S3E1: Ciara

Welcome to The Room Podcast. My name is Madison McIlwain and I'm a partner for seed stage investments at DefyVC.

And I'm Claudia Laurie, a co-founder of Pryve. We're a founder and funder who are in the room where it happens. If you're a first-time founder or an emerging venture capitalist, We're glad you found us. We share inspiring, authentic, and insightful stories from founders, funders, and operators who have been in the room and provide tactical feedback on their early aha moments and learnings along the way. Before we dive into this week's episode, we have a short message from our partners.

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We're excited to kick off season 3 with a very special guest, Ciara. A Grammy Award-winning artist, Ciara has built a name and an empire for herself through talent, grit, and generosity. Ciara has, of course, brought us iconic songs such as "Goodies," "One Two Step," and "Level Up." She's also released a total of 7 albums, since the age of 19. You may not know that Ciara is also the founder and CEO of Beauty Marks Entertainment, through which she produced her most recent album. She has continued to take the road less traveled as a songwriter, song producer, and leader in the music industry. Not only is she an entrepreneur, an inspiration in music, but she continues to expand beyond her roots. Today, she is the co-founder of the House of Love, Respect, and Care, and the Why Not You Foundation with her partner, Seahawks quarterback Russell Wilson. There seems to be nothing she can't do, and it was an absolute pleasure to dig in deeper on some of her early experiences in music and discussing her vision for the future of empowering more women like herself to fulfill their dreams. On today's episode of "The Room," we explore insights and themes such as digital media's transformation of the music industry, having a level-up mentality to your career, and surrounding yourself with people aligned to your vision. We certainly left our conversation asking, why not us?

And we hope you do too.

Let's open the door.

Hi, Ciara.

It's so wonderful to have you joining us in the room today.

Hey, I'm excited to be here. Thank you guys for having me.

But we're gonna get started with kind of part of your early career and taking us all the way back to your early days in the music industry. I think almost all of us know that Your first single was "Goodies," but I didn't realize in doing my research coming into this conversation that you actually co-wrote the song. Has being a singer and songwriter always been your passion?

I've always loved both equally, and obviously music came first. Just the pure excitement and feeling that music gave me was always special. And then obviously when I learned how songs were created, I definitely thought, "Maybe I could write some of my own songs one day." And it's been a blessing. It's— I don't think it's something everyone can necessarily do from the beginning, so I know that it really is a blessing and a gift that God that God has given me. And I was writing very early in my creative process. So it's always been very, very important to me to be able to express myself. When you write your music and you're part of the process, it allows you— for at least for me, it allows me to express myself in my truest, truest form of who I am. When you're listening to my songs, you actually are getting a good bit of who I am through my music. It's not just about me singing a song.

I love that. I think that's a untraditional type of founder that we, we typically interview tech founders or people in that bubble, but you've been a song founder and writer really your whole life. And we're gonna touch more on this later about how today you're a CEO and a board member and the definition of an entrepreneur in so many categories. But outside of the song and music world, did you ever think you would go on to become a founder in other capacities?

I've always had a big vision. I've always been a big thinker. So that's just been who I've always been, that girl since day one. And I used to say when I was younger, because I never really got to have a true legitimate 9-to-5 job, the way my career took off and started, I started right out of high school. So I never really got the true opportunity. I think a lot of my fans know, but some people may not know, is that I had a strong desire and passion to do hair. And I always said that, like, what do you want to do when you get older? First I thought I wanted to be an attorney, and then I was like, I don't want to do that. And then they were like, what do you want to do? I think I'm going to run hair salons. I think that's what I want to do. I love doing hair. And so I've kind of always had an entrepreneurial mindset. I've always had a curiosity for it. And it wasn't that I was just gonna do hair, I was gonna own a lot of hair salons. So that was always my attitude and how I kind of thought of things. And so I guess you could say I've kind of always had that entrepreneurial spirit and the desire to create and run my own company. I just wasn't quite sure exactly what it would be. That's the spirit of who I've always been.

I love hearing that. I think it's interesting. On our show, we have different people. Some people say, I've always, I've been born to be an entrepreneur. Ever since I was a little kid, I was running lemonade stands. I was wheeling dealing in the neighborhood or looking to start hair salons. But then other times people are like, no, this was never gonna be me. This was not my path.

I actually don't know how I got here. And so it's cool to see that today, looking back, this was just a part of the journey for you.

And we're excited to touch on some of those more traditional business founding experiences later. But take us back to the release of Goodies. I just, you mentioned it was just right out of high school. I can imagine your life changed quite dramatically, really quickly. Maybe tell us a little bit what it was like being a young woman in the music industry in the mid-2000s.

Oh my goodness. It was super exciting. Big dream come true for me because I really did, I always had a vision of becoming an artist and my ultimate goal was to be successful. And so it was a blessing to be super successful right outta the gate. And I'll tell you a funny story. I was at my graduation the year before I put out goodies. And at that time, they sent cameras with me, cameras to follow me because I was already signed to Arista Records. And so the idea was to kind of trail me on my journey as I was about to enter the whole new world of the music industry and putting out music and releasing albums and all that good stuff. And they asked me on the camera, they said, Sierra, where do you see yourself a year from now? And I was in my country, super country Atlanta accent. So I said, I see myself having number 1 song on the Billboard chart. And it's kind of crazy because there's really a power to manifestation. I really believe that. I always say, when you speak, you have a chance to tell your life story. So when you speak, say great things. And literally a year later, my song "Goodies" was number 1 on the Billboard charts for 8 weeks long in the 2000s. It was really exciting because I came in on the cusp of when digital started to impact music. So I got a chance to have— the experience of the old school traditional way of releasing music where there was a physical CDs were just as important, or they were the only way. And then obviously vinyl before that, and still vinyl was in the mix. It kind of, kind of started to become a bit more of a special item for people to have vinyl because that was starting to change as well. DJs mix differently on different boards now. They don't need vinyl the same way they used to. And now that's kind of become a specialty item as well. But I entered, I started Goodies was the last song of mine that was, at least in the beginning of it, was in the physical, physical CD space, and digital was really new. So the Spotify, Apple Music, and all these different musical music platforms were fresh, and your— the way that your song performed on a Billboard chart wasn't impacted so much by the digital performance. And so when I put out my song One Two Step, that song was in the mix of, okay, now digital performance is going to impact the performance of a record. And so I got to witness the old school or the, the more traditional way of how music was released and digested, and then also the new school way. And I really feel blessed because I do believe having that knowledge about the old school way of doing things really prepared me as an artist. There's things that we used to do back in the days that they don't do so much anymore. Artist development. I didn't grow up doing music from the beginning, in the beginning of my life. I literally started my vision, my idea to become an artist when I was in high school. So I always tell people, your dream is the possibility, or just where you come from doesn't determine how far you go in life, and your dream starts and ends with you. And the moment that I began to envision myself doing this, it started to become real. Especially on the entrepreneurial side, I feel even that experience from way back then has— it empowered me. It prepared me for all that I'm doing now.

Thank you for sharing kind of those impactful moments in your career. I think it's honestly so cool that you had that video footage that your label started recording right before you released your first album and started releasing albums. I think being able to get those inklings that something really big was going to happen is pretty special. And a lot of times we ask our guests what was an aha moment in their career journey or a moment when everything clicked. When did you realize you had made it as a singer, and what did this realization unlock for you personally and professionally?

The moment that I realized that I had made it probably was— I don't know if this is really the most— the best answer because there's a— I think there's probably a couple of moments, they're just not all coming to my mind. But I definitely can say winning a Grammy was pretty huge. At that time, it was the ultimate goal, the ultimate place to get to. It's the highest award you can get. To acknowledge your success and to celebrate your success and to cement it? Well, I definitely felt even more motivated. I definitely say it's kind of interesting when you, you meet that opportunity or that moment at such a young age and also at such a young time in the process. But I really felt the only way is up. Now that time has gone by, I would say that the definition of success looks a little different. So, back then it was, I wanna get this. Oh, I can't wait to get a Grammy. But now it's, you realize that there's more than one way to cement your success or to define or celebrate and yeah, to cement your success. There's just more than one ways to do it now. Right. And there always has been more than one way, but when you're at different stages, you have a vision of what that looks to you. And success means so much. It means so much more. And it, I would describe it differently than I would back then. And so— but I definitely felt inspired. I felt the only way is up. And the world was moving really fast. So I honestly— I wasn't even able to fully soak it in because in the beginning for me, it was— first song was number 1. Second song was top 2 song. Third song was top 3 songs in the world. And so when that's happening, the world's going really fast. So you're just trying to stay— you're trying to keep up and also stay ahead. So I was just— there were so many things I was focusing on. And ultimately, I, if I look back at it, I think that the vision that I had, it's, I'm exactly where I env— would've envisioned myself. And I believe I'm exactly where I'm supposed to be in my process of it all.

Certainly seems that period of your life was a catalyst to keep leveling up. And we're going to touch on that a little bit more in a second. But first, we had to ask a couple of questions for you. Did you invent the one-two step?

I have to credit Missy for that. Well, she and I, so it's funny because with one-two step, I got surprised— it was a surprise to me that she and I was going to do a song together. So it was one of my dreams to do a song with Missy Elliott. And at that time, I was working with the producer Jazzy Fae, who was a big part of my first album and just me getting started in front of the world. He was a phenomenal producer. And at that time, he was producing hit after hit after hit. And he knew that I wanted to work with Missy. And so he got in contact with her team and sent her over this beat. And then she sent back— a demo to the record. And so "One Two Step" was actually in the hook of the record. And then I kind of jumped in. And I guess you could say I co-wrote the record with her from afar. But first of all, I was taken aback that it was Missy coming through my speakers. I'm, what the world? This is crazy, because I really wanted to work with her. And then she had the words "One Two Step" in the hook. And it was a bit of a different melodic structure to that record. And then I just kind of jumped in and— tweaked some things here and there, and then added my touch to it. And so the words— so the theme of "1, 2 Step" was in the record when she sent it to me. But visually, I was a part of creating the "1, 2 Step" dance. So yeah.

And that has definitely blown up, especially with newer creators. I'm sure that was probably a really sort of special record for you. Could you tell us what your favorite album out of the 7 was?

It's between my first album and my last album. It's between Goodies and my last album, Beauty Marks. Both songs— both albums are significant to me and in my life and in my career. With Goodies, that was how it all started for me. And I remember being really young and writing on my goal sheet that I wanted to sell 3 million albums. That was one of my goals, to sell 3 million albums once I got discovered. And I was really blessed to sell 5 million albums on that album. So that was really motivating. And then fast forward to now with Beauty Marks, now that I'm running my own label, And that's another dream that's come true for me. And it was really a huge success to have songs level up on that album and also to just see it all come to fruition and to see myself putting out an album under my own label imprint. I felt really empowered and really proud of that moment. And the idea behind Beauty Marks is that all the scars you get from the obstacles you face in life are your beauty marks. And it's, it's really significant for so many reasons. So I, I think it'd be a tie between Goodies and Beauty Marks.

You mentioned Level Up, and that's also the name of your Apple Music radio show. Tell us a little bit more around the concept behind leveling up and what really inspired you to write this.

Yeah, I was inspired by my life journey. To level up was— the idea was to motivate and hopefully encourage others, myself, everyone out there to be your best self. Don't settle. I kind of had some of my level-up-isms. Be your own boss. Haha, take risk, just different things that came to my mind that were the definition of how you level up. Be fearless, being your best you, being you, dropping dead weight, removing people or whatever it may be that get in the way of your vision and your journey and people that don't align with you and who you are and don't add value. Drop that dead weight. There were all these different things that I thought of that were synonymous with the idea of leveling up. And I was also 8 months pregnant when I was making that song and also making my album. And that felt pretty powerful to have my little precious Sienna, my little princess, in my belly. Also that she— it was a she. And there was my first girl. And so there were so many thoughts running through my mind. And I just felt putting that energy out there. And my ultimate goal was to inspire others. And it was just how I looked at my life. I felt if I reflected back on my journey that every step of the way, even in the midst of the not-so-pretty moments and the not-so-pretty part of my journey that I was always trying to find my way to level up. So yeah, I wanted to pour it into the form of— I wanted to make it in the form of a song.

Thank you for sharing that. That's really just an inspiring story and a message that I'm sure not only your children but many other kids will continue to take with them hearing that song. And that song has really found its audience on emerging dancers and creators on TikTok. What's your take on these platforms for future creators?

Oh, it's amazing. It's a whole new world. It's a massive world too. It's really cool though, because these platforms, they are a huge asset and support to artists myself, or every artist, right? It's really cool because when you see all these creators being creative to your song, it just only adds more life to the record. And I think for me, with Level Up in particular, my mission was to impact. And so it makes me feel— and also I want to make the world dance. And so when I see people dancing to my music, that brings me the ultimate joy. It brings me the feeling I can't even put it into words because it's really a dream come true. And it's kind of wow. It's amazing to see how many people have been impacted on the journey. Even doctors doing their own Love Love videos. Not only seeing the dancers and creators, but just people that— doctors, nurses, I mean everyone, grandmas, little girls. When you see— your songs impact everyone, every age, every person, it's pretty powerful. It's pretty— it's inspiring. And I'm motivated. I'm like, OK, how can I make another record that can have the same impact? And it's a blessing to be doing this 15— as you mentioned, 15 years. And that's not including the other years that I had to get to that point of putting out my first album. So it'd be like 19 years doing this thing. But it's a blessing. And it's so funny you mention that because I have another song now called Got Me Good. That's supposedly really blowing up, blowing up on TikTok. And I'm about to go do me a TikTok video myself.

I love that. I definitely watched a couple of those Level Up videos myself. They've come across my feed.

I think I've seen the doctor one, which was really fun.

We talked about you releasing your 7th album, which is Beauty Marks. But what we didn't touch on is that you're actually the CEO of Beauty Marks Entertainment, which is your own music label that you started yourself. What prompted you to start Beauty Marks the label?

Well, it was interesting because I, I'd always had the dream to create my own record company, but I started to desire it even more because I was having kind of bumping heads with the major recording system that I was in at that time. And I'm like, gosh, it's so hard to always have to wait on someone to make a decision for you. I know the answer. I believe I know the answer. No, I know I know the answer. And I just want the opportunity to put the music out when I want to, how I want to. And so I was kind of getting frustrated with that process of having to wait for someone else to make a decision for me or to say if something's okay or if it's not. And then I was having conversations at the time with a really cool friend of mine that I will forever be grateful for, a guy named Monte Olson. And we talked about just the power of when that opportunity would come, what it would be to be able to run my own label and just how it works on the business side. And just kind of learning that, the power of owning your masters and everything. And I'm like, gosh, I look forward to that day when that can happen. And then I also have to give my husband a lot of love and credit as well to my my thought process because Russ was in it with me. And he could feel my frustrations and pain more than anybody else. It's just my desire being able to put music out and do it how I want to. And so we were up late nights studying people, people that create their own record labels. There was Frank Sinatra. I mean, there was so many artists that you didn't even know they were doing it themselves. And why not me? Why not? We can do this, right? And so crazy timing and how it all worked out. I had my last meeting with the label, and that was to kind of play my project and present it and say, I have this song, Level Up, the video and everything, and this is what I envision. And they just didn't see the vision, the same vision that I had. They didn't see the vision in Level Up, and that was my moment. And so I had the dream to run my own label, and my dream came true in that same breath, in that same moment. And I took off running. I asked for my masters back, and I thank them because they gave it back to me.

That's such a good reminder to entrepreneurs everywhere who get a lot of nos. And in this case, the no was to Level Up, which is a now iconic song that we just talked about impacting hundreds of millions of people on platforms like TikTok and through channels like Apple and Spotify.

And if the world didn't have Level Up, I mean, I think we would all be very sad.

So I am just in awe of your can-do attitude and the why not me question asking. Um, that empowered you to go after building your own business and becoming a CEO and founder through Beauty Marks Entertainment. And I was doing a little bit of research on how rare it is for women in the music industry to be such owners of their own career path. And according to USC Annenberg Inclusion Initiative, about 17% of recording artists are female, which is so much lower than I thought in 2017. And meanwhile, only 2% of music producers are women. And only 12% of songwriters are women. So I'm used to seeing these kinds of low numbers on the technology side of the world, but it really did surprise me when some of my favorite artists are female, that this is also true in the music industry. And so my question for you, Sara, is really, you've been in the minority now as both a female producer, a songwriter, and then let alone a Black woman in the industry. How do you think about building a better future for your adorable daughter and sons?

That's a really good question. You gotta stay fast on the mission. I can't let off of my vision and the things that I wanna do. And I do think that when people see examples of how someone persevered or how someone believed in their vision and committed to their vision and was fearless in the process of achieving their vision and, and goals, I think that's a great example, right? I think about women before me. I talked to my good friend, Missy Elliott. The other day on my Level Up radio show. And she was telling me how when she had the opportunity to start everything, it kind of just actually— the timing for her was she was also prepared for a really cool moment that she didn't know was going to happen. But she got the opportunity to get on a song. And then once she got on this song, everything took off from there. But she was telling me how when she was getting— they call it a bidding war, where so many labels are coming to the table because they know that this person is going to be a star. This person is going to be big. We want in. This is what we wanna spend. We wanna pay, we wanna, this is what your deal is gonna be. We're gonna pay you X, X, and X. So there's a bidding war from all these labels. And she said when she landed on the place that she wanted to be at, she said, I'm not gonna do this unless I can have my own label. And I think about how powerful that was because that was back in the days when it was even more, the percentage numbers that you just said were less. And I love that she was fearless. I love that she was a risk taker. I love that she, stood for her vision and her self-belief and who— and believing in herself. And so I think that women like her, if it wasn't for women like her and just women that have really stood firm in their vision and their beliefs, if it wasn't for those women, then I wouldn't even have the opportunity, right? So I think about that. And I want to— I too, I want to take that same stance in everything that I do. And I think that leading by example is going to be one of the best ways for my daughter to see I can do whatever I believe I can do. I really believe that when we walk into rooms, especially rooms with, with men, I don't think I even realized the disparity. I don't think I realized the difference, to be honest. That's how committed I was to my vision. I think you have to kind of be that way. I think if you think so much about who you are in a room, sometimes you start to overthink the process. Hey, yes, I'm aware that I am the, one of the few representations of females in this room, but at the same time, I'm not gonna be so focused on it that I get distracted on what my ultimate mission is. And so, I think that you gotta have that attitude. You gotta have a vision. You gotta believe in that vision. You gotta believe in yourself. I always said all it takes is one person to believe, and that person is you. And if you have that, there, there's the opportunity. And so, I just think it's important to continue to lead by example. And then when there's opportunities, being here with you girls in the room. I think that these platforms, whoever it may reach and touch, whether it's— if it's just one person, we've done something. And so I think that it takes all of us to come together and to commit to all that we know is possible within us. Because everything that you want to do and become and achieve, it's in you. You just have to discover it and know. And once you figure it out, go for it. And don't let off. Don't let off the gas on your vision. It takes all of us. That's the light that will shine back to the other young girls that watch us or that watch me and say, oh, she did it, I can do it. Because I didn't grow up with having a lot. I said to you earlier, music isn't— it's the foundation but not the limitation. And coming from where I came from, I still had this massive vision of where I wanted to get to. And so I think that what's important also for girls to know that I said your dream starts and ends with you. It's within you. So it's what do you want to do? If you want to do it, you can do it.

You're feeding my soul right now with this wisdom, Ciara. Thank you.

And as you were talking about going into this, these rooms, sometimes when you're the only woman there, something you said to me a little while back was, you have to play the game to win the game. And I feel like you've really been playing the game in all the right ways and found yourself at the top.

Thank you so much. I really appreciate that. Yeah, you do. You have to be aware of your surroundings. I say you gotta play the game to change the game. Yeah. Play the game to win the game is great too. You gotta play to— you wanna play to win. But yeah, I think it's— I always say there's more, more than one way to skin a cat and to get things done. And I think that you just have to, you know, know your audience, like know where you are so you know how to communicate to whoever you're speaking to. And sometimes there's also a way to get things done without— like I had to learn as a woman, we're emotional. So, and when I started, I was super sincere and I, I still am, but there's some moments where you gotta leave that at the door. You can't have like emotions at the door. People can't hear emotions sometimes, especially when you're dealing with men, just to be honest. They gotta like— you gotta have your facts right, and you gotta be firm on your facts. And I've had those moments where, yes, you know, I, I may have been called a bitch behind my back, just to be honest, because I had an opinion. But I mean, like, you know how they say she's like— there's that saying like for a woman, she's a that, because you have an opinion. There's those moments, but then also you, you learn the power. You learn about the power of who we are, what we possess as women. Like we're very powerful. And so you got that. And then you also learn when you're in certain spaces or environments, like, okay, you know your audience. And sometimes you don't have to— there's a way for you to deliver, deliver a no without saying no. Sometimes there's a way for you to deliver, I don't that without saying, I don't that. So it's, you figure that out, you start to understand that, and then you're, you're able to lead in the process. That's ultimately leadership, right? You know, I always say good leaders, they know when to lead, but they also know when to follow. And so it's a combination of all of that. It's to play the game to change the game. Sometimes we may walk into a room, we, we're so honest and honesty is great, but there's a way to convey your honesty to whereas you can get the other person to understand it. There's a time and a place to express yourself in certain ways and know how to express yourself to really get the job done. And so it took me some time to figure that out. And yeah, it's been, it's been awesome though, to kind of adopt that habit or philosophy.

Well, you're changing the game in so many different contexts. Obviously, we've talked about all you've done in Beauty Marks, but we want to switch— and your whole career, really. But we want to switch gears a little bit to talk about the announcements I'm seeing coming out about you every week. And I think one of the biggest ones has been the launch of your fashion house over the past couple of months, the House of Love, Respect and Care, which you're partnered with on your life partner, Russell Wilson. Tell us a little bit more about the House of LR&C.

Yeah, the House of LR&C has been really fun. Both Russell and I, we launched our fashion house and we have a really amazing partner in our president, Christine Day. She helps us keep it all, put it all together. She actually was the, she's the former CEO of Lululemon. She helped, you know, start Lululemon and also other companies, Starbucks. And that's also really cool. Talk about girl power. It's been really fun working with someone like her. And both Russ and I have a strong passion for fashion and we also have this same strong passion to impact. And so we're on a mission, obviously it's through fashion, but again, the ultimate mission is to hopefully be able to impact everyone through fashion. And we have, we also adopt the philosophy and model of we give, we give away 3% of the proceeds. We give away first before we make any money. We're that kind of company. And we give the proceeds to our foundation. It all goes through our Why Not You Foundation and where our mission is to inspire the youth to lead with the Why Not You attitude. And it's been really amazing to be a part of incredible organizations, Friends of the Children, where you help provide a mentor for a child in need of education, and that's least likely to succeed. But the success rate of organizations, Friends of the Children, have been amazing because there's a 98% success rate. And to see these kids grow and have an opportunity to have education and then go off and be successful is pretty phenomenal. We also have our Why Not You Academy that we just launched recently as well. It's a charter school. And so being able to, again, empower the youth and provide that opportunity, that access and equity has been amazing. And so— and also we've been able to be a part of helping— helping be a part of raising money to cure cancer. I was going to say cure cancer, but to be a part of raising money to cure cancer. It's been a blessing. And to see that, to see the success in that world has been amazing, especially through immunotherapy. I say all that to say we have a passion for fashion, but also the same amount of passion to impact. And the idea is building a foundation on love, respect, and care. And we are a B Corp pending company. Sustainability is very important to us. Again, it goes back to impact and also being thoughtful and wanting to make a difference through fashion as well, I would say. And so it's been really fun though. It's been, it's been, we're learning so much in the process because there's, there's a lot of stuff on the back end that you don't think of when you think about creating your own fashion line or company, and in this case, a fashion house. But we've been really enjoying ourselves. We have Goodman Brand, which is Russ's company that he started years ago, and it's top 2, the top 2 men's line in Nordstrom, and, and it's also just rocking in general. And so that's been amazing. And then also we have Human Nation, our most, our newest brand that we've launched under the fashion house, and it's a Gen Z streetwear brand. And it's been really fun doing that. And then there's some other cool things that are brewing that I can't wait to share, but it's been a lot of fun.

Awesome to just see you go after the things that you're passionate about. And you mentioned a lot there, and I think there's a lot to unpack and we don't even have time to discuss all of the incredible initiatives you're involved in. So we have House of LR&C, we mentioned earlier, you have your own radio show, Level Up, on Apple Music, and of course the Why Not You Foundation and Academy. The work you're doing specifically with Why Not You really aligns with our goals of The Room in opening the doors so that more folks who are not traditionally exposed to certain conversations or certain pieces of knowledge can then go inside The Room and really pursue what they're passionate about. Can you tell me more about what you're doing more people to be empowered and asked, why not me?

And I think it goes back through our, our Why Not You Foundation, just really being consistent with that message and Again, I think my journey is a great example of why you have to say, why not you? You know, if they say, why not me? Again, I didn't have much growing up. I was a military baby, so it was a blessing to be able to travel the world because of that, but we didn't have much in our journey. But man, I had a big dream. I didn't have a lot, but my dream was pretty massive, and I believed in it. And so I think that that's just a simple fact of it all. You just have to simply ask yourself that when you're trying to think of something. No dream is really too big. To be honest. Some things now we can't get crazy. We know it's okay. That's just unrealistic. When I asked myself before becoming or deciding I wanted to be entertainer, I was running track in school. I was a fast, I was fast, but I wasn't the fastest girl on the block. So I was like, I'm not breaking any records. So we know I'm not gonna say, why not you go and be an Olympian? Because that's just not realistic. You have to say, you do ask yourself in the process, why not me? There's a lot of firsts in this world. How does someone think of, how does someone become the first to do like, oh, it's like creating a light bulb. Like how do you think of creating a light bulb? Like that's a big vision. Well, if that person had to be, why not? Right? So, I just think about those many, those many moments and within myself. And so, I just, I think it's important just to encourage every young woman out there to know that, as I mentioned earlier, you have all that it takes, everything that you need to thrive and survive and achieve your goals. It's within you. You just have to channel whatever those goals are. You have to channel your vision of what you want to become and do. And literally write those goals out, speak life into those, to your plans, and go after it.

The year that I graduated from high school, Sierra, was the year that the Seahawks and Russell Wilson, they won the Super Bowl. And so I, on my high school graduation speech, my whole speech, we're obviously huge Seahawks fans in the McIlwain family.

I wrote about why not us?

And I took Russell's coining phrase there and I said it to over my all-girls high school. Why not us? What are we gonna do? And I still love that phrase. And thanks to the way that you and Russell have been amplifying that vision, and I'm so excited for more people to be asking this question for themselves.

Hey, that's awesome. I'm excited too. That's, that's motivating to hear you say that again. It's really powerful and it's real, but why not you? Why not you be able to go out there and do all that you wanna do? Why not you dominate in Silicon Valley? Why not you have an incredible podcast called In the Room? Both of you girls. Why not, right? And it's real, right? So you have to believe it.

You mentioned something around being the first to do something, and I just, for myself personally, made a bit of a career change half a year ago and am now starting my own business and, and doing things for the first time, like quite a bit. And I think just even hearing you say, why not me? I can just hear and reflect on so many moments in that founding journey where I had those questions and eventually got to the point where I was, yes, why not me? But even people who have been hearing those messages throughout their life need to be reminded how real that is and how you should just go after it. So to echo Madison's earlier point, this conversation is definitely feeding my soul and I'm going to leave this a lot more just refreshed and motivated to keep chipping away at what my vision for myself is. And to that, I think a lot of this conversation is going to resonate with a lot of our audience. And a lot of young women who are starting their careers. What advice would you have for them and what advice would you have given yourself at the onset of your career and journey as an entrepreneur and artist?

Yeah, the advice I think is you gotta have patience. Oftentimes, you know, we wanna get to exactly where we wanted to get to right when we want to. And I think that you just have to be patient in the process. I think that's so important. I, I think that's one of the words that really resonated with me, especially after having kids. You have to have patience. Kids, boy, they will test you. So I would say that having patience is so important. You would hear them say patience is a virtue. They would say that, I'm like, okay. And then you go through life experience and you're like, it really is. So I would say that and trust the process. You gotta trust the process of your journey. It's not gonna be all— it's not gonna always be pretty. I think knowing that going into it is important too. We all can have high expectations for a situation and for ourselves and our dreams that, but you gotta know there's gonna be a process to it all and you gotta trust that process. So those are two things that I would think about that, that, that I could say to my younger self, be, be patient and trust the process and also enjoy the moments as they come. Like I said, you guys, when I won a Grammy, it was definitely an aha moment, but it was also, the world was moving so fast. So I was so focused on my next move. I was so focused on the next thing and It's also healthy to enjoy the process, to enjoy the moments as they happen because you can't get them back.

Well, we're definitely enjoying this moment right now. This is a very fun one for us. And as we come up on time, Sarah, I wanted to ask you our hero closing question, which we ask everyone on The Room.

Who is the woman in your life that has had a profound impact on you and your career?

Oh man, that's— That's tough. I mean, I would say we talked about her before this podcast happened, but I would say my best friend, Yolanda Frederick Thompson. She's my makeup artist, and I've known her since I was 16 years old. And you guys can do the math on that, whoever's listening, because I'm not going to tell you how old I am. But it's pretty amazing to look back, and I feel she was heaven-sent. I really do. When I think about when I first started, my mother and father, they were amazing, but they didn't know the music industry. And they were learning it as I was learning some things. And there were some parts of the business that I actually ended up probably learning even quicker than they did because I was in it and I had to still kind of run things even then. But I would say that Yolanda, she, she was amazing. She's amazing because she's almost double my age, not to mark her age as well, but she looks, she looks, we're pretty close in age. She does. She takes really great care of herself, which inspires me too. She was, I was a single mom at one point in time and she was a single mom too. And who would've known that her journey would've helped me out when I, when I came to a certain part of my journey and just her intelligence, her, her wisdom, just how she, her daughter, she went to Wharton and to see that success in her journey, it's motivating. Again, why not you? Right? You go back to that place. And so I just think to see all her great, to see all the, the great things that she's done and to see how she loves others, how she cares and how she's so She's very headstrong in her vision as well. And so there's women like her that motivate me and inspire me. And so gotta shout out Yolanda today for being the amazing woman that she is.

I love that.

Thank you so much for sharing. I, I know firsthand in my life, the, the power of female friendships has brought me, it's brought me into this room with Claudia and this room with you. And so I love that, that you're touching on that power in your own life.

I want to encourage every woman, shall I say, to just really tap into your inner self. Take a moment to pause and reflect on your journey and reflect on where you are, where you're trying to get to. If you're in a tough moment, that moment is temporary. Adversity is temporary. And so remind— I want to remind every woman about that. And okay, cry through it, hurt through it, and you're going to get through it. And then reset, self-evaluate, self-love. Self-care is the best care. Love on yourself. Take care of yourself, and then you set yourself up for the, an incredible amount of opportunity to go and do everything that you want to do and to, and, and be everything you want to become. So thank you guys for having me. Thanks for having me in The Room. And this has been awesome.

Thank you for listening to this episode of The Room. If you're new here, please subscribe and write us a review wherever you listen to podcasts. We've had some pretty incredible guests over the past two seasons, so also go check them out. We'll be back next week with an all-new episode, Tuesday, May 11th, 10 AM Eastern, 7 AM Pacific. See you in the room.

All opinions expressed by Claudia and Madison and podcast guests are solely their own opinions and do not reflect the opinion of The5AC. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

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