Why I Left My Hollywood Dream Job To Become an Entrepreneur

Speaker A: I ended up chartering a 747, filling it to the brim with pajamas, and we saved Christmas.

Speaker B: Little Sleepys is a bootstrap D2C sleepwear brand with a community of over 2 million customers built almost entirely on product quality and word of mouth.

Speaker A: All of a sudden, I had wait lists with thousands of people on it. It's the worst, best problem to have.

Speaker B: Today. Meredith's here to talk about validating a product before spending a single dollar on ads and what it took to hand off the CEO seat. Meredith, thanks so much for being here.

Speaker A: Thank you for having me.

Speaker B: You had this, like, what I call, like, a very big girl job before this. You had a very serious career. I did film, yes. You were VP of development and production for Universal Pictures. This is, like, as somebody who comes from this world, also, like, a lot of people's dream job.

Speaker A: It was my dream job. Yeah. I felt like for years that I had my dream job, and I loved it so much, I thought I was gonna run the studio. One day. I was all in, and the business started shifting. Right. As we've all definitely seen by this point, I had kids, and suddenly the constant travel and the late hours and all of that wasn't as glamorous as it once was. Just my priorities changed and Fast. Fast. Yeah. And I also realized at a certain point that I, uh, was starting to be on autopilot, and I wasn't being creatively challenged like I was before. And I just started thinking, like, is there something else that's gonna fill my cup more?

Speaker B: So you go on maternity leave for your second child?

Speaker A: Yes.

Speaker B: There's something kind of marinating of, like, maybe there's something else out there for me.

Speaker A: Yeah, that's exactly right. I always considered myself an entrepreneur.

Speaker B: You did?

Speaker A: I did. Yeah. So did my family. From the time I was little, I was always creating businesses. What was your first? Oh, my God. My first was built almost entirely, actually. I was six or seven.

Speaker B: Today, Meredith's here talking about.

Speaker A: I would take a large branch stand in front of my house, on my street, and I would stop cars and make them pay.

Speaker B: Me, a tool Masters, your companion for starting and scaling a business.

Speaker A: You weren't even, uh, hustling anything? No, no. Just to drive through.

Speaker B: That's a grift.

Speaker A: Yeah. Yeah.

Speaker B: Right, right.

Speaker A: Yeah. From an early age, I had this, like, hustle in me. I don't, uh, know where that came from. You know, I had a scrunchie business. I had. I always had some sort of side hustle going when I was in college, I had this ebay business to, like, really support myself and pay my rent. So I always had some. Something going on. And I was attracted to the movie business because it was really entrepreneurial. You know, making a movie and putting it out into the world, it's. It is, it's making a product.

Speaker B: People describe it as Sisyphean, to like,

Speaker A: get it really made. It's like a miracle every time it happens.

Speaker B: And the founder's journey is very similar. Right?

Speaker A: Yes.

Speaker B: You had that muscle developed to some.

Speaker A: Exactly. Right. Yeah. I felt like when I was thinking about, well, what else can I do erroneously, I thought, okay, I have no transferable skills. Right. Like, what can I take and apply this to something else? I thought I didn't, but I was so wrong. I think a couple things were the muscle that got me through. One was the work ethic. Um, because in the film business, you know, you sort of notoriously pay your dues. I was in the mailroom, I was an assistant for years before I got promoted to an executive. And I worked these really intense, really long jobs doing everything and anything. And the attitude that we were taught was this, I can do it, I can figure it out attitude. It was like, keep your head down, do the work. If you don't know how to do it or you don't know how to just figure it out and get it done. And I think that's really what carried me through building a company was that same mentality. When you're overseeing a movie, you're managing like a thousand workflows at once, which is also very similar to running a company.

Speaker B: Totally. And it strikes me that there's this other parallel of having to be really left brained and right brained at the same time. Right. Like as a producer, you know, there is like a deeply creative component to it. And you're also managing budgets and you're having to operate in both spaces simultaneously.

Speaker A: Exactly. And that. That is a sweet spot for me where I can sort of teeter between both sides.

Speaker B: I have a newborn at home.

Speaker A: Congratulations.

Speaker B: Right now. Thank you very much. So I can, like, feel into this acutely, like the Genesis story of little sleepies. But you're on maternity leave, you have a newborn, you already have another kid, you're exhausted.

Speaker A: Yes.

Speaker B: What is it that you're looking for and can't find that makes you want to pursue this company?

Speaker A: Gavin had a problem that my first child never had, which was he had eczema, very common, and babies. And I was trying, of course, everything to calm it down every lotion and potion and whatever. Nothing was working. And at some point, I looked down at what he's wearing all day, which were these just, you know, sleepers, and I realized, wait a second, I think these are actually irritating his skin worse. So I go online to order him something better, and I start doing research on what fabrics are good for eczema, good for sensitive skin. And I start reading about bamboo fabric and how it's amazing for that. So I thought, great, let me order him a bamboo sleeper. Shocked to find there's almost nothing available. I found one option that was a very, very expensive boutique brand that I didn't think was cute, but I ordered it anyway to try it, and it came and it felt amazing. And it helped his skin.

Speaker B: That's gotta be satisfying.

Speaker A: You're like, I figured it out. But as I'm changing his diaper in the middle of the night, I'm like, why is this so annoying to snap and unsnap or button and unbutton? And, like, no one wants to be dealing with that as, uh, when you're exhausted at three in the morning, changing a diaper. And my son, who is very tall, grew out of that sleeper in, like, I don't know, two weeks.

Speaker B: Now this expensive thing is no longer useful.

Speaker A: Yeah, that was the birth of the idea. I started really focusing in on. Wait a second, there's something here. No one's doing this. The whole industry of baby and kid sleepwear is dominated by these legacy brands that, like, no one has any connection with. Right. There's no emotional connection to those giant big box stores. And meanwhile, it's such an emotional time. Bedtime, right? You're cuddling your baby, you're reading them a bedtime story. There's nothing sweeter. And I just started to get really excited about that space, so decided I was going to build the perfect sleeper.

Speaker B: At that time, are you like, this is it. I'm going to pursue this. And I see this opportunity. And I can also see that this is potentially my exit from my other career. Or does it not feel that solidified to you?

Speaker A: It wasn't that much of a eureka moment. It was more of a curiosity. Uh, it was like, huh, I really think there's something here. This is really interesting. I know absolutely nothing about this space. I don't even know anyone in this industry. But let me start trying to see if I can figure it out.

Speaker B: It ended up taking two years before Little Sleepy's was able to launch. Yes, it's a long road.

Speaker A: It was A long road.

Speaker B: Was it longer than you anticipated?

Speaker A: Well, I still had my day job, and so I was sort of exploring this nights and weekends. First of all, I had to research how do you even get something made? Started researching factories around the world. And I had samples made from, I think, 12 different factories, which took a really long time. And you're going back and forth and you're improving things and you're perfecting things. And so that was. That was a long process to get it right. Hadn't been done before.

Speaker B: The manufacturing piece, I think, can be so mystifying to so many people and is sort of like, can stop you before you even start because it is so complex. You said you got 12 samples.

Speaker A: Yeah. 12 different factories, and they were all wildly different.

Speaker B: You're giving each of them the same directive.

Speaker A: Yeah.

Speaker B: And they're coming back to you with different products.

Speaker A: Yeah. I mean, it wasn't professionalized. Like, my team is now sending them instructions on what to make. Before, it was just me sort of sending them a drawing and some measurements, and it was really scrappy. So that's why I wasn't getting consistency, which I know now, but I did not know that then.

Speaker B: Totally. I mean, for people who do want to make something, whether it's children's sleepwear or makeup, uh, or pickles, do you have any advice for how to navigate that process, especially when they haven't done it before?

Speaker A: It's really hard. It's really hard. I think if you want to manufacture overseas, China is really amazing to work with. I think going to one of their trips, trade shows is probably what I'd advise someone to do now. I didn't do that. I did everything online. I went to the depths of the Internet to find any manufacturer who would speak with me, and a lot of them wouldn't.

Speaker B: Because you were untested.

Speaker A: I was untested. I wasn't interested in placing a large order. I didn't have a company name. Um, a million reasons.

Speaker B: When you ended up landing on the manufacturer that worked, was it about them being able to churn out the product that you wanted? Was it about the relationship that you were able to cultivate? What were the pieces that clicked?

Speaker A: It was. The product was perfect. Uh, finally, from one factory, after going back and forth, the product was perfect.

Speaker B: This was like, what has been your hero product? Right. The zippy?

Speaker A: Yeah.

Speaker B: Talk to me about when you get that sample that ends up being, like, your prototype. You're like, okay, we've landed on it. What did it have?

Speaker A: So. So it has a Double zipper, which is key for solving those middle of the night diaper changes. It has fold over feet cuffs, so you don't need socks. And it also prevents the problem of, in a traditional sleeper, the feet are built in. And if your child has big feet like mine, that's the first thing they're gonna grow out of.

Speaker B: Right.

Speaker A: So a lot more room to grow. The material was amazing. It was super, super stretchy. I also put in fold over handcuffs because babies scratch themselves and you want to sort of trap their hands so they can't do that.

Speaker B: Were you using Gavin as your guinea pig for this whole thing?

Speaker A: Yes. Yes. So at this point, he's already almost 2, so he's a little big for it. But yes, I was still putting him in it. There is this magic to little sleepy sizing where. Oh my God. I think I was putting my daughter Sienna in it at that point too. And she was already four, four and a half. It fits. I mean, the stretch is so insane. It can fit a, uh, kid for years. So they were my little models and testers.

Speaker B: I've heard you say that even at this stage of the game, you weren't really treating it yet like an all in endeavor. You've said that you were looking at it as an experiment.

Speaker A: Correct.

Speaker B: What does that mean?

Speaker A: I knew I had a great career, even if I had sort of fallen out of love with it. So to me it was, can I prove this concept out? I knew I loved this product. I knew I would buy this product, but I didn't really know if other moms would feel the same way. So my plan was, let me order some minimum quantities, put it out there, see what the response was. If it doesn't work, okay, yeah, I've lost a little bit of money, but I can go back to the film world and get another job.

Speaker B: How much money did you invest?

Speaker A: I invested less than $20,000. Wow.

Speaker B: Really?

Speaker A: Yeah, for my first production run. Wow. And I did absolutely everything myself. I was scrappy to a fault because it was my money. So every dollar that I spent hurt.

Speaker B: Right. Yeah. I'm thinking like you were accustomed to dealing with budgets and line items.

Speaker A: Yeah.

Speaker B: But when it's your cash, it's a lot.

Speaker A: It feels a lot different. Yeah.

Speaker B: It changes the way you spend.

Speaker A: Yeah, it really does.

Speaker B: So you put most of that money into inventory.

Speaker A: Um, almost entirely into product. Yeah, product.

Speaker B: And one photo shoot, it launches. And you're not really putting any marketing spend behind it. So how are you getting the word out?

Speaker A: Zero marketing? I didn't spend Money on marketing until well over a year into the business. I put the word out through family and friends, through mom Facebook groups, which I had already sort of seen the power of.

Speaker B: I'm learning.

Speaker A: Yeah. Yeah. And that was really where I started. And I was not expecting much. You know, I had a few thousand pieces of product shipped to my garage, and the plan was, let's give it nine months, see if I can sell through this. And if not, okay, no big deal. I'll go back and get another job in film. Looking back, I think that timeline I gave myself was absolutely ridiculous.

Speaker B: It's really short.

Speaker A: It's really short. Yeah. Uh, what happened was sort of the impossible, which is I sold out of that product within a couple of weeks.

Speaker B: Wow.

Speaker A: Yeah. And all of a sudden, I had wait lists with thousands of people on it.

Speaker B: Why do you think it caught fire in that way?

Speaker A: Really? What's still kind of the magic and the secret sauce of the brand, which is our customers are our marketers? Um, that is a completely organic thing that happened. But because the product is great and people love it and people are excited about it, and because they want to take pictures of their kids in it, they are putting the word out for us. You know, you're taking a matching pajama family shot. You're posting that on Instagram, and all of your friends are saying, oh, my God, where did you get those pajamas? So that's just what happened. And it. The compounding effect of that just grew really, really quickly. I mean, it was. It was very overwhelming.

Speaker B: You're speaking to this thing that happened really organically that you weren't anticipating, and you're seeing the success of it pretty much immediately. Do you then at some point parlay that into, like, more of a strategy in terms of your marketing?

Speaker A: I didn't even make a marketing hire until I was a few years in and already doing, I don't know, um, $12 million in revenue. It was so organic. And I had also, from day one. This is really important. Had built this community that I think is really part of the DNA of our brand, which is our own Facebook group. I mean, today there's, like, over half a million members in it. Wow. But at the time all. All of a sudden, people started joining this group pretty quickly without me promoting it. They were just. I think they were so excited about the product and were so in love with it. They were searching little sleepies wherever they were, and they were finding this Facebook group. And then later, I started inviting people to join, customers to join. But the Facebook Group grew really organically too. And so those customers in that community also, they're all ambassadors for the brand.

Speaker B: When you have a child and they're in some kind of distress and their only way of communicating with you is crying, you're just so desperate to find anything, to find the solution. And when you do find the solution, it's like it curries such immediate loyalty. It makes so much sense to me that people would be like the moment they found that this thing worked for their child, they're fought in.

Speaker A: Yeah, yeah. I didn't even really talk about the eczema connection. Believe it or not, in the early days, it was really more about just the softness, the comfort, the functionality, the patterns. That's what drew people in. And I think once they got them and they put them on their kids and they saw those benefits, it made it even better.

Speaker B: You sold out in a couple of weeks.

Speaker A: Yes.

Speaker B: You thought it would potentially take all the way up to nine months. You mentioned, like, good problem to have, but. Yes, a problem to have.

Speaker A: Yeah, it's the worst, best problem to have.

Speaker B: How did you navigate it?

Speaker A: Oh, my God, so much stress. I also had a real manufacturing snafu in those early days. On my second order, I got in product that was 80% defective. So that was another huge hiccup from the same manufacturer. From the same manufacturer who had done a great job with my first order. And I think I've heard this is pretty common with factories. Very short sighted of them because that was the end of that relationship.

Speaker B: Oh, my God. So now you're to some degree back to square one.

Speaker A: I was back to square one. But I had the benefit now of knowing that I could place larger orders and satisfy some bigger manufacturers minimums. And so it opened me up and I pretty quickly found a factory who was amazing and they still make a ton of our product today.

Speaker B: Do you think it's fair to say that if you're doing something as an entrepreneur that needs to be manufactured to prepare for something in that process to break?

Speaker A: Oh, my God, for sure. I mean, I think running a business in general, everything that can go wrong will go wrong. It's like your day is just. What fires am I putting out today? I mean, it's nonstop.

Speaker B: Are there other really big ones that jump out at you?

Speaker A: Yeah. Well, I'll tell you one of my favorite stories. This one's so crazy to look back on. So it was 2021. The business has absolutely exploded. And I decide to make a really, really big bet on holiday. I, uh, mean, we Couldn't keep anything in stock. But Holiday was like, there was the biggest frenzy over Holiday.

Speaker B: Pictures in front of the tree.

Speaker A: Yeah, yeah. Matching family pajamas. Photos, photos. Mr. Hanukkah, like nothing better. So I think I'm semi risk averse, but I really like invest all of it into Holiday. Right. Mhm. So the product is ready in China. This is 2021. So it's peak Covid supply chain issues. I think we needed something like 10 containers to transport it all to the US and I could not even book one.

Speaker B: Oh my God. And the clock is ticking.

Speaker A: And the clock is ticking. We spend, I don't know, a month or two trying to book containers and we can't. Uh, it was, I mean it was absolutely insane. They're already going for like seven times the usual cost. And it doesn't matter. You can't get them cause they're all taken up. We're now at the point where we're not going to make them in time for launch. Right. And if you have Christmas pajamas that arrive in January, you know, good luck to you.

Speaker B: Yeah.

Speaker A: So, so that was incredibly stressful. I decided to start calling plain charter companies and I ended up chartering a, uh, 747.

Speaker B: Oh my God.

Speaker A: Filling it to the brim with pajamas and flying it over. And to do that, I mean, it was literally like cold calling. And you, uh, have to pay for it way in advance. It was a million dollars. Literally a million dollars. And I had to go to the bank. I didn't even have like a banker relationship or anything. I had to go up to the teller and say, hi, I'd like to wire a million dollars. And they were like, and do you know this person? And I said no. And they were like, have you done business with them m before? And I said no. And they were like, okay, well, you know, there's no recourse if you don't get this the service that you ordered. And I was like, yeah, yeah, I got to do this.

Speaker B: It was like, it's like when you send the $20 Venmo and Venmo's like, are you sure you know this person? Because we can't give it back to you. But it's a million dollars.

Speaker A: But it's a million dollars. Yeah, yeah. So that was probably one of the most stressful time periods of my life. But it worked out. The plane made it, we got the product and we, we saved Christmas.

Speaker B: Saved Christmas, yeah. Uh, oh my God. My heart rate actually like sped up while you were telling that story. Like it's Stressful.

Speaker A: It's insane. Yeah.

Speaker B: It feels to me like there are these moments that at once make you so much more resilient but maybe also take years off of your life.

Speaker A: Yes, exactly.

Speaker B: Yeah.

Speaker A: And you're just like, what is my life in those moments? Like, what am I doing?

Speaker B: You, more recently, a few years ago, stepped out of the CEO role.

Speaker A: I did.

Speaker B: Maybe you'd had enough headaches. Why? Why did you make that decision?

Speaker A: The business had been in such insane hypergrowth that, I mean, a. I was exhausted. It had been five years of really doing nothing but like eat, sleep, work, and making a ton of sacrifices. And the business was at this place where we needed structure, we needed software, we needed to hire 100 people. I mean, it was insane. And there was so much focus on the parts of running the business that I don't love. Like, I. I love the creative stuff and I love strategy. And this was more. It's more operational legal, hr. And I just started feeling like I was getting a bit drained and not really able to focus on the things that I'm best at. So I was really excited to bring in a CEO.

Speaker B: It takes self awareness to recognize, hey, maybe this isn't really the right thing for me anymore. I think it also takes a degree of humility because there's like an ego component with this CEO title. Did any piece of you grapple with the letting go?

Speaker A: Honestly, I was so grateful to have someone fantastic come in who was a professional CEO, had done all these things, knew what to do versus me, still figuring it out as I went along. And I was figuring it out, but again, I sort of like lost the passion for what I was doing because it was so, to me, bogged down by those parts of the business that I didn't love.

Speaker B: So where's your focus today? Are you still involved?

Speaker A: Yeah, I'm still really involved in design, product development, strategy. I talk to my CEO once or twice a week.

Speaker B: There's like this timing component to this whole thing. Right. Which you can't really control for, but, you know, you have this very real need in your life with your son's eczema. Uh, but it also aligns with this moment when you're ready for something new professionally. Does it strike you that this little sleepy kind of couldn't have come to be if those two things hadn't aligned?

Speaker A: Oh, I think about it all the time.

Speaker B: Really.

Speaker A: It's like a sliding doors moment. Yeah. I was really. I was looking for something else to do. I was. I did want to start a business and this idea came to me at exactly the right time, and it hit the market at exactly the right time, too.

Speaker B: What do you think was right about that moment?

Speaker A: There was nothing else like it. There was true white space and it really, it got people's attention because it was. It was novel.

Speaker B: Could you see yourself starting something else?

Speaker A: Yeah.

Speaker B: Really?

Speaker A: I'm sure that I will, yeah.

Speaker B: Do you have any ideas percolating?

Speaker A: Nothing. Nothing solid yet.

Speaker B: What do you think is the key to making a successful transition from one career to the next? I mean, you had said that you didn't really see how your skills would be transferable. This is something that comes up time and again. Yeah, right. A lot of people come into being a founder and they're not like, oh, I've been a founder since Trump. They had some other career. Yeah. And they can't see how what they've been doing will apply almost every single time it ends up applying. Do you think that there's a way to see that sooner?

Speaker A: I think if you have the work ethic, you know that about yourself, that I think that is the number one necessity because obviously no one's driving you but yourself. And you will never work that hard in your life. So you have to have that ability. I think, number one. Number two for me, I think, was the way that I did it was I looked at everything that I had to do in the lens of my previous job. Like, I sort of had to make those parallels. Like, I used to work with writers and give them notes to make a script better. Now I'm working with artists and giving them notes to make a pattern better. I'm still predicting what the consumer is going to want in one to two years. So sort of making those connections helped, I don't know, sort of make it feel like I knew what I was doing even if I was just making it up.

Speaker B: Where do you think Little Sleepies is going in its next iteration?

Speaker A: Oh, my gosh. I think the one thing that we've always been really good at is giving parents what they want and what they're missing. So for us, it's going to be a real focus on innovation, continuing to innovate fabrics, products, product lines. We have so much stuff coming out I'm not allowed to talk about, but really excited about.

Speaker B: Oh, my God. But I'm like, as the mom of an 8 week old, I'm like, what are we wanting right now?

Speaker A: Yeah. Yeah, you'll learn.

Speaker B: Meredith, thank you so much for being here. Thank you for having me and thanks to you for tuning in. Be sure to subscribe so you never miss an episode. And we'll see you next time.