639: Katie Gatti Tassin (Money with Katie) - Building A Media Business, The Morning Brew Acquisition, Knowing Your Retirement Number, & Living Up To High Expectations

0:00This episode is brought to you by Insight Global. Insight Global is a staffing and professional services company dedicated to being the light to the world around them. If you want to learn more about the CEO, Burt Bean, and Chief Revenue Officer, Sam Kaufman, check out episode 424. We had a fantastic conversation talking about my partnership with the great people at Insight Global. If you need to hire one person, hire a team of people, or transform your business through talent or technical services, Insight Global's team of 30 ,000 people around the world have the hustle and grit to deliver. Hiring can be tough, but hiring the right person can be magic.

0:45Visit insightglobal.com slash learning leader today to learn more. That's insightglobal.com slash learning leader. Welcome to the Learning Leader Show. I am your host, Ryan Hawk. Thank you so much for being here. Go to learningleader.com for full show notes of this conversation and all podcast conversations. Go to learningleader.com. Now on to tonight's featured leader. Katie Gaddy Tasson is the host of the Money with Katie podcast and author of the newsletter of the same name, both acquired by Morning Brew in 2022. Katie provides fresh personal finance advice with a unique outlook coupled with deep self-taught knowledge.

1:36Before founding Money with Katie in 2020, she worked professionally in marketing and user experience design for Southwest Airlines, Dell Technologies, and Meta. She's also the author of a new book called Rich Girl Nation, Taking Charge of Our Financial Futures. During our conversation, we discuss the benefits and sometimes problems of having extremely high expectations. I have a feeling a lot of people who choose to listen to this podcast have this issue. Then Katie takes us inside the process of Morning Brew, acquiring her company, including the initial DM she got from their CEO and how quickly the deal came together.

2:23Love those inside stories of how something happens. And then we focused on what it means for you to become financially free. How to better understand what that number is for you. Ladies and gentlemen, please enjoy my conversation with Katie Gatti Tassin. Katie, it is so cool to have you here on the Learning Leader Show. Welcome. Thank you. It's so good to be here. I loved reading the dedication in your book because it's kind of spicy. And I think that's a cool way to start. You said to the anonymous guy who works in finance, in quotes, that used to relentlessly comment on my nascent website in 2018, urging me to quit writing about money and to, quote, keep it to myself.

3:08I hope you're well. Can you tell me more about your motivation from this guy to kind of like, it felt like a little bit of a chip, you know, a little spicy. Tell me more about this and some of the motivation to do the stuff that you've done. Yeah, isn't that nice? What a good first impression I'm going to make on your community. They're like, wow, she can really hold a grudge. Yeah, this is somebody and an experience that always stuck with me because I think when you start to put yourself out there, if you are building a business or you're trying to, I don't know, make a mark on the world with your work, it is going to involve facing criticism and facing feedback.

3:48And not all that feedback is going to be positive. And that's something that I've dealt with a lot over the years. But that was really the first time very early on when I was publishing a blog for, I don't know, probably like 16 people who read it, my mom, my neighbor, people I went to college with. And I had gotten really interested in personal finance kind of overnight. And so this blog that I had been writing that was formerly about dating and my career, and whatever, I kind of transitioned it really abruptly into a blog about money. And this was like this person that I dedicated the book to who I don't know who it was.

4:30It was just some anonymous person. I kind of consider them like my first troll or my first hater. And it was this, this moment where every time I would publish something new, like without fail, this person would comment and would leave me these long screeds basically saying like, you shouldn't be writing about this. I'm a financial professional and you don't have the qualifications to have opinions about money online. You should really stop writing about this. And as I was turning in the book and I had to write the dedication, I was like, I'm pretty sure I'm the only one of the two of us that's written a book about money.

5:06So I'm going to dedicate it to them. So good. You also write about though, specifically your mom and the acknowledgement section for all the quiet days spent sitting on the floor of the Lentz Branch Library and wandering the stacks at Barnes and Noble. Your dad's in there too, right? About being your number one fan and kind of always having your back at the kitchen table. Can you talk to me about your upbringing with your mom and your dad and how they set you up or what impact they've had on you as you've gone on to build such an amazing business? Oh, that's a really good question. And I'm impressed you read the acknowledgements.

5:43My parents were extremely supportive of me when I was a kid. They were also people who had very high expectations for the things that I was doing. So if it was school, it was straight A's or bust. They didn't really have high expectations for me in sports because I'm very uncoordinated. So they let that one go pretty early on. But they were always supportive of my interests and they always really doubled down on doing your best and working your hardest. And I think in a lot of ways, I'm an only child, so they really funneled all their ambition into me. But I think in a lot of ways that has been the biggest blessing and the biggest curse for me is that I am an incredibly driven person because of the people who raised me and the way I was raised, but I also have a really hard time with turning it off.

6:44I can become very narrow-minded and obsessive about the things that I'm doing. And I think that if you are an entrepreneur in particular, that can be a really useful trait. You can kind of weaponize that because I mean, if you're willing to put in really long hours, really focused hours, seven days a week, like you're going to get results. But I have found that over the years, as things have progressed, that is also a quality that I have to really be mindful of, because if I don't watch it, work will completely consume me. And I think that my parents now, something that's a little bit ironic is that back in the day when I was in school and, you know, taking all the AP classes and just was like that kind of kid, you know, very type A, very ambitious.

7:37Back in the day, I would spend a lot of time doing homework and there was a lot of focus on my grades. And I think now as an adult, they're often the ones that are like, remember, there's more to life than like money and success. Okay. Remember that like you can slow down a little bit. So I think sometimes they will feel like, oh gosh, what have we done? Because she really like took it and ran with it. But yes, I was very fortunate to have parents who both supported that drive early on, really cultivated it, but also taught me a lot about money and made money something in our household that was just another topic of conversation.

8:19I knew how much money my parents made, which I think is kind of unusual. Like I've told people that over the years and they're like, really? I remember asking them when I was relatively young, like, well, how much money do you make? And, you know, they told me. So I never really thought of it as something that was taboo. But my mom was a very diligent manager of our household finances, too. I would say relatively young age, there was an emphasis on like, oh, you always pay your credit card bill off in full every month. Oh, it's really important to save. And at the time you're a kid, you have no concept of monies, right?

8:50Yeah, yeah, whatever. Okay. But I do think that a lot of that, even just the ability to talk about money openly in my home made it a lot easier for me now as an adult. and especially as a young adult when I was just getting started and kind of trying to figure out, okay, what is my financial strategy going to be? I didn't have a lot of the hangups that I think some people have who are not as fortunate or whose parents maybe didn't have as like transparent and frank of relationship with money as mine did. Such a gift, I think, for parents to be that open and transparent because now it's, I mean, now you've built your kind of business and life around it.

9:30I want to go back though, Katie, because I sense you have this extremely high standards dedication to excellence. And this is something that I personally deal with. So this is a selfish question, but the problem is when you can't turn that off, the people that sometimes are collateral damage are the people you love, love the most. Meaning I have these unrelenting standards standards that are not really attainable for myself. But the problem is you then kind of put those on the people around you, like your spouse, your kids, and that can be a problem. I know from first-hand experience, and I am literally dealing with this as we speak.

10:14It never goes away. And I'm curious, how do you manage that with your husband or other people that you're really close to that you have such high standards and a demand for excellence of yourself and a crazy work ethic. I know that's part of who you are, but again, that could come out in a bad way with the people you love. How do you manage that? Oh man, that's such a good question. I think for me,

10:41I try and sometimes succeed, sometimes fail to keep it in perspective as far as like what I'm what I'm asking that work ethic to do. So if I'm talking specifically about myself and that standard of excellence that you've referred to, I think that that's that's interesting because that is actually something that we kind of say internally in Team Money with Katie is like, okay, there's a standard of excellence for this work. Is this hitting that standard? Is it reaching that standard or not? Are we proud of this? So we actually use that phrase, which is kind of wild that you picked up on that. But I've been working with a coach over the last, I'd say, 16 to 18 months.

11:26And something that we unearthed probably about a year in together is that part of the stress and the drive and the ambition, I guess you could call it, around the work is in many ways coming from this pressure that I'm putting on everything that we're doing to essentially reflect back to me this affirmation of you're smart. Yeah, you're working really hard. Yeah, you're good at this. Like asking the work itself to be an affirmation of these things that I hope are true about me. So I guess you could call it maybe a vector of imposter syndrome, but I really think it's more so about when you're putting that level of pressure on everything that you're putting out into the world to be the best thing that you've ever done, it has a way of really sucking the fun out of it.

12:28And so I think when it comes to managing that impulse and applying that impulse to other people who are not asking for it, I have found one-on-one coaching to be really, really important and really helpful. I think that a lot of the challenge with managing that impulse comes from the fact that it is just the water you're swimming in every day. So you often, I didn't really even realize that I was doing it. And so, you know, you might be experiencing the same argument over and over again, or you might have this pattern that you feel like you're stuck in. But until I started working with a coach and started talking to somebody about these feelings and these tendencies, I didn't really have that 360 view to be like, oh, that's where that's coming from.

13:21That's why I'm doing that. That's how that feels in my body when that impulse creeps up. So that is something that I'm really thankful for, just that outside help, that outside perspective. And I think that if you are somebody who works really hard or works for yourself or manages a team, it is really important to have that kind of third-party objective voice that you really trust, who you can tease some of this stuff out with. It's been invaluable for me. Is this like a business coach, a therapist, all of the above? What is the person? How did you come about making the decision to work with the coach?

13:57I need this, by the way. Big time. I also think high performers want and need coaching, but it's hard to find the good ones. I don't know the right, you know what I'm saying? So I'm curious about how did you come up with this idea? What is the person's technical job? All the details behind it. I think that part of the reason it's really hard, well, twofold. One, there's a lot of grift in this space, and it's hard to know qualifications ahead of time, and it's hard to gauge effectiveness ahead of time. So that can be a hurdle. It is a hurdle, but it's also expensive. And I think that for me, as someone who tends toward saving money and investing money and writing books about how to do those things better and more efficiently and how to optimize that, I was really reticent to hiring somebody because I was like, what is someone going to tell me that I don't already know?

14:55oh, you know, I had tried therapy in the past and it was fine, but like, it didn't really give me, for me personally, it didn't end up being some like life altering experience. So it was really a series of conversations that I had with a friend, her name's Tara, who runs a multimillion dollar ed tech company. And she was a person that as you get, you know, those people that you meet were like, they're just so themselves. They're so embodied. They're so confident. They're so authentic to themselves and kind of certain about what they want and not afraid to try things. That was, that's how Tara is.

15:36And she and I had this conversation about coaching and she asked me if I had ever worked with coaches or been in mastermind programs or done anything of that nature. And I kind of was like, no, I think all that's bullshit. Like, I think all that is grift. Like, you know, this is coaches, coaching coaches as a pyramid scheme. And she was kind of like, huh, that's interesting. Like, I've invested a lot of money in this work. And I could point you to that's the person that helped me 10x my business. That's the person that helped me finally break free of this limiting belief that was really holding me back.

16:10And I was very skeptical. I think I'm kind of a cynical person by nature. And I tend to, I'm a cynical optimist, we'll say, but I tend to try to think more at the systems level than at the individual level. And so I kind of wrote off a lot of it. But after a while, I was like, you know, but I can't deny the fact that she's getting results that I'm not getting. And she seems tapped into something that I'm not tapped into. So like, what could it hurt? So I had posted on Instagram toward the end of 2023. Hey, I'm looking to hire. I'm trying to level up next year. I really want to take things to the next level.

16:49I feel like I've had some success in business and things have been going well, but I feel like I'm kind of at a crossroads. And in order to really kick things up a notch, I got to figure this out. I need somebody who can help me get there. So I was originally looking for a business coach because I'm thinking I need tactics. I'm thinking I need strategies. And then I get this email from a girl that I went to high school with who was like, hey, I think that you would really, really like this coach that I've been working with. Her name's Elizabeth. And I was like, well, what kind of coach is she?

17:23Does she do business coaching? Does she know how to scale? You know, is she familiar with media? Like, I'm asking these types of questions. She's like, no, no, no. She's a life coach. And I'm like, whatever. life coach. Okay, sure. So I end up taking a first like referral with her though. Cause this woman gift, this woman I went to high school with gifted me a session with her. And so I prep my Google doc ahead of time. I'm like, okay, these are the three directions that I see my business going in. These are the three different paths. I could see these options. I think we could scale this way.

17:51We can do this. We can do this. I send her this Google doc ahead of time. And we sit down for this first session together. And she's like, okay, fuck your Google doc. She's like, you are way too in your head. You are way too concerned with like the minutia. You don't even know where you want to go yet. Do you even know what you want to do? And I was like, no, you're right. I actually haven't spent any time thinking about what I actually want. And so the first hour that we spent together, I think we did like a meditation. It was completely different than what I was expecting, but I left that session with what felt like a huge leap forward in clarity.

18:30And I was like, yeah, I got to work with this person. There's something here. She's doing some stuff that I, I am not tapped into. And we ended up, I basically asked her, you know, she presented me with these two options. You can do the year, you can do monthly and both are expensive. So I'm like, oh gosh, I don't know. So I sit with it for a while. And we basically worked something out where I said, I really want to do this, but I need an off-ramp if this is snake oil, basically. Like, I feel really good about that first session, but what if that's all you got, basically? The skepticism continued.

19:08And she was like, sure, sure. If at three months you don't think it's working, you can break the contract and we'll be done. By the three-month mark, I was like completely sold. And yeah, it's one of the best, it's one of the best investments in myself and in my business that I've ever made, because even though she's not there to talk to me about these different strategies and tactics, she helps me work on myself. And I think what I've learned is that as a business owner, as an entrepreneur, as somebody who has had that experience of kind of creating something out of nothing and like shepherding something new into the world, I think a lot of the answers are in here.

19:52And I had just gotten way too in my head and kind of forgot that, you know, I have the resources and if there are other resources I need to go need, like I will, even the first step is being able to recognize where your gaps are. And so it's been a really good experience, but yeah, it was just not what I was expecting. I think life coach is just a terrible name though. They should be like a performance coach or something. Like when I hear that phrase, Katie, I'm like, nope, not happening. Like they should just rebrand it or something, if that's what you call it. Cause like I, it's, there's, there's, as you said, there's just so much grift in that arena, but that's interesting.

20:33I may want to talk with you more about that later. I don't want to get off track for the rest of this though, but you mentioned being an entrepreneur were in your business. I vividly remember when the news came out that you were being, or your business, you, your business was being acquired by Morning Brew. As someone who has a media business and the different elements that go with that, it was super interesting to me that Morning Brew was a media company that had built itself up and scaled, got acquired themselves, and now was acquiring you, I was like, whoa, I need to learn more about this. So can you talk to me about what was going on up to that moment?

21:15And then what made you decide to agree to the acquisition with the Morning Brew team? Totally. So I write about this story in a little more detail in the book in chapter two as part of this. Basically, there are multiple ways to earn more money, right? You can either earn more money working for someone else, or you can go the entrepreneurship route. And so having done both now in my career, I wanted to kind of write a hybrid chapter that dives into all the finer points of kind of both paths. So that's what I did. But this particular experience, I learned a lot from it because I had been running Money with Katie.

21:53I'd started it in April, 2020. And then I had been running it on my own as a solopreneur from April 2020 until around November 2021. So call it about 18 months. And things were going really, really well for me. I had kind of stumbled into a solid monetization strategy. And I had also just gotten a job working in user experience design for Meta, formerly Facebook. So I had this great, cushy tech job with good benefits on one hand. Then I also had this kind of nascent personal finance media company that was growing month over month at a really solid clip. And I was seeing a lot of success with it.

22:40So I was really kind of content, but also looking ahead to go, okay, my side project, my side hustle is earning twice as much as my full-time job. Through ads, right? Through ads, through digital product sales, through affiliate revenue. So I had several. It was a well-diversified. That you figured out all yourself. Yeah. I mean, it was. And that's kind of the thing is like, even for the ads, people are like, how did you sell your first ads? I mean, I literally DMed the businesses that I wanted to work with. And they're like, hey, I'm Kate. I mean, I don't know where the confidence came from. I honestly think it was like when you can kind of have it's naivete that ends up working in your favor where like, you don't know any better.

23:25You don't know that that's weird. So you're just like, whatever, I'll just DM them and be like, my blog's great. You should definitely sponsor it. And like, to my shock and awe, people were like, okay. So that was, that was how that all kind of came together. And you know, it was like the product similarly, just responding to this is what readers are asking for. And I think it'd be fun to make something like that. So why not? So it was a very, it was a very easy breezy kind of like love at first sight business in that sense, where the first 18 months, it was really fun to, to build it. And so I was looking ahead though, to 2022 and going, all right, I really want to go full time with this, but I'm nervous because it feels really, it feels like I have this other career that has just kind of taken its next step.

24:15I just moved from a good company where I was paid decently to like one of the tech companies where you can make a lot. And I was like, oh, this is like a prestigious job. You know, if I really want to be a UX writer in my career, I don't want to throw that away, but my heart was elsewhere. So I'm like really weighing this decision to try to take it full time and penciling out all the numbers of, well, what would that look like? And what would be the worst case scenario? And that was around the time that I get a, I think a DM on Twitter from Austin Reif, who was the CEO of Morning Brew at the time and one of the co-founders.

24:50And he was like, hey, I think what you're doing with Money with Katie's interesting. I'd love to talk. So at the time I figured, oh, they're probably trying to spin up a personal finance for women thing. Like he just wants to ask me if I have any learnings to share. Basically we talk for 30 minutes and at the end he's like, all right, I'm going to cut to the chase. Like we want to buy money with Katie. And I was kind of taking it back. I was like, what? No, like that, that's crazy. Like, why would you, why would you want to do that? Because I basically told him there's no way that this would be mutually beneficial.

25:26Either you're going to pay me the amount that I want to make from this and you're not going to make any money or you're going to make all the money and I'm going to be working for my own brand for like a pittance. And that's stupid. I kind of sat with it for a little while and, and originally was like really leaning toward no, cause I was having so much fun with it that I was like, I don't want to sell this to somebody else. But as we kept talking and as I, and I write about this, this kind of thought process in the book of like, okay, well, what is most important? Like, let's prioritize here.

25:57Most important is I want to be able to stop context switching. Right now I spend all day doing one thing and then nights and weekends do another. That's not like a super sustainable lifestyle in the longterm. So I know I want to do this full-time anyway. I want to make more money than I'm making now doing both of these things, but to do just one. And I want to learn because this is a media company that has$50 million a year in revenue. This is a media company that knows how to sell ads, right? I have no idea what I'm doing. I'm flying by the seat of my pants. So as we, as we continued the negotiation over the course of like the next six weeks, and I really started to think about the long-term play, the, um, the, the best advice that I got was from another, a friend of mine who also actually had, had recently sold a company to, I think Acorns, he was like, well, would you rather have a hundred percent of a grape or 25 % of a watermelon?

26:56Because that was kind of how we were framing the, like, I'll get to keep a percentage, but not the whole thing. And I was like, oh yeah, good point. So I ended up doing it. And in January, 2022, Money with Katie became part of Morning Brew. So now it's been part of Morning Brew longer than it was independent. They do own all of it. They I get a revenue share and I have a base salary as well. But the big lesson that I took away from that negotiation and that I really wanted to make sure I conveyed in the book for any entrepreneurs who end up in a similar position is your intellectual property is the most valuable thing that you are negotiating over.

27:37And it is probably going to be worth it to seed other terms in order to keep some of the work that you're doing to retain some level of ownership over the thing that you're creating. And there are a lot of other terms that I think are worth negotiating as well that I outlined in chapter two. But when my original three-year contract ended this past January and we were renegotiating a new one, that was something that I kind of came back to the table with and said, I have to have a termination clause in this contract that gives me a path to buying this back from you. I don't want to be in a situation ever again where if I leave or if something ends that I lose everything that I've built.