Dinah Chapman is not your average entrepreneur. A fierce advocate for bold living, Dinah’s energy is magnetic, and her insights are ignited by a lifetime of choosing purpose over pretense. She’s a keynote speaker, creative strategist, and self-described “disruptor with intention.” Her Paper Napkin packs a punch — literally:
"If it doesn’t set your f*cking soul on fire, it’s not worth it."
This is more than a quote — it’s a manifesto.
In episode 258 of Paper Napkin Wisdom, Dinah invites us to challenge the safe path, to unlearn the behaviors that keep us small, and to say yes to what makes us burn with aliveness. Through unfiltered storytelling and a raw, soul-baring presence, she shares what it really means to show up in life and leadership without compromise.
“We’re not here to exist. We’re here to create impact. And you can’t do that pretending to be someone you’re not.”
From career pivots to deeply personal revelations, Dinah leads us through her journey of alignment. At each turn, her decision-making lens is simple yet radical: Does this light me up? If the answer’s no, it’s a no. Full stop.
What struck me most was her reminder that discomfort is the price of transformation. She says, “People think ease is the goal. But the best things in my life started with fear, not comfort. Fire doesn’t feel good — it feels necessary.”
Her message isn’t about reckless abandon — it’s about deliberate passion. Dinah doesn’t chase every flame. She tends to the ones that fuel purpose, service, and meaning. That’s a crucial distinction for leaders and creators alike.
Dinah also unpacked the weight of expectations — especially for women in leadership — and how dismantling those scripts changed her life. From leaving a stable job to launching a business built around values, she exemplifies what it looks like to choose freedom over familiarity.
“You’ll never meet your potential if you’re still auditioning for approval.”
Powerful. Let’s dive into five key takeaways from Dinah’s unforgettable episode and how you can apply them in your own leadership journey.
🔥 5 Key Takeaways from Episode 258 with Dinah Chapman
1. Passion is the Ultimate Filter If something doesn’t ignite you, it will eventually deplete you. Dinah reminds us that energy is non-negotiable. Take Action: Audit your calendar for the next month. Cross out what doesn’t excite you. Replace at least one item with something that does.
2. Discomfort is a Sign You’re Growing Growth rarely feels good at first. If you’re comfortable, you’re probably not evolving. Take Action: Identify one decision you’ve delayed out of fear. Take one step toward it this week — even if it’s just a conversation.
3. Approval is a Trap Trying to please everyone is the fastest way to betray yourself. Take Action: Journal this question: Where am I seeking validation instead of alignment? Th
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Govindh Jayaraman (00:02):
Dinah Chapman. Welcome to paper napkin wisdom. I'm excited to have you here today.
Dinah Chapman (00:06):
Thanks me, too. I'm excited to be here.
Govindh Jayaraman (00:09):
So you shared a great paper napkin with me, and you censored it. But we're not going to censor it here, so it says if it doesn't set your fucking soul on fire, it's not worth it.
Why did you share that with me?
Dinah Chapman (00:25):
Yeah, I feel like this. Last year of my life I have made a lot of really big changes and leaps and decided that which I've done a few different times throughout my career. Made those big leaps and decided if it
if I'm not investing my time and my energy in shit that really just sets me on fire, and that is passionate for me, and that I love. It's not worth it. At the end of the day. I think once I had kids that like really set in for me of just like time is my most valuable
(01:04):
asset, and I want to make sure I'm investing it in things that just really
fucking set me on fire.
Govindh Jayaraman (01:12):
I love it so.
So setting you on fire?
That idea!
Is it always like
the 1st thing that I thought of? Is it always a positive, or is it just like I need to get out of something is like, is it a push and a pull? Or is it just a pull.
Dinah Chapman (01:32):
Good question. Yes, as I say, set me on fire. I'm like as a mom. You think that sometimes during the day, but, like set my fucking soul on fire for me is always in a good way, but sometimes good things come through fire. It's like really hard to get there. You have to make some sacrifices, or or can take some concessions like there's
(01:59):
there's a lot of layers to it, in my opinion, but the the core of like wanting to invest my time in things, and if it doesn't set your soul on fire not being worth it, it's all positive.
Govindh Jayaraman (02:12):
Yeah, so what does? How did you 1st come? I mean, you talked about being a mom
making you more aware of how valuable your time is, and I'm not just talking, you know, like jokingly about the 3 Am. Feedings. And you know my babies at night, because then.
Dinah Chapman (02:30):
Yeah.
Govindh Jayaraman (02:31):
Leaping. Time becomes very precious in those moments. But but
I'm talking about overall like, so being a mom helps you make that realization right.
Dinah Chapman (02:40):
Yeah, just the time. In general, you mean.
Govindh Jayaraman (02:44):
Yeah, about how how precious your time was.
Dinah Chapman (02:48):
Yeah, it's a mixture of like
I. Time slows down and speeds up at the same time, especially when you have children, and not that it wasn't
moving quickly prior to me, having kids, but I always had
(03:08):
carved out time. You have more time when you only have yourself to focus on. And so you can make time for things. And then once I had kids, I realized, like, Wow, life's moving so quickly, they're growing up so fast. The stages are moving so quickly. But then sometimes you're like, Oh, my God! That
day felt like a year, and like time is moving really slowly at the same time. So I just there is a push pull in that sense of time, and how precious it is, and just also realizing, like
(03:42):
you also would devote so much time to your work. You realize once once you have things that are, you're responsible for tying tie ties to you. Essentially, you realize, like where the majority of your day is going.
And that's when I realized, too, just like, Wow, what do you have kids? And you're trying to be mom and and work, and and you're all the things at once, after now having these like huge in time commitments and investments. That's when it really hit me in like a bigger way of time, being my most valuable thing, because it's time with my kids time to develop to a business time for myself time to sleep. All of those things kind of like play, a factor.
Govindh Jayaraman (04:25):
So
how did that change? So did the business come before the realization? Or did the business come after the realization after the napkin.
Dinah Chapman (04:35):
Well, I was very ambitious when I started my company, because I was on maternity leave from my corporate job, so I thought I had time. I was like, I'm going to be on mat leave. I'm not going to be working new 1st time, Mom, like, Hello! That was ambitious.
I and so it all kind of hit at once, honestly, because the business with the the new stage of motherhood I was entering, plus. I was still working in corporate.
(05:05):
So
probably like perfect storm for me to realize I had a lot of time on my hands to very little, and I was juggling a lot at once.
Govindh Jayaraman (05:17):
And is that where you sort of are talking about
how time slows down and speeds up at the same time? You know you were living this sort of like
weird reality around time.
Dinah Chapman (05:30):
Yeah, like. And I think a lot of
others could relate, not just working mothers, for sure. But when you have this like a very short period of time to adjust this completely new version of yourself and what your life is. Once you have kids, and then you go back to work. You are in this like warped reality of like groundhog's day, essentially work, work work. And then kids, kids, kids and trying to find that that balance. And I think that's
(06:02):
yeah, truly, when I was just like God, it's always about time. It's it's who and what your priorities are, what you're investing your time in what you have time for. You're working and investing all your time and work for, for then what? To be later have time to do the stuff you didn't do because you were investing your time and work.
(06:22):
and then your kids. All of a sudden they're grown and you lost that time. But you invested it in other places like, I just started to have that like realization at that time that I had to have a better grasp on like what I spent
my core hours on and like, really wanted to make sure that I was really passionate about it, and and could build.
(06:46):
could build a career and a and a company and a job around around that, and not. I've been fortunate to do that with little trouble, obviously, and not not everyone can.
Govindh Jayaraman (06:54):
So let's talk about that right like. So when when starting little trouble, I mean everybody, every entrepreneur's been through this, there's a whole bunch of really fun things that
bring us toward the business that we really love to do, that we would do all the time. And then there's other things about the business that aren't as much fun. Are you saying that setting your soul on fire means that
(07:22):
you only pick the stuff that you like within that, too? Or how? How do you differentiate those kinds of things?
Dinah Chapman (07:29):
Yeah, no good question. I think that
if you could, if it was always the good, I mean amazing, but so unrealistic, right? And like you can't.
It'd be very challenging to get to that stage if everything was just like easy
daisies and rainbows. But I think that it's if if the
(07:55):
if the day in and day out the core of what you're doing, if you don't love what you're doing, that's like the the critical part of it if you don't love what you're doing, and if it's not really like setting your soul on fire in whatever way that is, whether it's creatively, mentally stimulating, surrounded it with something you love or a cause you love. The work you put in is
(08:19):
worth it on a different level, like I could be prior to starting my own company. I was really really invested in the companies I worked for, like I enjoyed the work I put in a ton of time, and I enjoyed what I got out of it the job satisfaction. But at the end of the day like that that for me, working for somebody else building someone else's dream wasn't
(08:42):
doing it for me, you know. At the end of it I always was like, Okay, but when I can do it for myself, or when this is mine, and these hours are going into my building, my future and my dream like that's what it's still just as hard, and it's grueling and
honestly way harder when you're doing it for yourself. But it's the concept of all that hard work. The end goal is setting like. That's what sets my soul on fire. The creativity, the build, the hustle like being, and then being able to like, reap that reward, all of that goes into it. So it's definitely not just like picking and choosing the good stuff. And if if it doesn't, if it's not fun, it's not worth it.
Govindh Jayaraman (09:23):
Yeah. So you're not saying that you're not saying every every single task has to be.
you know, sunshine and lollipops. You're some of it. Some of it's a bit of a slog.
Dinah Chapman (09:35):
Way more of it than I realized.
Govindh Jayaraman (09:37):
Yeah. But but the other side of it, what you're saying is making that vision come true.
That's what sets your soul on fire.
Dinah Chapman (09:48):
Yeah, fully working, working towards it.
Govindh Jayaraman (09:51):
So when when you started when you started this, you know, like
creating a clothing brand, that's not easy to do right. There's a there's a whole bunch of moving pieces.
Is this something that you knew before starting? Or did you figure it out when you started.
Dinah Chapman (10:15):
I never thought it would be an easy road, but, to be honest, when I started little trouble I was thinking it was going to be like an Etsy side hustle like I was like, I'll just kind of do this on the side. I was working as a marketing director for a large skincare company
managing a team of 13 people, and I was like again 1st time, Mom, very ambitious on maternity leave like I got time on my hands. And I'd always wanted like had that entrepreneurial spirit since I was a kid like selling wrapping paper, you know, on the golf cart to my my neighbors, and I.
(10:53):
But I didn't realize
A that it would grow and scale as quickly as it has. And then B, the things I thought would be challenging sometimes have been sometimes have been easier, the unexpected that I wasn't anticipating the learnings for me, that just were so outside of my wheelhouse, and I was like, Oh, God, I'm doing this now for myself. And there isn't like a support system that there typically is in corporate
(11:22):
that has been
eye opening so a little bit of both. I never thought it'd be easy, but I also kind of thought I was going to be running like a very small hobby.
Govindh Jayaraman (11:32):
And and when did it? When did you realize that it was catching fire.
Dinah Chapman (11:41):
Well, I sold out of hoodies in like peak heat in a California summer.
And I was like, Okay.
that's not what I expected. I kind of thought again. I was gonna like, have this inventory for a long time. See it? See how it goes. And and we sold out really quickly. It caught wind on social media. And then I was like, Okay, cool. See if I can like. Do it again. Place to reorder a little bit bigger.
(12:10):
and then it just kept selling out, and I kept catching the eye of like a few creators here and there, or just like really good social media traction. I had some like viral videos on Tiktok, unbeknownst to me, and so probably. But still I was so head down in corporate at the time. Still in my role, my role required so many hours
(12:35):
that I was just still kind of like it has viability. But it's also just cool. And I'm gonna like get to it eventually, probably like a year in
when and again, like the time investment. It was not all fun. I was working 60 h in corporate had a newborn, and then I was packing orders in my garage between 10 Pm. And 3 am. Between feeding like and then working my corporate job again. So I honestly have kind of like blacked out.
(13:06):
If I'm being honest. The pictures I have that my husband took of me are like crazy me like with the baby pack, and orders at like midnight
but so I was so head down for that period of time, and then at 1 point
my husband like was like, Where are you gonna put your like new shipment? And I was like, what do you mean like? And the he was like, have you like? The garage is overflowing, the office is overflowing, the living room has been taken over, and so then we had to get a shipping container and put the shipping container on our property. And that's when I was like, Okay, this has like serious legs. And if I make the leap away from corporate and like, dedicate myself to this.
(13:51):
I can make this like a full time thing.
And and yeah, so that's when probably a year and a half in, and I'm about to hit my 3 year mark but and the 1st year
was again just like me, very much packing orders when I could doing such a little amount of of effort in into it. And then the shipping container was probably the tipping point.
Govindh Jayaraman (14:15):
Yeah, right? So shipping heart containers kind of also hard to walk past. Right? Like you. You.
Dinah Chapman (14:21):
Totally.
Govindh Jayaraman (14:22):
Cute.
You're confronted by a
40 foot container that's sitting there going. Oh, I guess it's a something right? Yep, yeah, right? So
what? What prompted so so obviously, you couldn't deny the size and the scale, and how this is happening? Right? So that that was part of it.
(14:43):
But when did you realize how much this was giving you? How much of this was feeding your soul like you were setting your soul on fire? How much did you, because there's a i think, for a lot of us
like you just said it sort of just happened. And it grew. And then you found yourself kind of accidentally on purpose in this place.
What did you realize how important it was to you.
Dinah Chapman (15:06):
Yeah, it's a great question. It was when
I would get through. Well, a I was in corporate, and just like the grind, right of just like
the hours, the team, the building, etc. And I would I would find myself like using little trouble as like a creative outlet. And like that was where I was just like
(15:34):
energized again, like I was. I was working, but it was like filling my cup. It was hard work, but again. It was like Re. I was really passionate about it, and I was building something for myself, like there was purpose to the work. And so that's when I knew it was like important to me, but then, when it came down to.
I need to like, make a choice.
(15:55):
I can't. There are not enough hours in the day anymore for me to do this. It's not sustainable, and it's like, either.
take the leap and scale it, or, you know.
avert, because it's at that point. It was like, I'm either gonna let it just kind of simmer here and be a what if
(16:17):
or I'm gonna choose to really put forth all my energy and like, take the risk on it.
And I had many people ask me like, Why don't you just sell it now? It's like there's viability. Someone will buy it from you. You're doing really well in corporate. It's a sure path. Blah blah blah! And I was just like God! If I let this go, it will be like the biggest. What if
(16:42):
for myself of like but I what what could I have done if I had like been gutsy enough
to to do it. And that's when I was like, no, if I'm gonna pick something, I'm gonna pick myself, and I'm gonna like pick. My own idea.
Govindh Jayaraman (16:57):
And that's kind of what you're talking about. That's that moment where you decided to pick the thing that set your soul on fire right, the safety and the stability of the job.
Yeah, or this leap, this this leap into
entrepreneurship which you were already doing. I mean, you started the business, but
(17:19):
like little trouble, was already growing.
Dinah Chapman (17:21):
Just safety, net.
Govindh Jayaraman (17:22):
Yeah, but yeah, you you you took your toe out of the water and you dove in right? So
after you did that, did you have like an Oh, crap moment like, or was, it was just all good.
Dinah Chapman (17:35):
Yeah, I have them all the time. I still have them. I have like such. I always have to in my career. I don't know if it was from. I started
I like interned straight out of. Well, I interned in college straight out of college and got like straight into the workforce. I was always like very entrepreneurial, and very like stoked to like start my career. So I was always like the youngest person in the room always in, and I climbed the corporate ladder really quickly.
(18:06):
And I found myself in like very cool roles and very cool meetings and very cool cities like throughout my early stages of my career, but I think it almost formed like imposter syndrome.
because I feel that still, even though, like I've scaled tons of businesses from, you know.
5, 7, 10 million to 30, 40, 50 million, and, like my like, my bread and butter is in direct to consumer marketing and brand marketing, so I've like I knew I had it in me to do it for myself. But even in those roles
(18:40):
I've I would catch myself
like second guessing things, or and now having like the Oh, shit moments all the time. So I don't. It's a mix of like every entrepreneur, I'm sure has it. But I also think when you're like dedicated to your craft.
and you're good at it. There is also still this like imposter syndrome that that can set in. Yeah. So I talk myself out of that often to be like, no like, be be confident you're going to make mistakes. But, like you. You know what to do like. You've got it in you.
(19:14):
But I mean, yeah, I have. Oh, shit moments, even like I'm like God. Was that the right color. I should have picked 36, and I picked 1, 82 like.
Govindh Jayaraman (19:22):
Right.
Dinah Chapman (19:23):
So there's Con. And then there's also a constant like big oh, shit moments like we don't have the safety net we had before, or like.
Govindh Jayaraman (19:31):
Yeah.
Dinah Chapman (19:32):
Yeah, all the all the bills have stayed the same.
Govindh Jayaraman (19:35):
So you you talked about that you had the brand marketing background. But you know you took the leap of faith into a little trouble and doing it on your own.
The thing that I find really interesting is even within this, when you, when you're picking, maybe
when you're picking between things to do in the business? Right options?
(19:58):
Are you able to quiet the pressure and noise, to still use your soul as the barometer is, that is, that still leading you the way? Or do you find it harder now that you've got momentum
to use your internal barometer? And how do you communicate that to other people. What are you doing.
Dinah Chapman (20:16):
Yeah, that's actually such a great question, and has come up recently because I will, I will squash.
Well, the answer is, yes, I listen to my internal barometer. Still, I feel like it's what got me here.
I've built this brand on
designing things that I, as a parent, would like. Like my aesthetic, my style, things I would buy. It's easy to have other people try to influence what you develop, what you design.
(20:49):
how it fits the quality, like all of those things, and I
was just on a call saying, like, I am relatively known for squashing something that maybe would sell well because of the price difference, but it comes at a cost or and but I just I'm like, I don't like it. I don't like it for the business. I don't like it for the brand. I don't want it to. I don't want that to be
(21:16):
the connotation or the association or the quality. So
I it is still easy for me to like quiet those
other opinions, and really stay true, to like what I have as the vision. But I I know that the bigger the brand gets, the more influence there is externally, that can be harder. So that's always been something I want to make sure
(21:43):
I stay really attached to. There are a lot of things I want to stay true to being the founder. I've worked for a lot of small small brands that brands that either scale and or have that like founder story.
And I've worked really close with a lot of those people.
So I I've pulled like what I love and don't love. You know. Of course, from what I've experienced.
(22:09):
and I think the big thing is like a staying true to like the vision
for the long haul, and then also like remembering what it's like being the one doing the work and like being in the weeds and being on the ground floor, and how quickly you can like, dissociate from that and detach from that. So those are 2 things I like, wanna make sure I don't.
(22:33):
I don't have, or don't do, moving forward as the company scales. But easier easier said than done.
Govindh Jayaraman (22:41):
Right.
How do you? How do you tell that story to your team
like? How do you share that fire with the team?
What are some stories that you share or or do you.
Dinah Chapman (22:55):
Well, currently.
Well, I guess in 2 there's like 2 answers to that. Currently, my
shockingly, my team is still like myself. I've got like some customer care support, and then my husband, who does a lot of like operations for me. But I've scaled this business
(23:23):
with my myself and age, like some
outside support, like some agency support. But building a team is like critical this year. I've just held off basically as long as possible for a multitude of reasons, but one of which is like, I really wanna make sure I'm in a position where, when I start to build a team I'm able to offer. The things I know are like very critical. So
(23:58):
that that's been a really large part of like wanting a little trouble to get to a spot where I'm not just bringing someone on for like a really low, hourly rate, to just like help me, or like multiple people at that to help me. I want to be able to offer someone like a really amazing place to be a place that I would want to be. And so.
Govindh Jayaraman (24:17):
Again. This is like interesting to me, because it's again
one of the things that I love about how you built. Little trouble is you built it for stuff that you wanted to have for your kids, right? And I think that we're our best when we are for others. What we needed in the world.
and you're doing that with the brand. But I like how you're extending that even to how you will build your team. And and I think it's also an interesting statement about where we are
(24:49):
now that you can find ways to scale a business pretty aggressively.
Without the the traditional large team right? You. You've aligned yourself with vendors and suppliers and and and partners and agencies
that share your values, and you can do it that way, too, right?
Dinah Chapman (25:14):
Yeah, it's crazy. I was just talking to my husband actually, about how I've been brought in
at this stage to other companies several times, and they have teams of like
1520, 25 people like full, full warehousing teams marketing a small marketing team. But I was always brought in to like head up or or build a marketing team. But I think that. And that's when, like the imposter syndrome I'm like, Get out of here because
(25:44):
the company is at this stage, where, like, I was brought in at this stage with amongst a team of people, and it's still just me. And so but yeah, to your point. It's there are so many ways a the hours you've just got to like, put in the work. But if you align yourself with. Yeah, the right partners. There's so many people there's so many things you can like outsource.
(26:12):
But like, keep keep close knit. I but I do wear a lot of hats. So I'm excited to like, build the team but I've just I just wanna make sure that when I do the offer I have for someone is
is like really comprehensive, and fits their lifestyle, and is what I would be proud of saying like, I'm hiring for X, and like, this is what you're gonna get working with me. And it's what I want to be able to maintain as I scale the brand. It's like very important to me when I build the team.
Govindh Jayaraman (26:48):
And I also like the fact that you know, you started off with this idea that I'm just gonna sell this stuff on Etsy small.
you you leaned into what you knew.
and you and you did it.
You offer something of value so that you didn't wait, for
I know you said you were on mat leave, so that was the perfect time. But you know I have 3 kids, and there was no perfection.
Dinah Chapman (27:13):
Whole pirate.
Govindh Jayaraman (27:13):
There was no perfection around those times. But so so
you started it. Then you started off small. So you didn't wait like you didn't need. You didn't go raise a bunch of money, you didn't.
You didn't wait. You just took a step
and then took another step, and then another step right, and each time you made sure that these steps that you were taking the time that you're putting in
(27:40):
was firing you up like you were you were on fire, you said about what you were doing. You're really passionate about it.
Dinah Chapman (27:48):
That's why it's like you can make. You can make the time for the Passion project and the thing that like lights you up like if it's if it that, and that's what I really mean at the end of the day with my napkin is.
if it's a drag, it's gonna be a drag
like if you're if it just is, there's nothing motivating about it. Nothing is yeah, like exciting you or lighting you up the whole. The whole experience is probably going to be a drag.
(28:18):
and I just when I was thinking about time.
it was just like, I don't want.
I don't want to look back and say, like, God, that was a drag, or I just had to like, get through that like I wanna be building. It's really hard. But I want to be building and have something that's like.
really, creatively inspiring and like passionate for me. That's what I want, and that's that's all part of the
(28:47):
like. If it lights you up.
This is where to invest the time, and there wasn't a right time to your point. I was just like.
if not now, when that was kind of how I chose, if I don't do it now, when am I going to do it?
And then, yeah, I have one foot in front of the other. And
and then I just kept saying, like, I'm gonna choose myself. I'm gonna invest in myself. And
(29:13):
if I put in. Yeah, the time and the energy it's gonna work out.
Govindh Jayaraman (29:18):
That's awesome.
We've been asking every guest to pay forward some gratitude that we got from an early guest of ours. Many years ago we had John Rulin, who is the best selling author of a book called Giftology. He started a movement around Gratitude, and his napkin to us was what you appreciate, appreciates. He suddenly passed away
(29:39):
recently, and to honor his memory and his legacy we're asking everyone to shout out, give some appreciation to somebody or something that has been instrumental, or.
you know, timely. So is there anybody that you'd like to shout out.
Dinah Chapman (30:00):
Yes,
Can I shout out 2 people.
Govindh Jayaraman (30:05):
Of course.
Dinah Chapman (30:07):
Does that work?
I
would shout out my husband 1st and foremost, just because the building years are really challenging. You need a lot of support in those years, especially when you're building during young childhood years as well. When I mentioned earlier, like sacrifice concessions like it all, it's all part of it. It's not.
(30:28):
It's not just like what you see on social media of building a brand. And you know I live abroad, and it looks like it's the cool. It's the cool thing running a business from your computer. It's what everyone wants, right? But there's like such a different side of it on the back end.
So just like gratitude to sticking, sticking it out and like being positive and
(30:52):
supportive through that as we're in these building years. But then, like a collective call out to the women, I've been able to manage and mentor in my previous lives. They've like really shaped me as a as a person, as a leader, and how I want to build and shape my company, and I wouldn't have
(31:16):
the forward thinking ideas, or the the hustle or the desire to to build what I want to build. If it wasn't for them. And I think that good people give back to mentors the same way, like everything's very reciprocal.
And so I'd I'd shout out all of the really cool women that I've worked with or managed in the past.
Govindh Jayaraman (31:41):
I love that. That's great. Thank you for doing that, and thanks for joining me, Diana.
Dinah Chapman (31:45):
Yeah, thanks, so much.
Dinah Chapman. Welcome to paper napkin wisdom. I'm excited to have you here today.
Dinah Chapman (00:06):
Thanks me, too. I'm excited to be here.
Govindh Jayaraman (00:09):
So you shared a great paper napkin with me, and you censored it. But we're not going to censor it here, so it says if it doesn't set your fucking soul on fire, it's not worth it.
Why did you share that with me?
Dinah Chapman (00:25):
Yeah, I feel like this. Last year of my life I have made a lot of really big changes and leaps and decided that which I've done a few different times throughout my career. Made those big leaps and decided if it
if I'm not investing my time and my energy in shit that really just sets me on fire, and that is passionate for me, and that I love. It's not worth it. At the end of the day. I think once I had kids that like really set in for me of just like time is my most valuable
(01:04):
asset, and I want to make sure I'm investing it in things that just really
fucking set me on fire.
Govindh Jayaraman (01:12):
I love it so.
So setting you on fire?
That idea!
Is it always like
the 1st thing that I thought of? Is it always a positive, or is it just like I need to get out of something is like, is it a push and a pull? Or is it just a pull.
Dinah Chapman (01:32):
Good question. Yes, as I say, set me on fire. I'm like as a mom. You think that sometimes during the day, but, like set my fucking soul on fire for me is always in a good way, but sometimes good things come through fire. It's like really hard to get there. You have to make some sacrifices, or or can take some concessions like there's
(01:59):
there's a lot of layers to it, in my opinion, but the the core of like wanting to invest my time in things, and if it doesn't set your soul on fire not being worth it, it's all positive.
Govindh Jayaraman (02:12):
Yeah, so what does? How did you 1st come? I mean, you talked about being a mom
making you more aware of how valuable your time is, and I'm not just talking, you know, like jokingly about the 3 Am. Feedings. And you know my babies at night, because then.
Dinah Chapman (02:30):
Yeah.
Govindh Jayaraman (02:31):
Leaping. Time becomes very precious in those moments. But but
I'm talking about overall like, so being a mom helps you make that realization right.
Dinah Chapman (02:40):
Yeah, just the time. In general, you mean.
Govindh Jayaraman (02:44):
Yeah, about how how precious your time was.
Dinah Chapman (02:48):
Yeah, it's a mixture of like
I. Time slows down and speeds up at the same time, especially when you have children, and not that it wasn't
moving quickly prior to me, having kids, but I always had
(03:08):
carved out time. You have more time when you only have yourself to focus on. And so you can make time for things. And then once I had kids, I realized, like, Wow, life's moving so quickly, they're growing up so fast. The stages are moving so quickly. But then sometimes you're like, Oh, my God! That
day felt like a year, and like time is moving really slowly at the same time. So I just there is a push pull in that sense of time, and how precious it is, and just also realizing, like
(03:42):
you also would devote so much time to your work. You realize once once you have things that are, you're responsible for tying tie ties to you. Essentially, you realize, like where the majority of your day is going.
And that's when I realized, too, just like, Wow, what do you have kids? And you're trying to be mom and and work, and and you're all the things at once, after now having these like huge in time commitments and investments. That's when it really hit me in like a bigger way of time, being my most valuable thing, because it's time with my kids time to develop to a business time for myself time to sleep. All of those things kind of like play, a factor.
Govindh Jayaraman (04:25):
So
how did that change? So did the business come before the realization? Or did the business come after the realization after the napkin.
Dinah Chapman (04:35):
Well, I was very ambitious when I started my company, because I was on maternity leave from my corporate job, so I thought I had time. I was like, I'm going to be on mat leave. I'm not going to be working new 1st time, Mom, like, Hello! That was ambitious.
I and so it all kind of hit at once, honestly, because the business with the the new stage of motherhood I was entering, plus. I was still working in corporate.
(05:05):
So
probably like perfect storm for me to realize I had a lot of time on my hands to very little, and I was juggling a lot at once.
Govindh Jayaraman (05:17):
And is that where you sort of are talking about
how time slows down and speeds up at the same time? You know you were living this sort of like
weird reality around time.
Dinah Chapman (05:30):
Yeah, like. And I think a lot of
others could relate, not just working mothers, for sure. But when you have this like a very short period of time to adjust this completely new version of yourself and what your life is. Once you have kids, and then you go back to work. You are in this like warped reality of like groundhog's day, essentially work, work work. And then kids, kids, kids and trying to find that that balance. And I think that's
(06:02):
yeah, truly, when I was just like God, it's always about time. It's it's who and what your priorities are, what you're investing your time in what you have time for. You're working and investing all your time and work for, for then what? To be later have time to do the stuff you didn't do because you were investing your time and work.
(06:22):
and then your kids. All of a sudden they're grown and you lost that time. But you invested it in other places like, I just started to have that like realization at that time that I had to have a better grasp on like what I spent
my core hours on and like, really wanted to make sure that I was really passionate about it, and and could build.
(06:46):
could build a career and a and a company and a job around around that, and not. I've been fortunate to do that with little trouble, obviously, and not not everyone can.
Govindh Jayaraman (06:54):
So let's talk about that right like. So when when starting little trouble, I mean everybody, every entrepreneur's been through this, there's a whole bunch of really fun things that
bring us toward the business that we really love to do, that we would do all the time. And then there's other things about the business that aren't as much fun. Are you saying that setting your soul on fire means that
(07:22):
you only pick the stuff that you like within that, too? Or how? How do you differentiate those kinds of things?
Dinah Chapman (07:29):
Yeah, no good question. I think that
if you could, if it was always the good, I mean amazing, but so unrealistic, right? And like you can't.
It'd be very challenging to get to that stage if everything was just like easy
daisies and rainbows. But I think that it's if if the
(07:55):
if the day in and day out the core of what you're doing, if you don't love what you're doing, that's like the the critical part of it if you don't love what you're doing, and if it's not really like setting your soul on fire in whatever way that is, whether it's creatively, mentally stimulating, surrounded it with something you love or a cause you love. The work you put in is
(08:19):
worth it on a different level, like I could be prior to starting my own company. I was really really invested in the companies I worked for, like I enjoyed the work I put in a ton of time, and I enjoyed what I got out of it the job satisfaction. But at the end of the day like that that for me, working for somebody else building someone else's dream wasn't
(08:42):
doing it for me, you know. At the end of it I always was like, Okay, but when I can do it for myself, or when this is mine, and these hours are going into my building, my future and my dream like that's what it's still just as hard, and it's grueling and
honestly way harder when you're doing it for yourself. But it's the concept of all that hard work. The end goal is setting like. That's what sets my soul on fire. The creativity, the build, the hustle like being, and then being able to like, reap that reward, all of that goes into it. So it's definitely not just like picking and choosing the good stuff. And if if it doesn't, if it's not fun, it's not worth it.
Govindh Jayaraman (09:23):
Yeah. So you're not saying that you're not saying every every single task has to be.
you know, sunshine and lollipops. You're some of it. Some of it's a bit of a slog.
Dinah Chapman (09:35):
Way more of it than I realized.
Govindh Jayaraman (09:37):
Yeah. But but the other side of it, what you're saying is making that vision come true.
That's what sets your soul on fire.
Dinah Chapman (09:48):
Yeah, fully working, working towards it.
Govindh Jayaraman (09:51):
So when when you started when you started this, you know, like
creating a clothing brand, that's not easy to do right. There's a there's a whole bunch of moving pieces.
Is this something that you knew before starting? Or did you figure it out when you started.
Dinah Chapman (10:15):
I never thought it would be an easy road, but, to be honest, when I started little trouble I was thinking it was going to be like an Etsy side hustle like I was like, I'll just kind of do this on the side. I was working as a marketing director for a large skincare company
managing a team of 13 people, and I was like again 1st time, Mom, very ambitious on maternity leave like I got time on my hands. And I'd always wanted like had that entrepreneurial spirit since I was a kid like selling wrapping paper, you know, on the golf cart to my my neighbors, and I.
(10:53):
But I didn't realize
A that it would grow and scale as quickly as it has. And then B, the things I thought would be challenging sometimes have been sometimes have been easier, the unexpected that I wasn't anticipating the learnings for me, that just were so outside of my wheelhouse, and I was like, Oh, God, I'm doing this now for myself. And there isn't like a support system that there typically is in corporate
(11:22):
that has been
eye opening so a little bit of both. I never thought it'd be easy, but I also kind of thought I was going to be running like a very small hobby.
Govindh Jayaraman (11:32):
And and when did it? When did you realize that it was catching fire.
Dinah Chapman (11:41):
Well, I sold out of hoodies in like peak heat in a California summer.
And I was like, Okay.
that's not what I expected. I kind of thought again. I was gonna like, have this inventory for a long time. See it? See how it goes. And and we sold out really quickly. It caught wind on social media. And then I was like, Okay, cool. See if I can like. Do it again. Place to reorder a little bit bigger.
(12:10):
and then it just kept selling out, and I kept catching the eye of like a few creators here and there, or just like really good social media traction. I had some like viral videos on Tiktok, unbeknownst to me, and so probably. But still I was so head down in corporate at the time. Still in my role, my role required so many hours
(12:35):
that I was just still kind of like it has viability. But it's also just cool. And I'm gonna like get to it eventually, probably like a year in
when and again, like the time investment. It was not all fun. I was working 60 h in corporate had a newborn, and then I was packing orders in my garage between 10 Pm. And 3 am. Between feeding like and then working my corporate job again. So I honestly have kind of like blacked out.
(13:06):
If I'm being honest. The pictures I have that my husband took of me are like crazy me like with the baby pack, and orders at like midnight
but so I was so head down for that period of time, and then at 1 point
my husband like was like, Where are you gonna put your like new shipment? And I was like, what do you mean like? And the he was like, have you like? The garage is overflowing, the office is overflowing, the living room has been taken over, and so then we had to get a shipping container and put the shipping container on our property. And that's when I was like, Okay, this has like serious legs. And if I make the leap away from corporate and like, dedicate myself to this.
(13:51):
I can make this like a full time thing.
And and yeah, so that's when probably a year and a half in, and I'm about to hit my 3 year mark but and the 1st year
was again just like me, very much packing orders when I could doing such a little amount of of effort in into it. And then the shipping container was probably the tipping point.
Govindh Jayaraman (14:15):
Yeah, right? So shipping heart containers kind of also hard to walk past. Right? Like you. You.
Dinah Chapman (14:21):
Totally.
Govindh Jayaraman (14:22):
Cute.
You're confronted by a
40 foot container that's sitting there going. Oh, I guess it's a something right? Yep, yeah, right? So
what? What prompted so so obviously, you couldn't deny the size and the scale, and how this is happening? Right? So that that was part of it.
(14:43):
But when did you realize how much this was giving you? How much of this was feeding your soul like you were setting your soul on fire? How much did you, because there's a i think, for a lot of us
like you just said it sort of just happened. And it grew. And then you found yourself kind of accidentally on purpose in this place.
What did you realize how important it was to you.
Dinah Chapman (15:06):
Yeah, it's a great question. It was when
I would get through. Well, a I was in corporate, and just like the grind, right of just like
the hours, the team, the building, etc. And I would I would find myself like using little trouble as like a creative outlet. And like that was where I was just like
(15:34):
energized again, like I was. I was working, but it was like filling my cup. It was hard work, but again. It was like Re. I was really passionate about it, and I was building something for myself, like there was purpose to the work. And so that's when I knew it was like important to me, but then, when it came down to.
I need to like, make a choice.
(15:55):
I can't. There are not enough hours in the day anymore for me to do this. It's not sustainable, and it's like, either.
take the leap and scale it, or, you know.
avert, because it's at that point. It was like, I'm either gonna let it just kind of simmer here and be a what if
(16:17):
or I'm gonna choose to really put forth all my energy and like, take the risk on it.
And I had many people ask me like, Why don't you just sell it now? It's like there's viability. Someone will buy it from you. You're doing really well in corporate. It's a sure path. Blah blah blah! And I was just like God! If I let this go, it will be like the biggest. What if
(16:42):
for myself of like but I what what could I have done if I had like been gutsy enough
to to do it. And that's when I was like, no, if I'm gonna pick something, I'm gonna pick myself, and I'm gonna like pick. My own idea.
Govindh Jayaraman (16:57):
And that's kind of what you're talking about. That's that moment where you decided to pick the thing that set your soul on fire right, the safety and the stability of the job.
Yeah, or this leap, this this leap into
entrepreneurship which you were already doing. I mean, you started the business, but
(17:19):
like little trouble, was already growing.
Dinah Chapman (17:21):
Just safety, net.
Govindh Jayaraman (17:22):
Yeah, but yeah, you you you took your toe out of the water and you dove in right? So
after you did that, did you have like an Oh, crap moment like, or was, it was just all good.
Dinah Chapman (17:35):
Yeah, I have them all the time. I still have them. I have like such. I always have to in my career. I don't know if it was from. I started
I like interned straight out of. Well, I interned in college straight out of college and got like straight into the workforce. I was always like very entrepreneurial, and very like stoked to like start my career. So I was always like the youngest person in the room always in, and I climbed the corporate ladder really quickly.
(18:06):
And I found myself in like very cool roles and very cool meetings and very cool cities like throughout my early stages of my career, but I think it almost formed like imposter syndrome.
because I feel that still, even though, like I've scaled tons of businesses from, you know.
5, 7, 10 million to 30, 40, 50 million, and, like my like, my bread and butter is in direct to consumer marketing and brand marketing, so I've like I knew I had it in me to do it for myself. But even in those roles
(18:40):
I've I would catch myself
like second guessing things, or and now having like the Oh, shit moments all the time. So I don't. It's a mix of like every entrepreneur, I'm sure has it. But I also think when you're like dedicated to your craft.
and you're good at it. There is also still this like imposter syndrome that that can set in. Yeah. So I talk myself out of that often to be like, no like, be be confident you're going to make mistakes. But, like you. You know what to do like. You've got it in you.
(19:14):
But I mean, yeah, I have. Oh, shit moments, even like I'm like God. Was that the right color. I should have picked 36, and I picked 1, 82 like.
Govindh Jayaraman (19:22):
Right.
Dinah Chapman (19:23):
So there's Con. And then there's also a constant like big oh, shit moments like we don't have the safety net we had before, or like.
Govindh Jayaraman (19:31):
Yeah.
Dinah Chapman (19:32):
Yeah, all the all the bills have stayed the same.
Govindh Jayaraman (19:35):
So you you talked about that you had the brand marketing background. But you know you took the leap of faith into a little trouble and doing it on your own.
The thing that I find really interesting is even within this, when you, when you're picking, maybe
when you're picking between things to do in the business? Right options?
(19:58):
Are you able to quiet the pressure and noise, to still use your soul as the barometer is, that is, that still leading you the way? Or do you find it harder now that you've got momentum
to use your internal barometer? And how do you communicate that to other people. What are you doing.
Dinah Chapman (20:16):
Yeah, that's actually such a great question, and has come up recently because I will, I will squash.
Well, the answer is, yes, I listen to my internal barometer. Still, I feel like it's what got me here.
I've built this brand on
designing things that I, as a parent, would like. Like my aesthetic, my style, things I would buy. It's easy to have other people try to influence what you develop, what you design.
(20:49):
how it fits the quality, like all of those things, and I
was just on a call saying, like, I am relatively known for squashing something that maybe would sell well because of the price difference, but it comes at a cost or and but I just I'm like, I don't like it. I don't like it for the business. I don't like it for the brand. I don't want it to. I don't want that to be
(21:16):
the connotation or the association or the quality. So
I it is still easy for me to like quiet those
other opinions, and really stay true, to like what I have as the vision. But I I know that the bigger the brand gets, the more influence there is externally, that can be harder. So that's always been something I want to make sure
(21:43):
I stay really attached to. There are a lot of things I want to stay true to being the founder. I've worked for a lot of small small brands that brands that either scale and or have that like founder story.
And I've worked really close with a lot of those people.
So I I've pulled like what I love and don't love. You know. Of course, from what I've experienced.
(22:09):
and I think the big thing is like a staying true to like the vision
for the long haul, and then also like remembering what it's like being the one doing the work and like being in the weeds and being on the ground floor, and how quickly you can like, dissociate from that and detach from that. So those are 2 things I like, wanna make sure I don't.
(22:33):
I don't have, or don't do, moving forward as the company scales. But easier easier said than done.
Govindh Jayaraman (22:41):
Right.
How do you? How do you tell that story to your team
like? How do you share that fire with the team?
What are some stories that you share or or do you.
Dinah Chapman (22:55):
Well, currently.
Well, I guess in 2 there's like 2 answers to that. Currently, my
shockingly, my team is still like myself. I've got like some customer care support, and then my husband, who does a lot of like operations for me. But I've scaled this business
(23:23):
with my myself and age, like some
outside support, like some agency support. But building a team is like critical this year. I've just held off basically as long as possible for a multitude of reasons, but one of which is like, I really wanna make sure I'm in a position where, when I start to build a team I'm able to offer. The things I know are like very critical. So
(23:58):
that that's been a really large part of like wanting a little trouble to get to a spot where I'm not just bringing someone on for like a really low, hourly rate, to just like help me, or like multiple people at that to help me. I want to be able to offer someone like a really amazing place to be a place that I would want to be. And so.
Govindh Jayaraman (24:17):
Again. This is like interesting to me, because it's again
one of the things that I love about how you built. Little trouble is you built it for stuff that you wanted to have for your kids, right? And I think that we're our best when we are for others. What we needed in the world.
and you're doing that with the brand. But I like how you're extending that even to how you will build your team. And and I think it's also an interesting statement about where we are
(24:49):
now that you can find ways to scale a business pretty aggressively.
Without the the traditional large team right? You. You've aligned yourself with vendors and suppliers and and and partners and agencies
that share your values, and you can do it that way, too, right?
Dinah Chapman (25:14):
Yeah, it's crazy. I was just talking to my husband actually, about how I've been brought in
at this stage to other companies several times, and they have teams of like
1520, 25 people like full, full warehousing teams marketing a small marketing team. But I was always brought in to like head up or or build a marketing team. But I think that. And that's when, like the imposter syndrome I'm like, Get out of here because
(25:44):
the company is at this stage, where, like, I was brought in at this stage with amongst a team of people, and it's still just me. And so but yeah, to your point. It's there are so many ways a the hours you've just got to like, put in the work. But if you align yourself with. Yeah, the right partners. There's so many people there's so many things you can like outsource.
(26:12):
But like, keep keep close knit. I but I do wear a lot of hats. So I'm excited to like, build the team but I've just I just wanna make sure that when I do the offer I have for someone is
is like really comprehensive, and fits their lifestyle, and is what I would be proud of saying like, I'm hiring for X, and like, this is what you're gonna get working with me. And it's what I want to be able to maintain as I scale the brand. It's like very important to me when I build the team.
Govindh Jayaraman (26:48):
And I also like the fact that you know, you started off with this idea that I'm just gonna sell this stuff on Etsy small.
you you leaned into what you knew.
and you and you did it.
You offer something of value so that you didn't wait, for
I know you said you were on mat leave, so that was the perfect time. But you know I have 3 kids, and there was no perfection.
Dinah Chapman (27:13):
Whole pirate.
Govindh Jayaraman (27:13):
There was no perfection around those times. But so so
you started it. Then you started off small. So you didn't wait like you didn't need. You didn't go raise a bunch of money, you didn't.
You didn't wait. You just took a step
and then took another step, and then another step right, and each time you made sure that these steps that you were taking the time that you're putting in
(27:40):
was firing you up like you were you were on fire, you said about what you were doing. You're really passionate about it.
Dinah Chapman (27:48):
That's why it's like you can make. You can make the time for the Passion project and the thing that like lights you up like if it's if it that, and that's what I really mean at the end of the day with my napkin is.
if it's a drag, it's gonna be a drag
like if you're if it just is, there's nothing motivating about it. Nothing is yeah, like exciting you or lighting you up the whole. The whole experience is probably going to be a drag.
(28:18):
and I just when I was thinking about time.
it was just like, I don't want.
I don't want to look back and say, like, God, that was a drag, or I just had to like, get through that like I wanna be building. It's really hard. But I want to be building and have something that's like.
really, creatively inspiring and like passionate for me. That's what I want, and that's that's all part of the
(28:47):
like. If it lights you up.
This is where to invest the time, and there wasn't a right time to your point. I was just like.
if not now, when that was kind of how I chose, if I don't do it now, when am I going to do it?
And then, yeah, I have one foot in front of the other. And
and then I just kept saying, like, I'm gonna choose myself. I'm gonna invest in myself. And
(29:13):
if I put in. Yeah, the time and the energy it's gonna work out.
Govindh Jayaraman (29:18):
That's awesome.
We've been asking every guest to pay forward some gratitude that we got from an early guest of ours. Many years ago we had John Rulin, who is the best selling author of a book called Giftology. He started a movement around Gratitude, and his napkin to us was what you appreciate, appreciates. He suddenly passed away
(29:39):
recently, and to honor his memory and his legacy we're asking everyone to shout out, give some appreciation to somebody or something that has been instrumental, or.
you know, timely. So is there anybody that you'd like to shout out.
Dinah Chapman (30:00):
Yes,
Can I shout out 2 people.
Govindh Jayaraman (30:05):
Of course.
Dinah Chapman (30:07):
Does that work?
I
would shout out my husband 1st and foremost, just because the building years are really challenging. You need a lot of support in those years, especially when you're building during young childhood years as well. When I mentioned earlier, like sacrifice concessions like it all, it's all part of it. It's not.
(30:28):
It's not just like what you see on social media of building a brand. And you know I live abroad, and it looks like it's the cool. It's the cool thing running a business from your computer. It's what everyone wants, right? But there's like such a different side of it on the back end.
So just like gratitude to sticking, sticking it out and like being positive and
(30:52):
supportive through that as we're in these building years. But then, like a collective call out to the women, I've been able to manage and mentor in my previous lives. They've like really shaped me as a as a person, as a leader, and how I want to build and shape my company, and I wouldn't have
(31:16):
the forward thinking ideas, or the the hustle or the desire to to build what I want to build. If it wasn't for them. And I think that good people give back to mentors the same way, like everything's very reciprocal.
And so I'd I'd shout out all of the really cool women that I've worked with or managed in the past.
Govindh Jayaraman (31:41):
I love that. That's great. Thank you for doing that, and thanks for joining me, Diana.
Dinah Chapman (31:45):
Yeah, thanks, so much.
Popular Podcasts
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
The Joe Rogan Experience
The official podcast of comedian Joe Rogan.
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Special Summer Offer: Exclusively on Apple Podcasts, try our Dateline Premium subscription completely free for one month! With Dateline Premium, you get every episode ad-free plus exclusive bonus content.