Building a Billion-Dollar Network for Women Executives with Lindsay Kaplan

HOST: Adrienne Garland: [00:00:00] Leadership isn't just changing. It's evolving in ways we're only just beginning to imagine. And women, we're not playing this game anymore. We're the ones reshaping the entire field, building models, movements, and businesses that serve more than just a few. On the She Leads podcast, you'll hear real conversations with women who've broken through all kinds of barriers, revenue, identity, borders, and expectations. There's no sugar coating here, just the truth told by those who are living it. I'm Adrienne Garland, entrepreneur, strategist, educator, and creator of live experiences, gathering women leaders together for over a decade. And this is the She Leads podcast.
[00:01:00] All right, so my next guest is Lindsay Kaplan. She's a true visionary and I want you to buckle in as you hear her many accomplishments thus far and I know that she's not nearly finished. Lindsay is the co-founder of Chief, the premier network for executive women launched in 2019 from an idea that's now a billion-dollar national brand with tens of thousands of members and representation from more than 10,000 companies. Chief has five clubhouse locations, New York, Chicago, LA, and Fran and Washington DC. Under Lindsay's leadership, Chief was named one of Time's top 100 most influential companies and Fast Company's most innovative companies. Recently, Lindsay stepped out of a day-to-day operational role and into a more strategic one, serving on Chief's board of directors as it continues to shape the future of executive leadership. Before Chief, Lindsay was a founding team member at Casper, where she served as VP of communications and brand marketing and helped to create and define an entirely new category, transforming Casper from a startup into a cultural phenomenon. Lindsay is also a partner at NextWave, where she invests in early-stage companies including Riley, Loop, Esargo, and Neptune. She also advises and invests independently in startups including Deem, Clay, Cooper, Hiveley, Kina Health, Conceive, and Roco. Lindsay has spoken on huge stages including this one here, The Web Summit, Collision, Fast Company, Innovation Festival, Slush, and Techrunch Disrupt on Brand Building, Startup Growth, and its challenges, leadership, and the realities of being a founder. But wait, there's more. Lindsay also serves as a Tech Stars mentor and an executive judge for the Webbby Awards. First question, Lindsay, when do you sleep?
GUEST: Lindsay Kaplan: [00:02:40] All the time. That's a funny question. It's why I took that job at Casper Mattress Company because I love sleep. I'm a night owl. And so, anybody who has worked with me knows that I do not do well until probably 11:00 a.m. like unless it is urgent. And I do my best thinking and you may get emails from me at 2 in the morning. When do I sleep? Generally between 2 a.m. to 9:00 a.m.
HOST: Adrienne Garland: [00:03:10] Oh, I. Well, listen, it doesn't matter as long as we get the those hours in that is all that matters and we need to get sleep for our health. I'm sure that you know that as a very successful person in this world. I'm so happy to welcome you here to the She Leads podcast. Lindsay,
GUEST: Lindsay Kaplan: [00:03:30] I am very excited to be here and I think what you are doing, the way that you have been working with women for so long and championing women in business is so admirable. So very happy to be on your show and talking about how women.
HOST: Adrienne Garland: [00:03:50] Oh, I I love that and thank you so much. I'm sure that you can probably understand that it's been a long journey and that journey is not always, you know, paved in daisies and and rainbows, but I I truly support women leadership and just building things that matter in this world.
[00:04:15] So, amen to be. Amen, sister. So, over the last few weeks, we've actually been speaking more and more to women entrepreneurs that have crossed that million-dollar mark in their business. It's the elusive million-dollar mark for so many and what it means to be in that exclusive community of less than 2% of all women entrepreneurs. So, we're going to talk about that a a lot today, but before we do, I want to learn a little bit more about Lindsay and what your background is, where you came from, and how you got to, you know, be in the position of starting Chief. So, let's take us back. Tell us a little bit about Lindsay.
GUEST: Lindsay Kaplan: [00:05:05] Where do I start? I have a pretty untraditional path towards entrepreneurship. Although entrepreneurship is in my family, I didn't I never expected myself to to be one. And yet, as I look back, it makes a lot of sense. And it makes sense because I think a lot of entrepreneurs don't like being told what to do, don't love following the rules, generally like to march to the beat of their own drum. And I have always thought of myself as more of a creative than a business person. I was an English major and creative writing major in college. Wrote half a novel that will never see the light of day. Moved to New York City and got my first job in book publishing because as an English major, I just assumed I would end up with words somehow. Got really itchy in book publishing, moved to magazines because that's a little bit faster. And then from there, as I was doing comms and marketing for magazines, this was in the mid early ops. And so this was when Facebook was just starting pages, right? So brands were just figuring out how to put themselves on the internet for Square. rest in peace was launching and I was an early adopter Tumblr all of these early social platforms.
[00:06:25] So there was a really interesting move for writers into social media into the blogosphere which pulled me more into digital marketing and social media management which pulled me more into my interest there which really rewarded creativity and writing. And from there that led me many many jobs later to that role at Casper where I was running communications. And what really drew me outside of just loving sleep and loving the challenge of taking something boring and making it interesting was the creativity that was needed to do that. And so, as a writer, I was really fascinated by building these stories. I know a lot of marketers say that they're storytellers. Again, wrote half a novel that will never see the light of day, but I love stories. I love puns. I love writing. I used to love Twitter back in the day before it, you know, went rogue. And so when I joined Casper running comms, running brand marketing, it was very much a playground of creativity.
[00:07:30] I was there for five years, grew a pretty big team of content strategists, writers, social media managers, PR people, and just started to feel like Casper had gotten big. It was almost on its way to IPO. And there was this there was this nag in me that if these amazing guys at Casper could be the founders, why couldn't I do it, right? Like as and it wasn't like a manw woman thing. It was a me thing of man like they're great. They're smart. They're wonderful. They were the founders. I wanted to do that.
[00:08:15] And so, you know, as fate would have it had a wonderful introduction meeting with my co-founder Carolyn Childers who had the idea for Chief and it was everything that I wanted as a feminist, as a businesswoman, and also as a role knowing that Carolyn is an amazing operator, businesswoman, HBS, consulting, banking background, up COO, phenomenal. And she was really looking for somebody who was more thoughtful around brand experience, community, story. And so that was the the perfect not just company that I was interested in, but also the relationship with her and again that drive to want to do something on my own.
HOST: Adrienne Garland: [00:09:05] I love that story so much and it's so interesting as you're talking I'm thinking so much about how writers and and creatives that so many of us maybe I'll put myself there got into that digital marketing realm and now with AI it's it's seeming to and I don't think it's it's going away. I think there's definitely a place for of course writers and creative thinkers, but it's almost taking that part out of the digital mix and that feels a little scary. But I I think that the creativity and the and the pulling together of different ideas is something that at least at this point only we can do. So I think having that skill is It's paramount. And so many of the women that I've spoken to lately have a creative background and almost say similar like I didn't I didn't intend to be an entrepreneur, right? It's it's a beautiful thing. I'm I'm also thinking it's very interesting to be a co-founder. That relationship is a very close one and so I I I want to kind of go down that path a little bit for just to to kind of get this conversation going because when you are in a relationship like that as you're building a business that you don't know what it's actually going to look like, what are some of those challenges that come up in that relationship as you're building something that's even beyond the both of you together?
GUEST: Lindsay Kaplan: [00:10:40] Well, I think there's challenges in any partnership, but particular particularly a VC-backed high growth startup has its own set of challenges in part because the expectation of moving and growing so quickly is there. Carolyn and I at the end of the day we we think very differently again I'm more of a creative and what we always found so much trust in was our shared values. We are just really grounded people who have very similar values. We were really clear about what we wanted to do with the business. We we have a very strong relationship as humans and we weren't friends prior to Chief but grew a really important friendship based off of those values. So for me that is the biggest piece of advice I could give anybody as they think about either finding a co-founder or a business partner or strengthening an existing relationship is really doubling down on those shared values and making sure that you come back to them time and time again. What was really fantastic for us was if we weren't sure of the answer, we would both tend to get to the same response but take different paths there. And there was nothing that felt more credible than saying we both agree on this in completely different ways, right? Like we're doing math completely differently and getting to the same conclusion. And that gut, that level of trust and and affirmation you get with a co-founder who's thinking differently than you is un that is so amazing.
HOST: Adrienne Garland: [00:12:35] I actually know I'm very good friends with a woman that is building an app right now, connections for women that is based on on values on shared values because she she builds communities and she feels that or she's seen proof that exactly for, you know, exactly what you said that having the shared values is is the success factor. So, I I just I love that advice. I think it's absolutely incredible.
[00:13:05] I'm I'm thinking so much because I talk all the time to to women entrepreneurs, women founders, and and that's sort of, you know, where my mind is. I also came out of corporate, so I I understand that world and the challenges, you know, for women and rising up through the ranks, having life, you know, life, and then having to make a decision. Do, you know, do you want to keep going up that corporate ladder? I know so many women that that choose to to opt out. They they leave and then they start something of their own. Chief is built for the the corporate woman leader, as far as I understand. What are some of the different challenges that are faced by women that are in the corporate world and wanting to lead within that type of environment versus the women that choose to start a business and lead in that way?
GUEST: Lindsay Kaplan: [00:14:10] Well, first of all, I commend any woman who wants to go and do something on their own. Certainly, I did. We built Chief though not to exclude women who were entrepreneurial, but knowing that there are a lot of amazing organizations like yours out there to support these women. And what we saw in the the market was a real lack of a space for women corporate leaders to come together. We saw women in business which always ended up being for younger women and then we also saw a lot to support women entrepreneurs. So for us, we looked around as women in corporate and we didn't see a lot of women left. And so the women who were left who are VP who are in the C-suite they made it and how do we make sure that they stay there so that we see representation so that they have a ripple effect and their presence and their leadership in these highest levels of power in corporate America can both be something that other women can look up to but also that again the differences they can make in the boardroom in the C-suite for other women in business so that's why we created Chief was particularly for that individual. And what we noticed was first of all just a lack of support for women at that level.
[00:15:30] So if if you weren't getting really expensive, you know, tens of thousands of dollars a quarter coaching, there wasn't that much there. An occasional retreat and then some networking that usually ended up with this woman becoming the de facto mentor. Because when you are a powerful woman, people want your advice. So, who's mentoring the mentors? So, we really wanted to create a membership so that she could have ongoing peer mentorship and build relationships and trust and support that wasn't a, you know, a one-off 3-day retreat, but truly something that developed and was with her over her high-level career.
[00:16:15] And then to answer your particular question around what challenges she's experiencing, yeah, so much of the challenges that I've seen come back to the same place which is most problems are people problems. Whether you are managing your team, whether it is dealing with the CEO, whether it is board dynamics, other executives, most problems become people problems. And who better to workshop those problems with and to talk through those problems and potentially to hold up a mirror than other executives who could give you advice, who could say, "I've been there. I've done that." Or, you know, you're a marketer, you're in it with a CFO. As a CFO, let me give you advice on how to best manage your relationship with the CFO. You know, you've you've been through this drama with your team. I've been there. I've done that. So, that's what I've seen. Most problems, and you could even bring that up further into the state of the world right now, most problems are people problems.
HOST: Adrienne Garland: [00:17:40] Very well said. It is. That is so true.
[00:17:50] What made you you choose to create a physical location that people could come together in because I I think that in many membership communities that are started especially now after co you know it's it's all about virtual convenience but this aspect of coming together in person in this this beautiful club environment feels so special. How did you conceive of of that and and why did you think that that was important?
GUEST: Lindsay Kaplan: [00:18:25] Well, we started Chief and we we raised funding in 2018. So, pre-COVID we had to be in person. We also knew that building a relationship with your peers having those in-person meetings was essential. And so, you know, as we had to transition in COVID and then out of COVID, we ended up in a hybrid model where we know the convenience especially for our member who's the busiest person in the world, you know, a successful woman generally busiest person in the world.
HOST: Adrienne Garland: [00:19:05] Yeah. When does she sleep?
GUEST: Lindsay Kaplan: [00:19:10] We we know the convenience of virtual has to be there, but we also recognize the value of in person and know that that is just a really essential factor in relationship building.
HOST: Adrienne Garland: [00:19:30] Do you see now post-COVID that there are that there is either more or less interest from women that do want to climb that corporate ladder? Is that a conversation that happens within the community of of Chief like this has been great, right? I'm I'm at the SVP or in the executive suite in the C-suite let's say, but I am done. Is is do those types of conversations happen in the community?
GUEST: Lindsay Kaplan: [00:20:00] Yes, very much so. And there There is nothing that pains me more and there is nothing that keeps for me the fire of Chief's mission alive more than those conversations when women are burned out. when they are you know women who are the breadwinners in their household are still doing the lion share of caregiving even if they are the bread winner. So burnout is coming from all different directions. It is coming from caregiving whether that's elderly parents whether that's children it is coming from the workplace. It is coming from the back to office mandates. Yes.
HOST: Adrienne Garland: [00:20:45] Which are adding a commute that you know she had relied and kind of filled up her schedule not needing to deal with.
GUEST: Lindsay Kaplan: [00:20:50] It is coming from politics. It is coming from exhaustion and the world needs Chief to make sure that women are not burning out and that they have a space where they can find camaraderie, support, connections, community to make sure that we do not end up in a place where we are sliding backwards.
HOST: Adrienne Garland: [00:21:20] Yeah. And that women are opting out. Yeah. I know that is a harsh reality. And I think that everything that you said, all of those elements weigh so heavily on women. And no matter how amazing and successful we are, you can only sort of carry that load for so long until you just feel like you have to put it down in order to survive for yourself. And I think that much of that is not on us, right? And the way that corporate has, we'll call it maybe traditionally been structured has really not been built for women. And so more and more companies are recognizing that human beings work at those companies and they need to make sure that they're supporting those human beings and those are the best companies to work for. How are some of the the really great companies that have maybe been around for a long time, how are they changing and modifying the the way that they treat their employees so that they do hold on to this incredible, you know, powerhouse that is women executives?
GUEST: Lindsay Kaplan: [00:22:35] To me, the number one factor is being flexible with a schedule. That is it. Because the most precious commodity for her is time. And when you are rigid about butt in seats between specific hours and that is the hill you will die on, you will see women leaving the workplace. You will see it in droves because she has too much responsibility and there is a lack of trust that people pick up on when you demand that they are in their seats. And I'm again I want to go back to what I just said. There is an important factor about being in person. It is why Chief has club houses. So there is absolutely a factor of meeting some in person and I think it very much depends on the role, the company, the type of business. That being said, what flexibility means company to company is different but flexibility with the schedule is the number one factor in retaining women in the workplace.
HOST: Adrienne Garland: [00:23:45] Now does Chief also work on the other side of things? on the corporate side of things. Of course, you're supporting the executives that are within that company, so that's going to benefit the company, but are there other conversations that happen with leadership at these companies so that so that they are also expressing what maybe some of their challenges are that that could be brought up in discussion with the women executives?
GUEST: Lindsay Kaplan: [00:24:25] So, Chief has a lot of enterprise relationships with businesses, businesses that know that they want to retain women leaders, businesses who understand, you know, very progressive businesses who understand that women are facing a different set of of challenges and the importance of Chief. So that is how Chief today works with businesses with these enterprise relationships. Companies who are saying put my whole C-suite, put all of my VPs into Chief.
HOST: Adrienne Garland: [00:24:55] Wow.
GUEST: Lindsay Kaplan: [00:25:00] And and and it's because they recognize again those those specific challenges and want to make sure that they are supporting what then Chief does is women you know we are working with the leaders in businesses right? We like every member of Chief is a leader is a business leader in her organization so we want to make sure that she has the tools she has the knowledge to go back to her her co-workers her colleagues and make sure that she is fully prepared to have those conversations and again create that ripple effect that will help other women in her workplace.
HOST: Adrienne Garland: [00:25:40] So, you have been building this for quite some time and you recently have taken on the more strategic board of directors role and sort of out of the day-to-day.
GUEST: Lindsay Kaplan: [00:26:00] Yeah, I I've been on the board since day one. My co-founder and I have both been on the board, but yes, recently we I think got very tired pre-COVID post-CO and this company, this mission deserves somebody with 100% capacity, energy, passion. And so I think, you know, Carolyn and I are so devoted that we knew this was not something that a one-month vacation or sabbatical could fix.
[00:26:45] This was time for us to say, you know, we've been I'm going to use a sports analogy, which cracks up everybody who knows me because I don't play sports, but I love a sports analogy. I've been around men too often. You know, I think she and I were on the field and playing every game and giving it our all and had skinned knees and, you know, a twisted ankle and at a certain point, it's not doing the team. It's it's, you know, we're not giving the team our best if we're out there with a skinned knee and and tired. And so, she and I both recognize that again, this mission deserves 100% energy in a way that after eight years I I personally physically didn't have anymore. And I could feel it. I could feel it. I mean, I got I got physically sick from the burnout, you know. I was too young to get shingles and yet, you know, I was just exhausted.
HOST: Adrienne Garland: [00:27:50] Hurt. Those hurt. Yeah,
GUEST: Lindsay Kaplan: [00:27:55] it hurt. I was out for six weeks and I think that was a moment where I realized I was I don't think of it as stepping back. I think of it as kind of stepping up into a Yes. Yeah. Like even though I've been on the board, it is a different role you play on the board when you are both player and coach, right? Than to just step back and say, I am no longer playing. I'm going to be on the sidelines and now I could be more strategic when I'm not thinking about what I'm doing on the field. I'm back to the sports analogy. I can't stop.
HOST: Adrienne Garland: [00:28:40] It's good. And you have a a different perspective and and it comes from a a deeper place. Yes, you're steering the ship. You know, you you've you've fully taken the you know, the this is where this organization needs to go. And I mean, holding space for so many women that are facing and continue to face so many challenges is is, you know, I commend you for holding the space for so many of those women for so long. Because no matter what I mean I I you know produce conferences and and after every conference I'm no good for days because you know you give so much of yourself you take in so much of everybody's energy and as positive and wonderful as all of that energy is it's a lot of energy and so.
GUEST: Lindsay Kaplan: [00:29:40] and I'm an extrovert I love people so in a way it's it reminds me of my dog. Like my dog's always like is up for anything and I'm like girl you are tired like you need a nap and I and I think that was me. I think you know all of us extroverted introverted when you love something you're always game and yet it doesn't stop you from being exhausted. It doesn't stop you from potentially getting sick from just burnout. And it doesn't mean that I didn't love it and have the passion and the energy. It simply just meant I was, you know, burning the candle at both ends, physically, mentally, and it was it was time, and I my co-founder felt the same way. It was time for us together as partners to say, "Let's make sure this legacy that we are building,"
HOST: Adrienne Garland: [00:30:50] Yes.
GUEST: Lindsay Kaplan: [00:30:55] Has the energy and can keep going into its next chapter.
HOST: Adrienne Garland: [00:31:00] What is That's such a perfect segue. What is the next chapter for Chief?
GUEST: Lindsay Kaplan: [00:31:10] Well, I think what we we brought brought on an incredible CEO who was the Chief member that we are really excited to because I think Chief is is I think change again this is somebody that is in my heart of heart a creative somebody that that as you could tell from you know wanting to march to the beat of my own drum I love change I think change and evolution is healthy and so I think the next chapter of Chief will be different and I think in order to write a new chapter, you need a different writer to write that chapter. So, I'm excited to see what the new CEO will write. And I'm excited to read the next chapter of Chief.
HOST: Adrienne Garland: [00:32:00] Oh gosh, that is so good. I I just love it. And I can't wait to see I always I admire Chief, you know, from afar and I think it is something that is so needed and I think I think a level of programming like you have at Chief is also something that is so needed not just for women executives but and then you know also for for I think women because I often talk about the fact that when we're sort of going through our our education we we're taught how to work for somebody at least I was right? We're taught how to be good workers we're not necessarily taught how to solve problems from an entrepreneurial perspective and and find that value. And I think to myself, wouldn't it have been wonderful to have been taught both? Because in a woman's life, there are es and flows. And if we could, you know, sort of lean into corporate when that was great for us and then dip out for a little while and perhaps know how to start a business and make that successful and then go back to entrepreneurship, however we want to surf that wave. Wouldn't that just be so amazing for everyone? Because I don't think that we're ever one thing for our whole entire lives. It like we change clothing, fashions change, right? So too should our careers and our professional lives.
GUEST: Lindsay Kaplan: [00:33:45] It is a quote, a Buddhist quote that I used very early with Chief as we were developing some of the modules which is no person can step into the same river twice because you are not the same person and it is not the same water, right? And and and that is why having community and having different communities available for women is essential and having support structures. I mean, I don't have to tell you but the United States compared to other countries does not have the support structures in place for women in business or or women in general, whether that is whether that is child care, whether that is maternity leave. And so, unfortunately, because these the scaffolding doesn't exist for women in this country. We need to build it ourselves and we need to find it ourselves and find those communities, find that that support and do it in a way that helps us in every facet of our life as we grow.
HOST: Adrienne Garland: [00:34:55] Yeah, Lindsay, I have loved speaking to you. I want to continue to speak to to you and to learn from you. And I think that that is the power of just podcasts like this and also communities, the community that you built, the community that I'm building. And it's been an absolute honor to hear from you. And I commend you for everything that you're doing to help not only women in in business, business and corporate, but also all of these startup founders that you are working with. It's it's it's the work and I appreciate you so much and thank you for taking the time to spend some of your time with me here today.
GUEST: Lindsay Kaplan: [00:35:45] Thank you so much for having me. Loved our conversation. Have me back. We'll talk more.
HOST: Adrienne Garland: [00:35:55] Okay. Awesome. Thank you so much. If this conversation moved you, inspired you, or made you think differently. Please take a moment to leave a five-star rating and review. It's not just about boosting the show. It's about amplifying the voices of women entrepreneurs who are leading with vision, building with purpose, and shaping what's next. We need more of these conversations in the world right now, don't you think? And if someone came to mind while you were listening, someone who matters to you, send this episode to them. If there's something on your mind about leadership, legacy, or what's next, I want to hear it. Head to sheetsmedia.com/voice and leave a voice memo or note. Your insight might just help shape a future episode. Make sure to follow the show and come back next week for more conversations you won't hear anywhere else. Thank you so much for listening. This is the She Leads Podcast Network.