Being Yourself with Kathryn Finney
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Hey there, I'm Dr. Maya Shankar, and I'm a scientist who studies human behavior. Many of us have experienced a moment in our lives that changes everything, that instantly divides our life into a before and an after. On my podcast, A Slight Change of Plans, I talk to people about navigating these moments.

Their stories are full of candor and hard-won wisdom. And you'll hear from scientists who teach us how we can be more resilient in the face of change. Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hello, and welcome to Haunting, Purgatory's premier podcast. I'm your host, Teresa.

We'll be bringing you different ghost stories each week straight from the person who experienced it firsthand. Some will be unsettling, some unnerving, some even downright terrifying. But all of them will be totally true. Listen to Haunting on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Welcome to Cheaters and Backstabbers. I'm Shadi Diaz. And I'm Kate Robards. And we are New York City stand-up comedians and best friends. And we love a good cheating and backstabbing story. So this is a series where our guests reveal their most shocking cheating stories. Join us as we learn how to avoid getting our hearts broken or our backs slashed. Listen to Cheaters and Backstabbers on the iHeartRadio app, Apple Podcasts, or wherever you listen to podcasts.

Most of us try to fit in. It's a basic human desire to feel like we belong. The problem is, for so many of us, trying to fit in is absolutely exhausting. So why don't we just try and be ourselves? Well, it comes with some risk. Catherine Finney decided to experiment with just being herself from a relatively young age. Turns out, it worked out pretty well.

She's now an investor, entrepreneur, philanthropist, founder and managing partner at a venture capital firm, and an author. And she loves just being herself. And her story, well, inspires us all to give it a try. This is a bit of Optimism.

Catherine, thanks so much for doing this. I so appreciate it. Thanks for having me. I'm so excited. The thing that drew me to you immediately was everything about you is bold. You have this amazing presence.

Oh, thank you. And I loved talking to you. And so my rule is when I meet people that I enjoy talking to, I would be selfish if I didn't allow other people to listen and meet you as well. You know, I was born like this. And it was a challenge, you know,

Because I had realized at a very early age that even trying to fit in, I wasn't going to fit in. I grew up doing grunge where everyone was like kind of dressing down and like flannel and all this other stuff. And I remember I was dressing down. I was in the car with my dad and he was taking me somewhere. And he was like, you are a big girl. You are 5'10". You have big hair. You have this big personality. You come in the room and people notice. Mm-hmm.

And there's nothing you can do about that. So you dressing down is not going to hide you. You cannot hide. That's just your lot in life. You walk in the room and people turn and look and say, who's that? Right. And this is like, I mean, this talk was at 14. Yeah. And he said, so give them something to look at. Oh, I love that. That advice, it would be a futile effort to try to not stand out. It wasn't working. Even though I wanted it to, it wasn't working.

So give them something to look at. You might as well be yourself. It's the easiest thing to be is to be yourself. But it's the nonconformist dilemma, right? Those who find comfort in nonconformity still have the deep human desire to fit in and belong. And the problem is the nonconformist doesn't want to conform. It's a dilemma.

It's not even that you don't want to, you can't. You can't. So, I mean, this has been my dilemma, right? Which is like you in high school. I had friends who were jocks. I had friends who were nerds. I had friends who were in the drama club. I was friends with a little bit of everybody. Didn't really belong in any of them, but had friends in all of them and knew that I wasn't a perfect fit in them and prided myself on the fact that I wasn't in a clique, but also, and I think this has been a theme for my whole life, have been in the constant pursuit of finding my group. Right.

Right? Because I never really belonged anywhere. You get a lot of comfort. And it's why we seek to be around people who are like us. Here we are, you know, in this modern world making a case for diversity. But the other side of it, the flip side of it is, but we find great comfort in being around people who are like us because we also desperately want to feel comfortable and feel like we belong. We're all looking for these places, even as a nonconformist, where I can just be Catherine and all my nonconformity. Right?

Right. Just me. I don't have to really think about it. And finding the group of people who you can be that with is really your life's journey. I have friends who I've had for 40 years since fourth grade.

And I also have friends that I've just recently met. And it's been this lifelong journey to cobble together this group of people who often become my sanctuary, where I can just come and be Catherine. Maybe I'm weird Catherine that day. Maybe I'm venture capitalist Catherine. Or maybe I'm just mom Catherine because I'm a mother. Whatever it may be, whoever I am that day or whatever identities I'm occupying at that time, I'm able to be them.

And those people accept me. And that has become really, really important for me. Finding spaces where I can just be me has been a key part of my success, to be perfectly honest. Because even though your nonconformity is what makes you successful, people still want to put you in a box.

And it's been the life's journey for me is to create that sanctuary in those people. It raises a thought to me, right, as we're talking, which is, is there such thing as a conformist? Is everyone a nonconformist in some way? And like, who says that being a nonconformist is actually a better way of living? Right.

Well, you know, the human brain is always trying to make sense of things, right? Our brain is always trying to put things into boxes, right? Because it helps us navigate the world. And so I think as human beings, we want to conform because it helps us understand things. We want to categorize things because it just makes life easier because of the billion things that our brain is processing, that's just one other thing we have to process, right? So we want to conform. And the quicker you realize it, the easier life becomes.

For me, even though I had that realization early in high school, it really did take a while. Even throughout my career, I was just always trying to conform. For many years, I was in the tech space. Tech has this image of the tech bro with the hoodie and the t-shirt. And so I spent over 10 years where I was being forced to conform. And so I was like in this constant battle of like, one hand, I need to conform because that's how we'll get the money.

But I'm a Black woman, so I will never conform no matter what, no matter how much I try. And this is constant battle. And it wasn't until really the pandemic where everything that we thought was true got tested, that I was able to break out of that into a

who I really am, which is this bold, bright person who's brilliant, but also kind of goofy, who's loud, but also introspective at the same time, all these sort of things. But I think we all want to conform in many ways. We live in a day and age now where I would call it the pursuit of hyper-individualism, where fitting into a group isn't even enough yet.

You have to subdivide, subdivide, subdivide, subdivide. And we keep adding languages and words to try and capture every little bit of nuance to describe who I am within a subgroup. And I understand it. And there's a healthy part of it, which is trying to put words to define who I am so that I, A, know who I am and B, know where I belong. If I can put myself in a box that feels like me, then I can find other people who are in my box. But the boxes are getting so small that

There's not a lot of room for anybody but me, or at least a very small group of us. I question the value of hyper-individualism. I understand the desire to put words to describe exactly who I am with all my nuance so I know who I am for my own self-identity, but there's a cost for that.

I'm now removing myself or excluding myself from a group of people to whom I do belong and who belong to me. I think we're in this time period in our world where you can define yourself down to the very atom.

Because of the internet and the global universal nature of it, you can find someone else who also defines themselves down to that very atom too. So you can find two atoms that are like each other, right? And that's the nature of the internet. That's the beauty of it, but it's also the curse of it too.

you don't see the other ways in which you identify with people. Those bigger categories get kind of pushed aside as you get smaller and smaller and smaller and smaller. And then we lose that connectivity. And this is where I think us nonconformists can help. Growing up in Minnesota, because I was so different,

I had to find ways to connect with others that weren't so obvious. I had to find a way to connect my humanity with others' humanity, else I would have been a very, very lonely teenager.

And I think that art is kind of being lost a little bit. Me being able to see you, Simon, and us meet and to be able to connect. And I don't know what categories you fit in other than you're this cool person. But I just knew as a human, at a very human level, I connected with you.

And I think, unfortunately, with the internet, because we don't get to be in the presence of people that much, and this is another result of the pandemic, we have lost the ability to recognize the humanity in each other. Yeah.

And it doesn't matter what category you're in. We're human beings. You and I are both human beings. That is probably the most important category that we fit in. And that alone should be enough for us to connect on some sort of level. Perhaps our desire to be seen as who we are as individuals and be so descriptive that captures the exact version of me that I am

is actually one of the things that's contributing to our division. And perhaps there's value in letting go of some of our individuality, not all of it,

But letting go of some of our individuality, like being okay with not being a perfect description of me, because there is a value in fitting in to the tribe, because ultimately I have to be an individual and I have to be a member of a tribe every day. I'm a member of a team. I'm a member of a family. I'm a member of a community. I'm a member of a church. I'm a member of order society. We are members necessarily of these things every day, as well as being individuals.

And we don't want to abandon our individuality to the point where we're only conformist to the group, but we don't want to abandon our conformity where we're so individualistic we no longer fit in anywhere.

would add to that question, how much of this is an American thing? Probably a lot of it. A lot of it, right? The other places in the world that I've lived, particularly in parts of Sub-Saharan Africa where I've lived quite a bit, this question of your individuality versus the greater good, the greater community, is

is not as much of a trying decision as it is if you're from here in the U.S. Yeah. And I think, unfortunately, U.S., we don't...

get to the community level unless there's a crisis often. I think that's true. And what's interesting is during the pandemic, we did come together, but we divided instead of into lots and lots of splinter groups, we divided basically into two groups. You're either like for a vax or anti-vax, for a mask or anti-mask, for a lockdown or anti-lockdown, and that was pretty much it. There was no nuance. And I think in that case, the lack of nuance

was as unhealthy as the excessive amount of nuance. So I think America has nonconformity pride. Even though we're very conformist, which is like so weird to me, right? Like,

We have nonconformity pride. We were founded by people who were like, we're going to be different. We're going to try something new. And we as Americans, we like being American and not like the rest of the world. You know, we don't even like being like each other. Whereas if it goes to somewhere like Japan, which is vastly more conformist, they have conformity pride. What is the value of nonconformity? I think at the end of the day, it is easier to...

be yourself and to maintain that throughout your entire life than it is to pretend to be someone else. And so by doing that, your life becomes more sustainable. The downside of that is I come from a group of people who our entire lives were told not to be ourselves.

As a Black woman, I have been told and I continue to be told not to be me, to be everything but me. How many times have you been told, tone it down? I mean, my entire life. I mean, today. I mean, you know, like even today. And here's the interesting thing about basically being a Black woman. One of the things that people often talk about is Black girl magic, right? And it's like, where does that magic really come from?

And it's because even if we tried to conform, we still wouldn't be accepted.

And so what happens is oftentimes we're like, fuck it. Like I know even if I try to be exactly what you want me to be, you're still not going to accept me. So there comes a point, particularly in almost every Black woman I know, we're just like, ah, screw it. I'm just going to be me. And we do things and it seems magical, but we're just being ourselves because we're not going to fit in your box anyway. Can I give a terrible analogy? Okay. Yeah.

So in my first apartment in New York City, I had a heating pipe that stuck out in the middle of my bathroom. And it was an eyesore, this freaking pipe, this heating pipe that went through my bathroom. And it was painted the same color as the walls. It was painted white. Yeah.

And then I remember thinking to myself, and I'll take your advice, which is I can't make the pipe blend in. There's no amount of camouflage or paint that I can put on this thing that's going to make it look like the wall. It's clearly a pipe that's sticking out to you, to your attitude, which is, ah, fuck it. And I painted it red and it became the best thing in the world. And people would like go to the bathroom and be like, Hey, love your pipe. Right? Because I know that no matter what I do, when I come into a room and,

I'm going to be most likely the only Black woman general partner there, especially a room of other VCs. There's only 10 Black women general partners in like the U.S. Yeah. So I could try to wear a Patagonia fleece vest, you know, and some like Allbirds shoes and some Warby Parker glasses and be like, you know, and try to do that. Or...

I can say, fuck it and do what I usually do is come in, you know, my four inch Louboutins, my like quirky glasses and my big hair because it is what it is. It doesn't matter what I do, whether I try to conform or not, I'm still going to be that red pipe. There's a very important nuance here that is missed, which is when you say, fuck it. And you just sort of like paint the pipe red. Yeah. There has to be a natural pipe there first.

And I think what happens is the desire to be the nonconformist sometimes becomes gratuitous. And the expression of nonconformity actually is not authentic, but it is looking for a way to stand out because I actually am trying to get something. So not everybody who paints the pipe red is...

is actually doing it authentically. I think you have to have gone through the struggle of trying to fit in and it's just not working. And that's the point where you go, fuck it, I'm painting the pipe red. It's a chicken and egg question, right? Do you have to know yourself before you can be a nonconformist? Or do you have to try and fit in and other people say you're not of us until you become a nonconformist? Or maybe the answer is both. Maybe it's just like whatever your journey is, your journey is.

I think it's both. I think you start to create a sense of who you are and a sense of self, and you kind of test it. You put yourself in different situations as you are creating who you are, and then you see how people respond. The thing about being a nonconformist is that it gives permission to other people to be themselves. It really does. Yeah.

The thing that I have learned, me being me has given so many other people the ability to be themselves and not just other Black women. The number of white guys who are like, you know, you came in and you were wearing this and because I knew you were going to be there, I decided I'm going to wear maybe a different Patagonia vest today. I'm going to wear like a bright red one. I mean, me being me gives permission to other people. So if you're really truly yourself,

It draws people to you, actually. Tell me about your book. It's called Build a Damn Thing, How to Build a Successful Company if You're Not a Rich White Guy. So it is about those who are builders when you don't have...

have all the tools that others are given? And how do you build something in this startup ecosystem, which can be very focused on putting people in boxes and can make it really difficult for you to build? So it was everything I wish someone would have told me. The highest compliment that I've received consistently has been, this is the first business book I've read where I felt seen as an entrepreneur, where I felt

the person writing it understood exactly the challenges that I have to navigate. And isn't that the great irony of conformity and nonconformity, which is when we choose to conform, we want to be seen. And when we choose nonconformity, we want to be seen. Both ways we want to be seen. Both ways we want to be seen. One of the things I talk about in the book, because a lot of it is not just like business advice, it's like stories. As a nonconformist, I think it's important to talk about

the totality of the experience, not just like I'm a not conformance and look, I was successful, but there was some prices I had to pay for it. There was a cost to it. There's a cost on both sides. On both sides. And so let me tell you a little bit about the cost so that maybe you can prepare yourself for it, or maybe you can make decisions differently. I think where the challenge comes in is when people don't talk about the cost.

Yeah.

You sure can't do it at home. And the only way I've been able to live a nonconformist life and be a nonconformist and be myself is because along the way I've had magical friends who have given me the safest space to be myself. And by the way, some of them were nonconformists and some of them were conformists.

You and I have said quite clearly that choosing to conform or not conform is not a better or worse. There's costs and opportunities in both. But in every case, some of those friends who are conformists just knew who I wanted to be, even if they didn't want to be like me. And they just held that space for my journey, which was really important. I think of something my ex-husband said at the toast when we got married at our reception. And he said...

Before I met you, my life was black and white. And after I met you, it became technicolor. He's very much, and I don't think he would mind me saying this, a little more of a conformist sort of guy, right? He's a tech dude, an engineer, a software engineer. And I always remember that because I think as a non-conformist who's just living her life, I'm just really literally being myself. Like it's right every day. Yeah.

To have someone who isn't recognize that. And I think there's this fear that if you're nonconformist, that people who are maybe a little bit more conformist are not going to want to be around you. That's absolutely not true. They admire that too. It can be a little stressful for them too. At the same time, I'm sure my ex-husband would say that as well. But they admire that ability to,

Because it's something that maybe they're not able to do. When we talk about diversity and diverse teams, you want some nonconformists, but not too many. Exactly. You want some conformists, but not too many. Not too many. The little bit of tension between the conformist and nonconformist, I think, makes for better thinking and better product. An old COO that we had said their job was, I'm the balloon and they were holding the string.

Their job was to let me float as high as the string could possibly go, but not to completely float out of the atmosphere. Like that still have some sort of tether to the earth. And I thought that was like a really great way to describe it.

the role of a conformist on your team. There needs to be more conformity pride in America. Our society, American society, we are all somewhat conformists in a world that values more non-conformists. And I think there has to be pride in both. They need each other. They're different and they both have fears. As you said, one floats and one is grounded and

they need each other to thrive. Yeah. Because if you're not grounded, you'll float into the atmosphere. Yeah. But if you're too much on the ground, you don't get to go high. You don't soar. Yeah. Right. So you need both. And everybody's a little bit conformist in some areas and a little, everybody's a little bit nonconformist in others, which is the way it should be. Exactly. So I'm going to attend to summarize this conversation. Here's what I have learned from you today. I like have this big, stupid smile on my face because this is a great insight. I now believe based on this conversation that

that the journey of self-discovery of being a nonconformist is the same journey as becoming a leader. Being a leader is the person who risks saying what they believe. It's the person who risks speaking truth to power. It's the person who risks putting profit aside because I got to take care of my people in this moment.

It's the person who risks running towards the danger because it's the right thing to do. It's the person who risks leaning on the side of ethics rather than expedience. All of that is an expression of nonconformity because conformity says put numbers before people. Conformity says hit the annual number. Conformity is pressure to the status quo. And nonconformity is unto itself conformity.

the journey of leadership. When we're willing to take the risk to say, I made a mistake,

before anybody else says it. When we take the risk to say, I don't understand before anybody else says it. To your point, what that does is it creates a safe space for others to say, I made a mistake. I don't understand. I think we should do it a different way. Becoming a leader is becoming a nonconformist because by giving myself permission to live out loud who I am, it does the same thing for others. And I've heard this in extremely well-led organizations.

people who work in those organizations, people who work on the teams of great leaders say, only here do I feel I can be myself. And I always was like, what does being yourself have to do with working for a great company? And now I understand because the journey of self-identity and nonconformity is the same journey as becoming a leader. Psh. Catherine, you're amazing. Thank you so much, Simon. Thank you.

If you enjoyed this podcast and would like to hear more, please subscribe wherever you like to listen to podcasts. And if you'd like even more optimism, check out my website, simonsynic.com, for classes, videos, and more. Until then, take care of yourself. Take care of each other.

Hey there, I'm Dr. Maya Shankar, and I'm a scientist who studies human behavior. Many of us have experienced a moment in our lives that changes everything, that instantly divides our life into a before and an after. On my podcast, A Slight Change of Plans, I talk to people about navigating these moments

Their stories are full of candor and hard-won wisdom. And you'll hear from scientists who teach us how we can be more resilient in the face of change. Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hello, and welcome to Haunting, Purgatory's premier podcast. I'm your host, Teresa.

We'll be bringing you different ghost stories each week straight from the person who experienced it firsthand. Some will be unsettling, some unnerving, some even downright terrifying. But all of them will be totally true. Listen to Haunting on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Welcome to Cheaters and Backstabbers. I'm Shadi Diaz. And I'm Kate Robards. And we are New York City stand-up comedians and best friends. And we love a good cheating and backstabbing story. So this is a series where our guests reveal their most shocking cheating stories. Join us as we learn how to avoid getting our hearts broken or our backs slashed. Listen to Cheaters and Backstabbers on the iHeartRadio app, Apple Podcasts, or wherever you listen to podcasts.