100 Monthly Subscription Boxes Later: Lessons, Laughs, and What It Really Takes to Keep Showing Up

This one's a big one. Our 100th monthly box is shipping out this week, and I'm taking you behind the scenes of what it really took to get here. I'm sharing the lessons, the flops, the growth, and everything I've learned from curating 100 different subscription boxes over the last 8 and a half years. Whether you're just starting or you're deep in the game, there's something in this episode for you. Come listen.

Welcome to the Launch Your Box podcast with weekly tips, tricks, and strategies to start, launch, and grow your subscription box. Now here's your host, Sarah Williams.

Welcome back to the Launch Your Box podcast. Today is a milestone episode for me, and honestly, I really didn't expect it to hit me the way that it has. I took a photo yesterday and I took that photo at the warehouse standing in front of our 100th subscription box. Like, 100 boxes is so crazy to me, but it made me a little bit emotional and I'm going to share a little bit about that today. But it made me emotional because it's 100 boxes. That means 100 different themes. 100 different times that I've curated the boxes, 100 months of packing, shipping, sourcing, and 100 months of creating moments of surprise and joy to my subscribers. And it's wild to think about. And so I wanted to use this episode to look back on the journey, tell some stories, um, that maybe I've never told before, and share some of the lessons that I've learned along the way and hope that I encourage you wherever you are in your own subscription box journey, whether you're on box number 3, box 33, or maybe 303, or maybe you haven't even launched yet. This one is for you. That photo moment yesterday hit me because it made everything feel real. I was standing there in front of my 100th box. We're not talking about 100 boxes. We're talking about 100 months of boxes. And I just stopped and I thought back to the beginning of this journey, that small-town girl who had no idea what this would become. And it reminded me why I started and how far I've come. So let's just start with how this feels. It feels unreal is the best word that I can describe for it. Like, kind of an out-of-body experience, like an unreal experience in this moment of like, did this really happen? Have I done this for 100 months? Have I really curated 100 boxes over the last 8 and a half years? And when you just put your mind and you think about 8 and a half years of something, like, that's a long time. Um, I got to thinking about Okay, here's some of my stats, right? Like, how many of these 100 months did I actually physically pack boxes? And I just pulled the calendar out and I started making notes, and I physically packed about 45 of these months myself, some completely by myself, a lot of them with 1 or 2 employees. But once we moved into the warehouse, I kind of was banned from packing, honestly. My team didn't want me getting in the way, and it was easy to push me off to the side in the warehouse because I have this office in the corner, and they're like, go back to your office. When we were in the brick-and-mortar retail store, there was really nowhere to go. Like, I had to pack because there wasn't anywhere for me to sit and work unless I was packing. So we were just like on top of each other at the old location. And there was just nothing else to do but pack boxes when it was time to pack boxes. So the biggest thing that changed in me as a business owner over this journey is really my confidence. And it didn't happen overnight, but gradually with every box, with every launch, with every live, with every way that I showed up, with every decision that I made in this business, I really started trusting myself more and I started realizing that I can do this And that belief in myself grew stronger and stronger every single month. So I want you to think about that. If you're just on the start of this journey, you're going to have so much personal growth. If I look back at 8 and a half years ago, Sarah business owner versus Sarah business owner right now, it is mind-blowing. How much I've changed. And that change just doesn't come as being a business owner, but that change happens personally too. The confidence that I have personally has changed along with the confidence that I've gained as a business owner. And every decision, every launch, every box that you do, you're going to start trusting yourself more. And I want you to just know that in the beginning it feels like a lot. And in the beginning, I never would have told you that I would have gotten here. I never would have told you that in 100 months I'm going to be sitting here, you know, celebrating that. I didn't even know if this would last a year, and honestly, I was afraid to even put a yearly option on my website because I didn't know if I would make it a year. And that's the truth. And I think it's okay to feel those things, but just know that your belief in yourself is going to grow stronger and stronger with every single box that you build every single month that you go through, every challenge that you have, is it's going to help build your character, it's going to help build your growth, and you're going to, you're going to change both personally and professionally along the way. So I'm going to take you back. I want to take you back to box number 1. And, you know, I was sitting here looking at photos today thinking about, okay, what was my favorite box, or was there some, some boxes that really stand out? And I'm going to talk about a few of those a little bit later. But without looking at anything, I know exactly what was in box number 1. And box number 1, ironically, was inspired by Lily Pulitzer. It had a very fun Lily Pulitzer type pattern on it. I wanted this box to be colorful and bright and fun. My first box went out in April of 2017, and so it was spring and I want it to be fun. But what's funny about that is that years later, actually this past year, I got to do a real Lily Pulitzer collaboration box. Like, I had full-branded Lily Pulitzer in my box, and it was my very first Lily Pulitzer collaboration. And so it was really, it's really funny to see that that was the concept of my very first box, to take it full circle and have a full-on collaboration box. Feels really special. And I, I don't remember much about that packing day, and the only really memory I have is because we took pictures. Like, pictures are the best memory makers, and here's just And just another tip about this. As I was going back and looking at pictures, I didn't have all of my boxes. I don't have pictures saved of all 100 boxes. So I'm going to challenge you, if you're in the 30 boxes or, you know, 50 boxes, go back and create a Google Drive and put all of your boxes in there by month. I have some saved to an old laptop. I have some in a Dropbox. I have some in a Google Drive. Create a place where you can put all of these. I never would have expected me to have to go back and find 100 boxes, but I don't have all of them. But I do have pictures that I found of that very first packing day. And I look at my face in those pictures and I was probably stressing over every little detail and overthinking it in every single way because I wanted this to be perfect. And so I want you to think about that. Like, I've also grown with that. A little bit, you know, like I still want things to be perfect, but that very first one was so special. What I really remember is about sourcing that, that first box. So I was using a vendor and I'd never ordered 50 of anything, so that was kind of my first like gulp in my throat. I, you know, I ordered 4 pieces, 8 pieces, 10 pieces max of things that I sold in, that I sold in my retail store, but I'd never purchased 50 of anything. So here I was picking these things out and buying 50 of them. And, and I told myself, worst case scenario, you sell 5 of these, you can save these for the fourth quarter because I have no doubt I will sell them in the fourth quarter. And that's what I told myself. I really didn't have a big understanding of how much to spend on each item. I really didn't know, like, to keep my size in check to fill the box. I was just figuring it all out in real time, and I just picked these items because of the pattern, and I knew it would fun and exciting. And so it was all, all these things we had to learn. But buying my first bulk order— and I say 50 as my first bulk order, now I buy stuff in the thousands— it was stressful. There was a lot of cash flow that I had sunk into this, and if this didn't work, I was now going to have to sit on this product until fourth quarter. But it was something I had to learn. And back then, I started to quickly add things to the boxes. So we get into month 2, 3, 4. I'm wanting it to keep getting better and better, so I kept adding more to the box, and I kept chasing like, oh, if I add one more thing, it'll just make it so much better. But what was happening early on is I was overspending, and those few extra dollars here and there were completely wiping out my profit. And so that's one big lesson that I've learned, is that more isn't better. And now I have a set budget, and I start with one big impactful item. I call it my hero item of every single box, and I curate the rest of the box with the rest of the budget around that one particular item because that one item shows a lot of value in my box. And more doesn't mean better. Better actually means better. So that's really how sourcing has gotten better for me too— staying in budget, not losing all of my profit. And I did it for a long time before I realized that I wasn't making very much, like maybe $1 a box. Like, that's how bad it got. And so keep your eye on those numbers early. That was not something that I did either. I think back to box number 1, and packaging has had a major glow up since then too. We started with brown boxes that we stamped our logo on and we just sealed it with tape and put some cute stickers and tape on the outside. And that was the first several boxes. When I hit 100 subscribers, which was month 4, I invested in our first custom turquoise box with our logo printed on it. It wasn't really anything special. I mean, I could have, I could have done a better job, but at that time I just didn't want to have to stamp 100 boxes anymore. So I just wanted something with our logo on it and I just put our signature turquoise color on it. And so that worked well for a long time. And then a few years later, we rebranded the box to the Monogram Box, and we upgraded the entire box packaging experience with our signature Quattrofoil print on it and things like that. So it starts with one thing, and over time you keep getting better. I got better at product sourcing. I got better at profit margins. I got better with packaging. And so I don't want you to feel like you have to have it all figured out in the beginning. It's okay to just start where you're at and keep getting better. But let's talk about some of the not-so-glamorous side. These are, these are almost funny, like these would be like my bloopers, um, or stuff like that, but I was thinking about the things that I could talk about today, and so I kind of did some, did some things like, what's the funniest mistake that I've made with my boxes? And I think if you would have asked me back then, it would not have been funny, but it's kind of funny now, and we laugh about it now. But I had a box one fall, I think it was 2020, but I'm not sure, um, and I, I did a t-shirt and I designed it. Oh my Gourd, like the gourd, like a vegetable, right? And so it was just a pun on a song from the '90s, and I thought it was funny and I thought my subscribers would love it. And I curated the whole box around these colors and stuff like that. And our subscribers did not like it. In fact, we got hate mail over it and Yeah, it was a huge lesson learned that I need to stick with things that are for the masses and not things that are just fun to me. And so that taught me a huge lesson about what my subscribers want, and it's not always what I think is cute and fun. Then I think about I think about the, the box that I got the most cancellations from. And so I was like, okay, what was the— I call it like it's the worst box, but I don't feel like it was the worst box, but it was the box that generated the largest amount of cancellations. And I hadn't had this amount of cancellations at that point, and it devastated me. But it was our one-year anniversary. And I thought, okay, I sent a lot of cute bags, I sent a lot of cute tees, a lot of cute accessories. I'm going to do something completely different for our 1-year anniversary box. And I did a bathroom-themed box with monogrammed towels, a cute little like cotton ball Q-tip container, a toothbrush holder, this whole like bathroom box. And OMG, people were mad. They were like, this is not what you normally send. We didn't— we hate this. And I got the largest amount of cancellations after that box ever. And I was so depressed. I think I laid in my bed for a few days, like sometimes just sobbing because I thought I completely ruined this good thing that I had done. And so that also taught me a big lesson that What people are buying is what they love. And I need to not worry about how much of something they have. I need to keep giving it to them. And I also got like I had some people that month that were my first subscribers and they said, this is not what I've seen you do. I'm very disappointed. I thought it was cute bags and t-shirts and earrings and stuff. And I thought, okay, you're right. That's what we do. Why did I change that? So that's another lesson. I also thought about what's been our biggest shipping disaster. And I remember, I believe it was 2021, but FedEx picked up all of our subscription boxes and they left the warehouse, went down the street, did a few businesses. And at one of their businesses right on the corner, they forgot to put their door down on the truck and it was open. They pull out into a busy street. Six-lane road and our boxes started falling out of the truck and they ended up all over the road in ditches. Some people at the stoplight jumped out of their car and stole them. Some of them were run over. That was a hard day. And it was— I learned a lot. I learned a lot about shipping insurance, contingency plans. I was sold out that month. I didn't have any extra and I had about 100 boxes. That needed to be replaced. Some were stolen completely, um, and some were completely run over and damaged. And, um, again, just things that can happen you would never expect to happen. It only had happened once in 100 months, um, and hopefully it never happens again. But, you know, it is what it is. And I, you know, I still have months where I second-guess like every single product. I worry it's not good enough. I worry that people people won't love it. And then I get the best feedback. They're, you know, the boxes I'm most unsure about are often the boxes that they love the most. There was one month where we were short on the main product. It arrived late, it was wrong. I had to scramble at the last minute and replace it because it wasn't the right color. It didn't match anything in the box. And I was so stressed out thinking that that month would be a huge disaster. So I scrambled and I made a hoodie instead. And it was— people loved that hoodie. It was the best alternate item at the last minute that I could have ever asked for. And I want you to remember that, that sometimes our best boxes come from that pivoting moment in our, you know, in our businesses. So let's talk about my subscribers and some of the surprises that we have dealt with in the, the last several, several months. So my subscribers always surprise me, and, you know, I love that they they surprise me with— what am I trying to say here? They surprise me in that what I love the most is rarely the item that they love the most. Some of the things that I add in as an extra, it could be something small, almost as a filler, is the item that everyone is raving about. And so what I love is fun is that what keeps our subscribers coming back? People ask me that a lot, and I will tell them all the time that it's seasonality. What keeps my subscribers subscribing month after month after month is seasonality. It plays a huge role because as the seasons change, their needs change, their styles change. They're ready for the next box, they're ready for the season. And there's also that mystery element. They love the surprise. So if you can provide a mystery element to your box, that's one of the best things that keeps people coming back. They're waiting for that next surprise. They can't wait. And I don't share it until after it hits their doorstep. So when they receive that box, that's the surprise element that they're going to get. That's where, um, That's where their experience starts, right there. I'll never forget a message from one of my longtime subscribers who said, your box is my monthly treat to myself. It makes me feel seen. I hear this over and over, almost monthly, because it reminds me that this box is more than just stuff. It's a moment. It's a connection. When we listen to our subscribers on a regular basis, when we ask for feedback, when we ask for comments in the chat, when we send a survey or cancellation, we know what's working and what's not. And when someone says, I'm canceling because I have too many tumblers or I have too many bags, guess what? We got to cut out that many tumblers, then we got to cut out that many bags. Um, but what we do is we listen to what they love and we really try to curate boxes what they— with what they love. And so people ask me a lot, what's your favorite box of all time? And I just honestly cannot pick a box. I can't, I can't pick a box. I looked at these pictures today and I went through and thought, okay, if— what would be my favorite box of all time? It's hard. It was hard for me to even pick 10 of my favorite box. I think about like what's our subscribers' favorite boxes? And I look— as I was looking through the pictures, our subscribers' favorite boxes are always our Christmas-themed box that we send out in November. There was a particular item a couple of years ago, maybe 4 years ago. It was a green sweatshirt and we sent out this green sweatshirt. It said Be Merry on it. And I see it every Christmas. I see my subscribers wearing it. They're sharing in pictures. I still have a a lot of local subscribers, so I'm seeing it on their social media. But that has been one of our favorite items, and it makes me so happy because, you know, I know that I curated and I made that sweatshirt. I designed that patch. I picked the color. We put those together. When I think about what's been our most shared box on social media, and that was our first ever Kate Spade collaboration. That was in 2020, and it was one of those things that I just walked into the Kate Spade showroom and said, hey, I have a subscription box and I would love to put some Kate Spade items on there. I don't know if I can afford that. Is there someone I could talk to? And that started a beautiful relationship with the Kate Spade distributor and I, and we have done several Kate Spade collabs. But that particular— that first one, it exploded on social media. So when I think about the most memorable boxes, that's one to me. Christmas boxes are one to me. And so it's hard for me to pick, though. I can't say like there's one particular box. I will look through the years and I will say, oh, that was a great one that year. Oh, that was a great one. But I can tell you the ones that catch my eye when I was going through all 100 of those pictures were the seasonal ones. Keep it seasonal. People love that. What would— if someone asked me, what would 100 monthly boxes, like 100 months of boxes, teach you? Like, what does that teach you? And so when I was thinking about that, I thought, what has 100 different boxes taught me? And really, there's no magic box that changes your business. But I think about the consistency that changes your business because month after month, showing up month after month, learning, evolving, growing, changing. We've talked about the changes. We've talked about the packaging changes. We talked about my buying changes. We talked like I've gone through vendor changes. We've gone through different packing processes. It's all evolving. And I think that it's consistency. These 100 months have taught me that you can do anything if you're consistent. It takes the long game mindset here. This is not a get rich quick business, but it's the belief that this month matters just as much as next, next month matters. It's really hard to say month matters multiple times. This month matters just as much, just as much as last month and the next month. And this month's subscription matters just as much as next month when I'll be launching. That retention matters, that in-between matters, that your subscribers are paying attention even when you think they're not. So if you're on box number 3 or 33, my advice is stick to your budget, be consistent, don't let extra money steal your profits. Listen to your subscribers, keep showing up. Every month in this type of business is a new opportunity. Every month you get to redo it. Every month you get to try again. Every month you have something new to talk about. And that's what I love about this type of business. That's what I love about having my subscription box business. And when I look back on those 100 boxes, I'm proud, not just in the growth that I've had of going from 44 monthly subscribers to thousands of monthly subscribers, but the heart that I've poured into every single month. This business was built from creativity. It has been built with consistency, and it has created community. And if you're on this journey too, I hope that this encourages you. You don't need to have everything figured out. You just need to be willing to get started and to keep going. And I just want to give you a heartfelt thank you for being part of my journey. Um, thanks for watching over these months, whether you've been here for 40 months or 4 months. Thank you for letting me share this milestone with you and sharing this podcast with you. I'll see you next week.