In short
Trusting yourself amid constant opinions (especially in fame, entrepreneurship, and fundraising). Mary Holland Nader discusses using vulnerability on Love Thy Nader, building financial confidence through plain-language education, and choosing purpose over image. David Robinson (SAP Customer Success) adds that listening to customers is key to explaining technology in their language.
Guests
Mary Holland Nader, Wall Street–trained finance professional and co-founder of Mary and Pip (an app/podcast initiative for “financial wellness” and demystifying money). She stars with her sisters on Hulu’s Love Thy Nader; her sister Brooks drove the fame (including Dancing with the Stars). David Robinson is head of SAP Customer Success in North America.
Key claims
Fame can be leveraged for good; jargon makes people feel “dumb,” so finance should be taught simply; negative opinions are often rooted in others’ insecurity; founders should trust intuition/values and avoid building solely for an exit; investors’ incentives create pressure; controlling influence matters when raising money.
Notable examples
Mary’s “idiot” label from finance jargon; Love Thy Nader sizzle reel and her rapid decision to quit her Wall Street job; “spears” feedback culture from the Air Force; “I can’t do this” reframed as “this is really difficult.”
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOSponsor Introduction
2:29 to 2:45
Introduction to the sponsor SAP, highlighting their focus on understanding people.
“It turns out if you don't understand people, you don't understand business.”
The Journey of Fame and Finance
2:45 to 14:00
Explore Mary Holland Nader's unique journey from finance to reality TV stardom.
“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.”
The Basics of Financial Understanding
14:00 to 17:57
Learn why basic financial literacy is crucial for personal health and well-being.
“is they're high on themselves and they make the rest of us feel stupid.”
The Basics of Financial Understanding
18:02 to 19:02
Learn why basic financial literacy is crucial for personal health and well-being.
“SAP's David Robinson has learned that the best way to make customers feel supported is to be curious and listen.”
Building Confidence and Trusting Yourself
19:02 to 28:00
Explore how to overcome insecurities and trust your intuition in business.
“It's the old sales technique of sell this pen to somebody.”
Trusting Your Gut: Lessons from Experience
28:00 to 29:00
Learn about the importance of trusting your instincts over external opinions.
“Like Steve Jobs was purpose-driven, never gave out dividends, didn't care.”
Understanding Mentorship in Business
29:00 to 30:20
Explore the differences between mentors and champions in a business context.
“Because we were given our intuition as like old time homo sapiens for a reason.”
Defining Your Business Goals
30:20 to 31:20
Discuss the significance of having a clear purpose beyond financial exits.
“If you work for a company, that might be a senior executive.”
The Cost of Raising Money and Growth
31:20 to 34:10
Examine the implications of raising funds versus organic growth.
“And that stuck with me before I even knew you from the very beginning when anyone asked.”
Feedback and Its Importance in Leadership
34:10 to 36:10
Understand the value of giving and receiving feedback for personal and team growth.
“But you raise 30 million, meaning you give away most of the company.”
Show all 16 chapters
Cultivating a Feedback Culture
36:10 to 42:00
Learn how to create an environment where constructive criticism is welcomed.
“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.”
Creating a Culture of Feedback
42:01 to 44:02
Learn how implementing a culture of constructive criticism through 'spears' can enhance teamwork and creativity.
“And these are private opportunities for feedback.”
Transforming Language in Leadership
44:03 to 46:32
Understand the impact of language on team dynamics and the importance of adopting a problem-solving mindset.
“I want to know what you saw in like efficiency in the company, but also did anyone leave?”
The New Breed of Entrepreneurs
46:33 to 50:42
Explore the evolving identity of entrepreneurs and the importance of authenticity over traditional success metrics.
“I mean, like optimism is quite literally a strategy.”
Countering Influencer Culture
50:43 to 56:01
Discover how to navigate the pressures of influencer culture while maintaining values and purpose in business.
“What benefit does that have to your team, to the people you're serving?”
Inviting Others to Discover Their Potential
56:01 to 57:25
Learn how to be an inviter and encourage others to realize their capabilities.
“Whether you call that an inviter or a door opener, there's many ways you can say it.”
Transcript
Automatic transcript. May contain errors.0:00Mary Holland Nader: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.
0:10Dan Cheshire:Correct. Yeah.
0:11Mary Holland Nader:And the minute you made that connection, you realized, huh, I can leverage this for good.
0:16Dan Cheshire: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? 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.
0:35Mary Holland Nader: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?
1:21Mary Holland Nader: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.
2:00Mary Holland Nader: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.
2:25Mary Holland Nader:This episode is proudly brought to you by SAP. 100 % of employees are people. 100 % of customers 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.
2:59Dan Cheshire:Stop. On my way.
3:03Mary Holland Nader:and the thing that i find so fun about you and your family so i want to understand so you're
3:09Dan Cheshire:from the bayou in louisiana down under like yep not like from new orleans or something no from the bayou so we're we're we grew up in baton rouge but we're from a small town called maringuan which i can't even figure out how to spell no it's it's basically it means mosquito in cajun french so not even french not even yeah cajun french okay because it's the air is so thick there's so many mosquitoes there you walk outside and you're just eaten I always got the most bites because I was the sweetest sister of course of course so Maringuin 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
3:53Mary Holland Nader:overalls and barefoot and like with a piece of straw in your mouth honestly yeah like it was
3:58Dan Cheshire:pretty like stereotypical like simon we had a pet alligator i'm not even kidding gary the gator yeah i'm not even kidding there's pictures of us he we named him gary was he just like in your
4:08Mary Holland Nader:backyard so when we were in mary or is he actually your pet we named him gary so he was our pet we
4:13Dan Cheshire: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 it's a nicer word for swamp it's a nicer word for swamp but it's a in a ditch a swamp in a ditch basically and we had a bayou in our backyard in maringwen not when we we grew up in baton rouge like in high school and stuff so this was in maringwen 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 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
5:07Mary Holland Nader:all true all true okay so you're so you're from the bayou the backwaters of louisiana yep and four sisters.
5:15Dan Cheshire:Three, four, including me.
5:18Mary Holland Nader:Right. Four girls. Four girls. And my understanding is that Brooks, who's the oldest.
5:24Dan Cheshire:Correct.
5:25Mary Holland Nader:That Brooks decided when she was young, my memory serves, that she wanted to be famous.
5:32Dan Cheshire:Absolutely. Okay.
5:34Mary Holland Nader:So the reason you have a TV show is because Brooks as a young girl decided you would.
5:40Dan Cheshire: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 yeah but there was a story that i will never forget we were such a tight-knit family and we 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 ourselves we have to pass the ball back and we would pass the ball around the conversation ball
6:10Mary Holland Nader:and make sure that you're always passing literally or metaphorically when we were together sometimes
6:14Dan Cheshire: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 going to be famous. I'm going to drive a pink limousine. Like there's going to be paparazzi. She's like eight years old at this point, talking, talking, talking about how famous she's going to be.
6:49Dan Cheshire: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.
7:07Mary Holland Nader:I mean, she engineered this.
7:08Dan Cheshire:She literally engineered. She is the definition of manifesting.
7:12Mary Holland Nader: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.
7:21Dan Cheshire:Yes.
7:21Mary Holland Nader:Okay. You're good at math.
7:24Dan Cheshire:Yeah, I guess.
7:26Mary Holland Nader:Well, I mean, you're in finance.
7:27Dan Cheshire:I'm in finance. Yeah.
7:28Mary Holland Nader:You worked for a big bank in finance.
7:29Dan Cheshire: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.
8:06Dan Cheshire: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.
8:16Mary Holland Nader: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.
8:24Dan Cheshire:Yep.
8:25Mary Holland Nader:What did she pitch?
Read the full transcript
8:26Dan Cheshire: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 like just a really fun Long Island, like 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 we were just being out we were like we're from louisiana we're making our way in new york and he was like you guys need a show and we were like what's it why are you saying we need a show and he turns out he's jimmy kimmel's agent baby just weird look weird crazy luck so he starts kind of like quasi representing us and this is before i was still at doish 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 they 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 could have they could have but there's plenty of plenty of drama there's plenty of brother sister shows where one with
10:50Mary Holland Nader:one who didn't want to do it. And you just think there's three sisters and they talk about the other sister.
10:54Dan Cheshire:That's true. I guess we don't even have that vocabulary in our sister language. Like it's all or nothing with us.
11:01Mary Holland Nader:Did you feel peer pressure?
11:03Dan Cheshire: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. Cause my sisters can't do it without me.
11:10Mary Holland Nader:But you don't have a desire to be famous or be on television.
11:13Dan Cheshire: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
11:57Mary Holland Nader: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're they don't necessarily dramatic dramatic well they don't usually go together right like you know you're not even in a category.
12:13Dan Cheshire: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.
12:32Mary Holland Nader:Because you don't care about the fame and the television.
12:35Dan Cheshire:Yeah.
12:36Mary Holland Nader:I mean, you're an entrepreneur. You haven't quite left finance. you started a business.
12:41Dan Cheshire:Correct.
12:42Mary Holland Nader:Mary and Pip. And the goal of Mary and Pip is...
12:46Dan Cheshire:To basically create financial independence for women.
12:49Mary Holland Nader: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.
12:56Dan Cheshire:Exactly.
12:57Mary Holland Nader: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, 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.
13:24Dan Cheshire:Yeah.
13:24Mary Holland Nader:You know, they speak to me in jargon.
13:26Dan Cheshire:Totally.
13:26Mary Holland Nader: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.
13:31Dan Cheshire:Yeah.
13:31Mary Holland Nader:And when I ask questions, they roll their eyes or they talk to me like an idiot. and so I just choose not to work with them. 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, and basic, basic stuff. Like if everybody invested a little bit and understood compound interest even, which now I understand, I wish I understood it when I was 23 years old. 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.
14:04Mary Holland Nader:And so some of us do it because we fear that they know more than us so we better do this.
14:10Dan Cheshire:Correct.
14:10Mary Holland Nader:So we get taken advantage of.
14:12Dan Cheshire:Yeah.
14:12Mary Holland Nader:Or we just don't do it because we feel dumb.
14:14Dan Cheshire:Yeah.
14:15Mary Holland Nader: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.
14:24Dan Cheshire:Right.
14:24Mary Holland Nader:You're not starting a business to make people, you know, day trading and hardcore investors. Exactly. This is basic, basic stuff.
14:30Dan Cheshire:The most basic. And let me ask you, like 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.
14:54Mary Holland Nader:I think money is the number one cause of divorce. Yeah. Oh, it is.
14:58Dan Cheshire:Yeah.
14:58Mary Holland Nader:Financial stress. Totally. You're right.
15:00Dan Cheshire:And people who live longer have lower stress. Correct.
15:03Mary Holland Nader:It's not that they just eat vegetables. 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.
15:14Dan Cheshire:Exactly.
15:15Mary Holland Nader: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.
15:25Dan Cheshire:You get it.
15:25Mary Holland Nader:You find yourself doing this thing. I'm sure at some point you're like, what am I doing?
15:30Dan Cheshire:Yeah. There's a lot of points like that.
15:33Mary Holland Nader: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.
15:43Dan Cheshire:Sure. You know. Yeah.
15:44Mary Holland Nader:I watched some of the show.
15:46Dan Cheshire:Which one? Tell me. I didn't take you for a reality guy.
15:49Mary Holland Nader:I'm not. And I watched a part of one of your episodes.
15:53Dan Cheshire:Oh, stop it. No, I don't even want to know which one. Was it my pitch?
15:57Mary Holland Nader:Yeah.
15:57Dan Cheshire: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.
16:07Mary Holland Nader:You actually have a license to practice finance. I do. Like you pass tests.
16:10Dan Cheshire: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 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.
16:43Dan Cheshire: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 going to be. I like Love Thine Aider 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 Thine Aider showed how dumb I was in that pitch because like I literally had no idea what I was saying.
17:14Dan Cheshire: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.
17:55Mary Holland Nader: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.
18:38Mary Holland Nader: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 challenge is 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.
19:07Mary Holland Nader:It's got ink in it. And you can, you know, write an essay and you can. But nobody ever says, do you ever record things, write things down? Like they don't ask any questions. They don't listen about somebody's life to help understand how this pen fits into your life. They start talking about the technology of the pen. Sure. You have to really be listening all the time.
19:29Mary Holland Nader:Where did you get this confidence to be okay looking dumb?
19:33Dan Cheshire: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 oh 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
20:00Mary Holland Nader:obviously this is the person who manifests her entire life exactly we should pay attention the
20:04Dan Cheshire:power of mindset's insane and then also like no one's gonna 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.
20:38Dan Cheshire: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 going to leave here and think of every word I said on this podcast and be like, could that be misconstrued?
21:00Mary Holland Nader:By the way, I do it too. 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? And I started, well, I'm really interested in British history right now. And I sort of 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. But I was like, oh, do you really want to hear this?
21:26Dan Cheshire:So great.
21:27Mary Holland Nader:So I go through that as well. Like, you know, things that make me fascinated.
21:30Dan Cheshire:Right.
21:31Mary Holland Nader:About something. Because you're like, no one will care. Because I'm in my own head. Like, nobody wants to know about. But we do. You know, the OG online dating.
21:40Dan Cheshire:OG, which was the most fascinating thing ever, by the way. You'll have to go and listen to. Listen to Growing Interest.
21:45Mary Holland Nader: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.
21:53Dan Cheshire:Profile.
21:54Mary Holland Nader:Profile. That's right.
21:55Dan Cheshire:But, you know, 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 like what are your growing interests correct you should and after you left he was like that is an example of why we have to include that segment like that was the most clippable entertaining part of the entire interview and i was like really like not
22:19Mary Holland Nader:all of my prepared questions other parts no there were other that were amazing and he really was
22:25Dan Cheshire:talking about how it showed your personal interest in 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 when you were 27 when you're dying like and even if they do get hung up on something you said or they say well you looked dumb in that you know yeah it's usually
22:50Mary Holland Nader: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 you know we've definitely all gone to a concert and be like that sucked yeah that person was terrible true you know people definitely have opinions about you and your sisters you know and even if they're fans of the show yeah 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.
23:22Mary Holland Nader:You know?
23:22Dan Cheshire: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 like recognized as a founder. I'm starting Mary and Pip to give everyone financial independence that I once hoped for.
23:38Mary Holland Nader:Purpose driven, yeah.
23:39Dan Cheshire: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 encouraged 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.
24:15Dan Cheshire: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 be 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 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 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 because I'm not usually not about all that it's like a
25:36Mary Holland Nader:You know, a little kitten hanging. Yeah, exactly.
25:38Dan Cheshire: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. Yeah. 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.
25:56Mary Holland Nader: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. I got 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. Totally. Very, very, very purpose driven. You know, Carissa Bodner, you know, from Thrive Cosmetics. Sarah Blakely, obviously from Spanx.
26:28Mary Holland Nader:Very purpose driven, you know. And there's a list of these female finders who they're not as famous.
26:32Dan Cheshire:Yeah.
26:32Mary Holland Nader:And yet their businesses tend to do very well.
26:36Dan Cheshire:Yeah.
26:36Mary Holland Nader: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.
26:44Dan Cheshire:Really?
26:45Mary Holland Nader:Yep.
26:45Dan Cheshire:I didn't realize they were both bootstrapped.
26:47Mary Holland Nader:Sarah Blakely bootstrapped her company and owned 100 % of the stock when she sold it.
26:51Dan Cheshire:Holy shit. That's insane.
26:53Mary Holland Nader:Yeah, I think Chris is the same.
26:55Dan Cheshire:Oh my gosh. Well, and you know, the biggest consumer in the US and the biggest spenders are women.
26:59Mary Holland Nader:I get this question 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?
27:11Dan Cheshire:Yeah.
27:11Mary Holland Nader:What do I do? And I always give them the same answer. I was like, you took the money. It's like.
27:16Dan Cheshire:Right.
27:16Mary Holland Nader: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?
27:24Dan Cheshire:Right.
27:24Mary Holland Nader:Like was it your ego that you took that money?
27:26Dan Cheshire:Yeah.
27:26Mary Holland Nader:And everybody says, I'm like, careful, careful, because investors, their business model.
27:32Dan Cheshire:Right. They have to sell you for their business model to work.
27:36Mary Holland Nader:So between three to five, five to seven years, you're going to start having pressure. And they're like, no, no, no, my guy's different. I'm like, no, it's not the short termism. And I think women tend to be more long term focused automatically. The challenge you'll have is an 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, didn't care. And he told investors, if you like me, invest in me. If you don't like me, don't invest in me.
28:09Mary Holland Nader:Like, what do you want from me?
28:10Dan Cheshire:That's the greatest, yeah.
28:11Mary Holland Nader:And like that takes, you know, balls of steel.
28:14Dan Cheshire:Yeah, I know.
28:15Mary Holland Nader: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,
28:41Dan Cheshire:I wish I trusted my gut.
28:42Mary Holland Nader: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.
28:55Dan Cheshire:Yeah.
28:56Mary Holland Nader:This aligns with your why.
28:57Dan Cheshire:Yeah. And if it doesn't, find a different way. Is it the same as intuition? Because. Yeah, sure. Right? Because we were given our intuition as like old time homo sapiens for a reason. Correct.
29:09Mary Holland Nader: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.
29:25Dan Cheshire: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.
29:34Mary Holland Nader:It's a cultural thing.
29:35Dan Cheshire: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. 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.
30:06Mary Holland Nader:And other people operating.
30:07Dan Cheshire:For them.
30:08Mary Holland Nader:Unless it's a mentor or a friend with no interest.
30:11Dan Cheshire:Right.
30:12Mary Holland Nader:And that's why I think mentors should be outside of your business. I like that. Like the difference between a mentor and a champion.
30:18Dan Cheshire:Yeah. A champion is somebody who's pushing you, helping you, but they're either in your company.
30:23Mary Holland Nader:Right. If you work for a company, 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.
30:35Dan Cheshire:Yeah.
30:35Mary Holland Nader:They're not investors. They have no financial interest. They don't know your boss.
30:38Dan Cheshire:Right.
30:38Mary Holland Nader: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.
30:44Dan Cheshire:Yeah.
30:45Mary Holland Nader:That's it. That's a real mentor.
30:47Dan Cheshire:Yeah.
30:47Mary Holland Nader:I think you're right. I think we do all these things.
30:51Dan Cheshire:Yeah, I know. And I think we're having this conversation at the perfect time because me and my business are, 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.
31:21Dan Cheshire: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.
31:32Mary Holland Nader:By the way, if you say that, it turns investors off.
31:34Dan Cheshire:Yes, exactly, which is good.
31:36Mary Holland Nader:You want to turn off the investors
31:37Dan Cheshire:who only want the exit.
31:40Mary Holland Nader:That's so true. Mark Zuckerberg is still working for the company he founded. Michael Dell is still working for the company he founded. you know sergey bryn and larry page who founded google yeah 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
31:55Dan Cheshire: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
32:05Mary Holland Nader: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 raise money? Do you actually need outside money? So I think of everything in terms of cost.
32:18Dan Cheshire:Okay.
32:19Mary Holland Nader:Right. By raising money.
32:20Dan Cheshire:Yeah.
32:20Mary Holland Nader:That means you get to build a business faster because you can, you can afford more staff and you can have three or four priorities at the same time.
32:31Dan Cheshire:Yeah.
32:32Mary Holland Nader: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.
32:47Dan Cheshire:Yeah.
32:47Mary Holland Nader:Not taking some of his money means the cost is I'm going to grow slower, but I don't have any outside influence. I just have to get better at prioritizing. I personally chose slower. Why are you raising money? Do you actually need it?
33:03Dan Cheshire:Right. I mean, I guess I could, like I'm raising money to hire more people,
33:08Mary Holland Nader:basically okay again how many people do you actually need i hate it when companies when founders say 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 oh 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 and they're big and slow yeah 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.
33:50Mary Holland Nader:And the answer is zero. Totally. Hypergrowth is good for the investors because that's their business model.
33:57Dan Cheshire: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.
34:08Mary Holland Nader:Took us 10 years to get 30 million in revenue. Yeah, exactly. Produces no articles. Yeah, exactly. You're right.
34:13Dan Cheshire:But you raise 30 million, meaning you give away most of the company. And that's like every headline.
34:19Mary Holland Nader:So I'm going to go back to what I said before, which is why are you raising money?
34:23Dan Cheshire:Right.
34:24Mary Holland Nader: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. Yeah. I've seen founders get fired from their own companies that they founded many times.
34:36Dan Cheshire:That is so terrifying.
34:37Mary Holland Nader: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.
35:01Dan Cheshire:Stop it. Yeah. That makes me want to cry for her. Oh my God. Oh yeah, yeah. We need like a female bootcamp, female founded bootcamp from Simon Sinek.
35:09Mary Holland Nader:I mean.
35:10Dan Cheshire:Like literally.
35:11Mary Holland Nader:I'm a huge fan of female founders.
35:13Dan Cheshire:Because you're mission driven. And I feel like there's, 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.
35:28Mary Holland Nader: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.
35:45Dan Cheshire:Right.
35:46Mary Holland Nader:I understand it's a bit of a gamble. Yeah. I know what investing is. Yeah. I believed in you.
35:51Dan Cheshire:Yeah.
35:52Mary Holland Nader:It didn't work out. You don't owe me anything.
35:55Dan Cheshire:Right.
35:56Mary Holland Nader:And when they would
35:56Dan Cheshire:call me for advice I'd be like here's my advice yeah but the decision is yours if you don't follow
36:00Mary Holland Nader:my advice that's fine it's your business yeah 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 totally because I'm investing in you totally and the idea and full
36:14Dan Cheshire: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.
36:51Mary Holland Nader:I want to go back to something that you said before about I can't do this.
36:54Dan Cheshire:Yeah.
36:55Mary Holland Nader:I think what we do is we start making our doubts our identity.
37:01Dan Cheshire:Right. And simple grammar changes can help. Yeah.
37:07Mary Holland Nader:Right. I can't do this becomes this is really difficult.
37:10Dan Cheshire:Yes.
37:11Mary Holland Nader: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.
37:17Dan Cheshire:Yeah.
37:17Mary Holland Nader:That's fine. I can't do this
37:20Dan Cheshire:not acceptable
37:21Mary Holland Nader:because that's a limiting belief instead of saying I suck at this today was a bad day 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
37:38Dan Cheshire:well it's so much easier to be pulled down from a pedestal than to pull someone up 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
37:52Mary Holland Nader:there was this guy that would write in uh to us and say you're a hypocrite I read your latest blog you're such a hypocrite you're an idiot you know 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. He was like, oh, I see. You're okay. You're not a hypocrite. Okay. I'm like, oh, phew.
38:23Mary Holland Nader:Okay, good. And then like six weeks later, I'd post something. He's like, you're a hypocrite. You're an idiot. Yeah. You know, and we'd go through the whole cycle again. And it occurred to me that I was investing so much time and energy with this one guy
38:35Dan Cheshire:who was saying horrible things
38:36Mary Holland Nader:because I was so worried that he misunderstood me and that I wanted to correct the record. And I was ignoring 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? And why don't I give it to the people who are supportive? And I'm just going to ignore the negative ones. And so literally, we would just do random phone calls and be like, hey, I saw your post about that the work is helping you.
39:06Mary Holland Nader:I just wanted to call and say thanks. And so one of the things that helped my work grow was I said, thank you to the people who believed in me 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 ours that
39:19Dan Cheshire:don't why is that that we only pay attention to the negative it hurts yeah because it hurts we love to complain it's why is it like is it a dopamine hit or something like i don't love i think that 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, if you have a health scare, then all you wish for is your health. Nothing else matters. You know what I mean? It's true.
39:49Mary Holland Nader:We screw things up as a company all the time.
39:51Dan Cheshire:Of course.
39:51Mary Holland Nader:And if somebody's angry, we'll do our best to put it right.
39:54Dan Cheshire:Yeah.
39:55Mary Holland Nader: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.
40:01Dan Cheshire: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, but it's like worse for them.
40:35Dan Cheshire:It's mean to give feedback, but sometimes
40:37Mary Holland Nader:No, there's difference to something.
40:38Dan Cheshire:It's mean to not give feedback, sorry.
40:40Mary Holland Nader:There's difference between nice and kind.
40:42Dan Cheshire:Yeah.
40:42Mary Holland Nader:Right? It's nice to tell people they're doing a great job all the time.
40:46Dan Cheshire:Right.
40:47Mary Holland Nader:But is it kind? Yeah, not kind. Right? But it is kind to be like, hey, bud.
40:52Dan Cheshire:Yeah.
40:53Mary Holland Nader:Someone else is going to fire you. This is not good. Yeah. Right? Now, it doesn't feel nice, but it's definitely kind.
40:58Dan Cheshire:Yeah.
40:59Mary Holland Nader:And so feedback is kind.
41:00Dan Cheshire:Yeah.
41:01Mary Holland Nader: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.
41:11Dan Cheshire:Interesting.
41:11Mary Holland Nader:And so the hard part about giving feedback is learning how somebody else can receive feedback. Because you feel like you're like, what, gave the feedback, checked the box, done, did the feedback. But did they hear the feedback? Were they able to process and internalize the feedback? That's a different conversation.
41:25Dan Cheshire:Right.
41:26Mary Holland Nader:So learning how to adapt the way you give feedback so that somebody can hear the feedback.
41:32Dan Cheshire:I love that.
41:32Mary Holland Nader:Some people like it, just tell me, just tell me. Yeah. Tell me blunt, like me.
41:36Dan Cheshire:Yeah.
41:36Mary Holland Nader:please don't give me a feedback sandwich. Don't tell me the nice thing that's really generic and then the really specific thing that you hate and the really generic nice thing. The classic sandwich. Please stop it. Just tell me what you need to know.
41:45Dan Cheshire:What can I fix? Like, what is it?
41:47Mary Holland Nader:You know? But some people need that. Some people want a feedback sandwich.
41:50Dan Cheshire:Yeah. Do you have feedback sessions with your team like once a month, once a quarter? The answer is we should.
41:57Mary Holland Nader:We are inconsistent. We know we need to get better at it. But we are getting better at scheduling coaching calls.
42:03Dan Cheshire:Coaching calls, okay.
42:04Mary Holland Nader:And these are private opportunities for feedback. for growth and feedback. Yeah. We've also developed a culture of where people are very comfortable receiving criticism publicly.
42:13Dan Cheshire:Yeah. How did you develop that?
42:15Mary Holland Nader: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 and at the end of the PowerPoint they go,
42:36Dan Cheshire:what do you think? Pretty good, right?
42:38Mary Holland Nader:And you can't really say 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. The Air Force was different. Same scenario. Somebody put together their PowerPoint, spent two weeks putting it together. 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 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 that people like bring it on very easy to implement and what we've developed
43:25Dan Cheshire:is this culture where basically no criticizing somebody's work is now recognizes it's not like
43:32Mary Holland Nader: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.
43:38Dan Cheshire:Right.
43:38Mary Holland Nader:And so we throw spears all the time.
43:41Dan Cheshire:That's amazing.
43:41Mary Holland Nader:Every presentation gets spears. People start saying things like, so, okay, this is going to need some spears, but like...
43:49Dan Cheshire:Let me know. Yeah, yeah, yeah.
43:51Mary Holland Nader:And somebody will be like, it's not really a spear, but I've got a toothpick, you know?
43:54Dan Cheshire:Oh my gosh, love.
43:55Mary Holland Nader:And it's, yeah, it's just part of the culture now.
43:56Dan Cheshire: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.
44:10Mary Holland Nader: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, yeah, yeah. And some people like you'd give them criticism. They're like, I can't do anything right. Yeah. You know, it's like, no, it's just had a little feedback. you know? And the minute we implemented spears, that kind of evaporated almost immediately. Wow. And everybody's kind of like, it's, am I wrong? I mean, like, that's right, right? Yeah.
44:40Dan Cheshire:That's amazing. No one's like a bully if everyone does it. And nobody's above a spear.
44:44Mary Holland Nader:Yeah. So I can present.
44:45Dan Cheshire:Yeah.
44:46Mary Holland Nader: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.
44:56Dan Cheshire:That's incredible. Okay. Well, Mary and Pip team, if you're listening, where I have so many fears. 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.
45:26Mary Holland Nader:Or for the people sitting next to you.
45:28Dan Cheshire:Or for the people sitting next to you. And it just immediately makes you think that there's no solution. 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.
45:44Mary Holland Nader:And I think that's one of the biggest responsibilities of founders or any leader, quite frankly,
45:48Dan Cheshire:or actually anybody on a team, which is correct the language.
45:52Mary Holland Nader:Listen for the language that creates false narratives, creates limiting beliefs. and simply interrupt the language.
46:00Dan Cheshire:Yeah. And that takes a certain level of consciousness.
46:04Mary Holland Nader: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.
46:10Dan Cheshire: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.
46:38Mary Holland Nader:Yeah, I think gratitude's the strategy.
46:39Dan Cheshire:It's just, yeah.
46:40Mary Holland Nader:I think gratitude's the strategy and perspective, right? I think what gratitude does is puts everything in perspective. Yes, exactly.
46:45Dan Cheshire: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? 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
47:05Mary Holland Nader:and you're giving me so you think i'm doing this just 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
47:13Dan Cheshire:never came on mine honestly like i i think you're just like my friend and you were like i'll give her a chance to like talk about her story mary and pip 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 can't be i could yeah i know 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 pod recently i was on like a forbes podcast and i was like why are you inviting me on and they were like we want to hear from you like so it's a constant battle with myself of even like, I shouldn't even be asking myself that.
47:51Dan Cheshire:But of course it comes up. So why'd you invite me? Tell me. Stroke my ego.
47:55Mary Holland Nader: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.
48:29Mary Holland Nader:And if you have an issue, don't take it up with me.
48:31Dan Cheshire:Right.
48:31Mary Holland Nader:I didn't invite myself. Yeah. If you don't like me, if you think I'm an idiot, take it up with them.
48:36Dan Cheshire:Right. Right? Oh my gosh.
48:37Mary Holland Nader:So that's number one, which is that I'm not accountable.
48:40Dan Cheshire:Love. Yeah.
48:40Mary Holland Nader: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.
48:45Dan Cheshire:Yes.
48:45Mary Holland Nader:I do have accountability if you like me or not, but I don't have accountability if you just disagree.
48:50Dan Cheshire:Yeah.
48:50Mary Holland Nader:Right? Somebody else has made that decision. So number one, you have to trust that I've made the decision.
48:54Dan Cheshire:So true.
48:55Mary Holland Nader: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.
49:27Dan Cheshire:Right.
49:27Mary Holland Nader: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. And the minute you made that connection, you realized, huh, I can leverage this for good.
49:46Dan Cheshire:Right. Right.
49:47Mary Holland Nader:And the reason you're starting Mary and Pip is to teach people things that I wish I had Mary and Pip. You know, I, 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.
50:01Dan Cheshire:Right.
50:02Mary Holland Nader:I'm in your psychographic.
50:04Dan Cheshire:Yeah.
50:04Mary Holland Nader: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.
50:12Dan Cheshire:Yeah. It's everyone's target.
50:14Mary Holland Nader: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. 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? So my question is, is why are you growing at the speed of light. What benefit does that have to your team, to the people you're serving?
50:50Mary Holland Nader: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, as long as it's a really, really good product. And that's what I've learned. Every stage of my product is not perfect. 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.
51:08Dan Cheshire:Yeah, same. Story of my life.
51:10Mary Holland Nader:And then we fix it and we're like, this is amazing. and then a week later we're like, this is not amazing. And you just realize there's always more to do. And I'm so grateful to everybody who signs up for Leaderful because 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.
51:40Dan Cheshire: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 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 you know i also think you're a
52:25Mary Holland Nader:good counterbalance to the influencer culture you know which is young people want to be influencers do you know the term selling out yeah like oh my god he's such a sellout yeah yeah well you know more and more people your generation when i say sellout they go 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.
52:49Dan Cheshire:Yeah.
52:49Mary Holland Nader:And then people go. Yeah.
52:52Dan Cheshire:Yeah, of course.
52:53Mary Holland Nader:Like the term selling out.
52:56Dan Cheshire:Yeah.
52:56Mary Holland Nader:It's not pejorative.
52:57Dan Cheshire:Right.
52:58Mary Holland Nader:It's actually seen as the model.
53:00Dan Cheshire:Yeah.
53:00Mary Holland Nader:And so 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. And then sayonara. And like the whole influencer model, the whole influencer model is gain popularity in any way and make money.
53:21Dan Cheshire:Whatever it takes.
53:22Mary Holland Nader:And then monetize. Like that children know what the term monetize means.
53:26Dan Cheshire:It's so sad.
53:26Mary Holland Nader:Then monetize those followers. Monetize that fame. Yes. And what I like about you, 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.
53:41Dan Cheshire: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 the invoice and your income is different every single month, then you're just going to say yes to any brand.
54:09Mary Holland Nader: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. And you say yes to things you know are wrong. Yes. Because I think a real sellout thinks that it's all good.
54:23Dan Cheshire:Right.
54:23Mary Holland Nader:The reluctant sellout. Yes. Oh, I like that. Yeah. Reluctant sellouts. Yeah, but they don't want. It's almost like. Because sellouts are sellouts.
54:29Dan Cheshire:Back against a wall. Yeah, sellouts are sellouts. There are still those.
54:32Mary Holland Nader:Those still exist. But I love this concept of the reluctant sellout.
54:35Dan Cheshire:The reluctant sellout.
54:36Mary Holland Nader:Which is I have to, but I don't want to. Of course. Because that means values alignment.
54:39Dan Cheshire:Exactly.
54:39Mary Holland Nader:And we like people with values.
54:41Dan Cheshire: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.
54:47Mary Holland Nader: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?
55:02Dan Cheshire: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.
55:39Dan Cheshire: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. 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 asks me what i do i lead with i'm a founder can i
56:00Mary Holland Nader:add please add always add you're a door opener i'm a door 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
56:16Dan Cheshire: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 this is an influencer which is why i'm here which is why
56:27Mary Holland Nader: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 you're why 20 years
56:38Dan Cheshire:from now you will have founded something 20 years ago and you still want to be a founder 20 years on
56:43Mary Holland Nader:probably not and founder i feel like it's a little diluted now it's it's it's current right yeah so So from this day on to the day you die, you invite people in, make them feel safe so that they can discover what they're capable of.
56:56Dan Cheshire:Totally.
56:57Mary Holland Nader: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, 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.
57:09Dan Cheshire:And hopefully any company I found in the future is to invite people in.
57:13Mary Holland Nader:It always will be if it's true to you.
57:15Dan Cheshire:Yeah. No, that makes total sense. Well, I'm an inviter. There you go. Why am I here? I'm inviting people into my life to learn about.
57:21Mary Holland Nader:Gain confidence and all the things.
57:23Dan Cheshire:Yes, to learn how to gain confidence as a young girl.
57:25Mary Holland Nader:Mary Holland Nader, you're nothing but joy and fun.
57:28Dan Cheshire:Likewise, Simon.
57:34Mary Holland Nader: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.
From the publisher
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 at https://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: https://www.maryandpip.com
Want to keep up with Mary Holland and her sisters? Check out Love Thy Nader on Hulu: https://www.hulu.com/series/love-thy-nader
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Chapters
Chapters
00:00:00 From Wall Street to Reality TV: Using Fame as a Tool for Good
00:02:57 Growing Up in the Bayou: Four Sisters and a Pet Alligator
00:07:19 Why Finance? Growing Up With Money Anxiety
00:08:25 Meeting Jimmy Kimmel's Agent: The Accidental Origin Story
00:10:29 Quitting Wall Street for Reality TV
00:12:58 Why Finance Makes Everyone Feel Stupid
00:14:14 Mary and Pip: Translating Finance for Real People
00:17:23 Becoming Confident on Camera: From Mortified to Vulnerable
00:25:22 The Power of Positive Self-Talk: Mirror Affirmations That Actually Work
00:28:31 Trust Your Gut: When Smart People Give You Bad Advice
00:30:09 What Does A Mentor Actually Look Like?
00:33:27 Gazelles Get Eaten: Why Hypergrowth Isn't Always Good
00:42:24 Spears: The Feedback Technique That Changed Everything
00:45:32 Correcting Language That Creates False Narratives
00:54:02 The Reluctant Sellout: When Freelancers Are Forced to Compromise
00:56:02 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: http://simonsinek.com/
Leaderful: https://simonsinek.com/leaderful
Podcast: http://apple.co/simonsinek
Instagram: https://instagram.com/simonsinek/
Linkedin: https://linkedin.com/in/simonsinek/
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