From Sibling Rivalry to Startup Success: How to Build a Successful Business with Family with Maggie Sellers & Katie Sellers

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1:03In case you missed it, you're allowed to be hot, smart, and rich. So let's get into it. Wait, why don't you plot together? Let's make it a fake. Okay, ready? One, two, three. One, two, three. Okay. Rolling. rolling katie sellers are you ready to get hot smart rich i sure am are you nervous a little bit is this your first podcast no i've i've done other lots of other podcasts but none on film like look at the way i'm sitting right i was actually gonna start this out by being like this is the business visually so like you're super put together i'm a little bit more not But tell me about your outfit today.

1:49Why did you wear this? Well, burgundy is my favorite color. And the color of our business. And red is the color of our business. It's also the color of the past year or the season. Okay. Which we'll get into later. I get so many compliments on these jeans when I wear them. Okay. And I just thought it was cute. But I think the meaning of it is when you saw what I was wearing, you said to me, why are you wearing that? What are you going to wear? What are you wearing? And even down to the shoes, I was like, why are you not going to put on normal shoes? Yeah, I think, again, it goes back to like do what you're best at.

2:25And what we were just talking about is how different it feels when you have a microphone on versus like we've been saying to each other for the past 24 hours since you got here, like save it for the podcast. Save it for the podcast. Save it for the podcast. Because things are just so much better when it's natural. Yeah. And that's why I asked you to come on, which this is technically going to be, I think, episode two. Yeah. But we're filming it before episode one. Yes. Because there's nobody. Just to get the heebie-jeebies out. Yeah. There's nobody else in the world that I feel more myself around.

2:55And I feel like the one thing that's so hard is everybody tells me you're so much better in person. When I meet you, I'm like, oh my God, I want to be a part of that. I still struggle to translate that onto the video side of things. Yeah. So I'm hoping that today you can help just relax me and we can just get into it. Just bring out. Yeah. Yeah. Okay. For sure. So where I wanted to start was obviously our history of working together. And maybe actually. I think we need to do an intro. Let's do a little bit of a backup. Why don't you just tell the listeners? Hopefully there's some new people. Who are you?

3:27Okay. My name is Catherine. No. No, I'm kidding. I'm Katie. I'm Maggie's. Oh my God. Your voice just did the change. Did it? Yes. Just be natural. It's so hard to be natural. I'm Katie. Okay. I had to do media training at Missouri and it was so hard for me. Like I still can't do it. Okay. I'm Katie. I'm Maggie's sister and business partner slash co-founder of HSR. And I am based in Toronto. Yeah. And we're in LA. So we're a bi-coastal duo. Yeah. Which is honestly like the best of times, the worst of times, you know? Like it works in our favor a lot, but it also then the opportunities to sit down.

4:10What'd you do before? and my background I always explain to people on the phone like you and I are very have a lot of similar experience but different at the same time so I I don't know what side of the brain is the right and the left but if you're the left I'm the right okay and we cross over and but I would also say I would argue that you're kind of both actually I am kind of both but like so am I in our normal roles we have clearly like I'm the right you're the left and we converge yeah but okay so my background is similar to you. I went to business school, but then instead of being creative, I went into accounting at a big four.

4:47I worked at Ernst & Young for almost six years, which is a long time. Three years in Toronto, three years in San Francisco working in large publicly traded technology clients. But when I lived in SF, I really caught the startup bug. So when I moved back to Toronto, I am creative. I love consumer. I love products. I love interior design, clothes. So I was like, I'm never going to be happy learning about mining and banking in Toronto. So I wanted to find a business where I could work in consumer and be creative. And so I literally just like, wait, one second, I have to interject. You didn't just want to be in startups.

5:27You decided to go into crypto before like anybody was in crypto. And I remember when you did that, I was like, why is she going into a currency that doesn't exist? so I went on to crunch base and I literally like listed businesses that were headquartered in which there weren't very many cool businesses back in the day no so I literally wrote a list of businesses and Missouri was one of the only consumer brands at the time like looking back at that time I think there was only two consumer brands I would have wanted to work for back in the day which is like Missouri and uh Nudestix Nudestix yeah based in Toronto it still was even And like Nudestix was super, super early.

6:06They hadn't probably raised money. So I might have not even been aware of them at the time. Yeah. And then there's brands like Shopify. But anyway, Majori was the top of the list. They weren't hiring. So you're right. I did end up working in crypto in like 2018. I back in the day put$500 into Bitcoin. Do you still have it? Yeah. How much is that worth? It's not worth as much as you would think. It's like it's five figures, but it's not. From$500? Yeah. Okay, Slay. Yeah. Which in the last couple of weeks, it's actually, I just keep going in and checking. Wait, that's amazing. I can't even remember the logins to any of my accounts to get my crypto.

6:45Well, you should find them. Yeah. Okay, keep going. Which was a very interesting experience, but also a little bit, you know. Sketchy. Sketchy. Early days of a new type of currency and business. No regulation. and then Mejuri literally posted a job for director of finance in 2019 while they were raising their series B from NEA and it was like a five-month process but I eventually got the job wait and we need to tell a little backstory on how we actually first started working with Mejuri so tell it we had a blog Katie and I have tried a million different businesses together we've done gift wrapping we've done calligraphy calligraphy we've we've done so many things at sea like making cards yeah and it never worked out because we always ended up fighting um but we did start a blog called pepper and piper back in the day yeah and it kind of has the undertones of what hsr has turned into which is really interesting and our first ever brand deal was with majuri it was and And I remember going to their store opening in 2018 on Dundas and vividly Nora and Ayla, who I worked with for a long time at Majuri, were standing at the door greeting people.

8:01And yeah, we got this deal to like, and I still have that. Promote the store. That stay gold t-shirt to come to the store opening. And then it was full circle. I ended up leading their finance team for three years. Okay. And B, don't be humble. Tell a little bit about how big the company was or how many people you even managed by the time you left. So I joined in May of 2019. They just raised Series B. So it was still sub nine figure. It was like low eight figures in revenue. And by the time I left, we were, you know, approaching that half a billion dollars in revenue. We'd raised Series C and D, had reached a unicorn, had reached a unicorn valuation.

8:44in 2021 and uh I was on the executive team and managed a group of 25 people on the finance team you know what's so interesting when you repeat your story back to us is like we grew up in such a risk adverse household like so risk adverse so risk adverse I can't even tell you but I do remember one thing that dad would say to us when we were little which was like if you want to have because here's the thing we did grow up extremely privileged in a lot of different ways but we always like I had my first job at 12. Yeah. Actually had my first the payroll. That's what our dad always say to us. We never had an option to move back home after we were done college.

9:19He was like, you're out on your own. Um, and so I remember there was a few things dad said when we grew up, he was like, if you want to be financially okay, have a salary for the rest of your life. If you want to be fucking wealthy, become an entrepreneur. Yeah. Yet he was so risk adverse that like the fact that I just literally bet on myself when it was like in the middle of COVID, I had another, no other options. And then you were in crypto, you left an amazing job at Missouri to come and join me when it was still so early is so interesting to me because those are such big risks that like, why do you feel like we took them?

9:57Well, actually, I don't think that, and we've talked about this, so hopefully you don't get mad for saying this, but I really did take the big risk first and foremost to start this right and then once there was legs and there was like opportunities and you were like wait you're getting deals with like Dell and you're getting speaking opportunities and you're changing people's lives then you took the risk to come yeah but why do you feel like you left well paying successful like high tier job at Mejuri to come and join me at what we're doing at HeartSmart Rich well I feel like you kind of said it before about me.

10:30I am also multi-hyphenate in a lot of ways. Like I can draw a self-portrait of myself that actually looks like me. Exactly like you. And I also can like figure out how to issue an S1 for, you know, like your annual financial statements. Sorry, what's that? I'm just kidding. And I think that has a lot to do with it. Like you said, I am multi-hyphenate in a lot of different ways. And I think like, even though I was in a great job at Mejuri, I was running a finance team. I wasn't a COO. I wasn't a CMO. And there as much as there was creative conversations that I was a part of, I wasn't making decisions or really being creative in a lot of ways.

11:12And so I was finding the hamster wheel of it's this month, it's this quarter, it's this year, it's time for taxes, it's time for this. I was like, I can't do this anymore. Yeah, for the rest of my life until I'm 65 and I retire, like it was not going to be stimulating enough for me, which is why I was like, I need to do something that's not just finance. Well, we should tell the story of what it was like when I asked you to come over and like what it's been like working together. So do you remember what I said to make you convinced to come? Well, I don't maybe remember the exact words, but I remember you were, I called you and it was May of 2020 or yeah, yeah, 2023.

11:51Yeah. And, um, My son had just turned a year old. I was taking an 18-month mat leave. Which is crazy that in Canada you get 12 months. 12. You can extend to 18. Yeah. And you were like, you should come to New York with me because I'm a founder maid. I'm a panel. My intern who works with us from Columbia Business School is coming and going to be part of it. And I was like, wow, this is so cool. And it was my opportunity in a mat leave world where you're literally at home all day, every day with a baby. to experience something new. And for me, that was like the first opportunity to see what you had really started to build.

12:29Yeah. And that for me was like the beginning of, okay, there's actually like legs to this. And it's so interesting because I think I grew up so much in the first year. I was kind of like, I mean, I wouldn't even say I've done it officially for a year before that, but I used to be so attached to things like titles and like my ego drove so many of my decisions. And I knew that I was out of place. And I say this to you all the time, I am the best thing that will ever happen to this business. And I'm also the worst. And there was a growing point where I was just like, I know that if I don't bring on help, like this won't work.

13:02And I don't. That is what you said to me. I'm the, I'm the best thing and I'm the worst thing, but I'm at a point where like, I can't do more than I'm doing right now without having someone else. Well, and I think that's what works so well about you and I working together is like one, the first day that you didn't even really start, but you were like in New York with me. I'm like, here are all the bank account passwords like here's like every bill that needs to get paid like here's this here's that but I think it's also been this like very fluid relationship where it's like every single day is new we're kind of learning together but I know one of my strengths is like I am I'm an amazing leader I'm an amazing charismatic leader I have vision you're very visionary very visionary yeah execution is like it's just not in my DNA and I can do it you can do it.

13:48I've done amazing things in my career only possible because I could execute. Yeah. But in terms of growing a big business, like I just realized I am never going to be able to manage even five people. Yeah. I don't have the patience. I don't have the skillset. And quite frankly, it's not what I'm good at. Yeah. You are amazing at people management. Yeah. So the way that we've even structured the business is so unique where it's like you kind of technically report to me. Yeah. Even though I don't report to anyone. No, even though I was going to say one of the things that's so interesting is like, not only did I give you the bank accounts the first day, but I was like, you should have a title of co-founder and you should have 49 % of the business.

14:25I just want 51. And now everybody ladders up to you, which works really well. Which I do think though is quite common in, let's talk about like in a creator led business, right? That is the way it shakes out a lot of the time because the creator is the person who is this visionary. I have all of these ideas. And to your point, you don't even want to be spending your time managing a team of five people because it's not what brings you joy or you're passionate about and I think this is what I wanted to say actually the number of times I get asked by people when I I I always introduce myself hi I'm Katie I'm Maggie's co-founder I also happen to be her sister we have the same last name I just like to get it out of the way same because there are some people who are like months later like at the nude sticks campaign shoot they're like so how long have you been working with maggie and i was like about 30 years and they were like what i was like yeah she's my sister so even though we kind of look alike talk similarly have the same last name some people still just don't get it and the number of people who are like oh my god like what's it like working with your sibling what is it like working with your sibling behind my back i only ever have the best things to say and it's it's similar to another like co-founder sibling duo that we know.

15:45My boyfriends? Yeah well I didn't know what you wanted to say. Just go. Like he says it's the best of times it's the worst of times and it truly in this business with the two of us would not work with you having any other business partner or with me because we live on two different coasts there's a very big time change and we call each other it's like six o 'clock in the morning your time or for me it's nine o 'clock at night it's the weekend it just wouldn't work if you're not family another yeah and then because you're so creative and it's a lot of it is your life eczema isn't always obvious but it's real and so is the relief from epglis after an initial dosing phase about four in ten people taking epglis achieved itch relief and clear or almost clear skin at 16 weeks and most of those people maintain skin that's Still more clear at one year with monthly dosing.

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17:21When did making plans get this complicated? It's time to streamline with WhatsApp, the secure messaging app that brings the whole group together. Use polls to settle dinner plans. send event invites and pin messages so no one forgets mom's 60th and never miss a meme or milestone all protected with end-to-end encryption it's time for whatsapp message privately with everyone learn more at whatsapp.com and there's things that like are i don't even feel like i am ready to deal with like on a personal level nor share but i know that i'm going to have to and i think that's one of the biggest things that's like one i'm so happy that we created this business in like the mission just so everyone knows is like HSR is to like empower women to know and build their worth and yeah it started off being very much like business 101 and then I was like fuck I don't just talk about business all the time like I am not a robot and I was really struggling with this dichotomy of like I have all of these other passions and things that like I want to talk about and I'm sorry but like I don't care if I don't grow as quickly I have to be able to talk about different things otherwise like I will burn out yeah and it like almost two years later, like I have not burned out.

18:33I never do because there's different seasons of my life. There are seasons. I will say you, you've learned how to take pauses though. Yeah. So you don't burn out. And we have gone through phases over the last year where you're like, I'm not in much, in as much of a creative mood. And we've learned how to manage that for you as the creative, which I don't think I could do. And this is like having spent time in talent management. It's like your manager is kind of a babysitter, right? Like you are dealing with like the highest fires and like the smallest fires. And I think for me, I don't, I never really wanted to sign with a traditional management company because what we do in my opinion is so much like, like I have such a bigger kind of vision for where I see HSR going.

19:15But I also feel like it's so highly personal and like, there's so much like finances that get brought into it that it could never have this whole venture arm also, right? It's not just like, Oh, oh, Maggie makes content on TikTok. You know, it's like we're, we have over seven figures invested in consumer brands and we raise money in SPVs. We do investor reporting. We have updates from our portfolio companies. We have to help portfolio companies. And that's also a whole other layer of like me coming in and your experience where like, I have later stage consumer experience and know what the expectation of these businesses are going to be that we're helping.

19:53And they're just honestly like, it was just so serendipitous that it all came together with like the experience that I had had and built what you had and the reason it didn't work for us to work together before even with Pepper and Piper like transparently is because we both were very early in our careers we hadn't had the experience of building on our own and developing different skill sets and knowing what our swim lane is and now that's really defined and you are the creative that comes up with the vision and I can help execute on that, which is what I like. Where we struggled before was like two creatives wanting to put their own idea of their DNA of what the creative was going to look like or the Instagram or the blog or the product, whatever.

20:39And like that didn't work. No, that didn't work. And I think that's like something that I have figured out later on is it's like you really need to get clear on what your role is going to be. And for me, it's even hard to say out loud like I'm not a great people manager because as a great charismatic leader I want to be able to be a good manager I'm just not yeah and so it's like being I think you are but yeah I I honestly don't think that I am though and I don't enjoy it at all I like get very annoyed very easily because you and I both say this all the time we can just do things better than most people which controversial I sounds bad but I agree I stand behind that like you are the only person that I've worked with that I'm like, if it can't be me, it should be Katie.

21:22Yeah. There's nobody else like that. I would ever trust that for. Yeah. But I do think it's really interesting because I remember when I first started dating my boyfriend, he had been working with his brother for like 17 years and they have a very similar archetype of person and they've worked incredibly well for this period of time. But he said to me when we first started dating, he's like, don't you think your sister is gonna get upset that like you're the one in the spotlight and you have the limelight and she's kind of behind the scenes no like literally and he was like oh and now once he's met me he's like got it yeah you know but so do you that doesn't mean that I can't be creative in my own ways though but like yeah I'm not gonna be the one to be the person who's hosting my own podcast or like posting on tiktok three times a day I do it in spurts where I'm like I need some creativity right now I kind of like this trend I'm gonna post something yeah and then I get my creative outlet in so many different ways where it's like the HSR holiday suite I'm doing all the creative I'm doing the tablescape and can I just say yeah I empower you to do that like often in front of people I say I don't want people to think this is all me like Katie you're the best at tablescapes at flower arrangements like that is flat lays the invitations and it's weird because you're like I don't that's not my skill set but you're the creative I'm the operator but that's my creative which is where it goes back to like I think we're such a unique duo and little fun fact about me I'm ambidextrous and I'm ambidextrous really triggering story we'll talk about later but I feel that I go really well between being whatever you said like the left brain and the right brain and so do you but it's taken this like magic dance for us to figure out when we lean in and when we don't because it we do fight yeah and I think one of the things that I'm working over it a lot faster than I do I get over things I'm like a dude like we I we get in a fight I talk about it and I'm like moving on and you're sensitive Sally over there being like you hurt my feelings we've been that way since we were little kids also yeah yeah I was always just extremely risky.

23:33Like I was always taking risks. I was always breaking bones. I was always trying different things. I started always trying different things. I started my first business when I was seven years old, taking care of our neighbor's pets or, and I was running to mom being like, Maggie's doing flips on the trampoline and I don't like it. Yeah. Like I was always just getting into trouble and like being curious. And I think it's so interesting. I did this Berkman test the other day, which is around like, it's a coaching method. Yeah. And I scored 99 percentile in science and I was like sir I think the results are incorrect like I was not good at science and math I was more of an English person and he was like no it's actually really interesting science is more towards your curiosity you're the most curious person I have met he has done 4 ,000 Berkman tests he said he's never met somebody like me you know what I scored one of a kind everyone I scored zero percent on administration not surprising which goes back to Like I don't want to look at statements.

24:30I don't want to be bogged down in details. And that's where I think you work really well with me. Yeah. And when we're doing even like case studies or business dives, we bring two totally different perspectives. Totally. Which now that we've been working together for a year, like we do also meld together on different things. Yeah. We need to talk about some drama though. But when we first started working together. So I can recall the biggest fight that we probably got into was around tone of voice. I love how you knew that um please describe your tone of voice in three words and then I'll go direct direct direct yes I would describe your tone of voice previous to us me having a talking with you was curt yeah direct and short yeah and that doesn't say short yeah that doesn't work so we kept getting into these little tips because I talk very excited.

25:27Well, actually wait, what are my three words that you would describe my tone of voice as excited, passionate, lengthy? Yes. So my, this is hilarious. I am doing a bunch of book hauls right now and I bought this book called smart brevity and my boyfriend saw me and he's like, Oh damn it. That's one of your Christmas presents because you talk so like lengthy it's so annoying but so I'm reading this book Smart Brevity which is all about how to condense how you speak because you just waste so much time with words I could talk and I still have no idea what I said yeah um but I do think that when we first started working together you would speak to the HSR community from email in like a very direct curt short tone and that didn't work which doesn't work yeah because HSR is like I said bigger than me it's a brand that we've built and birthed and it has a personality yeah and it's excited and passionate and I'm trying to be not so lengthy yeah but it was interesting because when I first gave you that feedback how did you feel well I think like where I'll back up and explain like where it sort of comes from for me of like the way I've developed in my career and why I speak like that in a lot of cases because I think like this also comes back to the convergence of like where we both are in our careers.

26:48I've worked up until like this past year in a corporate structured environment, right? Where you took risks a lot earlier in your career and left like from Salesforce, Freshie, Dosis, and then you were off doing your own thing where things are just different, right? Dealing with different types of personalities. Talent, et cetera. I was never in a role or a job where I had to speak to people to make them feel a certain way. You just had to speak to people. Wait, you had to speak to people. To get shit done. Yeah. And I grew up and worked in an environment where I was always the only woman at any table, any dinner, any conference room.

27:28Like whether it was Ernst & Young, even at Majuriat a lot of times. I was the female leading the finance team. But if I was talking to the bank or an investor or other executives, like there were other men who were part of those conversations. and I from I'm going to say a young age like working had to figure out how to speak and communicate to people in a way that was direct so that I didn't get stuck in the like oh you know she's just a cute little girl who doesn't really know what to say and is being overly pleasant etc and especially when it came down to managing people the way that I've had to like evolve the way I speak and manage people is like the whole you know care personally challenge directly from Radical Candor is like I just had to almost like trick my brain into speaking that way so that I could literally just get through the day.

28:24Yeah. Of all of the things that I had to do, managing 25 people, talking to investors, talking to the bank. Yeah. And so I just was never in a role where I had to like, you know, think about the community aspect of making people feel good. Yeah. And that's been a big learning of like, you know, sending you all that hot, smart, rich energy is like not the way I would speak over email. But now when it is to the community, I do. Yeah. But again, I will say like, there is an art and a science to learning how to work with people. Cause like I do deal with executives at investment banks and at venture capital funds, and I'm not sending them an email signing off, sending you hot, smart, rich energy.

29:03No, obviously not. But like, I think that again, working in a startup and like, this is where I always have identified patterns and there's patterns of successful startup founders. And And it's like they know when to do certain things and when to turn it off and on. And for me, I can be at – and this happened this summer. I'm at Wembley in the Queen's box. And I'm able to speak to someone that is super high up in society and in business. And they walk away being like, she was lovely, professional, direct. And then I can go down to somebody that is graduating college and is looking for life advice.

29:37Their boyfriend just broke up with them. And they feel relatable to me. and I think that is kind of one of my superpowers and it was something that was obviously hard for us to work through but I think we've gotten to a good point on it now. For sure. But it's also like something that you weren't even the first person who told me. Yeah. Like even working at Missouri, people are like, you know, you don't put any emojis in your messages and I'm like, why do I need to? Yeah, you're scary. Okay, moving along. So we're still TBD on when this episode is going to come out because there's just a lot of moving parts but I do think that there are some major themes in pop culture that I want to touch on and just get some hot takes on yeah so regardless if this is like a little bit out I still think it's relevant because this was like moments of the year so Pantone just named that mocha moose is their Pantone of the year 2024 what are your thoughts on that I mean I love a neutral so that you love a beige I love a beige do you love a sad beige I don't love a sad beige I've moved on from sad beige I think it needs to just be like I love a beige in the right context can I tell you something that I've thought that I've never said out loud about branding what I think I betrayed my millennial self for a minute when Gen Z started popping up everywhere like I loved Glossier branding I love I aspire to be the millennial decorator yeah and I was like I'm usually really opinionated and set in my ways and like I don't really like what's the word I'm looking for I don't really um like change my mind on things based on you're very hard to like change your perspective especially based on like what's cool I usually go against the grain but when Gen Z was building brands and they were colorful and fun I was like I want to be colorful and fun but then I kind of look back at everything and I'm like that's not me like I like millennial pink so I'm really happy that this year was mocha moose yeah I feel like I'm I'm kind of over brat summer and the green yeah I'm over it yeah and I think you know who's done no better job at capitalizing it than this woman is Sabrina Carpenter yes what are your thoughts on Sabrina Carpenter um I think she's someone who's taken the like the opportunity she's been given and is riding the wave because I saw something on Instagram before we were filming this that was like talking about the eras tour and like everything that has happened in the context of the era's tour in a period of time and Sabrina Carpenter started as the very first opening act for Taylor Swift was nowhere close to where she is today and it before the era's tour ended she released a whole new album and became a headliner of her own sold out arena tour or maybe not arena but state whatever not the one that Taylor Swift did but like scotiabank arena arena tour and so she's someone who really was like took an opportunity and really ran with it but she's also not an overnight success like when we were doing all of our you know getting our event ready for the founders we took to the concert it's like she has nine studio albums well that's actually what I wanted to bring up today because she just released me espresso which is her new perfume flavor so I was doing some research on it this is not her first perfume launch if you look back no you wouldn't have no idea no but i'm actually going to do a video on why celebrities launch perfumes before they launch their own line it's the smartest thing a celebrity can do alex earl if you are watching this like do not launch anything but your own perfume first and foremost there's why a few reasons like it's genderless so it's like you can sell it to both audiences it's one skew so you don't have to develop an entire if you're doing makeup and concealer and you don't have certain skin tones like you're canceled before you even start.

33:23Yeah. It's usually a licensing deal. So you will carry none of the risk from like an inventory perspective. Got it. And it's really easy because celebrities are unattainable people. You can't look like Sabrina Carpenter. She wears a wig. But you can smell like her. You can smell like her. And so there's a reason that celebrities do perfumes before they do anything else. But going back to Sabrina Carpenter, this is her fourth scent. Her first was - Wow, fourth? fourth in 2022 then she launched caramel in 2023 then there's cherry so this is her fourth look back and maybe we can have a graphic of what the old perfume bottle looked like it was horrific it looked like bath and body works and now it's like she's evolved to have like the culture she everything she's doing is playing into the culture while being authentic to her her first scent revolved around chocolate and food.