00:08:10.640I knew I wanted to have a successful career
00:08:15.500but I didn't know what that was going to look like.
00:08:17.940But you thought it might be like 20 years at Southwest.
00:08:20.880Yeah. I mean, I love Southwest. It was a great company. I loved the team.
00:08:25.240I think at the time I was making $66,000 per year full-time. And then I was making
00:08:33.400probably an extra $1,000 a month teaching fitness, but I was constantly on the go. I was
00:08:41.640never home. I was always really busy. It's very funny. I think, I mean, I never want to look into
00:08:47.620what people think about us. I think that period of my online life is firmly over.
00:08:53.120But I do think that you and I present on this podcast as being very similar. Like we have very
00:08:59.220similar sense of humor. We have very similar interests. People are always asking like what
00:09:02.660disagreements we have and we really don't have many. I think we work together very well. But
00:09:07.680there are moments where I am struck by how different we are. And one of them is how you
00:09:13.160were really good at being a corporate girl. Like you were good at having a job and I was
00:09:18.140fundamentally not. And it's really interesting to me that you ended up going in your own direction.
00:09:25.580The people that I know who are like you have just stayed and continue to thrive in corporate
00:09:30.600workplaces and the people that- The homeschool jungle freaks of the Fortune 500 companies.
00:09:34.420Exactly. And like the people I know who have started businesses are like often people who didn't feel like the workplace was working for them. And so you are very distinct in that way to me in that the traditional path actually probably was going to work for you. If you hadn't done money with Katie, you would be earning hundreds of thousands of dollars right now, probably.
00:09:55.420I would have been laid off at Meta. I would have been part of a tech layoff is what would have
00:10:01.740happened. You would have been one of the people in a in like a boardroom being like, so you're
00:10:06.160telling me that if we manipulate the minds of 12 year old girls, our shareholder price goes up.0.94
00:10:11.460Pull that lever, boys. Let's go. Every time they talk about like the evil of Instagram,0.91
00:10:16.900I'm like, yeah, shit, I probably would have been like, oh, amazing. But I think there was always0.98
00:10:21.840a part of me that really wanted institutional approval. And to me, getting jobs at these big
00:10:27.220Fortune 100 companies was institutional approval. That was like the validation that I had done well
00:10:33.220and that my college degree was not worthless and that I was a functioning adult. So like,
00:10:37.720I always was a striver. I always wanted institutional approval. But I was also very
00:10:43.740curious about and drawn to entrepreneurship. I just didn't really see a path that made sense
00:10:50.260for a while. Yeah, speaking of institutional approval, fun fact, right before I sold
00:10:55.760yesteryear, I was actively trying to get a job at either Salesforce or Slack.
00:11:02.180Can you imagine, everyone, I just want you to imagine Caroline as an account executive at
00:11:09.200Salesforce. I was desperate. So she was either going to be a novelist and the co-host of this
00:11:16.040podcast or the person that's like, hey, checking in on your CRM. Are we meeting your sales? I want
00:11:22.460to be very clear here. I was never going to be that. They never called me back. I was either
00:11:25.840going to be this podcast host and a novelist or a dog walker and freelance writer. Shout out
00:11:30.300Knopf. Shout out Jenny Jackson at Knopf. Thank you for changing my fucking life. Okay. You're1.00
00:11:35.980a Southwest girly and you become really obsessed with personal finance. Tell me about the making
00:11:42.220of money with katie hold on i just don't i feel like i'm like blurry for you to look at and it's
00:11:48.140annoying me oh it was just it was just my computer being greasy okay we're back let's go continue
00:11:57.720slacks number one employee this is why you had jobs and i did not hiring departments like literally
00:12:05.060i have done multiple zoom calls with like people who matter and i have looked like i'm glowing
00:12:10.540because of the grease over my camera lens.
00:12:13.580There's just like a piece of like cheese like stuck to it.
00:12:17.420You're like, oh, hold on, let me flick that up.
00:12:19.640Okay, so if you recall, I said that I worked for an airline
00:12:27.100two industries that were famously decimated by the pandemic.
00:12:33.500So in my story, the pandemic really changed my life
00:12:37.500because that was the inciting factor for all of it.
00:12:39.940So I told you I wanted to have this long career at Southwest Airlines. I told you I was very ambitious. And when we got sent home that March, and it became clear as the weeks were passing, the original back-in office date was April 15th. And even in Dallas, I mean, Dallas opened back up that summer, so it wasn't like I lived in a place that was shut down for years.
00:22:22.100He's like, babe, I noticed that you logged off at 7 tonight. Are you not feeling okay? Why aren't you working till 11?
00:22:27.400But that period was really fun. Those early days were really fun. And I started the Money with Katie Instagram that summer, partially because I was sharing my blog posts on my personal Instagram account, which had like, I don't know, 4,000 followers that were mostly people from college and like fitness people from Dallas. And I was like, I can't keep posting about financial stuff on here. Like, this just feels weird. I need to sequester this somewhere else.
00:22:52.480When was the moment where you were like, I was right. This is going to be a thing.
00:22:56.080When Money with Katie's followers surpassed my personal ones.
00:23:00.640Okay, well, fun fact, I was following you before you had 4,000 followers.
00:25:42.040They were really looking to bring a creator in-house, and they had a lot of money to spend on it. So I think that I sort of started it without realizing it at a time that allowed me to take advantage of circumstantial opportunities in the market that I wasn't really even privy to. So I think that timing is a big piece of it as well.
00:26:07.140Did you ever have a moment where you contemplated what it would mean to build a career and even a literal brand name that was defined by money?
00:26:17.500Well, I want to know what you mean by that question, because I think what I was contemplating and what I was always thinking about was not defining it by money, but defining it with Katie, making myself central to it.
00:26:27.520I think at the time when I started, it was like, oh, yeah, well, I'm Katie and I'm going to talk about money.
00:26:42.420Say more about that question because I'm curious what you mean.
00:26:45.360As your ambition has found new cracks to seep into over the years, I mean, spoiler alert, you started another podcast that isn't about money.
00:26:56.400So it's like the idea of building a brand that is defined by finance. And then at some point, whether intuitively or intentionally or not, you made a decision that you didn't want your career to be entirely defined by your relationship to money and other people's perspective of your relationship to money. So I'm wondering if you have had different moments of thinking about that through the years.
00:27:19.400I think early on, especially after the acquisition, which we can talk about, I felt like I had my career pretty laid out for me.
00:27:29.440It did feel like a big change. And I want to make that clear is like I went back and forth on whether or not to accept the morning brew offer for a long time, not because I didn't need the money that they were offering me, but because I knew that if it didn't work, I was going to spend three years minimum because that's what the contract length was.
00:29:12.660What if I throw everything I have at it with all the resources of this $70 million company, this media company full of professionals?
00:29:20.460And what if it flops? What does that say about me? It wasn't just the practical implications of like what it would mean for my career. It was also like, what are the practical implications about what this means for my identity as someone who has kind of assumed that this would work?
00:30:36.280Like, and then I built a media kit and the next people that I would DM about, hey, I also like your product. Do you want to sponsor something? Here's the price. And when people would agree to it, I'd be like, cool. So like, in a way, the original Betterment team that I worked with kind of defined the market value of Money with Katie early on because they were the ones who offered me a number that I was like, really? Like, you'll pay me that to write a blog post for you?
00:31:01.500it's so funny hearing these stories about people who build something successfully or become
00:31:07.100successful because i feel like the proverbial you will have this perception of like well you're
00:31:12.320waiting to be anointed you're waiting for someone to like decide that you can do something and the
00:31:17.100most common like unifying detail in these stories is like yeah i just did it like i just like i just
00:31:23.500like try i just like slowly figured it out and like dm'd someone and asked or like like you and
00:31:27.780I with this podcast. We just like, literally, we still don't have a theme song. Like, well,
00:31:33.060we have so just like, like side fucked this into existence. It's crazy. But I want to like0.93
00:31:44.520encourage anyone who's listening to this that it's just like, there are no morals to the story.
00:31:49.000You had 4,000 followers and a dream and you DMed Betterment being like, hey, I have skills that you
00:31:55.700might benefit from. And the worst case scenario is that they didn't respond. And I think you and
00:32:00.460I both could fill numerous podcast episodes about all the moments that someone didn't respond or
00:32:06.080all the like the dead ends. But I do think that there is something really freeing about realizing
00:32:10.500that the people who quote unquote succeed in any industry are people who are just like a little
00:32:16.280bit shameless. Well, it is delusion. That's why I use the word delusion because it didn't, I didn't
00:32:21.740know that like that wasn't something people did. So let's talk about the acquisition. So you had
00:32:26.560tens of thousands of followers at this point, if I remember correctly. And you have mentioned,
00:32:32.480which is a detail I didn't know until we started this podcast, that you had just received a job at
00:32:37.460Meta when you finally got an offer from Morning Brew. You were already making a very good salary
00:32:42.900off of it, but you didn't feel confident it sounds taking it on your own. I'm not a risk taker.
00:32:48.540Because you're saying that, like, by this point, Money with Katie was making several hundreds of thousands of dollars, but you didn't feel like it was stable enough to basically create a hole in your resume where you would depart.
00:33:05.400I would have been, like, out the door on the first sale.
00:33:08.400Well, I'm very risk-averse, but I also think the other part of it was, like, I started it in April 2020, and by the time I was making that much was, like, the following winter.
00:33:17.200I didn't feel like I had a long enough track record to justify blowing up my career.
00:38:53.720They take all the Morning Brew creators to, like, a chokie in the bottom floor of Morning Brew headquarters, and then they just, like, shove you in there, and that's where you live. It's like Coraline.1.00
00:39:02.820But they had never done this before either.
00:39:05.200I was in Out of My Depth, but I was also the first creator that they brought in.
00:39:09.040Wait, wait, what do you mean? So what were the other people?
00:39:11.540They were just people that had been hired by Morning Brew and, like, got their own franchises. So, like, Dan Toomey, for example, he is extremely successful, and he was there before me.
00:39:21.940but he was a morning brew employee who was really funny and really talented and they recognized that
00:39:28.920good on them and basically said you're really good at this you're gonna run the Instagram account and
00:39:34.380then they gave him his own show so interesting they had never like sought out external intellectual
00:39:41.060property to like acquire it and bring it in house before I was the first person that that happened
00:39:45.760to so my deal was also like that was the first time they were doing it either and so I had
00:39:50.740actually like a lot I think I was able to like shape it in a way that I would not have been able
00:39:55.200to had there been other people that preceded me looking back on it is there anything that you
00:39:59.940wish that you had asked for then or that like you feel like you've learned about what it means to
00:40:04.520basically be like working with intellectual property I find that really interesting because
00:40:10.060you and I actually it's interesting as different as you and I are we both sell our intellectual
00:40:14.820property and when we do the yesteryear episode I think that we'll see mirrors of that of what that
00:40:20.220means. I think in retrospect, I would have tried to negotiate a termination clause from the
00:40:34.000beginning, not because it didn't end up working out, but because that was a pretty scary thing
00:40:40.080to have to negotiate for three years in when they already owned it. In a different world,
00:40:46.560where the president of Morning Brew was a different person,
00:40:49.240that could have gone completely sideways.
00:40:51.260Right. They could have just said, fuck you.1.00
00:40:52.820They could have just said, fuck you.1.00
00:40:54.180This is a valuable asset and we don't have to sell it back to you.1.00
00:40:56.980We're going to keep it and do something else with it.
00:41:11.760And, like, I will only marry you if you agree to this.
00:41:14.480That would have been the proper time to say what is going to happen at the end of this contract if I want to walk away. Let's define those terms now when I have the most leverage over what those terms say. And so that's something that I would have done.
00:41:28.800I also think that another piece of it was like, I made an illusion earlier that I kind of felt like once this deal happened, like my career was set out in front of me because the former CEO and I were very aligned on like, we want money with Katie to be as big as possible. We're going to unseat Dave Ramsey. That's the goal. We are going to make this the personal financial empire. So we had all these grand plans. I was more than happy to be working constantly because I really wanted to make this happen and I had their full support. So it was like, oh, amazing.
00:41:57.880Like, all these people are really fired up about this, too. And I think because of that, when I was looking at that original deal, there were a lot of things that we had talked about, which were like, this is just the beginning. You're going to have more than one show. Like, you're going to host multiple shows. This is just phase one. You're going to have a show about entrepreneurship. You're going to have a show about this. You're going to host courses.
00:42:24.040And at the time, I was like really, really into that idea. But as the years went on, and like as I realized just how hard it is to have something interesting to say on multiple platforms every single week without fail for years, it's tough.
00:42:42.020Pause, because I want to get into that. But I just want to stop and recognize the moment where you have been working on this side hustle. And it's working really well, but I also understand your point of, I don't know if the money's going to dry up. I'm selling this wealth planner. Maybe this is a blip. Maybe this is just like one moment where I made some money. Maybe it's a fluke. Maybe people are going to find out I'm a fraud. All these feelings that I think most people have.
00:43:06.700my inner monologue in the shower every morning.
00:43:35.900you. We do want to build this around you. We do think you are capable of being as good as it gets.
00:43:41.260What did that feel like? That's such a good question, because I don't know that in the
00:43:45.180moment it felt that way. It felt like pressure. Okay, that's really funny that you say that.
00:43:51.340Stephanie Dandler, as a writer, talks about this a lot, and something she has said that I think
00:43:55.220about all the time is that she had a huge debut novel, Sweet Bitter, and people asked her all the
00:44:00.040time, what does it feel like to succeed? And she said it feels a lot like failure. Yeah, it felt
00:44:05.340like pressure you know what the scariest moment was actually when morning brew acquired me that
00:44:11.360january they made an announcement in the daily brew newsletter which has 4 million subscribers
00:44:17.680okay so scary i got 5 to 10 000 new followers overnight from that and i felt so exposed oh my
00:44:29.620I felt nauseous for days because I felt so vulnerable to the outside opinions of people in a way that I had not felt when I was just doing it on my own and people were finding it organically.
00:44:43.120To have the spotlight put on you and like, hey, this is our new Money with Katie creator and like, go follow her and she's great. I was inundated with DMs from like Morning Brew readers who thought what I was doing was shit for the first time.0.97
00:45:01.540Yeah, that was scary. And then the other thing that was kind of crazy about that first couple0.97
00:45:07.000of months that like January, February period is that there's an Instagram account called
00:45:11.160things I bought and liked, who kind of coincidentally, at the same time, she has
00:45:17.340like half a million followers. She's anonymous. No one knows who she is. She posted about me and
00:45:23.020said, I love her. You should go follow her. And I got more followers from her one story slide
00:45:29.200than I did from the Morning Brew announcement.
01:01:57.640in that time. Yeah. And then that's why we're here right now.
01:02:02.180Okay. So you're at Morning Brew. You're having a little bit of an intellectual rum spring.
01:02:07.180Can you imagine? They were probably like, God damn it. Seriously. I was thinking that the CEO0.99
01:02:12.540was like, son of a bitch. We hired this personal finance girl. Now she's talking about universal1.00
01:02:17.780health care. Like, fuck, this is not what we signed up for. They like start hiding copies1.00
01:02:21.700of Nordic Theory of Everything and every nearby Barnes and Noble. Yeah. So, okay. So you're doing
01:02:25.960this insane job and you're also moving from working on your own to working with a team so
01:02:31.660what was that like basically building out money with katie in a team so morning brew is still a
01:02:37.660pretty small company i mean i think i don't know the exact number of employees but it has fluctuated
01:02:42.400around the 200 mark for the time that i've been there so at first they plugged me into the audio
01:02:47.940department because i was editing the show myself and so they i met nick nick nick edited the first
01:02:53.880episode of the money with katie show at morning brew who edits diabolical lies so that's really
01:02:58.280fun he's our audio engineer we love nick he is extremely talented so anyway they plugged me into
01:03:03.460the audio department there were other people in the audio department who i worked with on some
01:03:07.860strategy stuff who basically were like hey the show needs to have an angle like you need to think
01:03:12.360about like how you want this to exist in the ecosystem like what is the purpose of this show
01:03:16.100questions that i had never really asked before because i was just yapping yeah and so i kind of
01:03:21.340got that sort of insight. I got plugged into the sales team. So the sales team is comprised of
01:03:26.820sellers and account managers, basically, or account executives. And so there were, I don't
01:03:32.200even know, dozens, dozens of salespeople that have packaged and made media plans for Money
01:03:37.980with Katie over the years. So I got pretty much like, my days of slinging ads in the DMs were
01:03:43.400over immediately. That must have been so nice to not have to think about that. Yeah, but it also
01:03:48.280introduced some challenges because they have questions for me of like, well, who can we work
01:03:52.480with? Or like, oh, this brand wants to do this. And I'd have to be like, oh, I don't really want
01:03:55.800to do that. You're kind of trying to be a good sport of like, well, this is a business that
01:03:59.700needs to make money. You need to do ads. Cue our ethical consumption episode.
01:04:04.840Yeah, yeah. I mean, that's the reality of running a media company. Most spaces is like you have to
01:04:10.120take advertising dollars. So there were sellers. For a while, I was on YouTube. So there were video
01:04:15.980editors that worked on Money with Katie. There was a couple of video editors who produced the0.98
01:04:20.860videos. We made a full-time hire in May of 2022 as an editor position. And then that kind of morphed
01:04:29.400because that wasn't really what we ended up needing. It was still something where the amount
01:04:36.980of part-time involvement with people, it was kind of like, okay, we're trying to figure out and like
01:04:40.880build the plane as we're flying it here. Like what kind of help is going to be most helpful?
01:04:44.480And then there was also the design team who was involved. So the Morning Brew designers worked on the brand and, like, helping me streamline the visual identity. Oh, and then editors. Yeah, there was, like, the newsletter side of things. So, like, there was a fact checker assigned.
01:05:01.740So there was a lot of different hands that got involved. And then about six months later, they assigned a second full-time person to the brand who was fulfilling kind of a different role. And then that individual was on for about a year and then left the company entirely and we didn't backfill.
01:05:23.920Because by that point, I had kind of made clear that I think I need to do less. Like, I don't know that this workload is sustainable for me. And so we had pared back the work a little bit.
01:05:36.560When you talk about telling Morning Brew that you wanted to pare back, what was that decision like when you're someone who wants to make everyone happy and you want to meet expectations? Was that hard?
01:05:47.940yes yeah asking to do less i felt like a failure i did i felt like i couldn't do it
01:05:56.560was that before or after you and i met i finally told them i wanted to pair back after we met
01:06:02.720okay interesting because i think i was i wanted to do other things like i just i and i didn't feel
01:06:07.900like i had any time and really the opportunity to do less came up when it was time to renegotiate
01:06:15.360my contract. There was the termination clause that got added, but there was also in media,
01:06:20.840your work product is considered inventory from an advertising standpoint. So how much inventory do
01:06:27.640you have to sell to your partners? And every episode has five ad spots and every newsletter
01:06:34.780has one or two pieces. So the sales team is really looking at it from an inventory perspective. And I
01:06:39.840was basically going to them and saying, I would like to cut the inventory that you can sell in
01:06:44.640half. That's like not what you want to hear from somebody that works for you. We're gonna have to
01:06:51.740make half as much money on this because I can't keep up with this output anymore. Yeah. And that
01:06:57.660sucked. That did suck. Yeah. They were very gracious about it, like to their credit. I think0.99
01:07:03.360they understood. They did not give me a hard time about it. But again, at the end of the day, it is
01:07:08.780a business. So, like, all of these factors went into the final contract and, like, what was
01:07:14.980negotiated as far as, well, what is it going to mean if your first contract was negotiated based
01:07:21.280on this amount of work and this one is going to be negotiated based on these other terms. And so
01:07:25.440there are going to have to be consequences for that because we're going to make half as much
01:07:29.640money, basically. Yeah, it's really interesting to hear it from that perspective because I think
01:07:34.740you have like an annoying work ethic it's infuriating you work such long hours and I
01:07:41.820think that yes you were working insanely long hours of the last few years but I think
01:07:45.520you are also someone that as I've gotten to know like you enjoy working you are someone who really
01:07:51.340enjoys working and it's interesting to hear you talk about this in the context of us kind of
01:07:56.320spinning up diabolical lies because it's like for you to be able to recognize that you have
01:08:03.020different reservoirs of energy and they can't just all be pooled into one. Like your reservoir
01:08:08.620of energy for you and I to be doing voice memos that turned into a podcast wasn't something that
01:08:13.520you could just like pour over into money with Katie. And so I think I'm curious to know what
01:08:19.880it was like to meet me. And on a more serious note, like what was your experience as someone
01:08:27.580who is in the middle of a very intensive contract
01:08:49.840So when you met me and we started talking,
01:08:53.300we didn't know what it was going to be when we met.
01:08:55.400We didn't even know, are we starting a media company? Are we starting a podcast? Are we just trying to be friends? What was that like for you to be navigating basically, like, this new world of time, energy, intellectual interest, business opportunity, while you're also navigating, like, something that is already operating on all four cylinders?
01:09:15.620Let's keep in mind, this happened before I even sold yesteryear. Like, I was someone that you just, like, were interested in, but I had no credibility.
01:10:05.680And I think I also may have been just coming off of co-hosting a second show, but I had just come off of a period of time where I felt really spread thin.
01:10:15.480but I also think that I was starting to think about the future because it was kind of becoming
01:10:20.320clear to me that the way that I had described the way that I felt about money with Katie in
01:10:24.880the very beginning where it was so easy and it was exciting and I was just like bursting with
01:10:29.160ideas and energy I didn't really feel that way after a couple of years I had started to feel
01:10:35.640like I was slowing down I had started to feel like I was burning out and I was starting to feel like
01:10:41.400I'm losing that spark and I'm losing that excitement and I need to find it again
01:10:46.300because that is critical to me feeling like this is worth it yeah and so I was trying to conceptualize
01:10:53.840who am I what is my role here like Ezra Klein on Ta-Nehisi coach interview being like
01:10:58.880what's my purpose what role am I playing I was having an Ezra Klein what's my purpose what's
01:11:05.020my role crisis of faith I think internally about whomst among us hasn't had an Ezra Klein
01:11:10.660who am I? Yeah. What am I? The difference is that I did not publish an article called
01:11:17.880Charlie Kirk was practicing politics the right way. So it never got that bad. But when I met
01:11:22.820you, I was in the middle of kind of a crisis of identity of like, where am I going with this?
01:11:27.940What is the point? What is my end goal here? Because all along, like there has been sort
01:11:32.660of this North Star that like I am realizing now isn't actually where I want to go. I was
01:11:37.780kind of having to admit to myself I think I want to be a writer the sentence no one ever wants to
01:11:43.820admit the scariest realization yeah yeah so I had that realization of like I think I want to be a
01:11:50.600writer I think that that's the thing that I care the most about and so I had invested in hiring
01:11:54.800an editor who I felt like could take my writing to the next level I had like brought someone on
01:12:01.420externally that morning brew was not involved with and you paid out of pocket right yeah to edit my
01:12:07.120work because I wanted to get better at writing. I wanted that to be something that I could sell
01:12:11.860another book and, you know, make that more of my thing. I wanted longer lead times. The thing about
01:12:17.480publishing a show twice a week and a newsletter every week is, like I said, you constantly feel
01:12:23.000like you have to have interesting things to say. And because it's always on, we don't take breaks.
01:12:28.740We ended up building in bi-weeks to the show because I just could not keep up. I didn't have
01:12:33.840that much to say after 300 episodes. And I never wanted to say something just for the sake of
01:12:38.600saying it. I didn't want to be producing stuff just for the sake of putting something out there.
01:12:41.860That felt terrible to me. I think we've taken one week off the newsletter in four years.
01:13:54.380But I was watching your videos and I think, I don't know, it's hard to describe. I think there are so few experiences in life where you just have kind of that moment where I'm like watching your videos and I'm like, oh my God, she's saying the thing that I've been struggling to say. Like, this is a person who actually gets it.
01:14:11.840and then I think I was just so blown away honestly by like your intellect and your ability to
01:14:19.880communicate ideas in a way that I had not had that experience in a long time I just like knew
01:14:25.380I wanted to meet you and then I went to DM you on Instagram and I saw that we had talked in the
01:14:30.580past and I was like wait I already know her what the fuck because I used to respond to every DM that0.95
01:14:35.540I got yeah so proof I was an early follower yeah crazy I just want to pause here and say again0.97
01:14:41.180i was just saying things on tiktok and you were so established i did admire you i was so impressed
01:14:48.680with what you had done and i was someone who had never not only had i never received like any
01:14:53.800institutional anointment i had gone viral but that meant nothing and so when you reached out
01:14:59.320like you were my first ever moment of institutional anointment oh wow it was like oh a person that i
01:15:04.780admire has decided that i am worth being admired as well and again this happened like
01:15:10.520three to four weeks before I knew that I was going to sell yesteryear at the point I was
01:15:16.200just writing another manuscript I'd written plenty of manuscripts in the past had no thought that this
01:15:20.740one was going to sell you asked me to go on your show and I remember when I did the show with you
01:15:25.960I remember thinking like this doesn't feel like a money with Katie episode it was topics that I
01:15:31.300now realize you were exploring a lot but it's kind of like that was a little bit like a first
01:15:35.260diabolical lies episode yeah where you and I were like moving all over the place that's really funny
01:15:40.740Because you told me you were working on a novel.
01:16:09.840I'm knocking on wood. But let's be real, like, it's the lead novel for 2026. It's a big deal.
01:16:16.480And you are also very humble about that. But that was also kind of like a, I always, I joke that I'm
01:16:22.600like, it gave me some confidence that I have good taste. Because I was like, wow, I sniffed that out
01:16:28.040early. In the town square, like the elderly man who's like naked with a sign being like,
01:16:32.620nigh the world is ending but I think that our creative chemistry was so apparent meeting you
01:16:39.640gave me a very similar feeling to the way that I felt starting money with Katie which was just that
01:16:45.200kind of oddly peaceful feeling of like oh this is gonna work oh this is it you know yeah I think I
01:16:51.060had that like when you know you know feeling about our creative dynamic and about that so quickly
01:16:57.200that again there was just not a whole lot of overthinking to your point we still don't have
01:17:02.460a theme song. I think we were just like, okay, let's do it. Like, obviously we're going to do
01:17:06.040this. But that was, it was helpful because it was really clarifying for me, I guess is what I'm
01:17:10.980trying to say, is that I was in a period of the wilderness career-wise. I did not know where I was
01:17:16.260going. I did not have a North Star. I knew that what I was doing was not what I wanted to do
01:17:20.640forever, but I didn't know where to orient myself and where to start working hard again. And I think
01:17:27.500this kind of clarified for me that I didn't have to be a one-trick pony.
01:17:32.980So you and I meet about a year and a half ago, spring 2024. You are, it sounds like,
01:17:40.060in the process of starting to renegotiate your termination clause, right?
01:17:44.820I had just started, yes. My lawyer and I had just started working with Morning Brew
01:17:48.860to renegotiate the new contract because it was going to end in January 2025. And so it took us
01:17:56.300like six to eight months to get it all nailed down. And so what was that process of the following
01:18:02.180year and a half like of facing down? Like you're going to make huge changes with Money with Katie.
01:18:08.480You're basically taking on this unknown where at first Diabolical Lies was kind of shoot the shit,0.78
01:18:13.600but it rapidly evolved into something where you and I are basically doing 20-hour sprints on these0.54
01:18:21.120episode outlines. What did that look like in the final year and a half for you in terms of
01:18:25.580workload, in terms of where you were spiritually and emotionally, intellectually? Answer all of
01:18:32.140those. Well, one big open question in the beginning was, is Morning Brew even okay with
01:18:40.260me doing an external show? Yeah, I remember we didn't know. That's about something other than
01:18:44.680money. And they were. They were okay with it, especially because it was about something else.
01:18:50.880And the negotiation process, I wasn't entirely sure if I was going to get it back.
01:18:57.940I think that there were periods of time in that process where we were really trying to get into the weeds of the terms and like, what is going to make sense?
01:19:04.660Where I was kind of thinking like, should I just let them keep it and move on?
01:19:09.040Is it worth it basically to fight really hard to get the IP back?
01:19:12.480Why is it so important to me to own this?
01:19:16.560And I understand that this is a contract, so you can't reveal everything about it. But can you give any like rough strokes about what were the terms that you were kind of struggling with that made it seem like you didn't know if you would be able to get it back?
01:19:31.440The way that they would be paid and what they would be paid. So in the same way that when I initially signed the first contract, it was the question of, is this amount of money worth it to me to sell them my brand?
01:19:44.280Because you had sold 100% of the equity and now you were trying to buy back 100% of the equity Taylor Swift style.
01:19:49.900That's right. It was the same question but reversed. Is it worth it to me to get it back? What is it worth to me to own this? But ultimately it was important to me to own it because I think it was a body of work that spoke to how far I had come.
01:20:04.880I think the person that I was in April 2020 when I started and the person that I am now believe radically different things about the world. And I'm really proud of every single one of those essays and all of those interviews. And I'm really proud of what The Wealth Planner became.
01:20:22.960And it was ultimately just important to me that that body of work was mine. And so I think that weighed heavily in my decision. And I think at the same time, I didn't want to not be Money with Katie anymore. I wanted it to look different.
01:20:40.540So there are also the practical implications of like, what is the value of this asset now? And the value of that brand recognition and my name is on the book that's print, you know, so like there were pieces of it that ultimately I felt like I could not walk away from.
01:20:58.620Yeah, I think to add to that, something that I think about a lot, you and I talk all the time about what this is, what this podcast is. Do we want to do a bigger cadence? Do we want to get an employee? Do we want to do live events? Do we want to sell a book? Do we want to turn it into a media company? Like, we are constantly like, what is this?
01:21:19.980And I think that for both you and I, we are now at points as well where like diabolical lies is still like our slutty little side chick for both of us. It's like this thing that is pure pleasure. Genuinely. I have moments like this all the time where I'm like, I've messaged you before kind of saying like, it's almost like one of those corny TikTok videos, you know, that piano where it's like, and it's like, this was the part that you were hoping for all along. And it's like a picture of a baby foot or you're like in Capri or whatever the fuck.0.78
01:21:49.420That's how I feel about this, where I'm like, you and I talk all the time about the future,0.93
01:21:53.280but this project, we have allowed it to become this really bizarre, cool, creative project
01:22:00.380that we have no expectation on because we both never knew if it would work.
01:22:05.440Even, I mean, we joke about the redistributions.0.91
01:22:07.880We had no fucking clue we would be able to donate that much.0.90
01:23:01.140as opposed to if you had basically given away Money with Katie
01:23:05.500or signed a certain deal that ensured that you were basically separating with it,
01:23:09.500I think that there would have been immediate pressure
01:23:11.520for you to basically figure out the next thing immediately.
01:23:15.400But now you're in this position where you know what Money with Katie is. You know you want to do the weekly newsletter. You want to keep writing essays. But you also want time to not be building something in the same way. And I personally feel really grateful that you have been able to negotiate for Money with Katie in such a manner that it allows you and I to keep making decisions that feel a little bit aberrant with diabolical lies.
01:23:40.640Yeah, there are moments where there is the moment internally where you just have a good feeling about something and you can't really explain it.
01:23:50.680But I think the more practical thing that I would point to when I felt like Diabolical Lies was working and that my gut feeling was correct is that Money with Katie podcast launched mid-2021, late 2021.
01:24:08.580And it took up until this year to hit a download number on every episode that Diabolical Lies was hitting in the first seven to eight months.
01:24:23.840With no paid advertising, with no media company behind it, with no social media behind it.
01:24:28.980But that was the moment where my gut instinct was confirmed true, where I was like, oh, I actually have a benchmark for how podcasts typically grow and how hard it is to get one to this level and how much effort and resources it takes to get it to that level.
01:24:43.940And I think when I saw the way it was working and saw it hitting those benchmarks, I was like, okay, it's not all in my head.
01:24:52.720I think that for me, the bigger side of it really was that I had felt a little intellectually stagnant.
01:25:00.040Even though I was still learning a lot and reading books, I just didn't feel like I was growing in the way that I wanted to.
01:25:06.180And I think that working on this podcast and working with you changed the way that I think in a way that I started to feel again, oh, I feel myself growing intellectually. I can, like, feel the way that I'm thinking about these problems changing.
01:25:21.620Could a jump scare cut to me making you listen to, like, an eight-minute monologue about a woman's gangbang at a spa in fucking Portland, Oregon? I'm like, are you growing, Katie? Have you changed?0.96
01:25:36.180You're like, so I watched eight hours of porn for this episode.0.98
01:26:16.520Something that I have noticed with you over the last 18 months is that you and I would talk a lot about cadence.
01:26:23.600And I think at the beginning of our, I guess, like working relationship, I would kind of say maybe a bit insensitively, like, I don't think anyone can release something interesting every week.
01:26:34.500And I was trying to be empathetic to you. Your relationship to the concept of cadence and to the concept of the time you want to take over the last 18 months that I have known you has shifted from the perspective of a businesswoman to the perspective of an artist.
01:26:49.520to see your perspective on cadence change,
01:27:18.720the demands of commerce, and the demands of intellectual creativity. And to see you kind of
01:27:24.500navigate that has been really interesting because you currently have not one but two businesses that
01:27:30.660do require cadence. Like, as much as our cadence is much lower, you and I also have to fill an
01:27:35.740episode for, what, two hours on average? That's a totally different type of conversation. And so
01:27:41.300it's exciting in a way where I'm like, I don't know what she's going to do. I don't know. Like,
01:27:44.700I know what you and I want to do. But the thing that I was talking about at the beginning of this
01:27:48.480conversation for you to essentially walk away from something that was like, you could have kept
01:27:54.200doing a million things to keep growing money with Katie and keep expanding, but instead you are
01:27:58.920essentially saying, no, I need to go try something else. It's not just you turning to money with Katie
01:28:05.740and owning it yourself. It's not just you committing to diabolical lies. It's the third option as well
01:28:10.620of what would it look like if I had time that was not banked to anything? And that is a very
01:28:16.700exciting thing for someone who is a writer. Like, who knows what you're going to write, honestly.
01:28:22.920Yeah, who knows? I don't know. I'm a little stressed about it, gotta tell you. A little
01:28:29.340stressed about that. So you negotiated to buy Money with Katie back. Diabolical Lies is now
01:28:35.980something that is, like, fully operational, if I guess you could call it that. But it is still
01:28:40.120very bare bones. You and I basically switch off doing episodes. This is kind of rough,
01:28:45.360And it's not exactly like this because we're always kind of communicating about the podcast, but it's basically two weeks on, two weeks off where you have an episode and I have an episode. How did it feel to announce that you had bought back money with Katie and how are you feeling now?
01:28:58.820It felt surreal. It felt like the culmination of years of soul-searching. And it felt, in a way, sort of similar to how signing the original contract felt, in that it was a big celebration, and it also is really scary.
01:29:17.820That same risk-averse side of me still exists. There is definitely a side of me that has that feeling of this does feel like a leap. Because, you know, I think anyone else, objectively speaking, would be like, dude, you have this great cushy media job. You're in a great company. You're paid well to write and to produce this show. Why would you give that up? Like, why would you separate from something like that that's been so good for you?
01:29:43.200I don't know what my life is about to look like.
01:29:44.980I honestly think that it's going to be quite uncomfortable
01:29:47.400because I've been so 100 miles an hour for the last,