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Maggie Sellers Reum: I Was Tired of Being Told "NO", So I Became Hot, Smart, & Rich

54m 49s

Maggie Sellers Reum: I Was Tired of Being Told "NO", So I Became Hot, Smart, & Rich

Maggie Sellers recounts how a boss at Salesforce told her to change her voice inflection to succeed, a painful moment that shaped her mission to help women never settle in any area of life. She emphasizes the power of equity, learned from employee stock options and later investing in startups, often trading salary for ownership. A pivotal moment came when a founder asked her to take down a TikTok about a celebrity-brand deal, which felt like a death sentence to her business. This pushed her to become a creator and build a platform where she controls her narrative. She now runs "Hot Smart Rich" and prioritizes her personal brand, recently shifting from highlighting achievements to sharing her journey, using storytelling to connect with her audience. Maggie also relies on the AI tool Clawed for personal branding rules, calendar management, and email summarization, which helps her focus on important tasks over urgent ones. Her mission remains clear: empowering women to dream big and achieve financial freedom, business success, and personal fulfillment.

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I got a message from the founder of the company within 24 hours of the video being posted, asking me to take it down. That felt like a death sentence to the business that I was building. And I decided in that moment, I was going to become a creator, and I was going to build a platform that was so big that I could actually do things for myself and never have anyone tell me what I couldn't could not post about again. I'm a business woman, I'm not just a creator. Every single person that's listening to this, whether you're an employee or you're an entrepreneur, needs to understand the power of equity. I'm not special. I don't have a billion dollar exit. My story resonates so much because anybody listening to it that hasn't built a billion dollar company can do it too. My mission is very clear, and it is for women to never settle. Everyone was like, niche down, only talk about one thing, and I look at those people now, and I'm like, this must be so boring. If there's a creator founder, what is a good first step for them, what should they be prioritized with an opinion or belief that they should hold? You do not have to be for everyone, but you also don't need to people please to try to be for everyone. Most businesses that I have seen that have failed is because. - Maggie, thank you so much for joining us here at Creator Unplugged. Obviously, I've been looking forward to having this conversation with you. I think what you're doing in your empowering women of all different stages and walks of life. You are brilliant. We obviously had our conversation yesterday as well, but there was a really cool moment that I really wanted to ask about yesterday that I didn't get a chance to, and this is where we're gonna start today. I want you to bring me back to the moment with your first boss at Salesforce, and me probably even saying those words is like, "Oh my gosh." 'Cause I know in that moment that they told you that you couldn't be yourself, that you had to change the inflection of your voice or else you wouldn't be taken seriously. I know behind the scenes how hard you work. I know how much you care about your work. When someone tells you that, what are you feeling internally? - So to go back to that moment, I'm 33 now. This is when I was in my early 20s, I have some decades to have really grappled with that situation, but to your point, it's still painful to go back to that moment because I had just finished giving a presentation at Salesforce. I was the number one BDR worldwide, and we were closing business, millions of dollars. I was getting these amazing opportunities, and I remember I just finished a conversation in front of a larger group of people, and my boss at the time pulled me into a conference room, and I think it comes from a good place, but the conversation was, you're a lot smarter than you look. You're a lot smarter than you sound. The inflection at the end of your voice going up must be intentional, and you need to switch that if you ever wanna get ahead, not only in this organization, but in anywhere that you wanna work. And you know, you're just at a college, you're taking feedback, feedback is a gift, that's how I've lived my entire life. I love when I know where I stand with someone, but when it's something that you actually cannot change about yourself, and something that is not really something that you have the ability to put in the reps or put in hard work, which is what I've done my whole life to be able to succeed, your left thinking, well where is my opportunity going to be? And at that time, I don't come from a family of entrepreneurs, and I come from actually a very risk-adverse household, and I didn't really see how I was gonna be able to carve the path at that moment, but I remember it really sitting with me and thinking like, I was really scared. And going back to that moment now, it still brings up a lot of empathy for myself back then, but also a lot of gratitude, because without that experience, I don't know if I would have the mission that carries me through the hard times of being a creator entrepreneur, because I think there's hardships that come with being an entrepreneur, and then there's hardships that come with being a creator entrepreneur. And having rejection and facing feedback and having people not like me and misunderstand me, that experience at Salesforce, not only from being hung up on a hundred times a day from cold calling people, but also from bosses telling me things like that, is who, is made me who I am today. - Absolutely, and you said the word mission in us, knowing each other, you were so intentional about everything that you do. Now, looking back in even today, your work with HSR, if you were to put words to that mission, what are you ultimately trying to do with your personal brand with your podcast and with your businesses? - My mission is very clear, and it is for women to never settle in any capacity of their life, in their relationships, in their friendships, in their financial freedom, in their business, and in their way that they're going to feel proud to live their life, because they took maybe not the easiest decision, but the hard decision to get to a place where they never settled. And I've seen that play out across my entire life, and all the things that matter to me. So in our show, we really talk about femininity, money, business, relationships, and power. And I want women that listen and are a part of our community to never settle for anything in their life, to be able to dream as big as they want to achieve, what they want to achieve. - And the reason why so many craters, especially this new age of the creator landscape, the reason why you are such a great person, look up to is the idea of equity. It's the idea of ownership, and that comes from your investment background. You've sat on both sides of the table. You've been with the talent, you've been with the brand. And I'm curious from that background, working and investing, what has that taught you about ownership, about equity, that you ultimately now help all these women do for their own brands? - So that would actually go back way long ago to, even the time that I worked at Salesforce, when I was able to get stock for the first time. And I had no idea really like what that potential could look like. And I remember when I worked at Salesforce, I mean, they are so much bigger now than when I was even there like 10, 12 years ago. I felt like Mark Benioff knew who I was. And obviously he had no idea who I was. It was a publicly traded company, but just to see the progression of where I got to, where I was initially even able to be given stock as an employee, employee stock option plan, that's the first light bulb that turned off of like, what is this stock and how does it relate to compensation? And so much employees, anyone let's listen to this, that clocks in and clocks out, like you're given a salary, right? But your compensation package is so much more than that. And so every single person that's listening to this, whether you're an employee or you're an entrepreneur, needs to understand the power of equity. I learned through having an employee stock option plan. So when I went to my first startup after I was at Salesforce, I actually cut my salary in half so that I could have more equity upside in that company, that company ended up going public. And so I went on the road show with the founder and the CEO at the time and was really able to understand like, whoa, this is the dream state for every single startup that I work at in the future. And from that point on, except for one detour, I never had equity in the startups that I was building. And that was my first entry into what ownership even meant. Because it wasn't about the salary, it was about what is the opportunity, what is the upside? And I didn't learn by starting to invest my own money. From ESOP, I went to advising companies, I traded my skill set, my expertise, which at the time was marketing strategy, working with celebrities, bringing celebrities into the front of the brand for equity ownership. And it was all through advisory. Once I started having more disposable income, I was like, okay, I'm gonna spend $2,500 investing the first amount of money into a startup. Then it went to $5,000, then it went to $10,000, then it went to $25,000. The largest investment that I've personally ever made is $50,000 into one company. And then I've raised SPV, so special purpose vehicles, where I invest other people's money, going up to half a million dollars. So my journey, and I think why it's so unique, is that I'm not special. And I don't have a billion dollar exit. I'm not the founder of Jim Shark or Al-O-Yoga or Lulu Lem, and I know these are all active-ware brands, but these are exceptional entrepreneurial people that have built something from nothing. And my story resonates so much because anybody listening to it that hasn't built a billion dollar company, can do it too. And you can start very small and you can progress and you can get to a point where you really understand what it means to have ownership in something. - And the brilliance of your content, is you're taking such an important concept and you're making it accessible to people. Through you, you were actually one of the very first people to even talk about this industry behind the scenes. And that brings me to your first viral TikTok video, which we talked a lot about behind the scenes. But take me back to that moment where you're giving credit to your team, talking about this deal that you guys were able to put together. And is it true that that video wasn't able to actually stay up? I wanna hear the story from you directly. - So about five or six years ago, I developed a white space of a consulting practice that was really matching celebrities with early stage startups for equity, not necessarily just brand partnership sponsorship dollars. And I was doing that for someone else's company. I decided I ultimately wanted to do it for myself. And so I was matching celebrities into different brands. And some of the fun ones was like, little yawty into future mood and Joe Jonas into a beverage brand called Oza. And I matched a celebrity into a brand. It took two years of my life. And I remember when the deal went through, it's amazing, like everyone's so happy, sales increased by 1500% the weekend that it's announcing. I make a TikTok because as a brand development, business development piece of my business, it was being able to share the work that I was doing. - Absolutely. - And I got a message from the founder of the company within 24 hours of the video being posted, asking me to take it down. And it wasn't from her. It was from the celebrity's team calling the brand and saying this was a huge problem. And why is there information online about how things got done? They wanted to keep it very traditional celebrity world where it's not about the bells and whistles of how the deal got done, but you just see the final product. And I remember, I remember sitting in my bed and crying and thinking, how am I ever going to build a business if I'm not able to talk about what I'm actually doing? Like if this deal got done, my marketing is only gonna be word of mouth. And as someone who wants to be in control of their destiny, that felt like a death sentence to the business that I was building. And I decided in that moment, I was going to become a creator and I was going to build a platform that was so big that I could actually do things for myself and never have anyone tell me what I couldn't not post about again. - And that actually brings me to the moment you actually developed your personal brand, you developed your business page in parallel. So you did Hot Smart Rich and you had this idea in your head that you wanted this to be the biggest thing. It's cool because now you're in this world of trying to build your personal brand even further. I want to hear about that transition 'cause most business owners will come onto social media and they're thinking just the brand page alone, that's it. And they forget that people buy into people and as you start to recognize this, your evolution, your personal brand is becoming so incredibly strong. Can you talk about what made you want to pivot and actually focus and prioritize your personal brand just as much as Hot Smart Rich? - So five years ago, like I just said, when that moment happened, I was like, I need to build something online and I didn't really have the gumption to build the Maggie sellers at that time. Now I'm Maggie sellers' reign, but the Maggie sellers brand. And I had a vision of like, can I create a space online that is called her daddy meets how I built this? There is a white space there. Someone that owns business content in a pop culture way that's easy to understand. And the mission was so much bigger than it just being my personal brand that it was really focused on building Hot Smart Rich and having these fun, cool ways to break down these complex topics. But over time, there was a moment that actually happened a few weeks ago. And I spoke at one of the most prestigious consumer brand summits and a huge celebrity who just gave her keynote, comes over to my table for dinner and she gets introduced to me and she goes, oh my God, you're the Hot Smart Rich girl. And I mean, I love being called Hot Smart Rich, but I was also, okay, this is a problem because if I'm only going to be known as a silent face behind Hot Smart Rich and I know where the market is going and I know that the power is in building a community, a cult like leader, someone that people can look up to an aspire to be and learn from and show them the trials and tribulations, like I need to reposition my personal brand in the market to be just as strong as Hot Smart Rich and grow them equally at the same time. And so that moment was just a few weeks ago and that's when I went into hyper drive mode. I started working with Quad every single day, like rip apart my social media, tell me what I'm positioning to the world and interestingly enough, it's shocking what it came back with but it basically said, you are only leading with your achievements. You've achieved so much that all your Instagram is, all your TikTok, oh not TikTok, but all your personal Instagram is, is I've achieved this. I invested this. Look at me on this panel, look at this. You're not showing people anything about the journey and from our conversation yesterday, that's the number one thing you told me too. Like there is no storytelling, there is no crater vision framework, there is no pain, there is no pat, what's the second one? - It's pursuing. - You know it all. It's, trust me, I've been studying it all my life. I've been with my team, like this guy is a genius because it's so evident what the missing link has been with my personal brand. The thing I'm happy about is, I feel so good about the points on the board that I have and the experience that I can share with people that now the unlock is like following your crater vision framework and really putting that into practice to not go from 100,000 followers to a million followers. - 100% and for everyone listening in right now, the moment they go onto your page, positioning conversion is so strong. 'Cause the moment you open up your mouth, everyone believes you. You have actually lived, you call it points on the board, but you've had so many moments of success and then obviously encourages all these different people to pursue something similar. But then you're right, how do they see themselves in you? And I've had these conversations behind these things. I'm like, oh my gosh, Maggie, you should have a million followers. Why don't you have a million followers? It's ultimately this idea of people seeing themselves in your store and you have such a brilliant one. You actually mentioned this idea of use of Clawed and I was gonna bring this up because I love the way that you're utilizing it today and it certainly evolved. I think people as entrepreneurs as creative are gonna learn a lot from you. So how are you currently utilizing Clawed? You just called it your daily driver. Ultimately, what are the prompts that you're utilizing or how do you have it in your workflow at the moment? - I use Clawed for everything. It is scary if you go into that, how much of it it knows about me. So let's break it down by a few things that will be really relevant to your audience. Like personal positioning in terms of, for me, having a specific aesthetic has actually been very hard for me my whole life. I would say growing up, I was very tomboy chic and I love to wear like, I was very expressive. Like I would wear polka dot pants and a flower top and like things in my hair and my mom loves that about me because I was always a creative. It is on purpose that little Noss X wore a cowboy hat for the first three years of his career every single time you saw him. You almost start associating that hat when he was in his heyday with little Noss X, right? And I think for me, what was really hard was actually coming up with rules for how I actually needed to show up every single day because when I wake up on a Monday, I feel very different than when I wake up on a Friday. And maybe that's my ADHD, maybe that's what I'm doing in the day being a creative multi-hyphenant entrepreneur. Some days I'm having investment meetings and taking photos and I'm recording a podcast. I'm doing an investor update. So my mood really would depict how I would actually show up physically. And quad, I had it help me develop rules, language. When I paired certain things together and that set of rules has helped me develop hypothesis when I'm testing something like what is my audience actually going to relate to? And it's made getting up every single day and when you're making so many decisions as a CEO and as an entrepreneur, it lessens the amount of decisions that I'm making. Like I was able to throw this on in three seconds because it's part of the rule book now. But if I had been asked to get dressed for a podcast even six months ago, it would have taken me two hours. So that's one way, personal branding, personal image, knowing what's gonna look best on you for me, huge. The second way I use it a lot right now is for very, I actually have a very controversial opinion on personal assistance and EAs. I used to have someone help manage my calendar. And even if I have a space of an hour, I don't really want someone having ownership of deciding what I'm gonna do in that hour. I am the maker of my calendar. And so what I actually use quad for now, I have a personal assistant that helps me with a bunch of other stuff that's more in person. But in my emails and in my calendar, it actually helps manage. One is gonna be the best time for me to do certain things, creative thinking, big business decisions, having a financial meeting, even based around where I'm at in my cycle, which sounds crazy, but I ask quad, like when would be the best as time to have a P&L meeting on the podcast based on where I'm going to be in my cycle and what else I have going on that week. So quad is something that I use almost daily for tasks and sort of organization. The other huge two, it summarizes my emails at 8.30, 12.30 every single day. I ask it to highlight what's urgent, what's important and what can wait. And then I ask it based on what it knows about me, how to summarize what I absolutely need to know and then draft an email that is a response back to that person based on what it knows. So I used to be a slave to my email and something that my husband has taught me, which is one of the most important things he's ever shared with me is you need to understand what's urgent versus what's important. What is urgent is someone else's to-do list. What is important is your to-do list. And if you are chasing what is urgent and someone else's to-do list, you are never gonna get done what's important to you and move your business forward. And when I started having quad understand and be able to really decipher what is someone else's to-do list from what's my to-do list, I was so much more productive. And then the last thing that I use AI and quad for, because I do not ask it to come up with creative concepts for me, it's not writing scripts, it's not doing any sort of ideation. No one is me and that is my superpower. And being someone who is neurodivergent, I think differently regardless. I don't need AI to spit out things to me that everyone else is also going to have. But what it does help me is it helps me synthesize my thoughts. So for me, I think the best when I'm out on a walk. And I have so many ideas that going from trying to not step on the sidewalk and stepping someone's dog poo and cross the street with a red light 'cause I'm down looking at my phone, I now go for a walk and I basically talk into whisper flow or into claw directly for a solid hour about all of the ideas, everything that I'm thinking about, poke holes in my logic, poke holes in my thinking, and then help me prioritize based on everything else that I have going on, what is critical for me to execute on today and what is actually now on a content bank that I can resurface when I'm not actually thinking I'm that creative that week. I have a whole log of original thoughts that I've been keeping in clawed that I can resurface and go back to. - I love that because oftentimes us as creatives or as business owners, we have these assumptions that we don't even realize are our blind spots until something objectively can put a microscope to it. And so I utilize it all the time understand my audience, but that is one area that I think you're so phenomenal at. So when I think about that creator vision, I look at the second branch, the who, the target avatar. There's a psychographic associated with it. Of course, there's a demographic, which is sex, location, occupation, but the psychographic, what are they struggling with? What do they ultimately want? What are they desiring? You're so good at actually understanding that. Where does that come from? How do you understand so clearly exactly what your audience is struggling with? Is there something on a routine basis that you're doing to keep updated to that? I am obsessed with my community to probably a level that my husband thinks is concerning. I still answer and read almost every single DM. Nobody is in my personal DMs. Like no one on my team. And I am building this company from a pain point. And I think it's really important to understand like, are you building a vitamin pill or are you building a pain killer? And when you're building a pain killer, you are giving someone a solution that they need. It's like an Advil. You have to take an Advil or a Tylenol when you have a headache to relieve the pain. But a vitamin pill is something like, you know, I want my nails to be a little bit stronger. So I'm going to take collagen. It's a nice to have, but it's not a need to have. And what I realized about the community that I'm building for just to explain it's 25 to fifth year old women who their whole life they have had to choose. They have had to choose what they wear. Are they going to be judged for their earrings? Are they going to be judged for the inflection of their voice? There is no space for them to embrace who they are 100% authentically. And it's insane to me because as a consumer, these women control 85% of consumer spend. The math doesn't math. When we as women control 85% of consumer spend, yet the female founders that are building these businesses get 2% of ventured dollars. That doesn't make sense. And so I am that girl. It's me 10 years ago. How old is my 33? I'm turning 34 this week. It's me. Happy early birthday. By the way. 15 years ago starting to come into who I am as a woman, starting to really want to express my femininity and then going through these masculine corporate environments were like, "Trust me. I am a workhorse. I have big aspirations. I always have. I was always going to be the best at what I did." And that meant that I would have to choose who I was in the workplace. And I got so frustrated that it reminds me a lot of when I'm investing in someone. Do you have lower-case T trauma as a founder where you will stop at nothing to go and solve this problem because you can't sleep at night. And that's how I feel about my community. And it's not manufacturing anything. It's not trying to understand who they are. It's me. And it's at all the different life stages. And that's even how I invest now. It's like I invest in things that I know that I can actually add value to, that I can put through the distribution of hot smart rich. But knowing this audience is not challenging because I get the DMs of what we've done for these women. I get the messages. I see their faces when they come to these meetups. And it's because they were never served a place that gave them permission to be 100% themselves to win at life and to win in the workplace. We are very similar in the regard of how close we are in proximity to our audience. I am still answering my DMs. My team hates me for it. But I have to. Right? Because we want to prioritize what are they struggling with and what is the best way to find that feedback ultimately directly from them. So the fact that you're still doing that at your stage is really, really, really cool. I love your message because your message is all about not living yourself and finding your own desires, your own and being able to carve out that lane. Not smart rich. The name of it is an embodiment of that. You could even argue that is controversial. When someone hears it immediately, they feel something. What do you think about all these people that come online? Actually, it's a watered down version of who they are. What are you telling them behind this screen as they're watching or tuning into this? How can you inspire them to be like, no, actually carve out your own thing and feel emboldened to show up the way that you authentically feel? So when I first made this video that was like, I'm going to be hot smart rich. I was not in a great place. I was in a bad relationship. I was debating leaving. I was actually previously engaged and I felt a lot of pressure to get married because all of my friends were and I lived with him and I didn't have any family here and I actually felt very lost. I was starting to post on TikTok, but I was also doing this consulting business and I was also raising these SPVs and trying to figure out my own path. I remember posting this video and my hair was up in this messy bun and I had a filter on my face because I actually didn't even like the way that I looked and I said, I'm going to be hot smart rich this summer and I just took off. Those words together, but it wasn't, I've become hot smart rich and look at me. It was more like, I'm going to become this, come on the journey and building the audience from that low point of my life. People that were there at the beginning, when I got married and I did find my person, those people's messages were like, I've been here since you had your stuff in storage, you were figuring out your life in your 30s, all your friends were married or engaged, you had just called off your engagement. You definitely didn't look the way that you looked now because you've stepped into this power and I think that also comes from the authenticity of building it from that place of real want and need. So I think the same logic applies for someone that wants to build something today. It's like you have to find what's actually going on inside of you. And to your point yesterday, I've never been able to put it into words. Obviously you have. It's like create for the version of you two, three years before and I think that's so true. It's like what have you been able to learn over the period that was you? You're not manufacturing anything because that's when creating content gets really hard. And you are mimicking someone or you are seeing how this style that someone's doing it in, it gets exhausting. And I think for me, like I've never burned out from this. Like I haven't posted a video every single day like you have. I've definitely taken a week off, taken a day, which I wouldn't recommend. But I've been doing videos online for four years and I love it still. It still brings me equal to the same amount of joy. And I think it's because it's authentic to what I'm going through and people are now there for the journey. And I think one of the big things I did when I was starting was I wanted you to feel like we were out at dinner table. And we were going to talk about business, boys, relationships, investing, money, parents, family dynamics, like the whole thing. And I remember this was at the time that everyone was like niche down, only talk about one thing, become an expert. And I look at those people now and I'm like, this must be so boring. I love that. And you must burn out because how on earth would a human who is known for so many things and is multifunctional and can do so much, feel trapped to talk about one thing. And for me, I'm so excited about what's going to happen in the next, since I'm going to unlock the creator vision framework and get to talk about my story and full. And then all the other life moments that I have coming down the line, I don't ever feel like I'm going to burn out from this. This is just my personal brand because it's who I am. I have made content on this several times about me posting for last six plus years every single day and not having burnt out. And every single time I get a lot of comments people saying that I have no idea what I'm talking about that burn out is a topic that I shouldn't be creating content for. But there's a true obsession to what we do. And there's great joy when you feel alignment with it. And I think that's why it's so important to become the niche. Ultimately, if you're creating content about one topic for an extended period of time, of course you're going to evolve out of it. But people don't realize that. So they try to take a shortcut of I just want to get the reach now. So I want the search abilities. I'm going to choose a topic in niche now. But ultimately we want to be doing this for the next 10, 15, 20 plus years. And in order for you to do that, you have to create content that's extremely aligned to you and you do that. And you're like embodying it in real time, which is phenomenal. Can I say something there? Go for of course. I was actually going to say so obviously this is getting to bring in some of the rooms that I got to sit in. So are you familiar with slow ventures? No, please advise me. OK, so slow ventures is one of the most iconic Silicon Valley firms. I think they probably have, I don't want to actually say but like I think a million under under management. They just raised the first ever creator venture capital fund. So they are investing millions of dollars into creators that want to eventually start businesses. And the first time that this has happened. And what's very interesting about their investment thesis is that they are actually interested in investing in creators that have done exactly what you and I have not done, which is niche now. They are obsessed with one thing. They're known for that thing. So some of their investments have been into like a physical therapist, someone that has an audience and physical therapy. And then they want to have a business that is in that specific lane. They've done it in a gardener, a gardener creator that only talks about gardening and then they invest into that creator's holding company. Ultimately, hoping that that gardener creator is going to start a gardening business. The difference between you and I is we want the whole pie. You don't want to just build a business in one lane. Like I don't have to just invest in one thing because I'm one type of creator. So there's different ways to do things. And I think people have to think really critically about like what do you want with your life? Right? We're visionaries. We want that $100 million revenue, a billion dollar evaluation and not everyone wants that. Some people want, you know, a following that's dedicated. That's in that they can then launch a business that's gonna do one, four, five, 10, $15 million a year, and that is a win for them, and that's amazing. But I think the biggest piece of advice that I have for people is like, know what you want, because if you don't know what you want, how are you ever gonna build back from it? So as an investor, I'm pitched a lot of ideas, and I also see a lot of different archetypes of founders, and there's nothing wrong with what type of founder that you are, but you have to know what type of founder that you are. If you're obsessed with physical therapy, only talk about physical therapy then, and then start a business in physical therapy, and let that be your life. Don't let you and I stop you from that. But for people that want to be able to launch business after a business and get equity in that, and it's like, it's the me, you, Stephen Bartletz, like that is who needs to build their business completely differently than who, for example, slow vendgers is looking at investing in. Does that make sense? I'm saying that's a big difference. I believe it was in 2019, she could have been given a performance fee to perform at Uber. She decided to take it in stock options. I believe the 6 million turned into 9 million just a few years later. That example is so evident. That was obviously a very late stage start up. Uber was close to an IPO. I think her team around her was probably able to identify the opportunity and evaluate it very differently. But would you rather take 9 million or would you rather take 6 million in a very short year turnaround? Most of us would say the 9 million delayed gratification goes back to that. I think you show enough of those examples where Haley Bieber with Road, would she have wanted to do multiple one to five million dollar beauty deals or would she want to be able to sell her company to Elf in three years for a billion dollars? That juxtaposition is very clear to show someone when she's in the company. You're to show someone when you're like, oh, on the face of sunset bill of our billboard, you could have been the face for any beauty brand and made five million dollars. But you've sold your company for a billion dollars because you decided to bet on yourself and you decided to build equity. It's those types of pop culture examples that I try to share. That's why we call ourselves pop culture business because we use relevant people in pop culture, relevant companies to show people how cool and sexy business really can be. But again, it goes back to like what you want. It's not easy to sell a company in three years for a billion dollars and it takes blood and sweat and tears and sacrifice and a lot of it doesn't work out. But I think that you have to be able to show these people the outcomes of that so that they're understanding of like, what could the potential be? 100%. From your perspective, when you're doing your investments, you do it for HSR and you do it through personal investments as well. What makes a business sellable? For us creators, we're thinking about what's in front of us. We think about the actual content that we're curating. We want to develop businesses. We ultimately potentially want to exit. But all of this is completely new to us. And so I'm curious from your perspective, what actually makes a business sellable? Sellable at the end state to an acquirer. We're going up here. Okay. I would be lying if I said that in the age of AI, it's going to remain the same because I don't know. But how I have traditionally looked at investments, because there is a trap, great brand name, maybe not the best investment. How I typically do it with consumer brands, let's start there, is if it's a beauty or a food and beverage brand, the first thing I do is look at how big the market it. How big is this opportunity? If it's a small market, the upside just isn't there for the risk-reward profile. That's the first thing. The second thing I look at is who would buy this? And what is the white space in their portfolio? So someone like Elf, right? Let's take that. We just talked about the road example. Elf did not have a brand that was sold at Sephora that spoke to a more. not luxury customer, but someone that was not spending $8 on an Elf product but was spending $35 or $45 on a milk-lazing product. So they had a gap in their portfolio that by acquiring road, they could fill. They also had that same gap when they acquired Naturium, which is body, but that was obviously at a lower price point and it was at all to brand. So the first thing that I do is I look at all of the potential acquirers and I think do they already have a brand that is filling this specific gap in the marketplace? And if they do, the shrinking of acquirers goes down. So we are not in a great M&A market for beauty color cosmetics right now. So these brands that are five to ten years old for color cosmetics, you know, a few of them have tried to go out for sale to sell and there's just not the market of opportunity. And so whenever I'm thinking about an acquisition, I'm really. the first thing I do is market sizing, how big is this market? And the second thing I do is looking at the potential acquirers and do they have the white space in their portfolio that they would spend the money to acquire the customer? Those are the first two things that I do and from there it gets pretty tactical. Then what are the first mistakes that a crater entrepreneur is making? So let's say that a crater who's listening to this right now is like, "I love what she's talking about. I want to go and develop a business one day and I want it to be big." From all of your experience, what mistakes do early founders make, especially if they are content craters? When I look at my portfolio of 20-ish equity positions, the standout companies are the ones that have a founder that doesn't get in its own way. And I often struggle because there can be the best business in the world and you can see so much potential. It's like dating. Business and dating are the exact same fucking thing. Do not fall in love with potential. Fall in love with what is there. And I have founders. It drives me nuts. I want to pull out my hair. I'm like, "Get out of your own way. You are not the right person to lead this company anymore. You need to fire yourself." My favorite founder right now is Diana Cohen. She started Crown Affair. They just raised a series C for a hair care brand. It's a hard time to raise money and consumer. And when she came on my show last year, I said it very blankly to her. I said, "You fired yourself." And she was like, "What do you mean?" And she's like, "Well, I just hired a new CEO." And I was like, "Yes, because you fired yourself." You knew when it was the right time to get out of the way because your skill set was the ideation. It's the building of the world. It's the like bringing this thing from nothing to life. And now it's your time to keep doing that as the founder and as the head of crater and brand. But to have a new CEO come in and actually lead this business to be able to go and build a multi-hundred million dollar brand. When you're someone that's built something out of nothing like most craters have, both of us started on iPhones. I started my podcast on three iPhones. You showed me your broken iPhone 12. You're a magician. You are a magician. Don't let that magic get in the way of also being very critical to yourself and knowing like when to get the fuck out of your own way. A hundred percent. You have to be extremely self-aware. Especially when you have the concentration component and the operation component. I know what I'm weak at. And I think I have the most incredible team behind me in order for me to do what I'm good at. And I always say that I feel as though when we do shoots like this that have the easiest job in the room. Same, I just show up. I just show up. I get to be me. But it's the people behind the scenes. I think oftentimes people struggle with delegation. I've spoken with many craters and many craters who develop businesses who are very afraid of letting go of control. Because for the first time in their lives, they're actually letting people into the way that they operate. For let's say six years they've been creating content. They've been doing it by themselves. They've been thinking about the idea, the execute, the idea, the reap the benefits of the, and they just keep on going in a cycle. If there's a crater founder right now that is struggling with this idea of delegation, they hear you, right? They know that they have weak points. But they're still struggling internally with this idea of letting somebody take it on or bringing people on. What is a good first step for them? What should they be prioritized? What's an opinion or belief that they should hold? Because I know so many craters who listen to this right now need to hear from you. Somebody that has seen it at the highest levels to be convinced. Like, yes, it is time for me to let go some of this control. So I can speak from my experience because I remember when things really started happening. And I was like, I'm not a great people manager. Like, I don't really love like the day-to-day operational execute. I'm a visionary entrepreneur. I'm a community. I'm an investor. Like, I like to, I do not believe that investors predict the future. I believe we discover it because there's a lot of people who are not interested in this. I think that's the right thing to do. just people much smarter than us who are building the future. It's our job to discover it. But that's where I found joy and that's where I was the best. And I am a charismatic communicator. I love to be with people. It gives me joy. So the things that I started recognizing weren't my skill set, but we're going to be the Achilles heel of the business. I realize there is a rule that I need to fill. And it's someone that needs to be empowered. It's someone that needs to be able to be a leader. It's someone that needs to be able to come to me and have tough conversations. They are an equal. And for me, I'm very lucky that ends up being my sister. So my sister was a former accountant. She is a genius. She's an impeccable business leader and impeccable steward of capital. She is an impeccable people manager. And I love to take risks. She doesn't necessarily. And our yang to our yang is so critical for the way that our business operates because I have someone who does not want to do the same things as me. She would hate this. She would absolutely hate this right now. But she gets joy. She's having big business meetings right now. She's at the Beverly Wilshire. She's having three back-to-back meetings with whether it's huge agents or TV development or big investors. And that's where she gets to go and represent what we're doing in a different way. And I think you really have to find someone who has a completely different skill set than you. If you and someone that you work with, that is going to be an equal with you, wants to do the same thing. It is a disaster in the making, a disaster. And you need to have your own lanes. You need to know where you overlap. And you need to know where each other are going to be able to comp my each other. So I can talk about raising money from flight story to our area of the CEO. I love raising money. I love fundraising. I love selling the vision. That's what early stage fundraising is. Like you're selling a vision. And I led those conversations. I led that negotiation. I was the one that was like, I don't want any agent, any manager, any lawyer negotiating for me on my behalf. I'm going to do this deal because I'm a business woman. I'm not just a creator. And my sister, of course, she was on most of the calls. But she's the one once the call is done, taking that and actually executing it into the business and making sure that the manager, the agent, the lawyers are all actually looped into that. But she knows that her skill set is not necessarily what my skill set is. And I think for anyone that's listening, you have to be extremely self aware. You have to know what you're good at. And then you either have to hire for what your white space is. Or find, you have even with some of your companies, an equal partner that you can bring in that's going to offer a completely different skill set. And then you have to trust them. You have to let them go and do what they want and need to do. I can tell you this with 100% certainty. Most businesses that I have seen that have failed is because the founder doesn't know when to get out of the way. And that stems from people management. So who you choose to bring in is the most important thing that you will ever choose. - Can you speak to hiring? 'Cause this is a big part of what we do on a daily basis at this point with so much of creative college expanding we're always trying to hire the best talent. And that means that I'm in these interviews that means that I have to make the decision of, do we bring them on? Do we ultimately give them XYZ position? Do you have any strategy or help that you could provide to me? What should I be looking for as I try to bring somebody on to take creative college to the next level? - I have, this is a very common principle, but higher, extremely slow and fire extremely fast. And when we're hiring people, it is not like, hey, you have a call and it's great and you're gonna be on the team. It's like multiple tests. So for flight story, they have a culture test. This is like already weeding you out if you're gonna be a good fit culturally. I also use something called AkiMax, which is actually matching my personality. The way that I lead, I'm very direct. Like I match exactly the role that we're looking for. Does this person need to be proactive? Does this person need to be able to take feedback really well? My style, some people could call abrasive. It's just very direct and I'm very loud. So if you are very sensitive and you could be the best person for the job, you could have the skills that you could have the experience. But if our personalities don't match, which is what I use a test called AkiMax for, it's never gonna be a good fit for the job. And the other maybe more controversial advice I've also learned from my husband is, I don't need people learning on the job with my company. And when he said it to me, so my husband has a $2 billion fund. And that's tiny compared to someone like Sequoia or A16Z or like the huge guys in the world. And what he said to me that was really interesting as someone who's obviously built an incredible company is like, when you come to work for my firm, we are not training you. You have to be trained because we don't have the runway to have you learn on our dime. And I fundamentally believe that. I'm so happy with the trajectory of my career. I started cute. I started at Salesforce. I then went to a startup but close to going IPO. Then I went to my next startup that was building it with the founder and a co-founder and me in a room. The next startup that I went to, I joined when it had 20 people when I left it, had about 100 and so forth, right? So I've seen a lot of different iterations of startups. And one thing that I fundamentally know to be true is we are not the size of the business where we can afford for someone to learn on our dime. We need people that have some sort of expertise that have a real opinion that can add real value to our company. And one day, if I built a billion dollar company, sure, I would love for you to be able to learn on my dime, but we're not there yet. And so I think it's really important for you to think through like where are you in your business? And if you're young, there is nothing wrong with needing to hire people who can push the ball forward with every single role that you bring on. I worked at a startup where my first manager was used to managing 15,000 people. And when he was required to put a deck together, he could do that, but he could not execute the deck. And I was his only direct report. So I'm like, there was a disconnect between how he was actually going to take his experience and add value to that organization. He's a very valuable employee, but he wasn't the right fit for that role because we needed executors as much as we needed strategists. And so I think you have to be really clear on like, what stage of your business are you at? And then what type of person do you absolutely need to bring in to push the ball forward? - I love it. And there's so much that I'm learning. And something that I've learned a lot from you is about relationships. And I actually met your husband yesterday. And you talk so openly about your relationship together and what he's meant to you. Can you speak to that, to be a creator, to be an operator, to do as much as you do? It requires, I believe, a support system. It requires people in your circle that get your line of work and that will support you all the way through. What is your husband mean to you? - Oof. So my husband is not who I thought I was going to marry. I'll say that first. I, like I told you on my show, I always wore the pants in every relationship. I had the control. I was able to dictate what was important to our relationship, what we would value. And after a while, that was exhausting for me because I think specifically for female leaders, you don't get to express your femininity as much as you want to when you're in your work. Like I'm an extremely masculine version of myself to the point where I constantly feel like, people don't get to see the silly, carefree, feminine version of myself as much because I am very focused on results and vision and like pushing the team forward and creating something bigger than us. And I think being with my husband who is a true alpha masculine, who shares and takes on a lot of responsibility around our house, it's allowed me to be able to express a different side of myself that I haven't been able to have, even from childhood. Like I have definitely had relationships where I was the same version of myself at work that I was in the relationship and I didn't like that side of me. So my husband has given me the gift of being able to have the truest version of myself expressed in a way that I've never been able to before. And I think both of us work extremely hard. It is challenging. There are a lot of things you have to sacrifice. And there are moments where we don't get to spend the time together that other people would. And that's hard because we do have to both work. And I wouldn't have it any other way because for me being able to have an equal and be able to have someone that I can take real advice from and learn these things about what's urgent, what's important. He's been so helpful with my business of like, even understanding that I'm a maker. I'm not a manager. These things that he's learned throughout his career and through being 14 years my senior, he imparts that wisdom on me in a way where, even if it's just over a dinner conversation, I'm able to apply that for my business and that is a competitive advantage. My husband is a competitive advantage and I'm not embarrassed to say that. - I always say the micro-frontus competitive advantage as well because when you think about relationships, it's not even just the fiscal side, it's not even just the business component but we've talked a lot about this. where it's the spiritual, the mental, the ability to carry a safe space and know that that person is in your corner. And for me too, every single time that I post a piece of content, she's the final person that I ask for advice on. I know that you're very similar in the way that you work. This tees up my final question for you. I know so many people out there, the thing that's actually holding them back, tends to not be tactics or strategy, but there's a psychology associated with it. There's this fear of being seen. There's a fear of visibility. And maybe it's childhood trauma, you said, with a lower case of tears. But ultimately, there's something internally that's stopping them. They hear you speak right now. They hear this charismatic, this very confident person that's been able to build something that extends beyond you. Can you help me define what confidence means for the listeners? And ultimately, what is the first step that they can tackle on to be as confident as Maggie? Thank you for saying that I'm confident. I think that it's interesting because to get vulnerable for a second, there are parts of me that are very confident. And then there are parts that are still becoming comfortable with being seen, like the full version of myself. And I think that's why I was so focused on building hot smart rich, the business, because I could still hide a little bit of myself under being Maggie Sellers' Reign, which is the next iteration is empowering myself to be 100% myself. And I say that because I think a lot of people see me speak and I am very confident. And it's funny, my publicist was booking me on Inc. Founder House and I was speaking with two males. And she said, "Are you going to be okay on stage?" Speaking with two males in a male, and I was like, "Don't worry about me, I'll be fine." In this environment, I know the narrative, I know the controls, I know how to act. But I say that because there are sides of me that I'm excited for people to listen to this conversation and then follow along to hold me accountable to like, "Have I 100% come into myself?" So I say that before I answer the question of what does confidence mean to me? Because I think to me now, confidence is being able to show up not only online, but in real life as 100% your authentic self. Someone makes a comment, that's a microaggression, or someone makes a comment that you would normally just be like, "I want to people please and I don't want to upset anyone." No, in that moment, even though it's no one's watching and it's one to one, confidence is being able to show up as 100% yourself and not feel embarrassed or sorry for that. And that extends to being online as well. Like, you do not have to be for everyone, but you also don't need to people please to try to be for everyone. And so to me, being confident is no matter what the situation is, it's showing up as that 100% authentic version of yourself and not caring at all what anyone else is going to think about you. This is where ethos overlap. The idea of being the niche and being on a polygenic about it, you are changing the industry as we know it, right? The ultimate vision of creator ownership. And I know that I said last question, but I'm just going to do this here because we had this conversation yesterday. You talked about having people follow along your journey and to keep you accountable. I know what this next step is, but could you verbalize it to the world and what is that commitment that you're making this next chapter of your personal brand? So when you came over yesterday and this was sadly off the camera, but you described the creator vision framework for me. And I've been really good at creating the types of content that is educational and maybe aspirational and has shown the achievements. But I haven't really been able to walk people through the full storytelling narrative of the pain, the pursuit and the payoff. Yes. And that is the next iteration of really being able to show people like all the times the doors were closed on me, all the things that I've really overcome, all the bad relationships that I've been in, the dynamic that I've even had with my family, all of the things that I've been through, people still only know pieces of it. And I'm very excited to apply your creator vision framework to really bring people along on the journey of showing why this is so important for me and why this keeps me up at night and why I choose this over, like, traveling everywhere and just like being offline and not having to deal with the negativity because I think that is the next unlock of me and of Hot Smourich. You heard it here first. Maggie's road to a million followers starts today. Thank you so much for your time Maggie. Thank you so much for having me at the best time.

Podcast Summary

Key Points:

  1. Maggie's boss at Salesforce told her to change her voice inflection to be taken seriously, which was a painful but formative experience.
  2. Her mission is for women to never settle in any aspect of life—relationships, finances, business, or personal fulfillment.
  3. She learned the power of equity early through employee stock options, later trading salary for equity and investing in startups.
  4. A viral TikTok about a celebrity-brand deal was taken down after the founder asked, leading her to build a personal platform for creative freedom.
  5. She realized her personal brand was too achievement-focused and is now working on storytelling and relatability.
  6. She uses the AI tool "Clawed" (likely "Claude") for personal branding rules, calendar optimization, email management, and decision-making.

Summary:

Maggie Sellers recounts how a boss at Salesforce told her to change her voice inflection to succeed, a painful moment that shaped her mission to help women never settle in any area of life. She emphasizes the power of equity, learned from employee stock options and later investing in startups, often trading salary for ownership. A pivotal moment came when a founder asked her to take down a TikTok about a celebrity-brand deal, which felt like a death sentence to her business.

This pushed her to become a creator and build a platform where she controls her narrative. She now runs "Hot Smart Rich" and prioritizes her personal brand, recently shifting from highlighting achievements to sharing her journey, using storytelling to connect with her audience. Maggie also relies on the AI tool Clawed for personal branding rules, calendar management, and email summarization, which helps her focus on important tasks over urgent ones.

Her mission remains clear: empowering women to dream big and achieve financial freedom, business success, and personal fulfillment.

FAQs

She was asked to take down a viral TikTok video about a deal she worked on, which felt like a death sentence to her business. She then decided to build a platform so big that no one could control what she posted.

Her mission is for women to never settle in any area of life—relationships, friendships, financial freedom, business, or how they live their lives—by making hard decisions to feel proud.

She learned through an employee stock option plan at Salesforce, which sparked her interest. She later cut her salary in half at a startup for more equity, and that company went public, deepening her understanding.

She advises them to understand that they don't have to be for everyone, but they also shouldn't people-please to try to be for everyone.

She realized she was only known as the face behind Hot Smart Rich, not as herself. A recent event where a celebrity called her 'the Hot Smart Rich girl' made her see the need to reposition her personal brand to build community and leadership.

She uses it for personal branding rules (e.g., outfits), calendar management (e.g., scheduling based on her cycle), summarizing emails to highlight urgent vs. important items, and drafting responses.

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