenally, do you still think that you would be like, oh, eventually I’m gonna return to the world of corporate media?

Lindsey Stanberry: I never say never about anything. Like I said, yeah, like this, entrepreneurship was not on my to-do list. In the last five years, so it’s been a surprise to be here.

And so I think that I don’t really look around at other jobs. I work with this wonderful editor, Alicia, and last week I was doing my finances and she, she sent me a job listing and I was like, Alicia, don’t send me job listings when I’m doing,

Katie: doing the [00:36:00] books.

You’re like, are you trying to tell me something right now?

Lindsey Stanberry: Very happy right now, and I have so much I want to still accomplish, so it’s definitely not something I’m looking to do anytime soon. Should the like dream job come along? I don’t, I don’t even know what that is anymore. Like this experience has really changed my thoughts about what like a dream career means.

Katie: Oh, and how beautiful. To be like, wow, this completely changed my perspective on what a dream career is.

Lindsey Stanberry: It, I did my perspective on so many things on my own personal finances, on how much money is enough money. You know, I was with some friends on a girl’s weekend. This past weekend and we were shopping and you know, I can’t spend the way I did when I was making my fortune salary.

I can’t just shop. And I did a lot of emotional shopping in those years. And I always feel a little bad about, I always feel a little like [00:37:00] self-esteem drop when I like can’t shop the way I wanna shop. And then I had this moment where I was like, but that’s so stupid. There’s nothing in this store that you need and you have enough.

Why are you feeling sad that you can’t buy a new sweater that you don’t need? So it’s been a really interesting, there’s been a lot of reframing and thinking about priorities

Katie: a lot. Man, I think all the time about this, just the different ways that different people value autonomy. And I have never been fully self-employed.

So in a way, this conversation is very selfish. ’cause you did something that I’m about to do and I’m like, yeah, so how does it feel? Lemme know. Um, but I think I learned enough from the first two years of doing Money with Katie on my own, on the side. That autonomy is weirdly something that I value more than just about anything.

Yeah. Like I think the last couple of years I have been very fortunate in this role in the [00:38:00] sense that Morning Brew has been very generous to me and things have gone very well, and I was in a position where I could buy things that I never dreamed I would be able to buy. Yeah. It’s really fun and really gratifying for like 36 hours.

Yeah. And then you’re like, and now I have another expensive pair of shoes in the closet, and that’s great. I just think that there is a, there is a level of like deep fulfillment that I find from being able to do whatever I want that. Everything else kind of pales in comparison to, and I think that has been the core North star for me in going back and forth on this decision and like, is this dumb?

Am I giving up like the greatest job in the world based on a hunch? I’m gonna enjoy it more if I do it myself, even if I make less money, and even if it doesn’t go as well. And even if all of these things are true, I think what I’ve come around to is like, well, there’s really only one way to find [00:39:00] out, and that’s to do it and to see what happens.

Lindsey Stanberry: There’s also something to be said about doing hard things. I don’t think that we. Talk enough about how important it’s to do hard things and how gratifying it is to do hard things. Going back to like all the optimizations and how do we make our lives as smooth as possible, but like you get great stories when things go wrong.

Like it’s entertaining. It makes your life richer. You can sort of optimize your way out of having a rich life,

Katie: but oh my God, that’s such a bar, dude. Don’t optimize your way out of having a rich life.

Lindsey Stanberry: Yeah. Oh, and not even talking, you know, I’m like, obviously not talking about money in the bank. I’m talking about like.

Friends and family and yeah, like I still think that we sometimes lose that. I have to remind myself like, I wanna be here, I wanna be doing this. Like mm-hmm. I wanna be spending time. I want to be squeezing every minute out of every day. [00:40:00] And like, I think when you go off and you do this big thing, it’ll be really hard, but it’ll be exciting and you’ll like be learning all the time.

And that’s really cool. And the highs will be high and the lows will be low. And you can text me and be like, Lindsey. Why did you not interview me? I’m gonna,

Katie: I’m gonna, I’m gonna allow myself one crash out per week. Yes. Uh, that’s my, my crash out allotment. To your point about like, you need to hear this too.

I, I always joke that like the things that I say in interviews are the things that I need to hear. Yeah. And I had a little bit of a revelation recently and I wrote about it sort of in my end of year letter in the newsletter this week, but. I think because the last couple years I have put so much pressure on myself to make the most out of this opportunity that has really felt like the golden goose.

Anything in my life that looked like it would take any time or energy away from the time and energy that I had to work and basically build a career. [00:41:00] Was essentially clocked in my brain as like bad, avoid. So it was like any sort of hobby, any sort of project, buying a house, having children, getting another dog, like anything that looks like it was gonna require something of me, energy, time, et cetera.

I’d be like, oh, can’t do that, can’t do that. And it kind of hit me that like. What if the things that like take up the time and energy that don’t make money are good actually, like, which sounds so stupid to say out loud, but I think when you, when I have just been so one track mind for so long

Katie: Yeah.

Katie: That it really did feel like a significant shift to be like, no.

What if pursuing things that are going to be difficult and time consuming is actually going to be good for you and beneficial, what if those are not detractors? From this like other thing that’s more quote unquote more important. And I think that it actually did take me deprioritizing work in order to [00:42:00] even be able to notice that I was doing that.

’cause it was so subconscious that like value judgment.

Lindsey Stanberry: Yeah. That time away is so hard to take and yet so essential.

Katie: So something I noticed on your site is that one of the most popular articles is a very vulnerable piece that you published last summer called Some Frank Thoughts on Money, jealousy, and Loneliness.

Now, I remember reading this when it came out and I remember being like, whoa, this is fucking honest. This is the Lindsey equivalence of like cocaine I didn’t pay for in the bathroom. Stuff like that. Writing like that does tend to work. Yeah. Quote unquote work very well in women’s media. Mm-hmm. But I know that you don’t want the purse to be the Lindsey show.

Can’t relate to that feeling, uh, signed Money with Katie, but do you ever feel that tug or that temptation to put yourself more [00:43:00] or to put more of yourself into the material when you see pieces like that do so Well,

Lindsey Stanberry: I think I put myself in there enough. I think I give readers enough, and it’s really funny.

I’ll see friends I haven’t seen in a while and they’ll be like, I know how you’re doing. I read your newsletter and it’s like you read the newsletter, which is the little parts of my life I choose to share. Look, I’m a Brooklyn mom with one kid. I’m a nice white lady. Like I’m not that interested. I’m not, and that’s fine.

And so diversity of storytelling has been so important to me and I. I don’t think we’re there with the purse yet, but it’s something that’s like top of mind always is to make sure that we’re telling lots of different stories from lots of different women, from lots of different backgrounds and incomes and experiences.

And so to a certain extent, you know, opening myself up and, and sharing the pros and cons and ups and downs of [00:44:00] building this business have been a powerful way to build the business, frankly. So I share, I don’t think I want to share more. I don’t think people want to hear more. Like there was, uh, somebody canceled their subscription, their paid subscription earlier this year, and it was a really long, slightly mean note that was like, oh God, I’m tired of hearing from this writer about her experiences with her husband and.

Um, Alicia was like, does she know? Okay. Just you, like, it’s just you. Like you are, you are it. There is no writer. There is Jacquelin. Well, first

Katie: of all, very brave of you to actually read those. I don’t, I don’t. Right. When people, I, I’m like, I have all of those notifications turned off for diabolical lies.

I’m like, I don’t wanna know why you’re canceling. I don’t wanna know what it is you don’t like about me. That’s, keep it, that is entirely your business.

Lindsey Stanberry: You know, it was painful and obviously it’s still painful ’cause I’m still thinking about it and telling it to you on, on, you know, your national [00:45:00] podcast.

But I also think that there was a good point there, which is like, again, it’s not the Lindsey show, it’s supposed to be other people’s stories.

Katie: Well, ’cause you were an editor at Refinery, right? Yeah. So it’s like you are, you’re kind of still an editor. I’m definitely still an editor. You’re still identifying the stories and, and curating and like it’s your point of view that is shaping.

Yeah, the end product. But it’s not about you. It’s not about me, exactly. Mm-hmm. Something that’s kind of interesting too is when you talk about diversity of stories, I immediately started thinking about how. The incentives in corporate media kind of determine what stories get told. There’s a lot of content out there for people who earn median wages or above, like the voyeuristic content of like very wealthy people.

Right? And then also the median wages that like will attract a wide audience just by nature of being close to the middle. But I remember there was an Esquire piece that got published [00:46:00] sometime last year where it was a. Writer who had been homeless for a long time, and he was writing about that experience and just this very poignant, firsthand story.

And after I finished it, it was so moving and it just stuck with me. And I was like, I can’t believe this is the first time I’m ever reading a firsthand account from somebody who doesn’t have a house. Like why is there are so many people who are unhoused in the United States, like, why is this the first time I’m ever hearing from somebody like that in a, in a major publication like this?

I think that the same goes for stories that are firsthand about what it’s like to live in poverty. I think that’s why like books like Evicted are so powerful and feel so unique because it’s like we just, we really don’t hear from people who are living that close to the edge and speaking on, on their own behalf about what that feels, what that’s like, what those trade-offs are.

Lindsey Stanberry: Yeah. That they have agency and that it doesn’t feel like. Poverty porn or something like that, that they’re the [00:47:00] ones who are telling this story and not somebody else.

Katie: Yeah.

Lindsey Stanberry: It came up recently in the comment section of the Last Home Act ’cause it was another woman making over a hundred k. Somebody was like, I’m really desperate for you to be telling stories from people who are earning less.

And the truth is, is I just don’t have those entries. I would totally publish them if I had them. I just don’t have them.

Katie: There is some self-fulfilling there where like if you’re living paycheck, paycheck and barely scraping by, like you’re not spending your free time on substack like reading.

Lindsey Stanberry: Yeah. You don’t have the time.

If you’re like trying to figure out how to make ends meet, you don’t have time to sit down and write a home economics entry. Like I think that’s an important thing to. Remember and think about.

Katie: I bring up the incentives of kind of advertisers and demographics and all of that kind of stuff that goes into determining what a media company focuses on and what their right priorities are and things of that nature.

Because I think that there is something unique in the subscription model that, right, you have. [00:48:00] And that, I guess I have in, in half of my business life.

Lindsey Stanberry: Yes.

Katie: Where you don’t, you, you actually are not accountable to those forces.

Lindsey Stanberry: No. I would also say that I think one of the problems that corporate media has faced is that there was so much emphasis on growth and just being as big as humanly possible.

And at CNBC we used to be focused on unique visitors, so. Katie, we wanted you to show up and read a story today, but we didn’t care if you showed up tomorrow, like mm-hmm. Don’t come back, you know, until December. Then come back in December and read again. That attitude. Meant that a lot of stories weren’t being told ’cause they were just trying to reach the widest possible audience.

And I think that that’s the joy in some ways of more fragmented media. There’s definitely issues with it, but it allows me to really focus on the audience that I want and it’s gonna be a smaller audience. And advertisers always get a little nervous when I’m [00:49:00] like, it’s niche. But you also know that they’re going to be more engaged.

Oh

Katie: yeah,

Lindsey Stanberry: for sure. Let’s talk about you for a minute. Oh, okay. I wanna ask you a question. Okay. I just wanna know how you’re feeling about everything. It’s your second to last episode. It’s so exciting. Oh. But it also must be scary. Yeah. To put you on the spot.

Katie: Yeah. It is scary. Um, and I think what’s interesting about it is like, I feel like it’s kind of unfolding on two levels where like consciously I feel like I’ve done everything I can to prepare.

Right. I have really worked hard this year to get all the pieces in place. For a seamless transition. So I’ve kind of been joking that like the second half of this year after the book came out, it was like, okay, now that that’s done, time to transition to like doing double duty, basically trying to build up the independent side in the backend.

I mean like I need an accountant now. I needed a business manager. There were so many things that had to happen. Once that decision was made, and [00:50:00] I kind of realized I don’t wanna wait until January to start any of that, ’cause that’s gonna make me feel so stressed. Like I, I would rather have all that set up ahead of time.

Yeah. I’ll front load all the stress. So I feel like I’ve done everything that I can, and yet at the same time there is so much uncertainty and at this point it’s less uncertainty about like, is it gonna work? That part doesn’t really feel risky. But I think what feels risky is the fact that like, I don’t know how it’s gonna feel.

And I think for so long I’ve kind of promised myself that it’s gonna feel so much better. You’re gonna be in control. All the things that you haven’t liked about the last four years, you’re gonna be able to fix and things are gonna be great. Yeah. And I think finally being faced with the opportunity to test that thesis is a little bit terrifying.

’cause it’s like, well, what if it’s wrong? Yeah. What if the things that make me unhappy. Are still there. What if the things I don’t like are still there? What if, what if I’ve like built this up in my head that it’s gonna be this grand adventure and then it’s just not, and like [00:51:00] what would that have meant about this decision?

And the last, I don’t know, honestly, like I’ve been kind of dreaming of being an independence entrepreneur since I signed the contract to sell the business. So like I’ve kind of had that in the back of my mind the entire time. And there is a little bit of a existential. Fear, it makes total sense. I think in general though, I feel optimistic.

I feel good. I feel ready to like make some bigger swings and just kind of stop putting off the things that I’ve told myself I want to do. So, I don’t know, 2026 could be a big year for me. I might change everything about myself. We’ll see. I’m excited. I’m really excited for you. Well, thank you. And thank you for asking

Lindsey Stanberry: as an outside observer, I’m very proud of you.

It’s been very exciting to see your trajectory.

Katie: Oh, thank you.

Lindsey Stanberry: I, I know that you’ll do big things. I worry about a lot of stuff, but not you, Lindsey. Oh, thank you. It means a lot to me to be part of your origin story. Oh my gosh. Like I, that really like, it’s super cheesy, but it’s one [00:52:00] of the reasons why I do the work I do is really to help.

Women. And you know, we were talking about it not being the Lindsey show. Like this is why like I want to see you go out and succeed. That’s thrilling to me. That’s the whole point.

Katie: Oh my gosh. Thank you. I really appreciate that. And. The ripple effect of your work, your interests, your point of view. I mean living proof of it.

So thank you for joining me today for my penultimate episode. Thank you so much.

That is all this week for The Money with Katie Show and for the last time, I’ll see you next week. Our show is a production of Morning Brew and this episode was produced by me, Katie Gatti Tassin with audio engineering and sound design. From Nick [00:53:00] Torres. Devin Emery is President of Morning Brew.