Episode 124

Building a Business with Jessie Pepper

May 16, 2017

Jessie Pepper of Style & Pepper and the Marriage is Funny podcast joins us on the Being Boss Podcast to talk about building a business that doesn’t keep you “boxed in,” and evolving and changing when you are the face of your business.

Learn More about the Topics Discussed in this Episode
This Episode Brought to You By:
"The confidence that comes from looking good on the outside has such a huge impact on how we feel on the inside."
- Jessie Pepper

Discussed in this Episode

  • An overview of all the awesome projects Jessie has up her sleeve
  • Jessie's creative entrepreneur journey
  • How to keep yourself from being "boxed in" and evolve + grow your business in new directions
  • Building your business as a lifestyle brand
  • Starting with just one thing vs going after ALL your ideas
  • Choosing how you want to grow in your business


More from Jessie Pepper

More from Kathleen

Braid Creative

More from Emily

Almanac Supply Co.


Kathleen Shannon 0:01
Hello and welcome to being boss, a podcast for creative

Emily Thompson 0:05
entrepreneurs. I'm Emily Thompson.

Unknown Speaker 0:08
And I'm Kathleen Shannon.

Jessie Pepper 0:10
I'm Jessie pepper and I'm being boss. Today we're

Emily Thompson 0:18
talking to Jesse pepper about being a multi passionate, creative and what it takes to bring a passion project into fruition. As always, you can find all the tools, books and links we reference on the show notes at WWW dot being boss club.

Kathleen Shannon 0:34
Alright, you guys, imagine this, you're racing against the clock to wrap up three projects. You're prepping for a meeting later in the afternoon, all while trying to tackle a mountain of paperwork. Welcome to life as a freelancer, small business owner, Boss who's wearing all the hats. Challenging Yes, but our friends at freshbooks believe the rewards are worth it. the working world has changed with the growth of the internet, there's never been more opportunities for the self employed. So to meet this need, freshbooks is excited to announce the launch of an all new version of their cloud accounting software. It's been redesigned from the ground up and custom built for exactly the way you work. Get ready for the simplest way to be more productive, organized and most importantly get paid quickly. The all new fresh books is not only ridiculously easy to use, it's packed full of powerful features. You can create and send professional looking invoices in less than 30 seconds, you can set up online payments and with just a couple of clicks get paid up to 40 faster. And you can see when your client has seen your invoice putting an end to all the guessing games freshbooks is offering a 30 day unrestricted free trial to our listeners to claim it Just go to freshbooks comm slash being boss and enter being boss in the How did you hear about us section.

Emily Thompson 1:52
Jessie is a lifestyle expert on air host and the founder of a dress design called season. She lives in Long Beach, California where life currently revolves around her hilarious husband, their sidekick safety, and an ever growing number of tabs on her internet browser.

Kathleen Shannon 2:11
All right, let's jump right in. Jesse, we're so excited to have you on the show. Thanks for joining us.

Jessie Pepper 2:17
Oh my gosh, thanks for having me, guys.

Kathleen Shannon 2:19
I am super excited about what you have up your sleeve right now, which we will share with our listeners. But first, I want to talk about how much shit you've got going on. So like,

Emily Thompson 2:31
just to dive right in there. If

Kathleen Shannon 2:32
you have a website, which I think everyone knows, which is style and pepper

Unknown Speaker 2:37

Kathleen Shannon 2:39
That's like that's like your home base.

Jessie Pepper 2:41
That's my that's my little internet home. That's a good way to say it home base.

Kathleen Shannon 2:44
So that's your home base. And then you have not one but podcasts. True. So you've got marriages funny.

Jessie Pepper 2:51
Yes. And then the second podcast, I don't even know if you could call it an official separate podcast. It's, we call it a spin off mini series called The perfect wife.

Kathleen Shannon 3:00
I love that you gave yourself a spin off.

Unknown Speaker 3:03
Yeah, basically.

Kathleen Shannon 3:06
So both of these podcasts are a little bit more personal. I would say like we're you're really exploring the topics of marriage and being a wife. And then you are coming out with a dress.

Jessie Pepper 3:18
I am how random is that? It feels like oh my gosh, it's it's been quite the journey. But I honestly as I've been working on it for the past year or so it just feels like exactly what I meant to do. So we're launching a dress design and the lines called season. But it's really not a full line. So I don't even really call it that because it's just one design that I made. Myself basically about five or six years ago, actually, I need to figure out the exact date because people always ask and I don't quite know. But I sort of Frankenstein a couple of my different dresses that I'd bought together and made this prototype that I just wore for the last few years until last summer when I decided to start making a few more I really just wanted one for myself in black. Because I had it in in a pattern and I was like I wish I had this dress in black and I tried to find something just like it. I mean, I I tried everything I exhausted all of my like fashion connections to try to figure this out. Because I didn't really want I knew that I could sell myself another one if I needed to. But I just was like, I don't have time for that. So I was like okay, I'll take it to a seamstress and get another one made and black. And then when I started pricing everything out and finding the fabric and everything. I was like, dang, this is a lot of work. And if I'm going to do one, maybe I'll do a few other colors and then I had a few friends be like well make me one. And I thought okay, so if I'm making 10 Why don't I just make a few 100

Emily Thompson 4:57
I love it. So I went for Everyone who doesn't who isn't familiar with you, I'd love to hear like, how you how you got to the dress. Like all the things that you've put together tell us like the timeline of your first website, like, how did you get here?

Jessie Pepper 5:11
Yeah, so I've been blogging for about about almost nine years total, I guess in May, it'll be or May or June. And only as a full time, business has been a part of my full time business for about five years full time. And so it's always been related to personal style and fashion, I would say over the last few years, I've then started to introduce more lifestyle stuff. So Fitness, Health, beauty, all of the things that I love to talk about designing a flavorful life is what we talk about. So. So that was kind of the foundation for setting up my business. When I started blogging, I was posting outfit photos, both of myself and other people, and quickly started getting asked to do a lot of personal styling. So I was then doing that on the side, in addition to my full time job, and that was back, we lived in Kansas City. So since then, I launched a personal styling business really built that from the ground up. And then we moved to New York City, a lot of my clients that I was starting to service were more brands. And then also ad agencies wanting wardrobe styling for commercials and print ads and all that. So my husband had a great job offer in New York, I was like, Well, I'm already traveling there quite a bit for business. So let's do it. So we moved there. And we're there for about four years. And when we moved back to California, about a year and a half ago, my business model. You've been thinking about this a lot. It's my business model, I think, had quite a few hiccups. And I can explain more about that if you're curious. But yes, please just okay. Well, I mean, I think I think it was it was a combination of a lot of things. I think, before my business model was I had my consulting clients who I was mentoring, and helping them with their personal style, and their fitness and their health journey and kind of kind of similar to life coaching, but I never call it that, because I'm not a certified life coach. So I would, these people would pay me to mentor them through their personal style journey. And then I would have brands that would hire me to do on air hosting, and to post about their products on my blog, or social media channels. I'm the on air hosting stuff I still do. But the sponsored post, stuff started to really taper off when we moved to California. And I think it was for a few reasons. One, the market just became so saturated, to I don't know if it's because I hit a certain age, or if I'd been doing it long enough, but I just immediately felt like so jaded about it all. And Kathleen and I have talked about this off, you know, in real life, I guess, a little bit just because we've had a journey of both being in the blog industry for a long time. But then I also realized, like I don't, my life doesn't have the same need to put together these outfits and get dressed and take photos the same way that I did so easily before. And so I just was like, I need something new. And it's funny, because that was actually a really not to like over dramatize it, which I have a tendency for. But I that was like a very dark time for me last summer because I was just, I was distraught, I felt like I had to let my original business die in a way in order to make space for something new. And it's actually believe it or not a complete coincidence how closely that even ties into the word season, which is the name of our dress design. Because it was just really clear to me that I was trying to just keep adding new things like oh, well, you know, maybe I can now do this, and this and this and just trying to pile it all on didn't work. And it wasn't until I really like let go of everything I had been doing that. And not only let go but then like sat in the emptiness and the sadness of that for a few months before I finally was like, this has been sort of almost sitting here in front of me all along the dress design. And it's it's kind of funny to me that I never thought to pursue it before actually, people would ask me, what do you do for a living and a lot of times you know, you have like levels of what you respond to based on how how long you want the conversation to go. So sometimes I would just say, Oh, I work in fashion. And then the very next question is usually, Oh, are you Oh, you're a designer, everyone would always assume that and be like no and I have nothing against designers but that was never ever I didn't go to fashion school. I didn't I don't sketch. I was never a part of my desire. By but again, this like this whole dress thing kind of came about really organically. And when I thought I had nothing else to pursue at the Moment. That was when I started writing a lot about

just my career journey and the things that I want to pursue. And I'm lucky that I had some money saved up. And I'm lucky that I had a little bit more financial flexibility moving out here because, believe it or not, I mean, it's so funny, like, we our life out here feels so much better than our life in New York. But it costs so much less.

Kathleen Shannon 10:30

Jessie Pepper 10:31
Yeah, I mean, we live two blocks from less than two blocks from the beach, and our rent is at our places bigger and our rent is less than what we paid. And, you know, it's just, it's ridiculous. But it's so I had a little bit more financial flexibility. And that allowed me to take a leap of faith, I

Kathleen Shannon 10:50
guess. Okay, so I think that's the thing that I was really curious about is that you're doing all of these things. And I've known you long enough to know that like, you cannot box baby in the corner, like, I'm not gonna box Jesse in the corner. And that's one of the things that I really admired about you for the past five years, because whenever I was all about expertise, expertise, niche down niche down, what do you want to be known for? You were like, you cannot box me in like, it's a whole lifestyle. It's the whole shebang. And so then seeing the dress on top of it. I just couldn't help but wonder how do you have the time for all of this, but in hearing your story, now, it sounds like you did kind of have to let go not necessarily of blogging, but the business model of blogging. Yeah. And I'm so impressed with what you're doing with the dress. So I'm super curious to hear about your journey of actually producing the dress, because I think that we all have these ideas of passion projects from, Oh, I'd love to write a book of personal essays to design a dress to, you know, maybe like monetize a capsule wardrobe. Like, these are just a few ideas. So how do you actually start to bring I don't know, motivation or inspiration, and even just the logistics to making this a reality.

Jessie Pepper 12:11
So the logistics are such a bitch. I, I definitely like I enjoy the how things work part of life. And so when I was starting off this, you know, after I decided, Okay, I am going to pursue this when I was starting off on the journey of like, how am I going to get this made? I had a lot of fear, just because I kept thinking like that just the the risk seems so much higher, because you're you're investing capital into the process of actually like producing something. And I we can talk more about that in a sec. But I'm doing, we're doing a Kickstarter. So I had a little bit of grace there in terms of not having to plunk down like $20,000 or more. But still, the startup costs are for sure. Still there. And I wanted to bootstrap that. And so I was literally and still am like taking on air gigs, and taking speaking gigs. And putting, you know, a couple $1,000 here a couple $1,000 there and just like putting it straight back into season. So I'm using those other venues to like pay the bills and then fund this the the startup costs of season. But yeah, I remember that when that all started, I was reading the War of Art for the first time. And a lot of times with business books, which I love a lot of them. But when they get really buzzy and when everyone's talking about them, that's when I'm like myth. And so I read it I felt like after everyone else did, but I read it last summer and I like journaled my way through it.

Kathleen Shannon 13:46
And now like five years later, you telling everyone you have to read this book

Jessie Pepper 13:50
totally. And I'm like, this is why people were saying this before. Same thing happened to me last actually last winter with or like a year ago, a little bit over a year ago was essential ism. And that's one of the ones that like, you'll hear me say a lot of these things. I'm like, I I was so resistant to reading essential ism. And then when I read it, I was like, Fuck, this is what I've been needing, like this is this is this. This was me then deciding that like this little garden of silent pepper that I'd been trying so hard to build and had been successful in building I'm so proud of what I built with style and pepper and with that part of my business and I will continue to operate under style and pepper as like our parent company, as I say, season is just a branch of that now, but I had to like stop. Stop nurturing that, you know, and let it die in a way which is painful, like when you put so much blood sweat and tears into it. But it's funny back to the logistics when I was reading the War of Art. I remember so much. You know he really personifies Steven pressfield personifies resistance and fear so much. And that actually helped me. Because whenever I would come up against something in terms of production, where I'm like, I'm afraid to just like, go cold call a bunch of us based cut and sew factories, like, That's scary for someone who's never done that before, doesn't know what it's like, like, doesn't know, I have no idea how this works, I would then, you know, read a chapter of that book sort of accidentally, and be like, Oh, this is what he's talking about that fear is what I need to push past. And it's almost like wrestling with this little imaginary person that it's, it's it's just a part of the process. And it kind of adds depth to the story in a way I don't know, I don't mean to like, over, you know, idealize it. But it was very, very much a part of my journey, for sure. I love that I

Emily Thompson 15:50
have. So I have this thought in my head. Get out, we can work shop together,

Unknown Speaker 15:57
it's gonna be good. I can tell around

Emily Thompson 15:59
around how creatives especially we start businesses, because we want to do this thing. And we have this idea that we want to monetize. And I'm in the middle of this too, which is why I have to like process this out loud. And we do the good thing of creating this business model that works. And you do it really well. And then you change your mind. And not even so much that you change your mind. But you grow. And you decide that sure you can do this thing. But you could also do something else. And so I feel like over the past couple of years, we've been at the forefront of creative starting online businesses know what that looks like. But I feel this sort of shift in in most of us who started around the same time, kind of being over that first thing that we did, and ready to move on to the next thing. But having that weight of letting go of the thing we started in order to move on to the next thing. So I'd love to hear both of your thoughts on that sort of thought process.

Unknown Speaker 16:57
It's even a little bit of guilt. Yeah, I

Jessie Pepper 17:00
have I have a little bit of guilt I might have, you know, it's like, Oh, dang, you know, I don't know why I haven't haven't really figured that out yet. Cause I don't know.

Kathleen Shannon 17:12
So, you know, it's funny for me, because it does feel like it feels cyclical almost, which could probably go back to the idea of seasons. Because as I revealed on our last episode, I'm actually wanting to get back into personal blogging. Yeah, I feel like personal blogging without monetizing is the thing that helped me really process and be present in actively capturing, shaping and sharing my life. And at the same time, you know, it feels cyclical at the same time, you know, I had to really put braid creative on the backburner to really bring being boss the point where it is now. I mean, we've, we've been able to monetize it, we've written a book, we are traveling all over the world all the time. And that's taken a lot of energy. But at the same time, whenever I think about braid, creative, and what I created with my sister, I'm so proud of that and thinking about just letting it die, which is it was on the brink, you know, and not that it is because it's super healthy. We get a ton of clients, but there is this thing to putting your energy somewhere and what's going to happen with that. So now I'm even coming back around to braid and thinking, Okay, how can I help? My sister and my team over at Bree creative, re invent this into its next level and grow up? And I think the thing with evolving your business is that we're constantly thinking, I noticed creative entrepreneurs do this a lot whenever it comes to, like going back to a day job. And I put this on air quotes, and because the idea of going back, right, so sounds like

Jessie Pepper 18:50
yeah, you're reverting?

Kathleen Shannon 18:52
It sounds like you're reverting. So whenever I think about going back to braid, creative in my mind, I imagine, you know, knocking on my sister's work shed door and saying, like, Hey, can I have my job back, but it's more, it's different. I'm coming back to it as a different person. And that's going to evolve the brand in a different way. So I just have to constantly keep in the forefront of my mind that we are always moving forward. Even if something feels like we're going back to an old experience, whether that's a day job, or maybe you start consulting at style and pepper again in a few months or a few years. It's not going back. It's bringing who you've become to that original concept, I guess. And I even experienced this like in my personal relationships in my marriage in my relationship with my kiddo because he's changing all the time. So I think it's just giving our businesses permission to evolve and change and breathe right side along with us.

Emily Thompson 19:55
So I agree with that, then that really makes me think about so you know, Like, whenever we were branding ourselves back in the day for our first business is like, Alright, I'm gonna spend the next 25 years doing this thing. So here's my brand, stay here forever. I like I challenge people these days, especially if you're creative as to build a brand that's a little more flexible, like, definitely say what you mean and know what you're offering right now. But know that the decisions that you're making right now are not going to be the exact same decisions that you are going to hold true for yourself five years from now, or 10 years from now. So I think that there almost needs to be this like flexibility and branding these days that needs to hold space for where you're going to be three to five years from now, which I think is really important. It also makes me really interested to see where we will be in five to 10 years from now? Or will we find the thing that we want to do for 20 years and years on the path to get there? Or will we keep evolving to the point that we're all going to have like every piece of medium like living in our like under our umbrellas, we're going to make things or we're going to sell things and we're going to have TV shows and radio show and all the big

Kathleen Shannon 21:08
like, or Eiger I think in in current company, all three of us are going to be doing right.

Emily Thompson 21:14
Or your dress and your line, be it forever, you know, like the great forward to seeing where we all are in a couple of years.

Jessie Pepper 21:24
Yeah. And actually love that, that you're kind of verbalizing, taking that into account because I hadn't thought of that ever, maybe. I'm very like, I mean, I loved dreaming about the future. But I don't think I'd ever thought about it much in terms of like, how might my brand change based on what my actual output is? until fairly recently? I'm actually so our branding is being done by a past being boss guest. I'm pretty sure yeah, no, she's been on the show. I'm like I know in real life. Who is it? Becky?

Kathleen Shannon 22:03
Becky's and favorite? Well, so

Jessie Pepper 22:05
the reason I bring it up is because I actually I mean, again, I'm so lucky to be working with so many great friends we have like our team has just blown me away. But Becky is dear to me anyways, but her branding questionnaire I loved so much because she asks really good questions like, what are you going to be bragging about in one year? And then in three years, and then five years? And I was like, Oh, I don't know. I mean, I hadn't thought of that with season. I was just like, Look, man, I just want to get this dress made. So I can wear the color I want, you know what I mean? And so asking that sort of question, whether it's to answering it to someone else, or blogging about it or journaling about it, or even just answering it to yourself. I was like, wow, this is really helpful to me and better believe I was dreaming, dreaming big and am dreaming big. I mean, I have like really big ideas for this. But one of the things I like about what I'm doing is that it still relates somewhat to the lifestyle. Little like, mini empire that I was at one point building with Thailand.

Emily Thompson 23:06
And that's the thing is that you are the common thread. And so and we're writing the work chapter in our book right now. And so this is like so top of mind for me this idea of like I think creatives aren't building these exterior businesses. I think we're building life businesses, these businesses or like or business modeling our life in a way that we can create whatever, as long as we remain the common thread. We should figure out how it makes sense.

Kathleen Shannon 23:38
Be that said though?

Jessie Pepper 23:39
Yeah, so I agree with you. And I think that's how I've kind of operated up until this point. However, one thing I have been thinking about recently, kind of by accident was the idea of building this new business or this new branch of my business that has a little bit more of an opportunity for an exit strategy. Yeah. Which, again, like everything I've ever done, up until this point, not scalable at all. Like Truly, I don't have an info product. I don't like if you hire me, you get me. I do have employees, but it's like, are not employees, but they contract employees. But it's not you know, they're not delivering what you're paying for essentially they're helping me with the back end. And so now with this product, which product based businesses obviously are like this is kind of more the point or not the point but more just naturally like that. I didn't think about it either. Until recently, I had someone say Will you sell it like when you build this up? And you're and it's going really well and you're going gangbusters and and you want to do something else? What are you going to do to sell it? And I was like, Oh yeah, yeah, I guess like I hadn't even thought of that. It's funny because we actually had an interesting situation with marriage is funny, our main podcast that we do run a big hiatus right now. So I honestly haven't thought very much about it recently, but When we were going gangbusters on that, and during season three and really trying to monetize and figure out what we wanted to do, we were in talks with a company about them. And they do have they have a product and they offer something to people right in our wheelhouse. And it's related to marriage and relationships and communication, all this stuff. And so they were like, Would you ever consider selling so that you guys were the ones basically creating the

Kathleen Shannon 25:24
vibrator? No, no.

Jessie Pepper 25:29
Damn, actually, that would be really fun. Can you imagine we make all the jokes we want to do?

Emily Thompson 25:37
Right? There would be no mine at that point. I think

Jessie Pepper 25:42
I know. Exactly. So anyway, so it's interesting, because I wasn't until I had a someone asked me that, that I was like, Oh, actually, this, I guess, is one of the things I've done. One of the only things I've really done in the entrepreneurial world that does have less of a connection to me, Jesse. But obviously, I think my personality is infused throughout. And I think Luckily, I'm going to be able to use my existing platform to hopefully make it a thing. But I don't know, it's an interesting thing to think about.

Kathleen Shannon 26:17
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Okay, so one thing that I really want to point out whenever I'm looking at you creating the stress, which, by the way, I love the dress, it's so good. I was fortunate enough to be on your list and fill out a survey and you were like, talk about the dress. It's in your closet and I talked about my favorite pair of leggings because

Jessie Pepper 27:26
I know I totally did that with you. By the way. It was an anonymous survey, but I was like, I'm pretty sure this is

Kathleen Shannon 27:32
okay. I wasn't sure if it was anonymous. It

Jessie Pepper 27:34
was totally it was anonymous. Yeah, that's hilarious.

Kathleen Shannon 27:37
So but then I started seeing peeks of the dress on Instagram and I love the dress First off,

Unknown Speaker 27:43
thank you second

Kathleen Shannon 27:44
I love that. dreaming big four season and dreaming big for this brand isn't holding you back from starting small. And a lot of what you're creating kind of reminds me of I even sent you this in a text I was like you're gonna be the next Dvf like Diane Von Furstenberg ran, I guess. And she kind of known for that rap dress. And her brand has obviously expanded much bigger beyond just the rap dress. Right. And I also I tried writing a blog post about this the other day, but I couldn't quite articulate how I love that Kylie Jenner started with lip kit. Yeah, obviously her brand has exploded. And watching that has been really cool how you feel about the Kardashians and the Jenners is another thing altogether. You love this idea that with unlimited resources, she still started really small. And I don't think it's because I don't think it was just strategy. I really don't I think that there was some more figuring it out as she went and just publishing before she was ready. At least. That's the case by starting with just the lip kit.

Emily Thompson 28:50
And I just had a really expensive business coach that was like No, honey, just start with one.

Jessie Pepper 28:55
But maybe which is hard to do. I mean, I don't know if it was hard for Kylie but for someone like me, who is just creatively stimulated all the time. And I mean, I, I always want to do all the things, you know that and I, my enthusiasm gets the best of me and then I bite off more than I can chew. And then I'm like, flat out on my back because I am feeling paralyzed from everything that I'm trying to or wanting to do. But so I really appreciate even just the inkling of that comparison is so flattering, and I would love to be the next I mean, I don't even know if that's true if I would love to be the next Dvf but I would love to be someone who inspires and is known for creating things like her. And it's, it's true. It was again, I mentioned the story of how it kind of came about was a little bit of an accident. But then when I started on the journey, I was like oh yeah, and then I can do a caftan and we're gonna do a pair of pants and we're gonna do this and the one main thing that I know will tie All together is that I feel really excited about at the moment is using the type of silk that we're using. And so it was it right now where I'm kind of thinking of going in the future is all kind of related to these, like really flowy and mouth and multifunctional silk pieces. But it has been difficult to be like, no, you're just starting with the one not even just dresses, period, but like the one dress design. And part of why it works is because it is, you know, it's meant to be multifunctional. And so you really can it transforms into like, originally it was four ways and then at the photoshoot, we discovered a fifth way. And then the other day I was like it actually kind of is more like 10 ways but so I don't exactly know how the marketing stuff is actually gonna end up. But it's it's that multifunctional flowy silhouette that's really important to me. And that's kind of what I've built my own personal style around. And so I'm trying to, like you said, really, really, really hone in on that one thing and perfect it because like this is version one. But there's so many things about version one already that I'm like, you know what I bet if I had XYZ, I could just I could make that one little part just a little bit better. And so I'm excited to even do version two or three or, and I'm also excited to get user feedback. Like I want to know what people love about it, what people would change about it. You know, whether it's like something simple, like the length being different or whatever, or maybe it's something really technologically savvy, I'm very, very, I've always been super into technology across the board, but specifically within the fashion industry. I think it's fascinating what people are doing one of my total, like role models or whatever you want to call it. spirit animal is the CEO and founder of Patagonia Yvon Chouinard last name,

Kathleen Shannon 31:55
love Patagonia love everything about them.

Jessie Pepper 31:58
I know they're doing such great things. But just like what like learning more about that his journey and just watching the way that they have stayed not small, but like they've kept their company, I think it's a priority, it seems like for for him and for the company to stay nimble. So that they can respond quickly and efficiently to their customers. And then so that they can also take really great care of anyone else that's a part of the community. And he still owns 100%. So they don't have to, they don't have to deal with investors or stock drama or any of that stuff. And I just love that about them. And like I my goal with this for right now is to build something that sustains itself sustains eventually me. And then eventually I mean, me slash the team. Paying great people, and and then maybe eventually then we break out into other, you know, whether it's different pieces or garments or whatever, then great. Maybe it's a physical space. Maybe it's a weekend getaway, I don't know. But my goal is to just really stay focused, because that is a muscle that I have not really been great at building in my eight years of being a creative entrepreneur. And actually speaking of muscles, Kathleen, you always talk about how closely there can be ties between someone's fitness journey and their career journey. I love that specifically creative entrepreneurs, I think resonate a lot. And actually, do you guys listen to the podcast called how we how I built this or how we made this.

Kathleen Shannon 33:36
I just saw you post about that, Emily, that's the podcast you should listen to on your road trip.

Jessie Pepper 33:41
Oh, Emily. Oh my gosh, it's called I think it's how we let me just pull it up or like

Kathleen Shannon 33:47
how it was built or how I built this here it

Jessie Pepper 33:49
is how I built this. Okay. So it's how I built this. It's it's done by NPR. So you know, it's going to be quality. And yeah, and the host is darling. And so the episode about Patagonia. And so far, they're profiling like all these big businesses, which it but it's great, because they're really taking a very to me what seems like a very personal approach. And I like hearing the stories behind it. But the one with Patagonia was so good. And actually I thought of you Kathleen, because he talks about how we he was he was the host asked him a little bit about like profit margins and stocks and investors and all this stuff and profit margins. I mean, that's a different story. But that's something I'm dealing with on the daily and it stresses me out to no end. But I have really strong values. So I'm trying not to let myself be swayed by something like $1 sign. But one of the things he said is that there's two kinds of growth. There's, there's the kind of growth where you get fatter, and then there's the kind of growth where you get stronger. And I was thinking about that and like Yeah, that's true. Like if you're gaining weight, you're either going to be gaining fat or you're going to be gaining muscle. I mean, I guess unless you're gaining water, but you'd go into that. So

Kathleen Shannon 34:56
let's just use that into gaining muscle. Totally. Pour water,

Jessie Pepper 35:00
obviously totally So, but he was talking about, you know, you can still like a company could obviously take on a ton of investments. And there's tons of tons of ways to grow. But like, look at it from the perspective of do, do you want that kind of growth? And is that going to cause you like, for instance, with the fat metaphor, like, you could totally just like pound down the doughnuts gain a ton of weight that way, but then, are you going to be able to walk up a flight of stairs at your house, you know? Or would you rather gain the weight by doing a bunch of lunges and squats and lifting so that you're actually becoming stronger? And I was like, amazing. I mean, he's a genius. But how can I apply this to what I'm working on now? And so I've been thinking about that a ton over the past few weeks.

Emily Thompson 35:46
I like that. Shit. Kathleen and I were talking about this just yesterday.

Jessie Pepper 35:52
Which part the fitness thing,

Kathleen Shannon 35:54
and just how we grow and how we want to grow. And just remaining nimble is super important. And as you're talking about this, I'm also thinking about Sophia amoruso, who I have mad respect for and just seeing her journey and learning from her mistakes if she would call it a mistake or not of taking on investors and growing to too big in the wrong ways. Because I think she was super nimble and strong. Anyway, it's probably all working out for her. I mean, she seems like she's fine. But my question before we start to wrap up, I would love to know just kind of what a day in the life is like for you these days? Like how much time are you spending working on your different projects? And what kinds of different tasks and hats are you wearing to make season? come to life?

Jessie Pepper 36:44
Wow, that's a great question. Um, so I'm working on season right now I'm working on season 100% of my of my work bandwidth. We took a break from marriages funny around Thanksgiving. And then I cranked out my mini series that lasted through basically just like the week before Christmas. So when I started the new year, I was like, Alright, this is it 100% in. And in terms of day to day, which by the way, like that's been a challenge and a gift at the same time in terms of like letting everything else go for just a season. Because we know, we do want to get back to the podcast, and we will get back to the podcast, but it has to be after our Kickstarter campaign. And so we just have said, like, Look, we'll be back, but just hang on a second. That's been really hard. But also, it's been kind of beautiful to not feel like I have this other stuff weighing on me, when I'm in the midst of kind of my tunnel vision moment with season. So I'm just letting it happen. And it's been great in terms of my day to day, I mean, honestly, like, today's a little bit funky, because I had a bunch of like appointments and things. But a lot of times, I mean, I'm really big on my morning routine. So I take about two hours to do all of that. And then I start working there, usually about nine. And then it's a lot of like emailing the guy trying to get our, our strap hardware ironed out. And then phone calls with our production company in Chicago and trying samples on different friends and meeting up for photo shoots. And we're actually so we're launching the Kickstarter launches next month. And so everything I've been doing this week has been geared towards that I actually just brought on two interns, which has been exciting. And so a lot of delegation, in terms of like having them help me with some of the content marketing that we're putting together. A lot of pitching myself to media outlets, which also really fortunately ends up being many friends since that's kind of the space that I was in before was like the fashion digital media space. But I feel like I'm constantly just really trying to be intentional about my day. And it's worked out pretty well so far, as long as I as long as I stay on top of it and stay organized. And honestly like, that's another thing, the freedom from doing all of the other stuff that I had historically been doing is clearing up so much mental space for me. Like I honestly I feel like I'm like witnessing when I'm talking about it because it's just it's changed my life. And I'm like, if you haven't read essentialism, roll your eyes in you know, roll your eyes, because I'm blabbing about it and then go read the book, because it's really good. It's been a huge game changer for me.

Emily Thompson 39:34
I love that whenever you can focus wherever you can focus, guys seriously and not even try. Right things will change for you. But also, I think there's so much to be said about that prioritization, like knowing what it is that you're doing in this moment and knowing what, like you mentioned, like, going intentionally about your day, which comes from knowing what are the most important tasks, what's going to make the biggest impact what needs To be moved out the way so I can move the other things. That's how you get shit done.

Jessie Pepper 40:04
Yeah, and one other thing I was thinking about actually the other day back to the Yvonne, Yvonne. I think that's his name, the Patagonia guy. Um, it's funny because I was he said he told a story and I was actually applying it to my life in terms of personal style. But I actually really think what we're talking about right now is making me realize it's, it's it could be applied to to your work. And he was talking about how he for an entire year, you know, he's all into all the outdoor sports for an entire year, he decided to do all this fly fishing with just one fly one little like tool fly do Hickey thing, and not a big flyfisher. So I don't know what that would be like, but but he talked about how instead of like viewing that as some sort of, I think even use the word impoverished, like instead of letting him feel like, Oh, woe is me, I only have this one fly to use. He actually instead he tried to focus on being so good with that one fly, so that instead of constantly having to rely on the entire toolbox, he was he was like, Look, I can fit this fly in my pocket, you know, and it comes with me and I can I could be an expert at it and all these things like, and so he was talking about the fly and how that has applied to his journey at Patagonia. I was originally thinking like, oh, maybe maybe this because I've always said that having creative restrictions on yourself is where you can see so much growth and and I've experienced that in my personal style in terms of limiting my shopping in certain ways, or just even challenging myself to live out of a suitcase for longer periods of time because of our travels and stuff. And I actually, I love those moments where I'm like, Oh, this is like a puzzle. It's like a riddle or word. You know, it's just it's something for me to figure out. And I like figuring stuff out, especially when it's playing dress up. So with with our dresses, I'm like, maybe not only is the actual physical dress my fly, I'm doing a 30 day challenge right now. It's the only thing I'm wearing for the next 30 days, which I love right now. It's been really fun. But it's funny because I'm using it as my literal fly. But then I'm also pursuing season as my fly for this this time of my career because I I've had to say like, no, get over the woe is me feelings of giving up other parts of my business that I really enjoyed and just figure out ways to apply them to season and so if I love still talking with women, how can I find interns that want to be mentored? Or if I love still being on air? How can I turn my Insta stories and my youtube channel into something that like makes people want to watch I still get to do my hosting and, and it still applies to it. But that that story, like really hit home for me. And I didn't realize until now that I love it could be applied to our career as

Kathleen Shannon 42:52
well. And I love that in the idea that you have this one fly, which is either the business or the actual dress, you've actually uncovered that you have a lot more tools in your tool belt than just the fly.

Yeah. All right.

Well, let's go and wrap this up. I want to know what makes you feel most boss, huh?

Jessie Pepper 43:12
Um, it's funny, I was like, zipping around flustered and rushed earlier. And I was thinking about you guys, because I knew we were gonna chat and I was like, I remember thinking, I don't I don't feel boss right now. And then I was like, okay, and I really I wasn't rushed. Like it was an hour before we started so I really had more of a buffer of time than I was giving myself and my head but I thought okay, calm down, go get dressed, get your makeup done or not get your makeup get your makeup on, you know, which to me is not a lot I don't do a ton it but I was like just get ready. And then then start a non what you need to get done before you hop on the call with the girls and I honestly, I noticed such a difference for myself. When I take the time to put together even if it's just putting on a clean pair of leggings and like a minorly cuter t shirt than I had on five minutes before. I mean it can be so small but those things for me It helped me feel so much more boss and you guys had an actually you had a great blog post on being boss club. I can't think of the name of the girl the author but she was writing about lipstick.

Kathleen Shannon 44:24
And how I think that was Jessica Willingham. It was it was moody being boss.

Jessie Pepper 44:29
Yeah. And I retweeted that because I was like, Oh my gosh, this is so true. Totally resonated with me. And I think so when I take care of myself and when I feel put together, which often means having a cute outfit or my hair or my makeup on. I feel really badass. It sounds trite and it sounds frivolous. But I I'm such a firm believer that the confidence that comes from looking good on the outside has such a huge impact on how we feel on the inside. And so I just I will never apologize or back down from that

Emily Thompson 44:59
good. Pretty

Kathleen Shannon 45:01
So Jessie, where can our listeners find more and get the dress and follow along on your creative journey? Yeah, so

Jessie Pepper 45:08
our website is season everyday.com and we're on Twitter season every day and then Instagram which we're having a lot of fun with Instagram right now it's season dot every day and actually, I'm posting a lot of stories over there a lot of ways to wear the dress and it's been a ton of fun and I'm also everywhere at style and pepper, too. Awesome. Thanks

Kathleen Shannon 45:28
so much for joining us. Thank

Jessie Pepper 45:31
you for having me. Guys. This is a dream you're awesome.

Kathleen Shannon 45:36
This episode of being boss was brought to you by fresh books cloud accounting. Try it for free by going to fresh books calm slash being boss. And special shout out to Meet Edgar you can try them at Meet Edgar calm slash being boss. Thank you for listening to being boss. Find Articles show notes and downloads at WWW dot being boss club.

Emily Thompson 46:01
If you're a creative entrepreneur, Freelancer or small business owner who is ready to take your goals to the next level, check out the being boss clubhouse, a two day online retreat followed by a year of community support, monthly masterclasses book club secret episodes and optional in person retreats. Find more at www dot being boss club slash clubhouse.

Kathleen Shannon 46:24
Thank you so much to our team and sponsors who make being boss possible. Our sound engineer and web developer Corey winter. Our editorial director and content manager Caitlin brain, our community manager and social media director Sharon Leakey and our bean counter David Austin, with support from braid creative and indicia typography,

Emily Thompson 46:43
do the work. Be boss, and we'll see you next week.