A Bit of Optimism· Staffel 6· Folge 27

How to Trust Yourself When Everyone Has an Opinion with Love Thy Nader's Mary Holland Nader

Dienstag, 25. August 2026 · 58 min

MP3

Shownotes

Maybe this sounds familiar: you finally get the opportunity you've been waiting for, and the voice in your head says, "I'm not ready, I don't belong here."

Now imagine hearing that voice with millions of people watching.

Mary Holland Nader has lived it. She never dreamed of fame, but when Hulu's reality series Love Thy Nader came knocking, she traded her secure Wall Street job for the spotlight and put her new platform to work. It allowed her to launch Mary & Pip, a purpose-driven fintech company that takes a wellness approach to money, demystifying finance for those of us it usually makes feel dumb. She also brings that expertise to her new podcast, Growing Interest (where I was lucky to be among her first guests).

On the show, Mary Holland lets us join every step of her founder’s journey… even when it’s messy. Because she never wanted to be famous, but now that she is, she’s realized fame is leverage. And Mary Holland's committed to using hers to help and inspire others.

In this episode you'll learn:
➡️ How to survive a 180-degree life pivot
➡️ Why your gut doesn't tell you what to do — it checks your values
➡️ The "corny" morning ritual that transformed Mary Holland's confidence
➡️ How to stop making your doubts your identity (with one simple grammar change)
➡️ The difference between being nice and being kind — and why feedback is kind
➡️ The 2 questions every founder should ask before raising money
➡️ Why Simon gives his time to supporters instead of critics
➡️ The "reluctant sellout" + how financial stability protects your values
➡️ How to introduce yourself when you're more than one job title

Mary Holland is a new breed of entrepreneur — proof of what happens when you use your platform for something bigger than yourself. She stopped waiting for confidence to arrive and decided to build it… in front of everyone.

This… is A Bit of Optimism.

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This episode is brought to you by SAP. Bring it with SAP GROW. The AI Cloud ERP for any size business. Learn more atSAP.com/GROW (sap.com/GROW)

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Tune in to Mary Holland’s new podcast, Growing Interest, and you might just see Simon as a guest.

Improve your financial wellness with Mary & Pip. Head to: maryandpip.com

Want to keep up with Mary Holland and her sisters? Check out Love Thy Nader on Hulu: hulu.com/series/love-thy-nader

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Chapters
Chapters
• From Wall Street to Reality TV: Using Fame as a Tool for Good
• Growing Up in the Bayou: Four Sisters and a Pet Alligator
• Why Finance? Growing Up With Money Anxiety
• Meeting Jimmy Kimmel's Agent: The Accidental Origin Story
• Quitting Wall Street for Reality TV
• Why Finance Makes Everyone Feel Stupid
• Mary and Pip: Translating Finance for Real People
• Becoming Confident on Camera: From Mortified to Vulnerable
• The Power of Positive Self-Talk: Mirror Affirmations That Actually Work
• Trust Your Gut: When Smart People Give You Bad Advice
• What Does A Mentor Actually Look Like?
• Gazelles Get Eaten: Why Hypergrowth Isn't Always Good
• Spears: The Feedback Technique That Changed Everything
• Correcting Language That Creates False Narratives
• The Reluctant Sellout: When Freelancers Are Forced to Compromise
• You're Not a Founder, You're an Inviter: Finding Your True Identity

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Simon is an unshakable optimist. He believes in a bright future and our ability to build it together.

Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do.

Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game.

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Website:simonsinek.com
Leaderful: simonsinek.com/leaderful
Podcast:apple.co/simonsinek
Instagram:instagram.com/simonsinek
Linkedin:linkedin.com/in/simonsinek
Twitter:twitter.com/simonsinek
Facebook:facebook.com/simonsinek

Transkriptvom Podcast bereitgestellt · Zeitmarken springen hin

You have no desire to be famous, and yet you recognize that being on TV and having some fame gives you the ability to spread your message more efficiently. Correct, yeah. And the minute you made that connection, you realized, huh, I can leverage this for good. This season, it shows a much more confident version of me.

I can't control the edit at all. So like, why pretend to be someone I'm not? The more vulnerable I am, the more likely someone like your niece could watch and be like, oh, I see myself in her or I could do that, too. These days, fame isn't solely a byproduct of a career. The pursuit of fame has become a career.

We live in a world of content creators, influencers and reality TV stars who have literally made fame their job. Which is why I was excited to talk to Mary Holland Nader. Mary Holland, along with her three sisters, are the stars of the Hulu reality TV show Love Thy Nader. Except it was Mary Holland's sister, Brooks, who was the one who actually wanted to be famous.

Mary Holland just didn't want to let her sisters down. She had a secure Wall Street job and a clear path ahead. Mary Holland wondered, if I had fame, what could I do with it? Her answer? Leverage it for good. Mary Holland founded Mary and Pip, an app that demystifies money for those of us who don't really understand finance and all its jargon.

Just like we have mental and physical wellness, Mary Holland wants to help guide people to practice financial wellness, too. She also launched a podcast, Growing Interest, to further advance her cause. You might even see me as a guest on the show sometime. Mary Holland loves to teach, and she also loves to learn.

So fair warning, you may hear a little more of me than usual in this episode. Mary Holland took full advantage of our time together to ask me a bunch of questions. It's fair to say that in our modern social media world, counting followers is here to stay. So let's have more entrepreneurs like Mary Holland who are motivated to use that platform to serve others.

If you like this episode, please remember to subscribe. This is a bit of optimism. This episode is proudly brought to you by SAP. 100% of employees are people. 100% of customers are people. are people. And 100% of investors are people. It turns out if you don't understand people, you don't understand business.

Which is why I was so excited when I asked David Robinson, the head of SAP Customer Success in North America, about how he talks to customers about new technology. His secret weapon? Listening. You are now a famous TV star. Stop. On my way. And the thing that I find so fun about you and your family, so I want to understand, so you're from the Bayou in Louisiana.

Down under. Like, not like from New Orleans or something? No, from the Bayou. So we grew up in Baton Rouge, but we're from a small town called Maringuen. Which I can't even figure out how to spell. No, it's basically... It means mosquito in Cajun French. So not even French. It's not even French. Yeah, Cajun French.

Okay. Because the air is so thick. There's so many mosquitoes there. You walk outside and you're just eating. I always got the most bites because I was the sweetest sister, of course. Of course. So Marenguin is like where my grandparents are from, where we were all kind of grew up a little bit. And then we moved to the big city of Baton Rouge, which is a college town, the capital of Louisiana, but still very Cajun.

I mean, like, are you all wearing like overalls and barefoot and like with a piece of straw in your mouth? Honestly, yeah. Like, it was pretty, like, stereotypical. Like, Simon, we had a pet alligator. I'm not even kidding. No, please. Gary the Gator, yeah. I'm not even kidding. There's pictures of us.

We named him Gary. Wait, was he just, like, in your backyard? He was in our, so when we were in marriage. Or was he actually your pet? We named him Gary, so he was our pet. We obviously didn't like take him on a leash anywhere. That was way too dangerous. But we had a bayou in our backyard. You know what a bayou is, right?

It's like a ditch with... It's like the remnants of a swamp. It's like instead of a river to a larger body of water... It's a nicer word for swamp. It's a nicer word for swamp, but it's in a ditch. A swamp in a ditch, basically. And we had a bayou in our backyard in Marenguyn. Not when we... We grew up in Baton Rouge, like in high school and stuff.

So this was in Marenguyn. And Gary lived on like a rock just baking in the sun in that bayou. And so we would go throw rocks at him and like play with him. He's never attacked us or anything. We had to play with him from a bridge. Yeah. So it would be harder for him to get to us. And obviously we had supervision, but we were literally boondock, like running around in our diapers, in the mud, playing with random wildlife.

It was quite dangerous. So all the stereotypes that are going through my mind, all true. Exist. All true. Okay. So you're from the bayou, the backwaters of Louisiana. Yep. And four sisters- Mm-hmm. Three. Four, including me. Right. Four girls. Four girls. And my understanding is that Brooks, who's the oldest?

Correct. That Brooks decided when she was young, my memory serves, that she wanted to be famous. Absolutely. Okay. Mm-hmm. So the reason you have a TV show- Literally. Is because Brooks, as a young girl, decided you would- Oh, my God. Yeah. I mean, she knew from the moment she popped out of my mother's 23-year-old womb because my mom had us so young.

Wow. Yeah. But there was a story that I will never forget. We were such a tight-knit family, and my mom was a stay-at-home mom, and we would have guests over for dinner. We had family dinner every single night. And my mom always taught us the power of conversation and communication skills, which I'm so grateful to her now for.

But she would always say like, when we say something about ourself, we have to pass the ball back. And we would pass the ball around, the conversation ball and make sure that you're always passing the ball. Literally or metaphorically? When we were together sometimes, because my sisters, I couldn't get a word in.

I was definitely the quietest kid, but my sisters were all yappers, as you know. I mean, you know me and my sisters are more yapper than I am. And they talk even more than me. So sometimes we would have to have a talking stick and like only if you were holding the talking stick But I digress we had a friend over who was a writer.

He was my dad's friend from high school And he was like Brooks, you know, what do you want to be when you grow up? She's like I'm gonna be famous I'm gonna drive a pink limousine like there's gonna be paparazzi. She's like eight years old at this point and talking, talking, talking about how famous she's going to be.

And my mom goes, Brooksie, pass the ball back to Mr. Feynman. And she goes, oh, I'm so sorry. Mr. Feynman, how will you feel when I'm famous? So she's always had like a burning fire in her to be famous, which is crazy, but like it's worked. I mean, she has gotten herself on the map. I mean, she engineered this.

She literally, she manifest, like she is the definition of manifesting. So she's living her dream, literally her childhood dream. Yeah. It doesn't even matter how she got famous. She got famous. She's on TV. She's got a TV show. But you went into finance. Yes. Okay. You're like good at math. Yeah, I guess.

Well, I mean, you're in finance. I'm in finance. Yeah. You worked for a big bank in finance. I worked for a big bank in finance, but I honestly went into finance because we were so insecure financially growing up. And my dad pivoted from nonprofit work to finance, to wealth management. and kind of climbed his way with all of us out of the situation we were in.

And slowly as we got older, I mean, we were still lower middle class, but we were very lower class, like at the beginning when he was in nonprofit work. So I always associated finance with stability and money. And I was like, oh my gosh, if I know finance, I'll never worry about it. Because we always worried about money growing up, like it was a constant stressor in our house.

So that's why I studied finance at Georgia and got the big job at the big Wall Street bank because I thought this is going to pay me the most money and going to be the most stable. So I want to know, your sister's pursuing her dream to become famous. That's going fine. Yeah. She manages to get a TV show.

Yep. What did she pitch? Our origin story of the show is actually so funny. We were all out in New York, okay? Just being our crazy normal selves because we all go out in New York together. We met this couple, this really nice couple, and their daughter and her boyfriend. And it was just a really fun Long Island...

New York couple. And I feel like Long Islanders and like Northeasterns are very similar to Cajuns that we like to drink. We like to party. We're like very hospitable and welcoming. So we were all just like partying and having fun together. Okay. As you know. And so we were just like having the most fun out.

Turns out this is Jimmy Kimmel's agent. And he was like, you guys need a show. Like from Louisiana. We're making our way in New York. And he was like, you guys need a show. And we were like, why are you saying we need a show? And it turns out he's Jimmy Kimmel's agent, baby doll. So it's just weird luck.

Weird, crazy luck. So he starts kind of like quasi-representing us. And this is before I was still at Deutsche Bank as an analyst, like not even thinking anything of it. He basically pitched us to Hulu. They were like, this is an interesting story. They didn't know who any of us were. But they let us produce basically a sizzle reel, which is like...

18 minutes like a shortened pilot to pitch to the network so we filmed that when i was probably 23 24 sarah jane couldn't even drink yet like not even legal drinking age brooks was still married to her husband which is a whole nother story grace ann was still in college so we were all in a very different stage in life than actual season one was filmed the sizzle reel i was so anxious simon that someone at work would like find out about it i was still in such like impress the boss mode as an analyst.

And so we filmed it and then we didn't really hear anything. And I honestly thought like we didn't get it. So I was like, okay, perfect. I'm just gonna continue on my easy steady path. And then we get the call last January that was like, y'all got the show. Basically on the back of Brooks being on Dancing with the Stars.

She made a huge splash in the media. Everyone's talking about her. And they were like, this is actually interesting. They're all in different phases in their life now. Let's green light this thing. So we got the call last January. I basically had like two weeks to decide if I was going to quit my Wall Street job or pursue this show with my sisters.

But everyone's like, you made this huge choice, but it was a sister show. Like they couldn't do it without me. And Deutsche Bank wasn't. They could have. They could have. But. There's plenty of. Plenty of drama. There's plenty of brother-sister shows where one with one who didn't want to do it. And you just think there's three sisters and they talk about the other sister.

That's true. I guess we don't even have that vocabulary in our sister language. Like it's all or nothing with us. Did you feel peer pressure? A hundred percent. All right. It wasn't even an option to me. Like I was like, oh, well, of course, I'll just quit my job and do this because my sisters can't do it without me.

But you don't have a desire to be famous or be on television? No. I mean, now my desires have completely shifted that I'm starting a company. So obviously, it all helps the greater cause of distribution. But at the time, I was so happy being behind the scenes in the background. I was modeling with them by night, like doing covers.

And it was fun and creative because I like to be challenged. I'm very curious and just like to challenge my ability to do things. So I was like, oh, I checked the model box, signed with Ford. But I loved keeping those identities separate. And I think for a long time, even up until like this past year, society only rewards people who are really good at like one thing.

And now people are becoming more multi-hyphenate, but it's still hard to merge two completely opposite industries. Well, I mean, you're doing things that like one that requires you to be pretty. Yes. One that requires you to be smart. One that requires you to be sort of vivacious. Right. I mean, they don't necessarily.

Dramatic. Dramatic. They don't usually go together. Right. Like, you know, you're not even in a category. No, exactly. And like going to a boardroom, asking investors for money, knowing that they've seen the show where I'm like ripping my sister's hair apart and like being a crazy reality star, which I'm not even the craziest on the show, but it's just totally opposite industries.

So it's still tricky to find my identity as a blend of all of them. Because you don't care about the fame and the television. Yeah. I mean, you're an entrepreneur. You haven't quite left finance. You started a business. Correct. Mary and Pip. And the goal of Mary and Pip is... To basically create financial independence for women.

To basically do the thing that you wanted to do for your family. Correct. But now give that gift to as many people as possible. Exactly. And to translate it. Because I am what people in the finance industry refer to as an idiot. Stop it. No, no, no, no, no. Everybody thinks I'm joking. Really? Everybody thinks I'm joking.

I don't understand money. I'm not driven by money. And one of the reasons I've been a bad investor is... One of the reasons, you know, like even financial managers who I go and see in the bank, the reason I'm bad at it is because they make me feel dumb. Yeah. You know, they speak to me in jargon. Totally.

And I don't know whether it's because they automatically think that I understand it or they're just trying to make themselves look smart. Yeah. And when I ask questions, they... They roll their eyes or they talk to me like an idiot. And so I just choose not to work with them. Yeah. And I think a lot of people keep it to themselves.

They keep it a secret that we don't understand money or don't understand investing or don't know. And basic, basic stuff. Like if everybody invested a little bit and understood compound interest even. Correct. You know, which now I understand. I wish I understood it when I was 23 years old. Yeah. But the problem with the whole financial industry, a good portion of the financial industry, is they're high on themselves and they make the rest of us feel stupid.

Yeah. And so some of us do it because we fear that they know more than us, so we better do this. Correct. So we get taken advantage of. Yeah. Yeah. Or we just don't do it because we feel dumb. Yeah. And so I think what you're doing, you're making it simple to understand so people understand the basics of investing and finance so that they can provide for themselves and the people they love.

Right. You're not starting a business to make people day trading and hardcore investors. Exactly. This is basic, basic stuff. The most basic, and let me ask you, you said you don't even like talking about it because they make you feel dumb. And I feel like that manifestation of just holding it in and not talking about it creates such stress and anxiety.

There's just so many trends about longevity and it's such a buzzword. And I feel like everyone's trying to hack their wellness, but then they have such financial stress that is ultimately contributing to their overall- I think money is the number one cause of divorce. It's, yeah, oh, it is, yeah. Financial stress.

Totally. You're right. And people who live longer have lower stress. Correct. It's not that they just eat vegetables. Yeah, exactly. It's that they have lower stress. You would think more people would spend time to understand the basics of money for no other reason than for their health. Exactly. I'm glad you're doing this.

Yes. But this is what I find interesting about you, which is you have no desire to be on television. You're only doing it because all for one, one for all. I get it. That's great. You get it. You find yourself doing this thing. And I'm sure at some point you're like, what am I doing? Yeah. Yeah. there's a lot of points like you know and like the producers are editing it in a way that they can make you the good one or the bad one yep nobody really knows the real one yeah you know it's reality ish sure you know yeah i watched some of the show are which one tell me i didn't take you for a reality guy i'm not And I watched a part of one of your episodes.

Oh, stop it. No, I don't even want to know which one. Was it my pitch? Yeah. I was mortified. And so also, like, I had worked for so long to get my licenses and on Wall Street. Talk about, like, if they made you feel dumb, they made me feel... Right. You actually have a license to practice finance. I do.

Like you pass tests. I pass tests to practice. And I was also modeling by night and I felt so dumb just being like a pretty girl on Wall Street, like honestly. And I just felt like so out of place. You know what I mean? When I was there and then to quit. And I had never been a part of this entrepreneur world.

The founder world is a completely different world than the Wall Street world and the corporate world. Like 100%. In corporate America, it's cool to climb the corporate ladder. And, like, it's cool to get MD and to get the next, you know, title. In founder world, it's cool to take risks. But it's not very cool to be on a reality show in the founder world.

You know what I mean? So it's all different conflicting things. So I left and pitched... a half-baked idea. I didn't even know what Mary and Pip was gonna be. I like Love Thy Nader because season one was literally, if you just have an idea and you feel like you're too dumb to execute it or feel like you're not meant to execute it.

Like maybe I thought I could do something like this, but being on a reality show, I thought my LinkedIn was like torched on fire. I thought all my credibility was out of the window. So I love that Love Thy Nader showed how dumb I was in that pitch. Cause like I literally had no idea what I was saying.

I like had never given a pitch before for my own idea. I didn't even know what that was. And they were like, just do it on camera for the first time ever. You don't know what you're going to come off looking like. And so I was super nervous. And then this season it shows a much more confident version of me.

Because I had been in front of the cameras before. And because I know half of it's not included. I can't control the edit at all. So like, why pretend to be someone I'm not? And the more vulnerable I am, the more likely someone like your niece could watch and be like, oh, I see myself in her or I could do that, too.

We'll be right back. But first, we want to share an ad with authenticity brought to you by SAP. Too many people think the way to stand out in the market is to talk more about their product. SAP's David Robinson has learned that the best way to make customers feel supported is to be curious and listen.

Customers always will tell you exactly what they need as long as you're listening. It goes back to some other conversations you and I had about how proud technology people are about the technology. The technology becomes the main thing, not what it means to your day-to-day life. The ability to really listen is critical if you want to explain.

We need to make sure that we're always talking about something in the context of the customer, something that's in their language, something that relates to them. I may think I know what the challenges this customer is trying to solve. The ability to be curious of what that looks like and then distill that into something very simple to communicate is something that I enjoy doing.

I want to highlight what you said, which is to be a great explainer, you have to be a great listener. It's the old sales technique of sell this pen to somebody. And what people start doing is like, I've got a great pen here, it's got ink in it, and you can write an essay, but nobody ever says, Do you ever...

Record things write things down like they don't ask any questions They don't listen to about somebody's life to help understand how this pin fits into your life They start talking about the technology of the pen sure you have to really be listening all the time Where did you get this confidence to be okay looking dumb?

I've always been insecure to look dumb, for sure. Definitely always didn't think I was meant to be in a room that I was supposed to be in. But I think A, like my older sister instills a lot of confidence in me, Brooks, honestly, because she is just like so confident and she'll yell at us if we say anything bad about ourselves, which I love about her.

If I say like, ugh, I feel fat today, or like don't feel confident, look ugly, she's like, never say that about yourself again. Your body hears what your brain is telling you, you know, obviously. This is the person who manifests her entire life. Yes, exactly. So we should pay attention. The power of mindset's insane.

And then also, like, no one's going to remember you on your tombstone for, like, what you almost did or, like, your excuse for why you didn't do something. And so I think that my mindset shift, there's been a lot of internal work since the show came out. and like watching a show where you have no control over the edit like that is very vulnerable and because i filmed so many hours and there were so many scenes in season one that i was super nervous about how i was going to be perceived that didn't even make the cut and so this season i've been like well i don't even know if this is going to make the cut so i might as well just like give it my all and try and be myself and so there's like the show aspect of it but then there's also just thinking everyone is so worried about themselves everyone's worried about

themselves looking dumb no one is actually thinking like simon looked so dumb today during that like i'm gonna leave here and think of every word i said on this podcast and be like could that be misconstrued by the way i do it too i'm sure i was on your podcast oh my gosh and you asked me a question at the end and you said what are you interested in right now oh my gosh yeah and i started well i'm really interested in british history right now and i sort of I insecurely shared some of the things I was learning.

And I realized when I walked out is why couldn't I be like, okay, let me tell you why, you know, the Tudor period is amazing. Right. But I just, and I was like, oh, do you really want to hear this? No, it was so great. So I go through that as well. Like, you know, things that make me fascinated. Right.

About something. Because you're like, no one will care. Because I'm in my own head, like, nobody wants to know. But we do. You know, the OG online dating. OG, which was the most fascinating thing ever, by the way. You'll have to go and listen to... Listen to Growing Interest. The great name for a podcast, by the way.

Thank you. You have to go listen to Growing Interest to hear our conversation about Anne of Cleves, the original online dating... Profile. Profile. That's right. That's right. But it's so funny. You were thinking that. And meanwhile, probably at the exact same time, my podcast producer was like, because I was debating including that segment in each of my episodes because I have all these growing interests.

So I want to ask my guests, what are your growing interests? I think that's correct. You should. And after you left, he was like, that is an example of why we have to include that segment. That was the most clippable, entertaining part of the entire interview. And I was like, really? Not all of my prepared questions?

I thought other parts were quite good. No, there were others that were amazing. And he really was talking about how it showed your personal interest and like a little bit of your personality of like, this is what I'm actually interested in. So I think just realizing that everyone is so worried about themselves, which everyone says all the time, but it's like no one's going to remember you for some word you said on a podcast or...

when you were 27, when you're dying. And even if they do get hung up on something you said, or they say, well, you looked dumb in that, it's usually born out of their own story. That's something I've learned. When people say, nobody thinks about you, they're only thinking about themselves. Like, well, sometimes they do think about you.

Right, right. We've definitely all gone to a concert and be like, that sucked. Yeah, yeah. That person was terrible. True. People definitely have opinions about you and your sisters. Sure. Sure they do. And even if they're fans of the show, they have opinions about who you are. Yeah. I think what I've learned is that the opinions that others have of us are still very often born out of their own...

Insecurity. Well, not necessarily insecurities, but their own narratives. Right. And their own stories. Right. Well, and not to be corny sitting in a chair with you, but it's all about your why. I'm not creating Mary and Pip to be rich or to be featured and recognized as a founder. I'm starting Mary and Pip to give everyone financial independence that I once hoped for.

Purpose driven, yeah. Purpose driven. So whatever the reason is, is like why you're showing up and not necessarily like what people will say about you, but I will say one like practical outcome that I've done that I'm encourage my friends to do is similar to how Brooks does not let me speak bad about myself.

And it sounds so small, but it's so easy. Like we're all so sillily like self-deprecating and it's funny and like it's great to have humor about yourself. But when you are saying every day like I'm so fucking ugly or I'm so fat or I'm so this or like – I just look so bad. Like that was fucking horrible about any performance you did.

Your brain and body listen and your brain fills the gaps of things it doesn't see like and fills the gaps of things that it doesn't understand. So in the past year, I was so insecure about being this new founder because like my whole identity was Wall Street. And so when I pitched the show, I was like, first of all, don't know how it's going to be portrayed.

Don't know how I'm going to come off. I don't know if this is going to be successful or not. Like, it's not like I'm talking in retrospect, like most founders do, of how well I did. I'm like, people are actually seeing me start this. Now there's pressure. And I used to wake up every day and be like, I can't do this, basically.

Like, and I'm insecure to even say that out loud, but I did. I didn't think I could do it. I got a lot of opinions, which I feel like as a female founder, it's really easy to listen to a lot of people and a lot of opinions from Wall Street tech, because I was new to starting a fintech app. So I would just listen to everyone and I'd be like, oh, well, this investor said I should do this, so I'm going to do that.

And then someone else would tell me something different and I'd completely pivot. Oh, because their accolades are a little bit better. And then one of my mentors was like, your advantage as a female founder is that you think differently than all of these people, you know? And so like, you really need to trust your intuition and like trust yourself a little bit.

So I would actually like, so corny, look in the mirror in the morning and be like, I'm a founder, I'm a CEO. Yeah. like Mary and Pope is going to the moon. Like I would literally say that in the mirror every day. And I felt so corny doing it. Cause I'm not usually not about all that. It's like a poster with, you know, a little kitten hanging.

Yeah, exactly. I was like, oh my gosh, this is embarrassing but it actually transformed my confidence. And I would meditate and like try to be more conscious of my negative thoughts and notice when I thought them and notice when I felt insecure. So a lot of that, like repetitive rewiring actually contributed, I think, to me being much more confident.

I like female founders because they tend to be more purpose-driven. Men tend to be more competitive. And so for them, it's about, look at the amount of funding I got. You know, it's like, Yeah, but your business is stupid. Right. You know, we're changing the world. Yeah. Funding. Through efficiency. Through my pizza delivery app.

You know, men, it's about like how much. And women I find tend to be a little more like, no, no, but who's this going to help? You know, Sarah Blakely, you know, very, very, very purpose driven. You know, Carissa Bodner, you know, from Thrive Cosmetics, Sarah Blakely, obviously from Spanx. Very purpose driven.

You know, and there's a list of these female finders who they're not as famous. Yeah. And yet their businesses tend to do very well. Yeah. And they tend to be smarter about who they take money from and who they don't take money from. In fact, both Chris and Sarah know money from anybody. Yep. I didn't realize they were both bootstrapped.

Sarah Blakely bootstrapped her company and owned 100% of the stock when she sold it. Holy shit. That's insane. Yeah, I think Chris is the same. Oh, my gosh. Well, and you know, the biggest consumer in the US and the biggest spenders are women. I get this question of an uncomfortably high amount where a founder will say to me, you know, what do you do when your investor is putting pressure on you to make decisions that you know are bad for the business, but, you know, serve their short term interest?

Yeah. What do I do? And I always give the same answer. I was like, you took the money. It's like, right. Like when you were meeting investors. Did you choose the investor who believed in you even if they gave you less? Or did you choose the famous investor who gave you more? Right. Like, was it your ego that you took that money?

Yeah. And everybody says, I'm like, careful, careful, because investors, their business model, they have to sell you. Yeah. for their business model to work. Right. So between three to five, five to seven years, you're gonna start having pressure. And they're like, no, no, no, my guy's different. I'm like, no, it's not.

It's the short-termism. And I think women tend to be more long-term focused automatically. The challenge you'll have is, and every purpose-driven founder, male and female, has this challenge, which is the pressures will be overwhelming, especially if you have investors. And do you have the wherewithal to keep it going?

Like Steve Jobs was purpose driven, never gave out dividends. Yep. Didn't care. Yeah. And he told investors, if you like me, invest in me. If you don't like me, don't invest in me. Yeah. Like, what do you want from me? That's the greatest. Yeah. And like that takes, you know, balls of steel. Yeah, I know.

Looking back at my own career, the stupidest decisions I made, the bad decisions I made, the wrong decisions I made, the wrong advice that I followed every single time. It's because I thought somebody was smarter than me, had more experience than me, knew something that I didn't know. I better listen to them because they know more and I'm dumb.

And even though it doesn't feel right. They know more than me. And close to 100% of the time, I wish I trusted my gut. Close to 100% of the time. Because your gut isn't telling you what to do. Your gut is checking your values. And so you might get advice that you may or may not agree with, but your gut is saying this aligns with your value.

This aligns with your why. And if it doesn't, find a different way. Is it the same as intuition? Yeah, sure. Right? Because we were given intuition as like old time homo sapiens for a reason. Correct. You know, cavemen sort of were evaluating, can I trust this person because my survival depends on it?

Correct. And I can trust people who share my values. And if we're values aligned, this will work. And if we're not values aligned, you might just be stabbing me in the back. And so, yeah, we are gifted with this and we don't trust it enough. And I don't want to generalize that all women, you know, tend to suppress their intuition.

But I feel like we historically have been taught to suppress our intuition. It's a cultural thing. It's a cultural thing. Like even being polite to strangers, I feel like. Like I listened to My Favorite Murder, this other podcast, and one of their things is fuck politeness because women have been taught to be polite and it's gotten them killed, you know?

And it's like if your intuition is telling you that something's off, then it probably is. Yeah. And when it comes to raising, I think in the past year, you can't run a company or make any decisions for yourself unless you believe in yourself first. Otherwise, you're just going to be listening to other people's advice.

And other people operating... For them. Unless it's a mentor or a friend with no interest. Right. And that's why I think mentors should be outside of your... I like that. Your business. Yeah. Like the difference between a mentor and a champion. Yeah. A champion is somebody who's pushing you, helping you, but they...

They're either in your company. Right. If you work for a company, you know, that might be a senior executive. And you expect a champion to like, hey, put in a good word for me. Right. Where a true mentor has no ability to influence anything. Yeah. They're not investors. They have no financial interest.

They don't know your boss. Right. They have no interest whatsoever and no ability to help you other than just give you advice because they care about you and love you. Yeah. That's it. That's a real mentor. Yeah. I think you're right. I think we do all these things. Yeah, I know. And I think we're having this conversation at the perfect time because me and my business owner, we're about to start raising our seed round.

And right now it's really easy. There's so many VCs, private markets are booming. And I remember when we first sidebar, I first met you and I was telling you about Mary and Pip. You were like, what do you want to do with the company? And I was like, I guess exit, because everyone was telling me that's what you have to do.

That's the end goal. And you were like, do not build this company with the goal of exiting, or you're going to lose your why and your purpose. And that stuck with me before I even knew you from the very beginning when anyone asked. And it's honestly intimidating when I say, I'm not building this to exit, because investors don't even want anything to do with it.

And by the way, if you say that, it turns investors off. Yes, exactly, which is good. You want to turn off the investors. Right, who don't believe it. Who only want the exit. That's so true. So if you say Mark Zuckerberg is still working for the company he founded. Michael Dell is still working for the company he founded.

Yeah. You know, Sergey Brin and Larry Page, who founded Google, they've moved on since, but they had one job their whole life. Right. You know, Steve Jobs started Apple when he was 22, 23 years old, you know? Yeah. It's like my mom when she's like, which this is like so bad, but she would say like...

Whatever you wear out is going to attract that kind of guy. It's like the same type of thing. So if you're saying I'm building it to exit, you're going to attract all the money who likes the exit. Totally. If you say I never plan on exiting. Yeah. And so the other question is like, why do you need to raise money?

Do you actually need outside money? So I think of everything in terms of cost. Okay. Right? By raising money. Yeah. That means you get to build the business faster. Right. Because you can afford more staff. Yep. Right. And you can have three or four priorities at the same time. Yeah. If I don't take money, I can do one thing at a time.

So one is not better or worse. It's just different ways of doing it. So what's the cost? Well, the cost of doing four things at the same time means that I have to take money from somebody else, which means I'm going to sell some of my business and somebody else is going to have influence. Yeah. Not taking some of this money means the cost is I'm going to grow slower.

Right. But I don't have any outside influence. I just have to get better at prioritizing. Yeah. I personally chose slower. Why are you raising money? Do you actually need it? Right. You know? I mean, I guess I could, like, I'm raising money to hire more people, basically. Okay. Again, how many people do you actually need?

I hate it when companies, when founders say to me, I'm like, so tell me about your company. Like, we're hyper growth. Right. You know, we're a gazelle. Okay. What does that even mean? That means a hyper growth company. I like literally didn't even know that. And I'm raising money. Okay. A gazelle. Gazelles get eaten.

Facts. Elephants don't get eaten. Mm-hmm. And they're big and slow. Yep. Slow and steady wins the race. Show me one article. Pick a legitimate magazine, Harvard Business Review, Inc. Magazine. I don't care. Give me one article in any reputable publication that says that hypergrowth is good for long-term value of the company.

And the answer is zero. Hypergrowth is good for the investors because that's their business model. Yeah. Well, because you don't get an article for saying like we had, you get an article for saying you raised 30 million more than you would get an article saying you have 30 million in revenue. Right. Which is so bizarre to me.

It took us 10 years to get 30 million in revenue. Yeah, exactly. It produces no articles. Yeah, exactly. You're right. But you raise 30 million, meaning you give away most of the company. And that's like every headline. So I'm going to go back to what I said before, which is why are you raising money?

Right. How much do you actually need to raise? Yeah. Make sure that you always maintain a controlling interest, that no one can fire you ever. I've seen founders get fired from their own companies that they founded many times. That is so terrifying. There's this one founder I'm thinking of in particular.

She was a female founder, mission driven. Her numbers were better than her primary competition, which was a big funded company and like a huge corporation. And she did better numbers than them. Right. Her investors were putting huge pressure on her. They wouldn't let her spend money on things that were good for the company.

Right. They wanted to run a little too lean. And they kept putting pressure on her and they eventually fired her. Stop it. Yeah. That makes me want to cry for her. Oh, my God. Oh, yeah. Yeah. We need like a female boot camp, female founded boot camp from Simon Sinek. I mean, like literally. I'm a huge fan of female founders.

Because you're mission driven. And I feel like there's a... Females are better investors because we're long term. We're not impulsive. And I don't know. I don't know if like when male investors get in on female founded businesses, they just think that they know all because they're all hyper growth. I've lost money on investments because there were founders that I love them so much and I invested in them and the business didn't work.

And they came to me and they're like, I'm so sorry. I don't think this is going to work. And I say to them every single time, I'm like, I'd never invest more money than I can afford to lose. Rule number one. Right. I understand it's a bit of a gamble. I know what investing is. I believed in you. It didn't work out.

You don't owe me anything. And when they would call me for advice, I'd be like, here's my advice, but the decision is yours. If you don't follow my advice, that's fine. It's your business. And I'll always tell you what I think, but then you have to make your own decision. I'll never force you to make a decision, even if I have a vested interest in you making one decision versus another.

Because I'm investing in you and the idea. And full circle back to you asked what encouraged my confidence from season one as in the past year. One of the biggest contributors to my confidence has been being a CEO and being forced to make decisions quickly. Like I don't have time to ask a million people what should I do if my back's against a wall and I have to make a decision.

And I think that just being like making a decision, realizing that it goes correctly and right and like patting myself on the back and having gratitude and like, reflecting on my wins as well, instead of just constantly looking forward at the next thing, next thing, next thing has really helped my confidence.

I want to go back to something that you said before about I can't do this. Yeah. I think what we do is we start making our doubts our identity, right? And simple grammar changes can help. Yeah. Right. I can't do this becomes this is really difficult. Right. Yes. Right? How's building business? It's really difficult.

Yeah. And you can go to bed at night going, this is the hardest thing I've ever done. Yeah. That's fine. I can't do this. Not acceptable. Not acceptable because that's a limiting belief. It is. Instead of saying, I suck at this thing, today was a bad day. Yeah. You know? Or I have a lot to learn. Just simply making things, events or behaviors or small things I have found for me has helped.

And I learned the hard way. Yeah. Well, it's so much easier to be pulled down from a pedestal than to like pull someone up. Do you know what I mean? Like it's so easy to listen to people cutting you down and believe them and fall into the trap of saying, I just can't do this. there was this guy that would write in to us and say, you're a hypocrite.

I read your latest blog. You're such a hypocrite. You're an idiot. And we would like have a meeting about it and be like, how should we respond? And then somebody from my team would respond. He goes, oh, and Simon's too good to respond himself. And like, you're such a hypocrite, you know? Right. And so then we'd like have another meeting and be like, okay, should I call him?

And then I'd call and be like, Hey, and I'd talk him and explain my point of view. It was like, oh, I see you're, you're okay. You're not a hypocrite. Okay. Okay. I'm like, oh, okay, good. And then like six weeks later, I'd post something. He's like, you're a hypocrite. You're an idiot. Yeah. And we go through the whole cycle again.

And it occurred to me that I was investing so much time and energy with this one guy who was saying horrible things because I was so worried that he misunderstood me and that I wanted to correct the record. And I was ignoring him. Yeah. All of the people like, thank you. This helped me. This work has helped me build a business.

This work has helped me, you know, find confidence. And I was ignoring all of those people while having meetings about the others. I literally just said, why don't I take all the same amount of time? Yeah. And why don't I give it to the people who are supportive? Yeah. And I'm just going to ignore the negative ones.

Yeah. And so literally we would just do random phone calls and be like, hey, I saw your post about the work is helping you. I just wanted to call and say thanks. Yeah. Yeah. And so one of the things that helped my work grow was I said thank you to the people who believed in me. Wow, I love that. And started ignoring the people who didn't believe in me.

And you recognize that there's way more people who believe in you than there are that don't. Why is that that we only pay attention to the negative? Because it hurts. Yeah. Because it hurts. We love to complain. It's why is it like, is it a dopamine hit or something? I don't know. I think we have the sense of justice, I think.

Yeah. Yeah. I don't know. I don't know what it is. Or we expect things to go right and well. And so if things are going correctly, then like you don't notice when you're healthy, your health. And then if something happens or you have a health scare, then all you wish for is your health. Nothing else matters.

You know what I mean? It's true. We screw things up as a company all the time. Of course. And if somebody's angry, we'll do our best to put it right. Yeah. And but I want people to give me feedback so that we can make it right for other people, even if I can't make it right for you. Yes, I actually have been meaning to call you about like separately because I love receiving feedback because I love to grow and learn and whatever.

One thing that I know I need to work on immediately before I hire is giving feedback. I don't know if I'm just such an empath. I don't want anyone to think I'm mad at them, but especially like young workers who are coming on who just don't get the vision or they're just like time and again messing up.

I find myself just, let me just go in and fix it and let me just do it. And it's quicker and easier. I don't have to have a conversation. I like struggle with giving feedback so hard. Yeah. Yeah. But it's like worse for them. It's mean to give feedback. But sometimes... No, there's difference to something.

It's mean to not give feedback. Sorry. There's difference between nice and kind. Yeah. Right? It's nice to tell people they're doing a great job all the time. Right. But is it kind? Yeah. Not kind. Right? But it is kind to be like, hey, bud... Yeah. Someone else is going to fire you. This is not good.

Yeah. Right? Now, it doesn't feel nice, but it's definitely kind. Yeah. And so feedback is kind. Yeah. Now, the mistake that most people make with feedback is we tend to give feedback the way we like to receive it. but that's not necessarily the way others like to receive it interesting so the hard part about giving feedback is learning how somebody else can receive feedback because it's you feel like you're like what gave the feedback check the box done did the feedback yep but did they hear the feedback right were they able to process and internalize the feedback that's a different conversation right so learning how to adapt the way you give feedback so that somebody is can hear the feedback and

I love that. Some people like it. Just tell me. Just tell me. Yeah. Tell me blunt. Like me. Yeah. Please don't give me a feedback sandwich. Right. Don't tell me the nice thing that's really generic. And then like the really specific thing that you hate. And the really generic nice thing. The classic sandwich.

Just please stop. Just tell me what you need to know. What can I fix? Like what is it? You know? But some people need that. Some people want a feedback sandwich. Yeah. Do you have feedback sessions with your team like once a month, once a quarter? The answer is we should. We are inconsistent. We know we need to get better at it, but we are getting better at scheduling coaching calls.

Coaching calls. And these are private opportunities for feedback, for growth and feedback. We've also developed a culture of where people are very comfortable receiving criticism publicly. Yeah. How did you develop that? So it's a story I tell very often and I'm happy to keep talking about it because it's the most wonderful, powerful, easy to implement thing in the world.

I learned it from the Air Force. It's called Spears. So if somebody works on a presentation for Mary and Pip, they might work two weeks to put their PowerPoint together and then they come to the big meeting and they give their PowerPoint. At the end of the PowerPoint, they go, huh? What do you think?

Pretty good, right? Yeah. And you can't release anything mean. And if you point out an issue with the PowerPoint or one of the details or one of the ideas, they get defensive or they get upset, whatever it is, right? Because you're criticizing their work. Yeah. The Air Force was different. Same scenario.

Somebody put together their PowerPoint, spent two weeks putting it together. Yeah. They show up at the big presentation. I'm in the briefing. I'm in the room. And at the end of the presentation, the person who presents says, Spears? And they basically said, here's my presentation. Throw Spears at it to help me make it better.

I love that. And so we implemented Spears here. So now it's very common. It's so good. It's very common at our company when anybody says, hey, I've got an idea. And they'll present their idea. And they go, Spears? Or somebody will be like, I got a Spear for you. And the people like bring it on. Very easy to implement.

And what we've developed is this culture where basically criticizing somebody's work is now recognized as it's not like I think I'm smarter or you're not smart. It's that I had some ideas that can make the work better because we're all in this together. Right. And so we throw spears all the time. That's amazing.

Every presentation gets spears. People start saying things like... So, okay, this is going to need some spears, but like... Let me know. Yeah, yeah, yeah. And somebody will be like, it's not really a spear, but I've got a toothpick, you know? Oh my gosh, love! And it's, yeah, it's just part of the culture now.

And did you, like, from when you implemented spears, from before to when you implemented it to now... Yeah. I want to know what you saw in like efficiency in the company, but also did anyone leave? Like, could anyone not take that? No, no, no. So before we were pretty traditional, like, you know, hey, if it's not a problem, I have a few notes.

You did amazing work, but like this one little thing that I can make it better. If you're open to it, if you're open to it, you know? Yeah. And some people, you'd give them criticism. They're like, I can't do anything right. It's like, no, it's just had a little feedback. And the minute we implemented Spears, that kind of evaporated almost immediately.

And everybody's kind of like, am I wrong? I mean, that's right, right? That's amazing. No one's like a bully if everyone does it. And nobody's above a Spear. So I can present. And before, people would be afraid to give me feedback. And now... Somebody would be like, I got a spear and I go, bring it on.

So I'm welcoming of the spears too. That's incredible. Okay. Well, Mary and Pip team, if you're listening, we're implementing spears. I'm getting like such a bootcamp from on like my founder journey, which is so awesome. Like I want this type of advice. It's just hard to listen to my own intuition as well sometimes.

And I think over the past year, as I've built my confidence... as I've made those tweaks to your point, someone on my team was like, we're so fucked the other day. And it was like a minor inconvenience. And she said, we're so fucked. And I was like, please don't ever say that again because that creates a fight or flight mode in my body.

Or for the people sitting next to you. Or for the people sitting next to you. And it just immediately makes you think that there's no solution. Yeah. So instead of we're so fucked, like- What's step one? And that's what I love about being a founder is like you can take steps to find the right answer and it's problem solving.

And problem solving is so fun. It's like what we're made to do. And I think that's one of the biggest responsibilities of founders or any leader, quite frankly, or actually anybody on a team, which is correct the language. Listen for the language that creates false narratives, creates limiting beliefs, and simply interrupt the language.

Yeah. And that takes a certain level of consciousness. And it makes people smile. Yeah. Like, oh my God, we're fucked. No, this is just an inconvenience. Yeah. Like this will just be difficult for about a month. Right. And you know what also helps with that is gratitude practice. It puts things into perspective.

I think that's true. We're so fucked. But then I was like, at least we're working for ourselves and not on Wall Street right now. And we can make the decision to make the change and do this. That's right. And it's like, oh my God, you're right. Like we're in sunny California. We can go on a walk and figure it out instead of like sit at our desk.

So gratitude of the situation can also put things into perspective too. I think that's right. I mean, like optimism is quite literally a strategy. Like it is. Yeah, I think gratitude's the strategy. Yeah. I think gratitude's the strategy. And perspective, right? I think what gratitude does is puts everything in perspective.

Yes, exactly. You have so many episodes, like so many interesting people on your show, which is why I was so honored. Of course, before Simon, you know I was fighting the, what value could I add to his podcast? Really? You know, because there's always that. Do you want to know why I invited you? Tell me why, please.

Why do you think I invited you? I think you invited me because I invited you on yours and we're friends and you're giving me a chance. So you think I'm doing this like, well, she invited me on hers. I should probably have her on my quid pro quo. Yeah, quid pro. No, I've been on other people's podcasts that never came on mine.

Honestly, like I think you were just like my friend and you were like, I'll give her a chance to like talk about her story, marry and pep. But I still fight every single day that imposter syndrome of like. well, I don't even have a company yet, or I'm not an expert or a doctor or a scientist, or I wasn't in jail and like, didn't have all of these cool.

You can't be. I could. Yeah, I know. It's not too late. It's not too late. I'm only 27. I have plenty of years to be arrested, but it's always like, no matter every podcast, recently I was on like a Forbes podcast and I was like, why are you inviting me? And they were like, we want to hear from you. Like, so it's a constant battle with myself.

Yeah. of even like, I shouldn't even be asking myself that, but of course it comes up. So why'd you invite me? Tell me. Stroke my ego. When I go on a stage, I never tell people what my credentials are or how many books I've written. I tell them nothing. I just launch into my content, right? And the reason is, I don't have to prove that I'm worth being on that stage because somebody else has already made that decision.

So either they're an idiot and they made a huge mistake, which is always possible, or... They know what they're doing. Wow. And so I have to just trust that the person who invited me has a reason for me being there. So I don't have to prove to the audience that I have value on the stage. So true. Somebody else has already done that work.

And if you have an issue, don't take it up with me. Right. I didn't invite myself. Yeah. If you don't like me, if you think I'm an idiot, take it up with them. Right. Right? Oh, my gosh. So that's number one, which is that I'm not accountable. Love. I'm not accountable whether you like me or not. That decision has been made by somebody else or whether I have value or not.

I do have accountability if you like me or not, but I don't have accountability if you just disagree. That's somebody else has made that decision. So number one, you have to trust that I've made the decision and so you don't have to worry about it. That's number one. Number two, the actual reason I wanted you to come on, it's because I think that you are the new breed of entrepreneur that I think people need to hear from.

I think we're all exhausted from hearing from traditionally men who talk about their fundraising and their this and their that and their valuations. And yet they can't speak with any kind of... Vulnerability. Well, that for sure. But they can't speak about what value they're trying to give to the world.

Right. At all. You have no desire to be on TV. You have no desire to be famous. And yet you recognize that being on TV and having some fame... gives you the ability to spread your message more efficiently. Correct, yeah. And the minute you made that connection, you realized, huh, I can leverage this for good.

Right. And the reason you're starting Mary and Pip is to teach people things that I wish I had Mary and Pip. Mm-hmm, you can. By the way, I plan on it. Yeah. Right, I plan on using Mary and Pip because even though I'm not in your demographic, I mean, you're psychographic. Yeah. It's an industry that makes me feel stupid.

And I know the importance of this stuff. And I wish somebody would talk to me like a human and not like a target. Yeah. You know? It's everyone's target. So you're a young entrepreneur and I want to see you succeed. I want people to benefit from your product. And I want more entrepreneurs to be like you.

And so I think you're a counterbalance to the traditional entrepreneurial, you know, sort of story. Yeah. And that's one of the reasons I sort of, if I put any pressure on you, it's to do things the way you think they need to be done. Like, and do you need big investors? And do you need the famous this and the famous that?

Do you need to grow at the speed of light? You know? Right. So my question is, is why are you growing at the speed of light? Right. What benefit does that have to your team, to the people you're serving? Yeah. You know, what I'd rather you do is build a really, really, really good product. And if it's a little slower than you originally intended.

Yeah. As long as it's a really, really good product. And that's what I've learned. Like every stage of my product is not perfect. Yeah. It's constantly a state of improvement. The minute we launch something, we're like, this is amazing. And a week later, we're like, this really is not amazing. Yeah. Same.

You know, and then we fix it and we're like, this is amazing. Yeah. And then a week later, we're like, this is not amazing. And you just realize like there's always more to do. Right. And I'm so grateful to everybody who signs up for leaderful. Yeah. Because like you think it's great. And I was like, oh, I've got so much work to do.

Right. Of course. And the cool thing is I invite people to come on a journey with me. It's going to get better and better and better and better and better. Why? Because that's how I'm driven. And I just think you're very important to the entrepreneurial world. That's why I wanted you on. Thank you so much.

I feel like I'm learning more and more, especially with just putting... every mistake and like putting my whole self out there on season two, which is much, I feel like I've been much more vulnerable in season two. If nothing else, I just want to communicate to future young entrepreneurial women that you can do everything that you want to do.

And also like, even if you don't want to be famous and you don't want all of that world, like there is leverage that can be had to do good. You know, I have this platform now and we went to the Arctic for women's health and we can do all these things because we have this platform. So yeah. I appreciate you seeing that.

And sometimes I just overlook that. And I'm like, oh, well, why am I here? And you're like, you're here because you don't know why you're here. And a lot of people don't know why they're in the rooms that they're in. I also think you're a good counterbalance to the influencer culture, which is young people want to be influencers.

Do you know the term selling out? Yeah, of course. Like, oh my God, he's such a sellout. Yeah, yeah, yeah, yeah. Well, you know, more and more people your generation, when I say sellout, they don't know what it means. Really? And when I explain it, well, it means that somebody like starts cashing in on what they've built with brands that may or may not align with their values, but they're doing it for the cash.

Yeah. And then people go... Yeah. Of course. Like the term selling out is not pejorative. Right. It's actually seen as the model. Yeah, the goal. Influencer culture is get as many followers as possible and then cash out. Yeah. Then get as many sponsors and micro sponsors as you can get. Make it last as long as you can.

Yeah. And then... Sayonara. Yeah. And like the whole influencer model, the whole influencer model is gain popularity in any way. Yeah. And make money. Whatever it takes. And then monetize. Like that children know what the term monetize means. It's so sad. Then monetize that, those followers monetize that fame.

Yes. And what I like about you, you're the reason I say you're the counterbalance to the influencer culture is you have the followers, you've got the fame, you've got the TV show on Hulu, and you're leveraging it for service and for good. Well, my goal with Mary and Pip is to give people that financial stability so that they can choose brands that they align with.

Because freelancers, I understand why they're selling out. Like, it is stressful not having a steady paycheck come in. And that's why I started it originally for freelancers. Now it's pivoted more to anyone with kind of money anxiety, which tends to be women. But... If you're not making a steady paycheck and you're forgetting to invoice and your income is different every single month, then you're just going to say yes to any brand.

This is such a good point. I never thought about that, which is sometimes people are forced to sell out because of the inconsistency of the income. When you say yes to things you know are wrong. Yes. Because I think a real sellout thinks that it's all good. Right. The reluctant sellout. Yes. Oh, I like that.

Yeah. Because there's sellouts and then there's the reluctant sellout. It's almost like. Because sellouts are sellouts. back against a wall that, yeah, sellouts are sellouts. There are still those. Those still exist. But I love this concept of the reluctant sellout. The reluctant sellout. Which is I have to, but I don't want to.

Of course. Because that means values alignment. Exactly. And we like people with values. We like people with values. So people with values who are reluctant sellout maybe, like Mary and Pip is for them to help with that money anxiety. Okay, I have a couple questions here. Okay, you left the corporate world and you left behind structure and routine and predictability to forge your own path as a founder and reality star.

How did you adjust to the identity shift? I think I'm still adjusting to the identity shift. I think when I was on Wall Street, I completely separated my influencer model identity to my Wall Street corporate identity. And since I left to be on a reality show, I go into boardrooms and they might not have watched the show, but they know about it.

And then I go to an influencer event with my sisters and they don't know that I'm a fintech founder. So when it's like, what do you do? I am starting to get better at saying, oh, I'm a founder. I'm a founder. I'm a founder. Because that's who I want to be known as. For a long time, if I was in a room with influencers or models, I'd say, oh, I'm a model or I'm talent or I'm on the show.

I wouldn't even mention Mary and Pip. Or if I was in a boardroom, I wouldn't even mention my distribution or love thy nader because I wanted to be taken seriously as a founder. Yeah. And now I'm realizing the strength and being all of it. And who do I want to be? And who do I want to show up as? And recently for me, my confidence that has been founder.

So if someone asked me what I do, I lead with, I'm a founder. Can I add? Please add. Always add. You're a door opener. I'm a door opener. I'm an inviter. I'm an inviter. What do you do? I'm a door opener. I'm an inviter. What does that mean? Well, there are many ways in which I get to invite people in to discover that they're capable of more than they thought.

One of the ways I do it is as a founder. I love that. One is as a podcaster. One is as a friend. So if you're at an influencer event, you'd say, one of the ways I do that is as an influencer, which is why I'm here. Which is why I'm here. Or if you're in a boardroom, say, one of the ways I do it is as a founder, which is why I'm here.

I love that. You don't want to define yourself by something you do because... 20 years from now, you will have founded something 20 years ago. And you still want to be a founder 20 years on? Probably not. And founder, I feel like it's a little diluted now. It's current, right? Yeah. So from this day on to the day you die.

I'm an inviter. You invite people in, make them feel safe so that they can discover what they're capable of. Totally. Whether you call that an inviter or a door opener, there's many ways you can say it. Yeah. When somebody says, so what brings you here? I'm like, oh, I'm a door opener. And they go, what?

This is how I show up in the world. And one of the ways I do it is I founded this fintech company called Mary and Pip, which is why I'm at this event. And hopefully any company I found in the future is to invite people in. It always will be if it's true to you. Yeah. No, that makes total sense. Well, I'm an inviter.

Why am I here? I'm inviting people into my life to learn about. Gain confidence. Yes. To learn how to gain confidence as a young girl. Mary Helen Nader, you're nothing but joy and fun. Likewise, Simon. As always, thanks for listening. And if you liked this episode, please do remember to subscribe to A Bit of Optimism wherever you enjoy listening to podcasts.

And remember, new episodes drop every Tuesday. A Bit of Optimism is a production of The Optimism Company, lovingly produced by our team, Lindsay Garbenius, Phoebe Bradford, and Devin Johnson. And if you want more cool stuff or just to find out what I'm up to, visit simonsynic.com. Until next time, take care of yourself, take care of each other.

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