How to Buy a Business (and Make It Your Own)

Ann Shoket: Show cat. Ann Shoket: I was going to tell you and then I realized, no, we didn't. Yeah. Thank you for asking. Kathryn Finney: Yes, okay. Kathryn Finney: Welcome back to Build the Damn Thing, the podcast where I teach you how to use entrepreneurship to build the creative life in which you control. I'm your host, Catherine Finney. In today's episode, we're diving into legacy, leadership, and the power of women rising together. What does it take to lead a media revolution, challenge outdated definitions of success, and build community in a time when isolation is at an all time high? We're joined today by the iconic Anne Chilquette. CEO, media brand builder, bestselling author, and one of the most powerful voices in redefining success for women in the next generation. From reshaping Seventeen and Cosmo Girl to now leading the list, Anne's career has been a bold blueprint for purpose-driven leadership. Her bestselling book, The Big Life, is a rallying cry for ambitious women carving out their own paths. Her current mission? tackling the loneliness epidemic in the workplace and building spaces where women and non-binary leaders don't just survive, they thrive. So whether you're launching a brand, your platform, or just trying to figure out what's next in your big move, shoot, I'm gonna do that. Kathryn Finney: So whether you're launching a brand, growing your platform, or just trying to figure out what's next, this episode is packed with the kind of wisdom you don't wanna miss. Welcome in, it's so great to have you. Ann Shoket: I'm so honored to be here, Catherine Finney. What a joy to see you and to be in conversation with you and frankly, just to know you. Kathryn Finney: You have blazed trails in many ways. And there's the obvious ways that you've blazed trails by leading major magazines and publications. But then you've also blazed trails by also giving women a different path and helping women sort of rethink paths to success. And so where did you get started on this journey? Where did little Anne, nine-year-old Anne, where did you grow up? Ann Shoket: So I don't think I ever thought of myself as a trailblazer. I was always just doing whatever was next to whatever was curious and whatever new adventure popped up. There was never like a grand plan. Nine-year-old Ann was living in Littleton, Colorado in a really quiet suburb before Littleton, Colorado grew into like one of the largest suburban sprawls. But it really was. this like suburban yards, roller skating down the driveway, like jumping on the trampoline in my friend's backyard. But even then, when I was growing up outside of Denver, when I was in junior high, I started a collective of my girlfriends and we called ourselves Women of the World. And like here, you can just imagine like skinny Kathryn Finney: bit. Ann Shoket: 12 year old Anne, right, seventh grade at Douglas County Junior High. And where did I get the balls to think that I was a woman of the world? But I really did. Like I always imagined that there was something greater, something more, something out there that I wanted to see in the world. So that was what propelled me out of, out of Littleton, Colorado. Kathryn Finney: You know, that's the theme with a lot of great entrepreneurs and leaders is this thing of very early on, kind of having this vision for yourself, even though, you you weren't a woman of the world. Had you traveled out of the country at that point? Right. You didn't know anything, but you knew you didn't know, but you knew like internally, you knew that. Ann Shoket: I didn't know anything. Kathryn Finney: there was this bigger world out there and that you knew that you were a part of it and that you were going to help shape it. And that is a theme that we see over and over again with amazing people I interview of this idea very early on with many times no indication, but that there's this bigger world out there and that you're a part of it. And so you're in Littleton. Colorado, I have a picture of it in my head. Every time I think of like suburbs, I'm thinking from the 80s and 90s, I'm thinking of ET. You know how they were kind of like in the suburb, that suburb, you're right. Ann Shoket: Not that different, yeah. No, a little more Western, right? We had some tumbleweeds and it was definitely like that. But yes, it was the 80s and I was wearing roller skates and I was probably in the backyard listening to the Flashdance soundtrack or in my basement dancing to the Flashdance. Like, was the... Those were my icons, right? That was... Kathryn Finney: Hehehehehe Kathryn Finney: Right. Doing your little dance and like. Ann Shoket: That was the moment for that. And honestly, I didn't see... I didn't even, I mean, I didn't see people operating at a really high level. My parents were, my dad was an entrepreneur. He was in real estate. He would start a new business. He was always looking for the angle. And my mom was a therapist and she did run her own business, but she just certainly didn't consider herself an entrepreneur in that way. And so I really don't even know where I got the, Kathryn Finney: Mm. Ann Shoket: vision that there could be, should be more because we were in a town of suburban housewives, you know, in the eighties. Kathryn Finney: Yeah. But maybe, you know, being around your parents who were entrepreneurs, whether or not they define themselves as that or not, there is a little bit of risk taking that happens. One of the things that I found my parents, I grew up with my grandmother, who was definitely an entrepreneur and who I'm named after. in many ways, my life kind of echoes hers in many, many ways. But one of the things I said to people that know, entrepreneurship is very risky, and at the heart of it is your ability to take risks. And I saw my parents take a risk, and it paid off. And that made me very comfortable with risk taking. And so if you witnessed that at an early stage of your parents taking risks, your mom being a therapist, she wasn't a stay at home mom, she was a therapist, she was running a business, Whether she thought she was or not, she was. And so you grew up seeing that. You saw your parents take risks. You saw your parents be entrepreneurs. You saw that. And it's something about those of us who grew up with that become very comfortable with the concept of risk. Risk is not foreign to us. We've seen both the highs and the lows of it, right? And so we're more comfortable with that. So it doesn't surprise me that you were starting a club called Women of the World. Ann Shoket: Well, was something, there was something you said at the very beginning when you were introducing the podcast where you talked about leading a life that you are in control of. And that really resonated with me, right? That I wanted, I, I always wanted to be at the front of the class. I was always volunteering to be in charge. I always wanted to be in the leadership position. I wanted to be. the one who was in charge, not somebody else. wanted to make the decisions. And if it wasn't going to be a great decision, at least it would have been mine. And so I think that that I can see the early seeds of wanting to be the head of the group, wanting to be at the front of the class, wanting to be in control. And that theme of control, as soon as you said it, it sort of unfurled this whole journey of where can I make my mark? Kathryn Finney: Yeah. Kathryn Finney: I'm gonna leave. Ann Shoket: new adventures can I have and where can I find myself in a position of leadership and in greater control of my own destiny? So I can see that. Kathryn Finney: Is that how you got to New York? Is that what led you to New York? Ann Shoket: So after Denver, Colorado, we moved to the suburbs outside of Philadelphia, which is where my parents are from. And so we were a little closer to a big city, right? There was Philadelphia. I was hanging out with the punk rock kids at that point in time. There may have been some beer drinking in the woods. Don't tell my parents. But I really, I by that time really wanted like some sexy sizzle. Kathryn Finney: sure there was, you're right. Ann Shoket: in my life, right? I'd had enough of the quiet suburbs and I was like headed for New York. I was determined to be in New York. And so I came to New York to go to NYU and it was 1990 and the town like New York was on an upswing, right? It was a good time. were with it. It was back from its financial crisis. Things were getting like cleaned up. It was, it was before Rudy Giuliani, but like, it was a, it was a Kathryn Finney: Yeah. Kathryn Finney: Yes, the clubs were clubbing. Ann Shoket: The clubs were clubbing. It was amazing. And so I loved it. That was that like the sizzle of New York City was speaking to my heart and everything felt possible here. I am a junkie for possibility. And so everything really felt possible. You just had to like be at the right place at the right time, probably wearing the right thing. Kathryn Finney: That's something that, you know, when I talk to like younger members of our team who are, you millennials and Gen Z and I talk about that New York, because I lived in New York for a really long time with the school out in the East Coast and like what it was like to be 18, 19, 20 in 1990s New York, right, where it was much safer than it was in the 80s. It wasn't as sanitized as it became in the 2000s. It was just this sweet period in which there was a lot of possibilities and it was a lot of fun. It wasn't so driven by money as much as it was driven by coolness. It was like you could have all the money in the world but if you weren't cool. Ann Shoket: I think that's right. Kathryn Finney: If you weren't interesting, it didn't really get you invited to things. Money couldn't buy your way in. Now it's a very different world. And it was the possibilities that came out of that. And I find the folks who kind of came up during that period to be very interesting sort of leaders and entrepreneurs because of being in that sort of New York. And so your 1990s, your clubbing, I'm imagining you at Sound Factory, Total, Palladium, Palladium if you're at NYU probably. It's the limelight. Ann Shoket: I was at the, there was the limelight. There was an industrial club called the building. And then there was a rotating like R and B party called soul kitchen. And those were, those, those were my, those were my nights out. And then there was a lot of like late nights at seven B's in the East village. That, that's, can you, do you have a picture of this 90s? Anne. Kathryn Finney: Yes. you Kathryn Finney: Yes. I have a picture because I was probably right beside you on the floor. Actually, the very first nightclub I went to was Limelight. I was 17 and I was visiting a friend who I went to Phillips Andover with and I was supposed to be looking at colleges. I put suppose. Coming right from Minnesota and we went to the Limelight which... Ann Shoket: Yeah. Kathryn Finney: At that time, mean, anybody could just go to the Limelight. I mean, I think I could have brought, my son is nine. I think I could have brought him and I don't think anybody would have. The Limelight was a very special place and anyone who, again, was around in New York in that time will know exactly what I'm talking about in Limelight. It was an old church. It was in like 18th and 6th, right? Like 18th, 19th and 6th, old church that was converted into this nightclub where Ann Shoket: Yep. Kathryn Finney: really club kids, know, the closest thing I could give to anyone, a description would be kind of like living art, living human art mixed with like maybe drag performance. Like that's the only kind of description I could give of what a club kid was. And so it was really where the club kid culture really like started to become popular. And so we go to this club. Ann Shoket: Yes. Kathryn Finney: 17, again, no business being anywhere, but my friend was a New Yorker. And so she was going to clubs and she was like, 10, I don't know. And so we go in and it was so crazy. I actually saw someone OD on cocaine and I'm like 17 right from Minnesota. If you can imagine that, like fresh off of Northwest Airlines from Minnesota, like as Minnesota, as Minnesota can get. And it was like, I just remember being like, so like, my God, this person is like, and everyone's like, yeah, the ambulance is coming anyway. And they like, and I'm freaking out and they're like, yeah, it happens. Ann Shoket: You have to cultivate that nonchalance even in the face of like trauma and crisis. That is crazy. Kathryn Finney: I mean, you know, I have another quick digression of story, but when I had just moved to New York, I had a friend who went to Pratt and we're walking down the street. was 42nd and eighth. And this was right when that area started to become Disney Fied before Disney. For those of you who have spent time in New York or haven't watched movies from New York like Taxi Driver and stuff like that, you know, Times Square was like not a place to hang out. It was very suspect and very seedy. And we're walking down the street and we saw someone, dead person. And we went to a police officer who was near and we're like, you know, of course me, I was still fresh from Minnesota, like first semester of college, started to freak out. It was like, my God, there's a dead person. I he's like needs help or whatever. And the cop looked at him and looked at us and was like, look, I fucking called the wagon. What the fuck do you want me to do? He's like, it'll fucking be here. He's not going anywhere. And I was just like, and in my Minnesotan way, was like, you know, clutching, I'm clutching my pearls now. didn't, don't think I was wearing pearls at the time, was like, you know, cause it's like Minnesota, we don't do that. But you're, so you're in this New York, right? Which is very formative. And so how do you get from that to then running magazines and major magazines at that? Ann Shoket: Yes. Ann Shoket: So I really thought that I was going to write novels. I went to NYU to study creative writing and I was convinced I was going to write novels. And then I realized that writing novels does not pay the bills to live in New York City. I mean, I don't know why it didn't occur to me sooner. So I was like, Kathryn Finney: Where you're like thinking Diane was Daniel still like you were thinking like. Ann Shoket: No, I was gonna write cool indie downtown fiction. It was the era of short stories and I was writing, I had this whole vision for a novel of short stories that characters interwoven with each other. There's probably notes somewhere in a box that I will at one point in my life unpack. However, I was like, okay, gotta get a job. And that's when I turned to magazines and I started... Kathryn Finney: You Ann Shoket: my career because it was, I came out of college, there was a recession, just like millennials coming out of college. This was the era of Gen Xers who were, instead of hustlers, we were slackers, right? We were getting mick jobs and like everybody was gonna be a barista. It was the beginning of coffee culture. It wasn't even called barista. You were just pouring coffee at a coffee shop. And so I got whatever job I could and I ended up at the American Lawyer Magazine, which sounds deeply boring. Kathryn Finney: Hmm. Kathryn Finney: You Ann Shoket: And it was, it was deeply boring. However, it was run by this legendary journalist, Stephen Brill, who had cultivated this whole aura around himself that he was tough as nails and a hard ass and a loud mouth. And he ran the newsroom where he would like chomp on his cigars and storm around and he would put giant X's through people's copy and Kathryn Finney: Yeah. Ann Shoket: being in the room where that was happening, I was just a lowly assistant, but being in the room where that was happening was like a master class in journalism. We sat in a big reporter's pit. I learned how to become a reporter by listening to the other people around me who were on the phone, Mandelbaum here. I was like, okay, that's not my, I'm not calling somebody up and saying like, okay, Mandelbaum here. But then there were other people who would have very challenging perspectives in doing their reporting. Kathryn Finney: You Ann Shoket: And then I sort of learned this like deep curiosity. Can you explain that to me? I don't understand. Is this what you're trying to say? And I really learned how to be a reporter in that time, how to ask questions, how to think about why someone is telling you something and what is the story there more than what they are just saying on the surface. that... early experience. also happened to be that since we're here talking about being Gen X and being in the nineties flashback with me to 1994, June 17th, 1994, the day that OJ Simpson drove his white Bronco down the highway. That's when I was at the American lawyer and upstairs from the American lawyer was court TV, which they owned at the time. And so it was an amazing time to be. Kathryn Finney: Mm-hmm. Kathryn Finney: Yeah. Kathryn Finney: Ooh, yeah. Ann Shoket: talking about lawyers in the business of law. there were, like, I didn't know this then, but there were amazing journalists who were coming up at court TV who've gone on to become major broadcast news people who everybody knows. But this was the moment that we were living in. Who knew that the American lawyer would become like a cultural moment on June 17th, 1994? And so that's where I learned how to be a journalist. Kathryn Finney: right? Ann Shoket: I'll tell you, it seems like a big leap to get from American Lawyer to Seventeen magazine, but there was an important step in between. I went to go work for a teen news magazine. It was called React, and I went there to write about legal issues for teenagers, right? And it was the beginning. Kathryn Finney: Interesting, yeah. Ann Shoket: of the millennial generation, right? I remember we did a cover story about how the generation that we were writing to was the largest generation in years and how the millennials, right? It was before the year 2000, were going to impact our culture. it was a good, that was when I realized how much I loved the irreverence, the moment of searching, of becoming who you're gonna be when you are. a teenager, right? I didn't know, I had been, I hadn't planned, right, that for teen magazines to be an important part of my career. But that was, that was that turning point moment where I realized, I really love this. This is, this is where you're figuring out who you're going to be in the world. And, and yeah. Kathryn Finney: I think it's really interesting that you bring it up. As people are building companies, as entrepreneurs, one of the most important things you can do is to be a good listener, right? And also to be curious, which are two things you have in abundance. But also surrounding yourself with people who are frankly younger than you. It gives you a different perspective on life, gives you a perspective on the possibilities. You know, we're talking about possibilities. And, you know, there's a tendency sometimes as you get older to be a little fearful of those who are younger, right? They're coming up with ideas that, you know, may contradict what what you think is true, their truth may be very different. And so it's so interesting that you have taken this sort of curiosity, this Ann Shoket: Yes. Kathryn Finney: this idea of connecting with those across generations to sort of build your career. And so you find yourself, not by chance because you did the work, but you find yourself as, you know, editor in chief of Seventeen. And those of us who are Gen Xers and millennials have very fond memories of Seventeen, right? That's the best, right? Ann Shoket: Yes, was the best. It was the best. Kathryn Finney: And all the people who you had on the cover, I mean, just think of all the icons that were on the cover of that magazine. But you're at the top, right? You're at the top. How did you transition from that? Like what happened? You're at the top of your career. You're in magazines. You're going on fabulous photo shoots. I'm sure the closet at Seventeen. For those of you don't know, the fashion closet at these magazines are like legendary. Sex and the City did a whole episode where she was like in the Vogue closet. It's pretty massive and pretty amazing. And as editor in chief, you got to borrow stuff if you needed to for things. But yeah, how did that? You were at the top. Did you know you were at the top when you were at the top? Ann Shoket: never, they would never let you think you were at the top. my goodness. It was always, it was an incredibly high pressured situation. So I was editor in chief of Seventeen for the better part of a decade. And it was an iconic magazine and what a tremendous honor to sit in that seat. And I was always aware that it was a borrowed throne, right? That there had been a lot of other women who had sat in that seat and there, well, there was like one. Kathryn Finney: Yeah. Ann Shoket: There was one who would sit in the seat after me because the RIP magazines. I was always aware that this was a borrowed throne and that the rug could be pulled out at any minute. And look, I worked hard and hustled like crazy to make sure that wouldn't happen. And I'll tell you a story about that after because this is a really important leadership lesson that I learned from that. Kathryn Finney: Yeah Ann Shoket: you'd never thought you were on the top. You always thought there was more. There was always more budget to cut. There was always more money to make. There was always a celebrity that you weren't getting. And I do want to just say, though, like when I think about the covers, you're talking about the covers, right? Like we gave Rihanna her first cover. We gave Taylor Swiftie her first cover. That we did an amazing cover with Beyonce where she styled herself. It was so it was so great. Like I just want to like put the moment where you think about what was happening during magazine moments and that that just doesn't exist anymore. And so The magazine business really crumbled. People say, why'd you leave magazines? And I say, magazines left me. Like the business wasn't there. There wasn't the investment at the time in digital. It was such a crazy moment. remember, I'll tell you that the turning point moment that I knew it was over before it was over. The end of 2014. And I'll never forget. Kathryn Finney: What year was this? What year was this? Ann Shoket: I was sitting with one of the digital editors, digital directors at Hearst. And I said, listen, you have been running nonstop Disney content on 17.com. And I said, I'm over here trying to make a magazine that's going to appeal to major national advertisers. And I'm trying to convince them that we're not a magazine for eight-year-olds and for tweens and that we're a major player here. And she sat back in her chair and she folded her arms and she said, I don't care. That's what the internet wants. And that was the turning point moment where I realized, I don't work for the internet. I work for the 13 million readers of 17, but you work for the internet. you're not there. Where's the brand? There's no brand there anymore. And I think, I think we've gone back and forth and the pendulum has swung in digital editorial from, you know, big brand, small brand, influencers, aggregated content. there's a, you know, whatever moment we're sitting in now. But to me, after having run an iconic 75 year old brand that had been so important to generations of young women, that was the moment where I realized, okay, it's over. This brand, this is over. Which doesn't make it hurtless when it happened. Kathryn Finney: Yeah. Ann Shoket: But the writing was on the wall and there were and I'll tell you, this is the leadership lesson that I learned and I didn't learn it for a while. The day that I realized that it was not my job to save the magazine business was like all the weight had just been freed off my shoulders, right? This is not, I had spent my sort of the second half of my career thinking I'm going to save the magazine business. Is it going to be on iPads? Is it going to be on digital magazines? Is it going to be on social media? Let's hustle to try and find what's gonna save magazines. And the day I realized that that was not my problem, my gosh, what a revelation. And so this leadership lesson that really took me into the next phase of building my own brand, building my own business and building my own entrepreneurship was knowing what was my problem to solve and knowing what was not my problem to solve. Kathryn Finney: Mm. Kathryn Finney: You know, that's another theme that we've found throughout the podcast of with entrepreneurs and leaders of really understanding what is the problem you're solving and really understanding what are the things that are important to you and to basically not care about the things that are important to you. Like what is your capacity, right? And so one of the things I wanted to follow up on is like dealing with that uncertainty. You're in this business that's evolving. And to give a bit of context for people who don't understand what was happening. When I started the Budget Fashionista, which was one of the early, early blogs back before people. Ann Shoket: Yes. Kathryn Finney: even new blogging. We didn't even have WordPress or anything. That's how long ago this was. I remember going into my publisher, Random House, shout out Random House, still my publisher, for my first book. And we had a marketing meeting with myself, my agent, and the marketing department. This was for my first book, How to Be a Budget Fashionista. It was 2004. We had this conversation. And they were furious with me. furious with me because I was giving the book to any blog that wrote about it and included a link to Amazon. Okay, again, this is 2004, 2005. They were furious. When I say it was like a yelling match in this meeting and they're like, you're you're taking sales away from Barnes and Noble. That's all that matters. Blah, blah, blah, blah. Fast forward, my book is like 16 years later, it still sells, even though the information's outdated, I still like 10 copies every quarter. I'm like, who's buying this? But because, I mean, it sold really well. I'm happy, I get the royalties, thank you. But it's because of those links. And so to give people a context of what you were going through, at that moment, really traditional media did not see a Ann Shoket: Yeah. Kathryn Finney: future in the internet. saw it as a fad. They really did see it as a fad, as a competitor, as an enemy, as a fad, instead of embracing it early on. And it caused a lot of challenges. And I'm sure for someone like you, who's this visionary who sees the possibilities, it must have been like crazy infuriating to deal with it at that point. How did you deal with the uncertainty of that moment? Ann Shoket: Yes, as a competitor. Ann Shoket: So I actually was a real digital first editor. I was there saying, like, we need more money, we need more resources, we need more attention. Please stop telling me how many magazines I have to sell and let's start talking about how am I reaching the audience digitally? Because I launched a magazine, I launched a website in 1996. When I was at The American Lawyer, I had a side hustle where I launched a website. that made its way all the way into the New York Times at the time. 25 year old Ann Choquette was in the New York Times with her website, with her cool downtown website. And then I was, I launched the first magazine and website together at Hearst, but it was always like, oh, that's so sweet. Oh, that's so cute. You're over there being so cute. And I, and, and when I was at 17, we were, I mean, this is actually going to sound funny to say, but we were, we were like, making partnerships with MySpace. We were making partnerships with Facebook, right? It was the early days of social media that the founder of Snapchat, Kate in our offices, right? Like even before I think it had officially launched and he was yawning and tired. I was like, can we get you some coffee because this is gonna, you've got a big road ahead of you. And so. Kathryn Finney: Yeah. Ann Shoket: We were there trying to bridge the divide between the work we were doing to build a brand and to talk about something, to talk about really deep and meaningful conversations about becoming the person that you're meant to be. And how do you do that in a digital space? And so it was this, but it felt like such a strange disconnect to be the person who was the booster. for digital innovation and then at the same time to find myself. aligned with old media, right? To even have those words. I was like, this doesn't have to be, we don't have to be old media. There's opportunity, there's possibility here. But this is one of those decisions that like... This is part of the control. I been in control of my own destiny at that time, it would have gone differently. Kathryn Finney: And I think as entrepreneurs too, that's one of the things that we are attracted to is the possibilities. We can see around corners and through walls that other people can't for whatever reason. And that's one of the things that I think makes a person a good entrepreneur is to be able to see the possibilities and then to be able to execute on that possibility too. So not just see it, be able to execute on it. So you had a bit of an unplanned pivot. Ann Shoket: Yes. Evolution. I like evolution better. Yeah, it's not like I didn't, it wasn't a hard write. It was like, how do I take what I've done for the last, you know, two decades and find a new way to express that in the world and evolution. Kathryn Finney: Evolution, evolution, growth. Kathryn Finney: How did you get started on that? Ann Shoket: So it also happened at the same time. I had just had two babies back-to-back and so I was I had a when I left Hearst I had a two year old and a six month old at home and I had to also figure out how to be a mother and what did it mean to be a mother with tremendous ambition in the world and Kathryn Finney: Mmm. Ann Shoket: It was also the era where, when I was pregnant, I like practically hid my baby bump underneath the desk because it wasn't an era of bring your full self to work. It was an era of like, please don't bring your full self to work. And so here I was trying to figure out what it meant to be an ambitious person, an ambitious woman, an ambitious mother. And the very first thing I did, was join a co-working space, which sounds weird, but I wanted to be out and about and see what people were doing. And that's what I did. So I joined one here in New York called Noya House, still exists. It was a really cool kind of creative collective. They were doing a lot to bring entrepreneurs together, but it really put me in the space of human beings who were building their own destiny, building their own careers, building their own businesses. Kathryn Finney: Mmm. Kathryn Finney: Which co-working space did you join? Ann Shoket: And I could see how they were doing it. And I could also see how important the connections were, right? Being in the room, getting the invite, knowing how to building the relationships. That was how business got done. When you're not in a hierarchical top-down tower where all the people that you need to know are somewhere between the 42nd floor and the 17th floor, right? It was... it really opened my eyes to a new way of working. And it was the beginning of a real rise in entrepreneurship because like it was just when WeWork was launching, right? It was everybody wanted to have that sort of cool come and go freedom from the office workplace. Kathryn Finney: Yeah. And is that how you got to the list? Ann Shoket: So the second thing I did was join a women's community called The List. And I... Kathryn Finney: What is the list? And Anne and I both are a member of this community for a long time. Ann Shoket: Yes. And so the list is a network of high impact women and non-binary leaders who are devoted to helping each other succeed. And when I first joined, I didn't know what I was signing up for. was like, yeah, yeah, here, let's do, let's, let's be in community together in quotes. And I was gobsmacked. My jaw was on the floor to see the most powerful women in America. bold-faced names sharing with each other so vulnerably with so much generosity. I had never experienced anything like that before in my career. The magazine business was so cutthroat and competitive sharp elbows everywhere. And here was a group of women who were talking not only about business, but talking about life in with so much vulnerability. had I I I was terrified to even introduce myself and it took me a really long time to even jump into the conversation. But over a series of years, I built relationships, I built trust, I got to know the people who were there and... I acquired the business in 2020. The founders were ready to leave. Yep. The founders were ready to leave. I had in between, in between, had written a book and built a really huge community of millennial women around the book, the book, The Big Life. And so I really loved community building. It was to me. Kathryn Finney: Rachel and Glen is yet. Ann Shoket: the same thing that I did at 17. When I was at 17, even though we had 13 million readers, I imagined that we could all be in the school gym together hanging out. And that's how I, I'll put, yes. And so that's, but that's exactly right. That's the connective tissue, right? Is to get to the relationships you build are the key to your success. And they don't just happen to you and they require nurturing and time and trust and transparency. Kathryn Finney: all part of Women of Ann Shoket: And all of that I realized, I acquired the business in the depths of the pandemic. It was 2020. And so we needed each other more than ever. And I built this millennial women's network and I knew the ways in which we needed each other, the ways in which we could help each other. I saw the possibility for building a huge brand back to my brand building days. And that's what brought me to the possibility, right? Is what brought me to the list, to acquire the list. Kathryn Finney: You know, as more people are starting to experience this sort of concept of unplanned pivots or unplanned growth or forced growth, evolution, one of the things that people often don't think about is purchasing an existing brand, something that already exists, that already has some infrastructure. And not starting at ground zero. People think of entrepreneurship, you have to start at ground zero. You have to have the idea, have to Ann Shoket: Yes, evolution, evolution, yeah. Kathryn Finney: No, you can purchase something that's existing. And there's actually a lot of opportunities for that right now as more boomers are retiring. A lot of their children are not wanting to take over the family business. And so there's a lot of opportunities to do some acquisitions. And the good part about the acquisitions is that the infrastructure is already there. What are some potential downsides of an acquisition of an existing brand? Ann Shoket: When I acquired the list, came to it with my own vision of what the list could and should be. And not everybody was down for that, right? And I think that that's, it's an opportunity to make your mark and to do your magic for a brand and a business that already exists, right? You're bringing your own special sauce. And some of the people who aren't into special sauce, right? Aren't into your special sauce. And so that's... Kathryn Finney: Mm. Kathryn Finney: Yeah. Ann Shoket: That's part of the process. It's like, OK, noted. Got it. This isn't for you. This isn't the right thing. And you need to be aware. Am I evolving? Am I growing? Am I doing what's right here? And what's right for me might not be right for somebody else. You have to ask yourself, I think, those questions along the way. But I think that there's also quite a lot of education. People are complicated. community business is a really hands-on business and really like it nuanced human behaviors and so To bring people along to nurture their trust To explain much more explaining who I am what I do that I ever thought possible. I thought I was a known quantity I thought everybody knows me. No problem, but no that I've really had to I've had to explain Kathryn Finney: Hmm. Ann Shoket: who I am, where I'm going, how we're gonna get there together. You said earlier, Catherine, you talked about the question of what are we doing here, right? You said these are the questions that entrepreneurs have to ask themselves. And that was a question about a year into the list that I really asked myself. Okay, we've made the transition, the ownership is mine. What are we doing here? What is our purpose? Why are we here? And that was the question that sort of has guided me for the last several years into finding new possibilities for what a community can be. Kathryn Finney: Yeah, I mean, Simon Sinek talks about that, like start with why. And it's like, why do we exist? And especially when you come into any sort of known entity. I often think of the analogy with churches. And I go to a really well known church here in Chicago called Trinity United. And most people know it because it's the church where Reverend Jeremiah Wright was a pastor. Now he's Pastor Emeritus. There's a new pastor, Reverend Otis Moss, who's also become really popular because of his social justice. It's a very social justice in the church. you know, Pastor Moss talks about what happened when we transitioned from this iconic leader who is very loved and very beloved. I joined the church because of Reverend Wright, who I had met when I was a student at Yale. And he came in with very different ideas and still incredibly respectful and honoring the previous leader. He's very beloved, very respected. It's very clear that he respects and honors and loves him. But for other people that change in leadership, that change, right, especially when you have a community-based business or organization, which is driven by personalities, right, and driven by human beings, people had a hard They have a hard time with that, right? And you're coming in with your own vision, your own sense of identity, your own sense of possibilities. And like you said, bringing people along and knowing that you're gonna lose some folks. And so yeah, it may be buying a community network, it may be you're buying a restaurant, right, in your local neighborhood and. You know, people were used to the previous owner opening on Saturdays at 9 a.m. and you might decide, well, you know what, that doesn't make economic sense. I'm gonna open at 12 and then you lose customers like that. That's part of the challenge of acquiring an existing company is that that's a possibility. And so you're growing the list. I can imagine how challenging and lonely that must have been, you know, when you're kind of trying to bring people along. Kathryn Finney: And you write and you talk a lot about loneliness and how do we build community? And so how did the lessons you learn from not only trying to build community at 17 and trying to convince people who are so digitally unaware to be visually unaware, but then buying this community and then trying to really insert your own vision in. Ann Shoket: Yes. Kathryn Finney: How did those sort of challenges influence your ideas around loneliness and how to build community around? Ann Shoket: So glad we're talking about loneliness because this has been a really an epiphany for me. And I'm really late to loneliness. think a lot of people were talking about it before long before I was. But a couple of years ago, I was reading the New York Times and there was an article where the US search in general talked about loneliness being on being on par with the opioid crisis. Kathryn Finney: Viva. Ann Shoket: And I was like, say what? You're telling me that loneliness is as damaging to our lives, to our relationships, to our health as fentanyl? Like, was like, this is, I was like, that doesn't make sense. So I started, but all of my journalists, like, spidey senses went off. And I was like, let me, let me explore this. And the more I, the more I explored it, the more I kept asking myself this question. How is loneliness showing up in my life? And I realized that under the moments of greatest career stress were the loneliest moments. When I became the editor-in-chief of Seventeen, I was the youngest editor-in-chief at the time. I was single. I was separated from the team that had helped me rise up to that point. And I was plopped into the middle of a brand new team. there were days where I just would... collapse at the end of the week and cry on my couch because I had nowhere else to put the stress and no support system to help me through that moment. And so, I mean, I built a new system. The same thing happened when I became an entrepreneur and when I bought the list, it was the pandemic. So I was actually physically separated from the people who had been my support system. But I would say, I was talking to a coach and she said, who's in your boat? And I was like, nobody's in my boat. Kathryn Finney: Hmm. Ann Shoket: I was like, who? Get in my boat. She's like, all right, is your husband in your boat? I was like, fine, my husband's in my boat. Who else is in your boat? I was like, there are people who are rowing alongside me, but I need to get some people in my boat. And that was a real revelation for me, is I needed to build people who were devoted to helping me succeed. And it was the same revelation I had as I looked at our community, the list, that the reason, and the question I asked myself, right? Like, why are we here? Kathryn Finney: Who's in your boat? Ann Shoket: We are here because it is deeply lonely to be an ambitious woman and a non-binary leader. is profoundly isolating to be a person with a big idea who's trying to make it happen in the world, whether that world is in traditional corporate or whether it's as an entrepreneurship, and that we need each other to validate ourselves, to see ourselves through someone else's eyes. Okay, great. If she can do it. I can do it. If she understands the pressure that I'm having as a mother, as a partner, and as a business person, that makes me feel safer and seen and trusted. so, so not only my Spidey Sense and my understanding of seeing the people around me, but then we started to do some research. I partnered with a major research firm, BSG, and we brought in an agency, Berlin Cameron, and we did some research. 80 % of women are lonely because of their jobs. It gets worse as they get more senior. And the next generation, Gen Z, millennials, they're already starting at a higher level of loneliness. It's also worse for women of color, that not only are they feeling isolated and overwhelmed in the workplace, but they feel like they can't show up to work as their authentic selves. And so we really are facing this crisis of loneliness. So Vivek Murthy, the surgeon general, was absolutely right. But The solution is togetherness, right? The solution is your network and your community of support. And it is not enough for me to create that community of support for the 500 amazing humans who are members of the list. I wanna teach everybody how to create their communities of support. so we launched an initiative, 10 minutes to togetherness, to teach everybody how to build their own version of the list. Who are the people who will be there for you and will help? Kathryn Finney: Yeah. Ann Shoket: who will get in your boat. Who's gonna get in your boat? Kathryn Finney: In your boat. It's so interesting. In my book, a Damn Thing, we have a whole section about your personal advisory board, which is very similar of who and the roles that you need. And so who are the people in your boat? That's your personal advisory board, right? And I say, you know, need someone who's like the comedian, because sometimes you just need to laugh. You need, when you're an entrepreneur, Ann Shoket: Yes. Kathryn Finney: or leader in general, you're so involved in sometimes a solution. Sometimes you're so involved in putting out fires that you don't see the levity in life, right? You're just so deep in it, the joy, the humor. I tell people my comedian on my personal advisory board is my son, who's nine. Ann Shoket: Yes, the joy. Kathryn Finney: And, you know, nine year olds just have a really interesting way of looking at life and how one time I was really stressed. I don't even know what I was stressed about. And he came in and he was telling me this like rap about toilet people, people who lived in the toilet. And I mean, it was some big investment. I actually remember it was one of our investments was just excuse my language was just fucking up. I mean, just. failed and it was a seven figure investment that we had made. This founder was just, and I was so stressed because it was going to be a big hit to the fund. And we had other pretty significant successes, but this one I was like, damn, because it didn't need to be that way. And know, my son saw that maybe I was stressed and decided to do his rap about people who live in the toilet. And I remember at that moment being like, my God, like. I just started laughing so hard I started to cry because it's like what, this is so absurd and it's exactly what I needed because I was so in the middle of something that I can't even change. And he just brought me out of it with toilet people. And so thank you for that. But then, you know, there's other folks that you need, right? So you have your comedian, the person who brings you out is the person who tells you about yourself. My long-term producing partner. Ann Shoket: Yes. Ann Shoket: you Kathryn Finney: Darlene Giller-Jones, she has a gentle way of telling me about myself, right? And helping me come out of wherever I may be at. Someone once said, you're kind of like the balloon and you're up there and Darlene's the person on the ground kind of holding you so you don't fly off too much. And so we need those people. need, when you're a woman and particularly a woman of color, your family often have requirements of you that are unrealistic. And you need somebody, preferably a family member who can tell people no. And my mother, who's almost 80 year old black grandma, says no in the most lovely but very clear and firm way to family members. Ann Shoket: Yes. Kathryn Finney: which is important because it allows me to maintain my relationship with these family members, because I can't write checks to everybody. I'm not going to invest in everybody's business. But my mom says no in a way that allows me to still maintain relationships, because I still want to maintain these relationships. so getting the people in your boat is so crucial to doing not just being an entrepreneur, but just really living, I think, especially in the world that we're in now. And so for you in your boat, have your husband, your mom. Ann Shoket: My mom is in my boat too. My mom is. brings like, you she's a, I said she's a therapist, right? So she brings like deep wells of understanding and empathy and compassion and doesn't always want to solve it for me. She's just happy to like listen. And so I really appreciate that. Yes. Everybody like if you've got a, if you've got a good mom, get them in your boat. Kathryn Finney: Hmm Kathryn Finney: Get them in the boat, put them in there. They like to be in boats. Moms like boats. Yeah. Ann Shoket: Yeah, yeah, I put you know, also in my boat. There are some women who are younger than me who are who are not a senior in their career. And I, I would not call it mentorship, I would say that we are supportive of each other. Right? I learned from them, I turn to them with questions that I don't know the answer to. I am endlessly supportive of their careers, if I can be like, I have built, I've built a great Kathryn Finney: Mm-hmm. Kathryn Finney: Yes. Ann Shoket: a lot of deep relationships and I'm happy to use them to say, like, can I open a door for you? I'm happy to do that. And at the same time, there are women who are a step or two ahead of me, who I am turning to to say, I know you've been through this before, or who can you introduce me to because I really, can't figure out how to unlock this. Those are the kinds of people. I do my 10 minutes a day. Kathryn Finney: Yeah. Ann Shoket: I do it really intentionally in the morning. I get my coffee. It's like a practice. It's like a muscle that I'm flexing. And so I have my coffee. I've dropped my daughter at school. I open my computer. I've got Good Morning America on the TV. And I will intentionally reach out to people and say, you've been on my mind. Or to say, your name came up at a meeting last week. I'm thinking of you. Kathryn Finney: Is it like a gratitude? Okay. Ann Shoket: I also always ask, how can I help you? Is there something I can do? What would be helpful? But even just the outreach, I've been thinking of you, keeps those relationships warm and strong. And when you're not surrounded by people, which we aren't very often these days, you can still feel supported knowing that those people are just a text away. Kathryn Finney: You I think you highlight something that I think is a really important practice. Just spend five minutes, quick text, we all have text, it's super easy, reaching out to someone, right? Just five minutes every day. Just, hey, I'm thinking about you, or hey, I just saw this, I'm gonna send it to you. It's really amazing how we don't do that, even though we have the ability to do that. Like, we don't, we don't. and say, you know, let me just reach out, let me just send this little funny text to people. And it builds community. And it's not necessarily about you, right? You're sending it to someone else and you, but it helps maintain relationships. It helps fortify your community, right? And it's not hard to do. Ann Shoket (01:00:02.854) This came out of our research also that the people who are less likely to feel lonely in the workplace and more likely to feel connected have these tiny little micro habits of connection. And if you're like, oh God, I don't want to go to coffee with anybody. I don't want to invite anybody to anything. It feels like a huge mountain to climb out of this loneliness hole, but it's tiny little things just to say, how are you? And not to write a whole email, just a text, even a LinkedIn message. Sometimes like an Instagram thumbs up, right? You show up three times on somebody's Instagram and they're like, I remember you. And so it is an exercise. It is a muscle and it is a habit. And it's not something that's natural for so many of us, right? We're busy. Kids, family, working out, feeding yourself, getting caffeinated, hydrating, like all of the... Kathryn Finney (01:00:32.398) Yeah. Kathryn Finney (01:00:39.318) Yes! Ann Shoket (01:01:01.668) All of the things on your time. spent 20 minutes today trying to sort out something with like New York City parking tax. Like that took a whole half hour of my time, right? Like we are busy. There's a lot of stuff we have to do, but I do really feel like those 10 minutes a day are an investment in my own support, in my own centeredness and in my relationships, right? That's, that's what grounds me. Kathryn Finney (01:01:02.284) Mm-hmm. Kathryn Finney (01:01:10.979) Right. Kathryn Finney (01:01:28.675) Yeah. Kathryn Finney (01:01:32.13) Yeah, yeah. Well, Anne, it was so amazing chatting with you and you have been such a trailblazer. I know you don't necessarily think in that way, but but you are. It is what it is. And you have been ever since, you know, women of the world. And so it's been so great having you on the podcast. I think talking about Ann Shoket (01:01:50.864) Haha Kathryn Finney (01:02:01.71) How do we build connections? How do we build companies? How do we build communities is super important. And as an entrepreneur, finding who's in your boat, building your boat, and getting the people that you need to be in that boat is the key to success. So thank you so much for joining us. Ann Shoket (01:02:13.882) Yes. Ann Shoket (01:02:22.97) I want to thank you for your generosity and your gentleness and your sense of togetherness. really, you show up and I think that that is the most important quality in a human being. And so I thank you so much for including me in this part of your journey. Kathryn Finney (01:02:46.862) Thank you so much. It's been my pleasure. So I'm going to do the closing now. I just wanted to give them a little pause. Kathryn Finney (01:03:01.854) Anne is a living example of what it means to lead with purpose, power, and possibility. From transforming media to building communities, she's not just writing her next chapter, she's giving us all permission to write our own. If you love this episode in Let's Be Real, how could you not build your boat? Make sure to hit that subscribe button so that you never miss a moment of brilliance like this. And if you got something from today's conversation, share it with a friend or drop a review and let us know. what you're building. Until next time, keep showing up and remember to build the damn thing.