People are our power—Lindsay Kaplan, the cofounder of Chief, a private network of women executive leaders.

How would you describe yourself as a child?

The first word I would use to describe myself as a child is actually shy. I was a very shy, sheltered, little girl and I didn't ever really feel like I fit in. And so, I was a bookworm. I threw myself into whatever nerdy pursuit I was in a moment whether that was Magic the Gathering or playing the flute. You name the nerdy activity and I would have checked that box.

I think a bit of that shy feeling came from a place of not feeling comfortable with the people around me and feeling like I didn’t really belong. I think the raw Lindsay was there—the inquisitive, curious, and funny Lindsay. But I was really held back by the feeling of deep self consciousness and it really impacted my ability to extend and be really happy.

Is there a piece of advice from a family member growing up that has remained with you?

No, I don't think so. I don't believe so. I didn't really grow up with a mentor. I grew up with a very close family. So I think there is no one piece of advice that sticks with me. And I've asked this same question of people before. But, I don't think life works like that. The best advice for you is not the best advice for me. I also think that advice comes in a conversation, not a sentence.

I don't think life is like a movie quote. I think it's very rare that people actually get that one sentence of advice from that one person. So the short answer is no.

Did you have any mentors or people in your life who deeply influenced your work and your career?

I come from a family of entrepreneurs. My great grandfather owned a factory in the garment district in New York City. My father and uncle own a restaurant with my brother. My mom is a real estate broker who is entrepreneurial in her own way as she does her own thing. She’s never had a boss, she’s kept her own hours. So I think I was really inspired by my family's ability to take their own path.

I think when a lot of people think about entrepreneurship they think about big fancy businesses. But my parents raised me in a small town in upstate New York. They raised me with really good values and an appreciation for working in order to support your family and create a meaningful life. Not working in the pursuit of, you know, the asterisks of success. Success is really about being happy. I didn't grow up equating large buckets of money with happiness. So I was raised in a household that really valued the spirit of entrepreneurship, but without the hustle culture.

Do you remember a time when your career felt like it took a turn and started to gain momentum? When did that happen and who helped make it possible?

Definitely. I moved to New York City after I graduated college and I didn't know anybody. I had no connections. I had no money. I was flat broke. All of my shoes had holes in them. All of my ballet flats which were very, very fashionable in 2006 had holes. I had mice in my apartment. But I kept the values of my family and went in pursuit of my career.

I started my career in book publishing, because as I mentioned, I was a book nerd. I was an English major and it didn't even occur to me that I could do anything else. I figured I read books, so I would have a career in books. I mean, what else would an English major do? That was not very creative on my part.

I think a turning point in my career came after I left publishing. I started at Oxford University Press. I got bored because, while it is a lovely, scholarly nonprofit, it is not very exciting to work in academic book publishing. I then jumped into magazines and had an incredible time working in magazines. I was meeting people and schmoozing and going out and really understanding the power of relationships. However, the real turning point came when the magazine industry all but collapsed in 2009.

I started working at a series of startups that, with the best of intentions, were either lacking a product market fit, or the founder was inexperienced for a myriad of reasons. None of these startups worked. And there's nothing more depressing than working at a startup that can't get off the ground. As a marketer, you feel like it's your fault because you're not delivering on the market. So that was really the turning point for me. It was when I realized I was failing and I didn’t know what to do next.

I think seeing failure is really important. It’s important to learn the lesson of what didn't work, sometimes more so than learning the lesson of what did work. While I was making a lot of connections and, you know, building myself up from a place of holes in my shoes, I was flailing and failing and hitting a career rock bottom. That was the turning point.

How has a failure or apparent failure set you up for later success? Do you have a favorite failure?

I think failing at all of those startups put me in a position where I either needed to leave New York City and go write a novel or get an MBA and obtain a deeper business acumen. Or at least get a degree that proved I had deep business acumen.

Then, out of the blue, I got a cold email on LinkedIn from a guy who I don't even think had a photo on his profile, which is so sketchy, right? And he asked me if I had any time to talk about his Mattress Company, which I also thought sounded very sketchy. But, I really believe in meeting people and forging relationships and there was just something about the word “mattress” that made me cringe. And I like that. I thought this guy must have had some guts to reach out to me to talk about his mattress company, especially when you looked at the failure of my LinkedIn profile. So I met him and one of his co-founders for lunch and thought, what the hell? Let's do one more startup. One more shot to see if I can make this work. And that became Casper.

It's funny, my husband reminded me that originally, I was so down on myself that when they offered me the job, I said no. I said no for a few months and I offered other friends to meet with them. I sent multiple people their way. Then, I remember they wrote me back and thanked me for sending them all these people and told me they’d still rather work with me. And that's when I said yes. I was like, if you think I can do this, I can give this one more shot. I like mattresses. I love to sleep. It seemed like a good challenge. It was a major turning point in my career, and it was because I took that coffee, because I had that at lunch. It was because we had that great conversation and that connection stayed there. All of that turned into something that was absolutely career changing for me.

Who are some of the most thoughtful people that you have encountered in your career? What do you think really sets them apart?

I have to mention my co-founder, Carolyn [Childers], who is—on the surface level—very different from me. She has an incredible Harvard MBA. She started in investment banking. She became GM of Soap.com, which was acquired by Amazon. She is a world class operator and I have learned so much from her.

The beauty of our relationship is that I'm creative and I go with my gut and she is the operator that pays more attention to the data than I do. We almost always get to the same place and yet we take such a different path to the answer. And there is nothing more reassuring than having gut and deep business experience, meet at that answer. She is strategic. She is still very good at the things that may be considered her weakest skill set. When she is great at something, she’s a genius. So, it's been a privilege to work with her these last few years.

Somebody else that I'm really inspired by is Amani Duncan. She's a Chief member and president of BBH, which is an incredible ad agency. Her career has taken her in such an incredible direction from working in the music industry to now being the head, as a Black woman, of one of the best ad agencies in the country. She does it with so much creativity, intelligence, and drive. I just deeply admire her.

And then a third person is Gabby Hirata who is the CEO of DVF. Gabby's younger than I and she went from owning supply chain and having this deep, deep knowledge around international supply chain and merchandising to running one of the world's best fashion lines. I just find her tenacity absolutely incredible. She's younger than me and yet when we meet, I'm taking copious notes. Age doesn’t matter when it comes to somebody with that much wisdom and that much tenacity.

What advice would you give a student coming out of college to help them succeed in the modern workplace?

Replace the word networking with relationships. Networking feels transactional; nobody wants to be networked. Your job in your 20s is to forge relationships and relationships cannot be transactional.

I also think people forget how easy it is to stay in touch these days. I am a huge, huge advocate of just staying in touch with people. It's so easy to send somebody a text with a funny link or, once a year, send them an email. The power of staying in touch is incredible when you think about the span of your career. You never know when somebody is perfect for a job you're hiring for. Maybe you know somebody who knows somebody that will change your life. I think the wider the net you have of people is one thing but the other is to learn how to softly stay in touch and how to do so in a way that feels real.

I also think there are talented people who think people will find their talent. That's not the way the world works. You will never be the most talented person. You will never be that. I'm a very big fan of zagging when other people zig. So if I'm a great writer, guess what? There's 1000s of better writers out there. So what can I do differently? Never bring a kazoo to the parade. That is something I tell my team with marketing. I teach startup marketing, so I tell them you will never have enough money to launch a proper ad campaign and get TV coverage. What are you gonna do? You have a kazoo. Therefore, don't make that super bowl ad because no one's gonna see it. You could be the best kazoo player in the world, but nobody's going to hear it if you bring it to the noise. Find an empty room where people are listening.

Is there anyone on an interpersonal level that you really admire, friend, family member, business associate, or otherwise, have you tried to emulate or adopt anything that they particularly do well in their own life?

I can't do that. I can’t incorporate who they are. I think that shy person I was when I was a kid was because I didn't fit in and I felt like a zag amongst the zigs, which manifested itself as a shy little kid. Today, I am a very proud waver of my freak flag. I am not a traditional business person. And that's okay. I am surrounded by traditional business people. They are brilliant. They have those MBAs. They are smarter than I am. However, they're not more creative than me. They don't have my gut and intuition. They certainly don't have my rolodex. Life is really short. I went through the transformation of feeling self conscious about being different and not fitting in as a child to being really proud of who I am as an adult.

I have no intention of trying to be something I'm not or stealing pieces from other people and trying to wear them to be somebody better. I just want to be Lindsay. I also think that people are cynical and smart and can sniff that out.

What is a question you wish more people asked you that you haven't had a chance to speak about?

This is a gross generalization, but I've noticed women in particular are asked about their careers: How did they get there? How are they balancing family? But I think women in general are asked less about the future.

I'm a time traveler. I'm obsessed with the future and the implications of what I'm doing and what the community at large is doing to impact society. So questions regarding the road ahead.

What does the road ahead look like? What are the important things that are coming in the next year, five years, ten years?

I can't predict the future. What I can say is that there is a reason people are gravitating toward the idea of wellness, meditation, horoscopes, etc. I think that humans are rapidly deteriorating when it comes to the power of connecting with others and experiencing real life. I think the pandemic exponentially impacted the way in which we feel around one another. And I think it's going to have really, really long lasting ramifications when it comes to the way people are voting, the way that we empathize with others, and the policies that will be put in place to care for one another. So I'm deeply worried about the state of America and I'm worried that the pandemic, again, exponentially destroyed so many human bonds and connections that we get when we are face to face with one another. We really retreated into our echo chambers. And without that human interaction going into our own prescribed universes, we are going to quickly lose touch with what matters for the fabric of society which is taking care of one another.

Can you recall a moment when your personal values were deeply challenged, but you held your ground despite everything pointing in the other direction?

Every time my six year-old has a tantrum, he wants to watch YouTube. I want to give in so badly. So badly. And once in a while, I do.

But I know it's rotting his brain. That's why I took his iPad away after the pandemic. That is the answer, I feel like every day as a parent, I am challenged. There’s the idea of who you will be as a parent and then there is this every day of dealing with kids. I think that one of the biggest challenges I have ever faced as a human being is trying to be a good parent to my kids.