From Corporate Burnout to 8 Figures: The Story Behind Little Trouble

0:00And that's when I realized like I could really just like head down and grind to make sure that I'm investing this energy and this time into myself and my own future versus building someone else's dream. Because I was always going to work that hard and I was always going to like care that much about my work. And it was just who is it for? And so that was like my driving factor and like to quiet the self-doubt of like why if I can do it for this person and then this person and then this person, I can do it for myself. I think the biggest thing to get from like zero to one was probably like correct allocation of inventory.

0:38I didn't know what I didn't know. So I just didn't understand my size curve, seasonality. I was tweaking every, it was like V1. I'm on like V90 of all of these products of like fit. Like that was just a really crazy time of just like trial and error and testing. Welcome to the DTC Insider Podcast, where online business owners come to find actionable tips and tactics to grow their businesses. Now, here's your host, Brian Roizentl.

1:15Hey, welcome to another episode of the DTC Insider Podcast. As always, I'm Brian Roys, your host. And today I'm here with Dinah Chapman, the founder of Little Trouble. Hey, Dinah, thanks for being on the show. I know it's super early there in New Zealand. Yeah. Hey, Brian, thanks so much for having me. I'm really excited. Yeah. So first off, thanks for meeting me this early. I know you live very far away. I live very far away from the US as well in Argentina, but you live far away as well. How long have you been living there? Yeah, I've been in New Zealand with my family for about two weeks now.

1:52But we were in Bali for about eight and a half months prior to that. So we just had like this breaking point in the States a while back and just said, like, we have to switch it up, do something super different. So we looked at each other said, when do we do it? And within like three months, we had sold our house, everything we owned. And then we moved about six months after that. And so, yeah, here we are. My time zones are my like arch nemesis at this point, though, because I cannot schedule calls months in advance to save my life because the time zone changes. So you still lead the business in the U.S., living in New Zealand?

2:33Yeah. So logistically, everything is the same. It's all in the States. I use a 3PL and I just manage it from my computer, essentially. So time zone is basically irrelevant when it comes to that, other than my sleeping schedule has been a little haywire. Yeah. And I mean, traveling is great. Like I, at least for me, I learned a lot every time I travel and especially to that part of the world, because it's, I mean, I traveled to the U.S. many times. I traveled to Europe, sometimes to the Caribbean, let's say to other places, but I traveled to Thailand as well. that's probably the closer I've been to Bali and I don't know New Zealand but to Bali and it's a totally different culture totally different values I was there only for a month right but it's great what you learn right yeah it's I'd been on this side of the world prior to this journey too I did over a year abroad in my early 20s but I was you know not married not with kids not running a business it was so different I was just like kind of a dirty backpacker but got to see how much I loved the culture in a lot of these different countries.

3:40And so that's why we ended up back in Bali was for like a cultural difference and a different experience and access to like other countries and parts of the world where, you know, Australia or Cambodia was like a weekend trip or, you know, a one week off trip verse. That's a once a year thing. If you're lucky from the States, just the access to different countries was a huge part of why we chose Bali as a hub. But yeah, it's the inspiration you get to from like immersing yourself in a totally different culture and kind of like being a fish out of water and just seeing so many different things that was like unexpected for me when we got there of just like overwhelmed with inspiration and product ideas and because it's so different and the style is different and it's like really cool so yeah that was that was fun for me on a personal level and then for my kids too like what a cool experience to just be immersed in different cultures and and that's what they're growing up knowing which is so cool like my four-year-old teaches me Balinese yeah I mean prior to that I mean to traveling prior you left the U.S.

4:51and before you started the company what did your life flip like in the US? Oh, God, like the normal just I was hustling like, and I am working more hours now. Like it's not that it's not the hours you invest. It's the way you do it. And in the States, not that there's anything wrong with like the traditional grind, but I think it can burn people out really fast. When I started Little Trouble, I was also working as the marketing director for a large skincare company. I was managing a really large team and Little Trouble started as a side hustle. So I was just like burning the midnight oil entrepreneur at night and weekends, mom 24 seven, and then marketing director with this large team of women I was managing.

5:33So just like drained in every category. But I had to have this start as a side hustle to really be able to get it to where it is now and have like my primary source of income as as my, you know, nine to five, which was not a nine to five, I was working 60 hours a week at minimum, and then packing orders at two in the morning and then feeding the baby, you know, at midnight and two at five and whatever. So yeah, it was just like, it's work, it's parenthood, it's entrepreneurship, if you have those three combined, but then it's also like drop off, pick up, like all the normal things we do 24-7-2 in the States with very little support unless you have like a family system around you.

6:15So it looked standard. Like we had, you know, we bought the house, we had all the maintenance and the yard work and the business and the school drop offs and the daycare and, you know, just really, really like the recipe textbook for burnout. And I was in corporate burnout at the time as well. So it just kind of was this like Jenga effect where we knew I was like one piece from just a toppling tower by by the time we made the choice to switch it up. And when did you know that Little Trouble was more than a side hustle? Yeah so it's been three years since I started the brand and the stages looking back like I don't even know how I survived so long managing both.

7:03It was obvious like I started in my garage and then it grew into a bigger garage. And then we had shipping containers on our property, which ended up not being allowed to be there. So we had to get a warehouse and like it just overwhelmed the shipping container, the garage, the inside of the house, the warehouse. And I was still working my corporate job. And I think I got into like hyper growth mode though, because I saw what was possible. And if I was reinvesting everything into the business, I was like, I'm just like dumping gasoline on this like very timely fire. And I had the capital to keep reinvesting.

7:39And so that's why I did it for so long was because I knew what the minute I really made the choice to step away and I put all my energy towards it. If I could get it to a place where I was operating on like a decent cash flow basis, then I could really blow it up when I was full time. And so that's why I like hung on for as long as possible. But honestly, six months to a year before I made the official move, it could have been my primary. I just realized like dumping that capital back into the business was like my ticket to rocket ship growth. And that's what I wanted. So just like put my head down and I probably contributed to the burnout to be fair.

8:16Like I, I maybe could have avoided a little bit of that, but a year and a half in is when I knew it was sustainable for myself to be my primary, but I didn't really step off the ledge until two years in. We have in the audience entrepreneurs watching or listening to these, you know, some of them ahead in the journey, some of them behind, you know, some are marketers as well, but regardless, they are all here to learn, no pressure. And being inspired by what you're saying because many of these people including myself you know we all have dreams right and many times we are afraid probably think it's not the right time or that we don't have the knowledge to pull it off or what if what if right so what could you tell to those people you know early in their journey in the same position that you were back then juggling you know a side hassle or even an idea while working at the nine to five?

9:18Yeah, for me, it was always like, I think when you like have the entrepreneurial spirit, you just like, you know, putting you, if you have that spirit, you're also most likely putting in like the sweat equity into your nine to five. Like those types of people have like ownership over their work and love to feel invested in their work. And so like you're putting in the sweat equity. it's just where are you putting it into who and that's when I realized like I could really just like head down and grind to make sure that I'm investing this energy and this time into myself and my own future versus building someone else's dream because I was always going to work that hard and I was always going to like care that much about my work and it was just who is it for and so that was like my driving factor and like to quiet the self-doubt of like why if I can do it for this person and then this person and then this person.

10:13I can do it for myself. It's more doubt when it's for yourself. So for me, it was just like quieting that voice. And I've really learned like over the last several years, you can love advice and you don't have to take it. And that was like a game changer for my thought process of like, I can love advice. I can love feedback. I can love talking to people and like mentorship, but it doesn't always apply to you because that like was the voice I had to quiet in the beginning. I was surrounded by a lot of people who had built successful businesses or brands or worked for successful businesses and brands, but not all of that advice was applicable.

10:50You know, a lot of people had different opinions on what I should do to move forward or what my like ticket to growth was. And I think that's just all part of like quieting the self-doubt. And if you're tried and true and you know you can do it for somebody else because you're working the nine to five, like you can do it for yourself. It's just a matter of investing it and knowing like I want the payoff for me and not this other person's business that I'm watching thrive. And it just shows that I can do it again. We can all have this many times false feeling that we are not going to reinvent anything and we are going to be selling similar things to what exists out there, you know, sometimes more and sometimes less different.

11:39There are some more competitive and less competitive spaces. In this case, in your space, you know, what was the main reasons you feel that you were able to stand out and grow? Because it's not an easy space. I mean, what space is easy these days anyway? But in your space, what was it like, again, for those people wanting to start a brand and say, oh, but there are many like this. How were you able to, you know, say, hey, you know, pay attention to little trouble. This is some this is what we're building. This is too fun. Yeah. Yeah. It's such an applicable question given the times to like my brand is very social media driven, like it was born on social.

12:18And then there have been especially like post COVID. It's kind of gone in a lull now, but there were so many like pop up brands. Like I was just getting like inundated with ads of like some real, some drop shipping, some totally fake. TikTok shop came into the play at the time. That was huge. Temu starting to sell mainstream products. All of a sudden, social media was inundated with these pop-up fashion brands. And that was kind of all happening around the same time. When I started Little Trouble, there was an obvious market opening for me, at least in the States. There were some other cool brands in Europe that were doing like cool alternative clothing for kids.

13:02In the States, very cookie cutter. Like it was really hard to find what I wanted. I know that because as a pregnant woman, you spend way too much time on the internet at night, like scrolling, looking for like products. Yeah. I've become every single day like, hey, I saw these, hey, I saw these. And it's like, could you please stop? Oh yeah. The like, the influx in packages you start to get once you're pregnant breastfeeding like that journey is like so crazy so i was like knew there was an opening for what i wanted um i was basically just looking for like alternative styles for clothes for kids clothes and the brands i liked that were cool like these like direct to consumer disruptor brands in adults clothing i wanted those for kids and it like didn't really exist, like cool technical cargos and cool bomber jackets and these pieces that I was seeing pop up all the time in these really cool D2C apparel brands for men and women.

14:00And I was like, wow, no one has a kid's line. And you'd think it'd be easy to like you're tried and true an adult, open it up for children. It's actually such a crazy market because kids grow so quickly. there's such a massive size run, the depth of inventory you have to hold. I mean, I had a education is one way to say it as I started this business of just sizing alone for kids clothes. But so that's how I knew like there was an opening because I just couldn't find what I wanted. And that's rare these days to not be able to find truly what you want. Now it's funny, three years later, I could find what I wanted on the internet now and I would probably not start have started little trouble had all these options been available.

14:44But it's kind of cool to know, like, especially in this like kids niche, I'm in in the States, I was definitely like first the table with a lot of these things. And but in terms of how to like stick out and stay amongst competitors, like sometimes I let it get to me, right? Everyone does. And that's when like the doubt or like imposter syndrome, or like, can I do this? Or is it worth it? There's all these options now is because like there are so many key brands that we know of that are like just North Star, right? For fashion, for marketing, for branding in general. But there's like 10 of those brands in the exact same vertical.

15:22And we like them all for different reasons. And so I just remind myself like there are so many types of people and we're split 50-50 on so many things in life. And sometimes we're like, how? But there's always people that want something different. And so I've just like kept that true to the core and said like if I can just build the brand in like the aesthetic and the style and the way I want, there are other parents out there who are just like me with like the style I want. I'm like it's very like millennial, like a little like Y2K vibes are coming back. Like it's just marketing towards a person who's in my exact stage of life.

16:03And you kind of like also said it just when we talked about scrolling, the parent category, the mom's pregnancy, it's like such, there's so much opportunity marketing to that demographic. The amount of things you need, the clothes are always, you're always sizing up. There's always new people getting pregnant. Like there's just so much potential. It would have to be such a saturated category for you to like not have an opportunity. but that's just how I look at like how I can stand out is I know who I'm marketing towards because it's myself. I'm in this current stage. I have a two and a four-year-old and I wasn't able to find what I wanted on the market.

16:44And something that I've done now is like the way I'm really looking towards continued growth is going at brands where we like love them and they don't offer a kids category. And we're like, do you want to offer a kids category? Because we have like the tried and true recipe down for sizing material testing fit like all the things so it's this like very turnkey like fit style customer base and then brand and aesthetic and parent customer base and like those the merging of those minds is like really interesting is that white label or we're approaching it from a collab perspective but there have been conversations about white label as well.

17:29And that's, that's a potential. That's great. I get, I get approached a lot about my blanks, which I actually don't have blanks. I do all cut and sew. And so I get a lot of inquiries about, can I buy your blanks wholesale? And that's for the material and the fit. So it's something that I would consider down the line. But for now, that is like a unique identifier a lot of the like kids brands that you buy from not knowing you are buying blanks or like a factory blank it might not be gildan but you're buying a factory blank and yeah that's that comes with its own box that you're kind of put in and so that's been it's like an avenue we could pursue but the exciting part for me is like brand collabs yeah you know the other day i was talking to somebody to a founder and we were talking about something that we all mention these days, right?

18:22That it's to be an entrepreneur, we need to be crazy. We need to be problem solvers. You know, it's a lot about that, you know, solving problems. So in this case, correct me if I'm wrong, but I have the understanding that this year you're getting to eight figures. So you have under your belt a lot of experience of problems solved at different stages of growth. So I wanted to ask you if you had to say or if you had to mention whatever you remember about the key challenges that you went through before the first million, one to five, etc. What can you say that is like those that left, let's say, a scar?

19:04Yeah, many. I think the biggest thing to get from like zero to one was probably correct allocation of inventory. I didn't know what I didn't know. So I just didn't understand my size curve, seasonality. I was tweaking every, it was like V1. I'm on like V90 of all of these products of like fit. And I mean, like, since it's cut and sew, like we're down to the centimeter on hood circumference or depth or ribbing or like the eighth material for the ribbing to make it like extra stretchy for a kid's head with more elasticity. Like it's, so the first hurdle was just like entry into market product testing, having enough depth to not lose momentum, but not having too much depth of a category or a fit that wasn't right.

19:54Like that was just a really crazy time of just like trial and error and testing. And also you're doing trial and error with your like initial customer base. So you want to set, you want to be off on the right foot. You want them to love the brand. You want positive traction and momentum and feedback and reviews. And so it's like you're testing at the most volatile time because this is what matters. This is like sink or swim. So I think that was, there were even some categories where like I held back, like I held the inventory, it hurt my cashflow, but I was like, we're not ready to like product or market test this yet because I need to make sure we like fix this or get this in a really solid spot.

20:31So someone has confidence to buy this versus releasing multiple product categories at once and having like fit issues or material changes and stuff like that. So really like it was just merchandising in the first zero to one mil of like, how do I have the right assortment, sell through, have the cash flow and continue to to expand, I think, from one to five. And I had some duds in there and from one to five operational challenges that I just like never expected. That was understanding, like even warehousing. I moved to a 3PL in that time zone and that time frame. I've moved to my I'm on my third 3PL now at this point and like the challenges logistically of moving like scars lost inventory bad customer experience damaged goods delays I mean like you name it we went through it when it came to the 3PLs that's like my biggest my biggest scar I think And then from going to five to 10, that's really a mind shift transition of like operationally understanding what's happening in the business to grow.

21:48It's the same. The same things are working, but it's like finessing and fine tuning those and then trusting my gut on like bigger decisions because momentum is the key for me. Like when I lose, when I sell out or I have an unexpected hurdle or something happens and I lose momentum, then it's like, how do I regain, refocus? And you have to put a lot of capital into one place versus spreading the capital out on inventory, which was kind of my original thing. It was just reinvesting, reinvesting, reinvesting, keeping inventory. Now it's like working off of cash flow and profit and continuing to product diversify, but also like really invest in the right places marketing wise for the business.

22:32So I think like operational challenges were just tenfold. They still exist, but I feel like we're a lot more experienced and I've got it down to a certain capacity on that front. really good relationships with my my factories and in facetime in that first chunk was really important with my factories and just like understanding the process from a to z now it's a mind shift and like how do i really invest in the right areas take those like big steps and keep propelling the brand forward because it's scarier at this stage there's a lot more at risk yeah i mean like they say kids you know little kids little problems bigger kids bigger problems i want them to grow up i don't want to for the problems to grow up to you know but every time i speak to you know older kids it's like teenagers or so it's like oh my god that's waiting for me i know so yeah but with the business happening and you're like that's in my future yeah so so here we interview brands of all sizes you know uh seven to nine figure is that we interviewed you know brands like patagonia and disney like giants but originally you know uh nine figure brands eight figure brands as well and they all say the same thing you know the more they grow the more complicated and the next thing they need to do in every single area of the business is different you know what they chase from zero to one in the future what about the team Are you still wearing too many hats?

24:05Yeah, I am still a team of basically two. So myself and then my husband is full time as of very recently. He does a lot of like operational stuff for me. His background is in supply chain, my background's in marketing. So it was a very nice alignment when it came to starting an online business. It was just me for several years. And then my husband is now full time as of like, I think December. So like, you know, only a few months, maybe not even sorry, no, two months ago. So I've been full time since October of last year is when I left corporate America. And so it's just me and my husband. And I have one girl in customer experience.

24:47So yes, to I'm wearing too many hats, but I have gotten really good at project management and utilizing soft. I mean, if you're a brand by yourself, and now your husband and this, like, congrats, first off, how do you do that? I mean, I feel bad about myself now. You know, the next time I complain, not being able or not having time to do something, I'll think about you. Yeah, it's been, like I said in the beginning, I work way more now than I did when I was like at burnout. But it's different when you're investing the hours in yourself and your own business and you see the benefit that you can reap personally and what you can build for your family or yourself whatever your motivator is it's different than investing those hours in like the corporate grind but in hindsight is there any particular role that you say i should have hired that person or for that role back then when i was doing x oh my god customer experience.

25:56I did customer service for way too long. I was like, it was just the bane of my existence. I cared so much though about every single word that was said between the brand and a customer that I just like could not relinquish control. It was the hardest thing for me was to outsource customer service. And everyone was like, there's all these companies now that you can like fully outsource it to, to like bots and AI agents and people. And I'm like, absolutely not because you like I understand the capacity of AI and the capability and all of these things and people love it or outsourcing customer service or other simple tasks simple tasks like that but I know when I'm talking to an AI bot or or someone who doesn't actually work for the company when I'm chatting to any brand or software or anything and I like despise that experience as a customer and so I just knew like that wasn't it for me and these women that I'm connecting with on social media like I'm building a brand as a real person and as a mom and that's what's like relatable about the brand and people like see my kids me them wearing it a lot of my stuff is like videos of me showing the products and talking about it and like me at my factory and so to then talk to someone like so disconnected just felt really wrong and I just cared so much I like interviewed a few people for it a while back and I just feel like got nerves and was like no like they're not right they don't have the tone like it was my baby right and like everyone thought they were talking to me because they had been for so long people literally still address the inbox hi Dinah and sometimes my I have one girl who works for me and sometimes she'll forward it to me and be like do you know them and I'm like no but they like know me I prefer that they know you because they do through what you post you know exactly yeah they all know me like i'm into my life and like my i am the one talking on behalf of the brand and so uh i should have hired it way sooner because i i'm telling you like i would be like my eyes burning at three in the morning and i'm like i only have 22 more tickets like i can do it um and so that was like the biggest relief when i did it And like just yesterday, she's gotten very busy.

28:11And I was like, we had our weekly and I was like, please, like we need to get you some help because I cannot lose you. You are like my saving grace. If I had to ever return to this in a full capacity, I would fully lose my mind. And so that's something that like everyone thinks that could have been easy. That's like the first thing you outsource and it's easy. But I just thought that that was the most critical piece of people feeling like they we're still talking to someone, me or a spokesperson of the brand who like talked like them, understood their kids, the sizing. Like I have a lot of people be like, mom brain, I ordered this in the middle of the night.

28:46What was I thinking? It's the total wrong size. And my response is like, been there. That's the worst. Like sending you a label. Here's your correct size. Like no hassle. Just like, and that's what I wanted. I didn't want it to be robotic like you're outside of our return window by two days it's like no they they told me a personal story that i can resonate and relate to and like we're going to do everything we can to a make them laugh and bring some like levity to the situation and b make it right and you can't achieve that with like an ai or a team that you don't know yeah i mean this might seem like And our intuitive, we see every, every person out there, something by self, like all of us talking about the AI hype and I believe it's great.

29:35However, I think in the past, you know, people were waiting for technology and now technology is waiting for people, you know, because we don't know how to use it. There's so many options out there, so many things. And we feel that the more of it we use, the smarter we are. And we forget that one of the core advantages that we will have these days as founders and as brands is to humanize, to keep the human touch. It's for now. We don't know in the future, but at least for now. Because many brands are going to think that they won because they optimized everything due to using the latest AI technology.

30:14But in the end, as you said, whenever we use AI, we all say great things about AI. but everyone is embarrassed or despised as you said when they are in the other seat you know whenever somebody sees linkedin with an m dash it's like it's ai yeah that like we are always in ai like so we use ai move the m dash and all this ai look stuff and then when we interact with that machine it's like i want a human right and it's like why i don't know but it's a competitive advantage actually um one more thing all that to that like everyone is obsessed and i talked to many founders work with many brands with the agency i speak with many founders every single weekend everyone is so obsessed with attribution to a degree that is not healthy i think it's it's great but everyone is the opposite with zero party data you know for those who don't know what This is the data that people, the users will only give you through customer calls, surveys, blah, blah, blah.

31:18So there's a goldmine of information to win this. In the customer service inbox. Yeah. Finding money in your pockets. I always tell founders because it's like, you know, think about this. Cost to acquire customers is going up. Margins are thinner. So instead of saying how can we decrease the cost to acquire a customer, which is valid. But there's a limit to how much you can do that. We should be asking ourselves, how can we make more money on the back end to not instead? How can we make more money on the back end to afford the acquisition of new customers as well? And part of that is by, I believe at least, and proof that many times is by aligning your marketing with the way your customers behave.

32:02Many brands don't have that. Many brands guess who their customers are that goes to their marketing. Like the other day, I told the brand through an analysis that 72, this is strong, 72 % of their customers were gift givers. They weren't buying for themselves. And half of them were giving those gifts to close family members. Their marketing didn't say anything about gifts or something like that. That's how blind we are these days, you know, because we're obsessed about did it come from Google or from Meta only? Yeah, that's like hits so true to home because in my world prior to Little Trouble, working for a founder and a team like, you know, a C-suite team, a small one.

32:46I started the company when they were smaller than me now, which is actually crazy and was there for five years, scaled them well beyond where I'm at now. And attribution was like always the topic. And it was so exhausting to a degree because it was like, I understand we care. Like I've been singing from the rooftops for a long time that attribution is like not the be all end all and a more of like an all boats rise situation. Like let's look at obviously contribution margin is really what we should be talking about. Not like ROAS and attribution and people just like a lot of brands don't know what contribution margin even is.