717 Ciara Stockeland:

The best entrepreneurs are not afraid to fail. Failure is part of the growth plan, and the sooner we accept and welcome it as our friend, as vital feedback, as the fastest path to learning and success, the further and faster we’ll reach our goals, as my guest today, the serial entrepreneur Ciara Stockeland says. Some of us may be born with that instinctive knowing, and the acceptance of our inevitable failures as we take the entrepreneurial path can also be learned. It’s all part of the journey.

MELINDA

Hi, I’m Melinda Wittstock and welcome to Wings of Inspired Business, where we share the inspiring entrepreneurial journeys, epiphanies, and practical advice from successful female founders … so you have everything you need at your fingertips to build the business and life of your dreams. I’m a 5-time serial entrepreneur who has lived and breathed the ups and downs of starting and growing businesses, currently the game changing social podcast app Podopolo. Wherever you are listening to this, take a moment and join the Wings community over on Podopolo, where we can take the conversation further with your questions, perspectives, experiences, and advice for other female founders at whatever stage of the journey you’re at! Because together we’re stronger, and we soar higher when we fly together.

Today we meet an inspiring entrepreneur who has owned and operated businesses since her early teens. Ciara Stockeland refused to accept the mold society had in mind for her, dropping out of college to open her first store, before jumping into franchising. Ciara launched a box for boutique retailers, building and selling within 18 months, and now founding a coaching program for retailers called the Boutique Workshop. Today she shares what she learned from failure along the way, including all the mindset hacks every entrepreneur needs to succeed – and much more, including the ins and outs of franchising.

It’s hard to really understand the entrepreneurial roller coaster until you’re on it. There will be joyous highs, unbearable lows, challenges seemingly out of left field, things you can’t control, pressures you can’t foresee, and all along the ups and downs, and twists and turns, of the ride, you’ll be learning and growing every moment – and over time, as you learn to accept failure as an inevitable and helpful part of your journey, you’ll find the highs and lows level out, and your business will grow as you overcome your fears, and dare to be true to yourself, with love and acceptance.

I know this to be true from my own journey and wish I could have shared this hard-fought wisdom with my younger self as I began my own entrepreneurial journey some 30 years ago. So, today what a pleasure to share the crazy journey with Ciara Stockeland, who like me has owned and operated businesses since her early teens.  As a serial entrepreneur, Ciara’s business mindset and tenacity – and a declared intention to live BIG – that is, Bold, Intentional, Grateful. Ciara’s vast experience in both retail and wholesale industries, after launching her first store and building a franchise business, led her to launch the first ever to market wholesale subscription box for boutique retailers, which she built and sold within 18 months.

These days Ciara runs the Boutique Workshop, a coaching program for retailers with a mission to motivate boutique owners to dream big and build simply. Also host of the Boutique Workshop podcast, Ciara is all about helping entrepreneurs and small business owners, twice testifying before two U.S. Senate Committees regarding the “joint employer” standard for businesses and its effect on small businesses and franchises.  Additionally, in 2015 she represented small businesses at a White House Summit on Worker Voice and again in 2018 for a Summit on Economics. Ciara has been recognized as a Small Business Champion through SCORE, has held a seat on the United States Chamber of Commerce Small Business Council and is a Profit First Certified Coach.

Today we talk about entrepreneurial mindset, what it means in practice to live BIG, how to ask for what we want, and learn to accept ourselves, let go of perfectionism and control, delegate, and empower your team – and much more, including the ins and outs of building a successful retail or franchise business.

Let’s put on our wings with the inspiring Ciara Stockeland , and be sure to download the podcast app Podopolo so we can keep the conversation going after the episode.

Melinda Wittstock:

Ciara, welcome to Wings.

Ciara Stockeland:

Hello. I’m so excited to have a conversation with you today.

Melinda Wittstock:

Well, 100% and I’m excited too, because we have something in common. We were both kind of entrepreneurial as kids.

Ciara Stockeland:

Yes.

Melinda Wittstock:

How did that express itself for you?

Ciara Stockeland:

You know what, as far back as I can remember, I was always looking, this sounds so bad when I put it this way, but I was always looking for a way to make some money, even as a little kid. I was the one with the lemonade stands, the garage sales, I sold rocks to the neighbors. I was like, I’d put on little productions and create homemade tickets. But I really think it was a desire to see what wasn’t working or where there was opportunity and then just lean into that. And I think it just manifested by selling things and charging for things.

Melinda Wittstock:

Were your parents entrepreneurial-

Ciara Stockeland:

Yes.

Melinda Wittstock:

… or was this completely out of the blue?

Ciara Stockeland:

No, my mom is not at all. She is not at all, but she’s very, very creative, so she has her own way to be creative. But my dad and my grandfather were both entrepreneurs.

Melinda Wittstock:

Oh my God. I think we’re twins, because that’s [inaudible 00:01:15]-

Ciara Stockeland:

That’s so funny.

Melinda Wittstock:

… my experience and I, for whatever reason, I was motivated to do this, when I was almost six and I went door to door demanding prepayment for my show.

Ciara Stockeland:

Oh, I love it. We would’ve been badass neighbors, little neighbor girls putting on the productions.

Melinda Wittstock:

Yeah. My mom was this figure skating coach, she’d been in the Olympics and so she was all about the choreography and all of that. And I was a figure skater and ballet at that age, so I had this whole choreography kind of thing going on and performance thing, but my dad was a stockbroker so I was just like, “Oh, well let’s try and sell 100 tickets to this.

Ciara Stockeland:

Yeah. Let’s do it.

Melinda Wittstock:

Why not? But I think sometimes, I always wonder about this, to what extent entrepreneurship is just something that’s in your DNA, or to what extent it can be learned, or even things that have to be overcome in the way that our education system is, where it teaches people to be kind of employees or like fit in a box rather than go and create kind of new things. What do you think? Is it something that can be learned?

Ciara Stockeland:

Yeah. You know what? This is so interesting. I don’t think, and I’m not science based at all with this assumption, but I don’t think people are born or not born as entrepreneurs. But I do think that certain people that are successful or find themselves in entrepreneurial journeys over and over are wired to think a certain way. I don’t know about you, but I would guess that you’re like me, I’m just not afraid to fail. I just, I kind of can’t, I don’t feel those things. So I think if I’m going to try something, because it’s a good idea, if it doesn’t work, no worries. I’ll figure it out, and I don’t have that fear.

I think that people that are very entrepreneurial, have some of those mindset qualities where they just try things, they can see opportunity other people can’t necessarily see. And then I think, what you said, we’re often pushed though into trying to fit into a mold. So when I went to college, I just, I couldn’t get my mind around just paying for school so that I could come out of school and sit in a cubicle. I just couldn’t do it. So I ended up dropping out. I never finished college, because I was like, why? I just don’t understand why I would pay for a job, I just don’t get that. So I think the entrepreneurs, like the ones that are crazy like us, that just do a lot of different things. We have those certain qualities, those mindset pieces.

Melinda Wittstock:

100%. Well, the failure is vital. You have to be willing to fail, to be an entrepreneur because by definition, just like a scientist, you are exploring and you see a problem and you’re trying to find the solution to the problem. And there’s so many revisions to that and so many hypotheses that need to be tested, and inherent to that is that you are going to fail. It’s part of the process, and it’s part of the learning, and it’s feedback.

Ciara Stockeland:

It is. Right? It really is. And the quicker you can learn to look at it that way too, so that you’re not riding this crazy rollercoaster of super high highs and really low lows, but you can level that out a bit in your entrepreneurial journey, the better off you’ll be as well.

Melinda Wittstock:

I love that.

Ciara Stockeland:

Yes.

Melinda Wittstock:

The leveling out, that has been something that has come to me over time where you have a wild success and it’s like, “Okay, cool.”

Ciara Stockeland:

Right.

Melinda Wittstock:

And then you have a failure and it’s like, “Okay, cool.”

Ciara Stockeland:

Yep, yep.

Ciara Stockeland:

You have to, otherwise you’re just constantly like, “Oh my goodness, this is amazing. I have so much money in my bank account.” “Oh my goodness, I have nothing. It’s going to come to an end. I need to quit tomorrow.” And that just exhausts you and you’re not productive and you can’t envision out your next part of the journey either when you’re so caught up in the high highs and the low lows.

Melinda Wittstock:

Well, one of the interesting challenges too, of entrepreneurship as you’re building your team and you’re hiring basically from a pool of people, largely who have been inculcated into that whole trajectory of being a good student, fitting into the mold, ticking the boxes and all of that. Right? And you want to kind of hire people who are going to be entrepreneurial, or at least entrepreneurial, or be able to innovate, like learn how to fail, all of that. So as you’ve built teams for all your companies, Ciara, how have you kind of inculcated that in your team members?

Ciara Stockeland:

Yeah. That’s such a good thing to think about. I, because I’m not afraid of failure, I’m not afraid of my team members failing either. So I’d rather have them try, and learn, and do, and then we pivot, or change, or adjust, or redo if we need to. As a practical example, this was early stages of my retail brick and mortar store. And I can literally remember where I was standing. I had this awesome gal, who she was fresh out of college and she was going into retail merchandising, and she, I just hired her for store manager. She had no confidence. And so I said, “I want you to dress the mannequins up front.” And she’s like, “Well, what do you want me to put on them?” And I was like, “I want you to pick, like I just want you to do it.”

Ciara Stockeland:

And she was like, “Oh, but what if you don’t like it? And what if…” She was just so, just no confidence. And I said, “Hey, here’s the deal. I want you to do it. And if I don’t like it, I’ll tell you, and we’ll just redo it. It’s not a big deal.” And so just empowering your people to know that you’re not going to go on a rampage if something doesn’t work out, you’re not going to stomp around the office, throw a temper tantrum or a fit, but you’re just going to work together to empower them to make decisions and do what they think is best. Because that’ll really build that, even if they aren’t entrepreneurial at heart, it’ll give them the flexibility and freedom to succeed.

Melinda Wittstock:

Yeah. It’s a bias towards imperfect action. Like I’d rather have imperfect action than long cycles of planning. You can plan for something and just get the plan completely wrong. And meanwhile, you missed the market opportunity, right?

Ciara Stockeland:

Yeah. And I think a lot of entrepreneurs, we tend to be kind of possessive, right? Because it’s our baby, it’s our idea. And so with our teams, we’re like, we feel like we need to manage it all and tell them how to do everything. But I have come to learn through many mistakes, doing it the wrong way many times, that I’m not good at everything. There’s some things I’m really, really good at, but there’s a lot of things that other people have much better qualification, they’re just built with much better qualifications for a certain task than I am. And so to give them the freedom to succeed in that, I have to let go and just let them do their job or learn or ask questions. And I think a lot of times entrepreneurs, because we’re so possessive of our business that we’re creating, we put our hands in everything and it really discourages our team from taking action, being innovative, and we don’t want that in the long run. That might work a little bit at the beginning, but that’s just going to cripple us as we grow.

Melinda Wittstock:

So Ciara, that’s so interesting because it means that as an entrepreneur, if we have any control issues we have to actually learn to let go.

Ciara Stockeland:

Yes.

Melinda Wittstock:

And I think there’s so many women, in fact, I can’t think of any interview I’ve done for the past 715 plus episodes where we haven’t, at some point, talked about perfectionism and how women are really prone to that and how to overcome it. Did you ever struggle with that? Or you, it sounds like you just kind of wired that you never cared about that, but so many women do.

Ciara Stockeland:

Yeah, I think I do in certain areas. Recently with the building of my most recent business, it’s a coaching consulting business, so that’s very different than brick and mortar. I found myself getting so busy with all these busy tasks, right? Like busy work. And I thought, well, I don’t care about delegating. I will delegate. What what’s going on? Why am I doing all these? And I thought, I don’t really know how. It’s not that I don’t want to. I need to really learn and teach myself how to delegate well.

So even after doing small business for decades, I’m still learning things. And while it might not look the same as it does from someone else who wants everything perfect, and so they hold on tightly, I’ve just learned that I need to keep being introspective and thinking about what could I change? What do I need to give over? What do I need to be really intentional about in order to keep leaning into my superpower as an entrepreneur even more? So I think we all struggle with it, it manifests itself in different ways, but we all do, for whatever reason, want to control everything.

Melinda Wittstock:

Yeah. Learning how to delegate is hard, especially if, as a woman, you find it hard to ask for things or find it hard to [inaudible 00:10:40]-

Ciara Stockeland:

I think that’s me.

Melinda Wittstock:

Yeah.

Ciara Stockeland:

I think that’s what it is with me. Yeah. I’m like, but I can do it. Why would I ask someone? I’m capable of it.

Melinda Wittstock:

We all have to overcome that. So getting good at not only asking, and asking for what we want, but also being able to receive it.

Ciara Stockeland:

Yes.

Melinda Wittstock:

That’s the other part, like just even being able to, I noticed that a lot of women, and I struggled with this for a while, like you get a compliment about something like, I don’t know, you were wearing and you find yourself saying, “Oh, what, this old thing?” Or you diminish yourself in-

Ciara Stockeland:

Exactly. Yes.

Melinda Wittstock:

… active receiving a compliment. It was kind of like, you’re sort of telling the universe, no, you don’t want to receive. And that, and as an entrepreneur, yes, you want to receive.

Ciara Stockeland:

Yeah. And I think it really, whether it be doing that with a compliment, or a gift someone wants to give us, and we’re like, “No, no, no, I can afford dinner. You don’t have to pay.” We gyp people, if I can say that, of the blessing of helping and speaking into our life. And we do that with our employees too. So I have an amazing EA, I love her and she’s always saying, she’ll text me, “Ciara, what could I do to help you today?” And it’s hard for me to think of what I can find to give her, but she finds joy in helping me.

I’m really working at being intentional, so actually yesterday, this just happened yesterday. I was like, “You know what? This would be an amazing job for Emily.” And I texted her and said, “Hey, Emily, you’re always asking me, would you be willing to do this?” And she was so excited I asked her, because that empowers her that she’s doing a great job for me, she’s part of the team. And so we need to really think about it from that non-self-perspective too, even though I could do this, how could I empower my team by letting them know I trust them with this project?

Melinda Wittstock:

Oh, that’s so important, especially if you’re running a type of business where you’re scaling quickly and you’ve got to hire a lot of people quickly. This is the situation I find myself in right now where, just looking at the financial model, we’ll have between 60 and 80 people by the end of the year, going from a team of 20. That’s rapid scale and I’m kind of like, “Oh my God.” And I realize that to give every employee and team member the care they need and be able to delegate, we need to have, man, we have to have good systems around that and good processes around it. But it starts with me internally, like where am I at in my own head?

Ciara Stockeland:

Yeah. I agree.

Melinda Wittstock:

To be able to-

Ciara Stockeland:

And that’s hard sometimes, isn’t it?

Melinda Wittstock:

Yeah. Oh, yeah. It is. Because, oh man, and I apologize to everyone listening who’ve heard me say this so many times, if you want therapy, become an entrepreneur. Because it’s going to, all these things are going to confront you, and at the end of the day, anything that’s happening in your external world is a manifestation of what’s going on within you. Like what you believe you deserve, what you believe your value is, all those sorts of things. On your entrepreneurial journey, Ciara, have you been confronted with things that have put you on a personal growth journey in that sense?

Ciara Stockeland:

Yeah. Always, always.

Melinda Wittstock:

Right.

Ciara Stockeland:

Yeah. I, well, and you know, one of the best ways to learn and keep yourself on that growth journey is to constantly surround yourself with people two steps ahead of you and two steps behind you. So having those people ahead that have been there, done that, “What am I missing? What can I learn from you? How did you…” A good friend of mine always says, “Ask them if you can tap into their genius.” So instead of saying, “Can I pick your brain?” Like we say, “Tap into their genius.” I love it. Or those people two steps behind us because when we’re teaching other people, we learn ourselves as well. So I think both of those pieces will help keep us moving forward in our own growth and grounded as well.

Melinda Wittstock:

I love that, the two steps ahead and two steps back, because you got to be in that continuum. And so many people say that who you’re being is really who you’re surrounded by, like the five or six closest people to you, you’re going to be the, probably the lowest common denominator of that. Right?

Ciara Stockeland:

Exactly. Exactly.

Melinda Wittstock:

And so then that presupposes that you have to be willing to sometimes be the, I don’t know, the stupidest in the room, you know what I mean? And not mind that. Right?

Ciara Stockeland:

Yeah. And be humble enough to say like, “You know what? I have a lot to learn.” But guess what, I get to be in the room, and that’s pretty exciting.

Melinda Wittstock:

Yeah. Because we always do. So take me back to your first adult business.

Ciara Stockeland:

Yeah. My first adult [inaudible 00:15:17]-

Melinda Wittstock:

Right? So you dropped out of school and then what happened?

Ciara Stockeland:

Yep. So at the same time that I was going to college, I was building my theater, my acting company, theater company. And I had started that when I was 13. So it started as just a hobby I was a homeschool kid and wanted opportunity. I was whining and complaining that there was nothing for me. And my mom said, “Well, if you want something, how about you just do it yourself?” And so I was like, “Okay.” So I started an little acting company, which ended up taking off. And I ran that for about a decade. We had homeschool, high school, public school, private school kids, all the way through college. We had a full on production twice a year. It was awesome.

Ciara Stockeland:

And through that, I started going to college, dropped out, got married, had a couple kids, and thought, you know what? I’m kind of done with… I’ve been doing this for a while, kind of done with the nonprofit thing, nights and weekends, let me go into retail, which is nights and weekends and holidays. So it was like I don’t know what I was thinking there. But in 2006 I opened my first retail store, and then built that, grew it, franchised it. So that took up another decade of my small business journey. And I learned a lot through that. So while the acting company was a great way for me to just learn how to manage people, how to ask people to pay for services, the next chapter, the retail, is what really showed me who I was as an entrepreneur, what I needed to learn, how much I didn’t know, how to deal with people, just a lot. So that was a big chunk and that would be probably my first complete adult business.

Melinda Wittstock:

And so what was the first, what were you selling in your first retail business?

Ciara Stockeland:

Yeah, so we were a high end maternity baby store. So a really beautiful boutique in downtown Fargo, North Dakota. It was kind of, 2006, like all over the country they were revitalizing downtown. So that’s like small town America was just kind of coming back on the scene. So we got in on that, we were one of the first little boutiques downtown in Fargo to redo the building and open up. And then my husband was in trucking at the time, and still is actually, but he was working for a guy who owned a company and they would sell, or they would transport a lot of product to high end department stores and they’d end up with claims. So for whatever reason, the product would be damaged, they’d pay the claim, and they were just storing all this freight in their warehouse that they had paid claims on.

And he came to me and he is like, “Hey Ciara, you have a retail store, would you mind selling, I’ve got like two truckloads of stuff.” And I’m always open to opportunity, so I said, “Sure.” So we rented this little hole in the wall, right next door to my beautiful boutique, handshake deal. He supplied the product, paid the rent, I managed the people and managed the store and we split everything half and half. And so that was my second concept. And then we ended up merging those two concepts, because we were heading into the recession then in 2008. And so high end maternity baby, wasn’t the best idea heading into a recession, but the outlet store was doing phenomenally well. So people loved buying whatever product they could find, treasure hunt deal of the day. And so we merged those and then that’s the concept that I franchised.

Melinda Wittstock:

Franchising has its own challenges.

Ciara Stockeland:

Yes.

Melinda Wittstock:

What did you learn along the way? Were you the type, like the McDonald’s type that worked out your process so everything was the same in every store, every experience, or how did you approach franchising?

Ciara Stockeland:

Yeah. I didn’t know what I was doing. I didn’t realize that franchising is very financially, it costs a lot of money to franchise. It’s just very financially intense because you’re supporting suddenly multiple small businesses. And because we had an inventory based franchise concept, we supplied the product. So we were essentially the bank for all of our stores because we would buy the inventory, bring it into our warehouse, send it out. I didn’t realize that when you franchise you suddenly find yourself in a completely different role than what made you successful in your business model. So I was really good at finding opportunities, finding deals, selling to people, merchandising, our stores were wildly financially successful, great margins.

But in franchising now you suddenly become someone that holds people to the letter of the law. It’s very operational, very systematized like you mentioned. And so that was hard for me because I just felt so trapped. Like suddenly I was in this role that I didn’t really fit well. Right? I was the enforcer. I was the operations person. I had to be super detail oriented. And what got me to a place where people wanted to franchise my business, because it was wildly successful, was a completely different skill set than what I found myself needing as a franchisor. So that was really interesting. And that’s what I always tell people when they come to me and they’re like, “Should I franchise?” I never say no, because it is a good business model, but I like to tell people, “You’ve got to have financial backing and you need to understand that you will be playing a completely different role than you are now as the founder. Unless you can hire that out.”

Melinda Wittstock:

100%, unless you bring in a really great COO.

Ciara Stockeland:

Yep, you can hire it out. And that’s why you need money.

Melinda Wittstock:

You need those operational people that are, who, just going back a little ways in our conversation, who love that. Like that kind of stuff makes their heart sing.

Ciara Stockeland:

Yes.

Melinda Wittstock:

But the visionary is not that person.

Ciara Stockeland:

Right. Absolutely not. And so if you don’t realize that and/or you don’t have the finances to hire the right people, you’re going to try to bootstrap a franchise and that’s very… It can be done. There’s a lot of emerging franchise brands that have been successful at it, but it’s a much harder path than if you would hire and bring that person in and allow yourself to continue to be the cheerleader, the visionary. So I would go, in the same day, I’d go between selling a franchise to someone, to cheerleading my current franchisees, and like, “Come on, you can do this. This is awesome. Let me help. Let me train. Let me coach.” Which I’m really good at. To, “You didn’t pay your royalties, you painted the wall the wrong color. Now I need to go back to the contract.” That’s really difficult when you’re doing all of those pieces.

Melinda Wittstock:

Yeah. It’s hard to cheerlead and enforce at the same time.

Ciara Stockeland:

It is. It really is.

Melinda Wittstock:

It’s just, because you’re sort of two different people and then it confuses the hell out of everyone you meet, right? Because-

Ciara Stockeland:

And you end up not being the cheerleader.

Melinda Wittstock:

Right. Right, right, right.

Melinda Wittstock:

I remember a long time ago, so back in my days where I was a London Times business and then media correspondent, because my own journey is I was this entrepreneur as I was a kid and a teenager and became very entrepreneurial in journalism, because I was on my school newspaper, which was a daily, and I created its advertising department, and I broke all these stories. And I ended up like a journalist, which is kind of entrepreneurial in the sense that you’re only as good as your last story. And I remember interviewing, spending 18 hours with Richard Branson on this whole piece. and I watched him like clockwork be the cheerleader, get everybody excited, and then leave the room and all his kind of operational people and lawyers would come in and then like do the hard negotiation, right?

Ciara Stockeland:

Yes. Yes. Yes. And he’s the smart man for doing that.

Melinda Wittstock:

Yes. And that’s the way, and it’s always influenced me.

Ciara Stockeland:

Well, it’s interesting now because in my current business I have a mastermind program and there’s certain participation requirements when you’re in it. And of course, building it up, I’m doing everything and I thought, okay, Ciara, lesson learned last time around. If you’re going to be the coach of the women in the mastermind and their cheerleader, their number one cheerleader, you have to hire someone that can enforce the requirements and the expectations. And so I have done that. I’m like, I’m not making this mistake again.

Melinda Wittstock:

That’s really smart because we, as women, we tend to spread ourselves too thin in myriad ways, and that’s one of them, by trying to be everybody and we can’t be everybody.

Ciara Stockeland:

Yeah. We can’t and we should lean into our gifting. Like I can cheerlead you, I can coach you, I can give you ideas. I can help you, even in a way, sometimes it’s tough love, but that’s very different than turning around and saying, “You didn’t enter your numbers. You didn’t pay your bill. You didn’t…” I need to be two, we need two separate people doing those roles. But I did not know that before. So I do now.

Melinda Wittstock:

It’s so, so important. So for anyone listening, that’s kind of in that, stop.

Ciara Stockeland:

Right. Just stop.

Melinda Wittstock:

Just stop.

Ciara Stockeland:

It will not, it will not help you in the long run, just saying.

Melinda Wittstock:

100%. And so what led you to do the wholesale subscription box? Because you were one of the first to work your way into that wholesale subscription box thing, which is like a really big, growing thing now. And it’s nice for recurring revenue and all of that good stuff. So what was the inspiration there?

Ciara Stockeland:

Yeah, I think, again, just looking, always looking at where is there something missing? What problem could I solve? And I knew from boutique-ing that a lot of boutique owners weren’t going to market like they had traditionally done. So in the past, if you owned boutique, it was almost like a rite of passage, bragging rights to say like, “I go to market, I go to LA twice a year.” Right? But people can buy online now. And there’s so many boutiques in the Midwest where it’s really difficult for them, and expensive to go.

So I thought, what if I could just bring market to them? And at the same time Etsy was growing. So what if I could find a way to help these independent wholesalers and makers get their product? They can’t afford to booth that market, but if they could get their product in the hands of retailers. And so knowing that subscription box, the convenience of it was working well, I thought, you know what? Let’s just put these two things together and create a wholesale subscription box. So we deliver samples to a retailer’s doorstep, easy peasy, they can buy, they can shop, they never have to leave their store.

Melinda Wittstock:

So smart. And so you do a lot of things though, too, like testifying for U.S. Senate committees and things around joint employer standards for businesses and much more. What led you there to be an advocate and end up in front of the U.S. Senate?

Ciara Stockeland:

Yeah. So I loved that work. That was a really awesome season. I was still in franchising and got really involved in the international franchise association. And I just like telling my story. I just have a heart for small business owners. And I think the vast majority of the population doesn’t understand the heart of a small business owner. They walk into a store when it’s convenient for them, they’ll buy if they want, but people need to know that behind that counter is someone who has invested everything they have, they have mortgaged their homes to do that business. They often don’t get a paycheck. They’re the last at the end of the day to be taken care of.

And so I just had the opportunity, especially through the IFA and then the U.S. Small Business Chamber too, to just get up in front of our legislators and just tell the story of a small business owner. Like just listen from our perspective when you’re talking about minimum wage or you’re talking about imposing new rules or restrictions. From a small business owner standpoint, I just want to tell you my story because nobody can refute your story. Right? They might not agree with your policy, but your story is your own. And so I really think it’s important for small business owners to get up and tell their story whenever they can. And so I was just willing and had the opportunity.

Melinda Wittstock:

I think that’s so important. I was talking to our board chairman about this the other day, because for the U.S. Congress, it’s sort of like small business is a hundred million dollar company plus. Right?

Ciara Stockeland:

Right. Right.

Melinda Wittstock:

And those aren’t the companies that are necessarily creating the most jobs, it’s the small business owners, the small enterprises, like five, team of five, a team of 10, a team, small or sole proprietors and the tax code does not support those kind of entrepreneurs. And there’s no real lobbying group up against the Googles, and the Facebooks, and the big techs, and big oil and gas, and all of those things that really have a voice in Congress. It’s actually really important. And I mean, entrepreneurs are so busy. It’s not like we have time to get together and create such a lobbying thing. But we were just talking about this the other day, that it’s actually really important.

Ciara Stockeland:

It’s so important. Yeah. Because if you look at, I live in Nashville area now, so if I go downtown Franklin and I walk up and down, there’s like 3, 4, 5 blocks of all these small business owners, or small businesses. Every one of those has, like you said, maybe five, maybe 10 employees, probably five, well, one to five. Right? But those are real people that are hoping that they can have a paycheck from the sales that you go in and make that week with them. And that’s just one little Main Street in our vast country. And so think of all the independent insurance places, and coaches, and consultants, and dental offices, and you think of all these small businesses. And it’s really important for us to stand up when we can, and just share that with people, that small business isn’t, like you said, a Google, or maybe even a little smaller, 100 people, 200 people, small business is like one to five employees. And a lot of times it’s a solopreneur.

Melinda Wittstock:

And it just, it’s the engine of our country.

Ciara Stockeland:

Yeah. And the small businesses are the ones who are paying for an ad sponsorship for the local little league. And they’re the ones who are donating for the fundraiser for the family who just lost a loved one to cancer. Like it’s the teeny, tiny, small businesses that are investing in their communities, that are giving back, that are hosting charity events. And we don’t think of that. Right? And so I think, yeah, I just had the opportunity to share, and I really enjoyed doing that. I would do it again in a heartbeat.

Melinda Wittstock:

I love that. Because it’s so much, I think as we get more and more experienced and successful as entrepreneurs, we have responsibility, I was going to say give back, but it’s actually giving forward because we never took away anything from anybody. We just created opportunity. We created wealth, we created jobs. We did all these things. So I like to say give forward.

Ciara Stockeland:

Yes.

Melinda Wittstock:

But it’s very, very important to do that. So congratulations on that work.

Ciara Stockeland:

Thank you.

Melinda Wittstock:

It’s very inspiring and more of us should do it. That’s really cool. So tell me about now the coaching and mastermind you’re doing, and your ideal clients, and what they get, and who you work with, and all those good things.

Ciara Stockeland:

Yes. So obviously a lot of background in retail, inventory, management, inventory based businesses, retail wholesale. And so as I wound down the subscription box and prepared to sell it. So when I launched the subscription box, my goal was to build something to sell. I didn’t want to manage a bunch of inventory again and all of that, but I just knew that there was a potential business model there and if I could get it off the ground and sell it, great. So that’s what I did. And through that launch of that company, I started meeting boutique owners that had all these questions. And they were always similar questions like, “Well, how much inventory should I buy? I don’t pay myself. When could I be profitable?”

answering over and over, and I thought, maybe I should start charging for my answers. I’m giving away a lot of free advice. And so I put together a beta coaching program. I think I had five women in and it was like two months or something like that. And we just went through the method that I had created for building, launching, operating a retail business. So I just taught them how to manage inventory, what margin meant, how to read financials. Just really simple things that a lot of times small retailers don’t know, and they feel a lot of shame and guilt around not knowing them, but they don’t know who to ask, and so then they just buy more stuff. It’s like the easy thing, “I’ll just buy more pretty things and sell them.” And so built that beta program, it worked well. We ran a couple different launches of it and then ended up launching the boutique workshop so I could really get the information out to the masses.

So that’s my core program, it’s a membership, group membership. And I knew I’d have a little bit of an uphill battle. I think group programs, group coaching gets a bad rap a lot of times because people sign up for things and they don’t really get help and they feel really lost. And so it was really my intent to make sure that if people join, that they felt heard and seen, and that they could get the information that they needed, that they’d have access to me. So we’ve been doing that for a couple years. It’s amazing. We’ve worked with over 1100 retailers.

And then my accelerator program just takes all of that up a level and we really work on benchmarking numbers. So when I had my store, one thing that I never liked was the fact that I never really knew how I stood in comparison in my industry. There’s no way to find that. So I feel like I’m profitable, but like what should a boutique make per square foot? How much inventory should I have? How much should I spend on marketing? And so in my mastermind program, we benchmark, we look at each other’s numbers, it’s phenomenal, so that you can truly benchmark and see, okay, here is my margin, where should I be against the peers that are similar to me in size, or in in the country, where they’re placed, or whatever? So yeah, so those are my two programs. I love it. I just help inventory based businesses break down their numbers, help them focus on what they need to focus on and really work to give them peace of mind and profitability.

Melinda Wittstock:

Ciara, I’m not surprised hearing all of that. That one of your mantras is about living big, and big, of course, being an acronym for bold, intentional, and grateful. Talk to me about how those things fit together for you.

Ciara Stockeland:

Yeah. I’ve really been thinking about this, probably over the last year, and it started with, we were just coming out of COVID and I was part of a women’s Bible study. I was invited to go and I wanted to say, no, I’m kind of, I’m actually a bit introverted. So I tend to want to just stay home. But I thought, you know what? I’m going to go out. I’ll meet these gals. It’ll be good. So there was a lot of ladies in it I didn’t know. And one evening the host just asked us like, “Hey, what have you guys been learning?” And I had just completed an Iron Man in October, last year in October. And so I was just living through that whole experience and what I had learned. And I said, you know what? I just really feel like we’re called to live big.

We’re just all living these small, fearful lives and we need to live big. We need to try hard things. We need to fall down and get scraped up and get up and tell someone where that pothole is so they don’t fall down. We just need to live into our life. And then I kind of left it at that. And the next week, one of the gals that I didn’t know, came back to the study and she’s like, “Hey Ciara, I want to tell you something, what you said last week really stuck with me. And I went home and I told my family, we have been living small and we’re going to stop.” And she’s like, we booked a family vacation, and she started listing off all this stuff. And I thought if that message could touch someone that quickly, it needs to be shared everywhere.

And so just thinking of like, what does living big look like? Just living that bold life of trying things that are so out of your comfort zone, but you know you should try. Being really intentional with the people we meet and the decisions we make instead of just living this hot mess life of like whatever happens, happens. And I’m just a mess. No, let’s be intentional. And then being really grateful every day for the opportunities and the people. And what’s interesting when we do this, that grateful attitude brings us back around to want to live even more boldly. And that bold living makes us even more intentional with our choices. So it’s just this amazing cycle that we can find ourselves in. And we just get off that hamster wheel of hot mess, out of control, overwhelm, fear, small.

Melinda Wittstock:

I love that. And so it doesn’t surprise me that you’ve been training for Iron Man. What got you into that and how has that impacted everything you do?

Ciara Stockeland:

Oh, it’s great. I’m in the middle of training again. I had a four hour bike ride today.

Melinda Wittstock:

Oh my God.

Ciara Stockeland:

Yeah. Four hour training session.

Melinda Wittstock:

That’s making me feel tired. I don’t know. I just do hot yoga, so-

Ciara Stockeland:

Yeah. Well, hot yoga makes me feel tired. The thought of that. So we all have our own thing, but yeah, so I was always a 5k girl. I want to exercise quickly, I don’t want to be in pain too long, and just, I’m not going to do anything long. I had a friend who does Iron Man and she kept bugging me and I’m like, “No, it’s just not my deal. I’ll come cheer you on.” And my husband, it had been on his bucket list, so he did one a year ago. Well, over a year ago now. And when I went to his Iron Man the day and was watching, I was like, “Oh my goodness, this is so amazing.”

And you look around at all the different kinds of people that are participating and you think, okay, that lady’s like 80 years old, that person is walking, they’re not running. If they can do it, I can do it. If my husband can do it, I can do it. And then I started thinking, how awesome would it be to do an Iron Man and use that as a coaching tool for my clients, to really show them that if you decide and commit to something, you can do it. If you have the right tools and the right support, you can do what you want to do. And so for those reasons, I decided to sign up, and now, now I had to sign up again, because now I need to get a better time than I got last time. So I don’t know how many I’ll end up doing, but I’ll be doing a Alaska in a couple months here.

Melinda Wittstock:

Oh, that’s amazing. So you got a lot on your plate. What’s next for you? What’s the big vision? Where do you think you’re going to be five, 10 years from now?

Ciara Stockeland:

Yeah. So I’m actually working right now and just simplifying down. That’s another lesson for another day, but have just learned that I can quickly make everything complicated and I don’t want to live a rat race life. And so I think, for me, part of living big is living really simply so that I have margin in my life to say yes to people and the right things. And I want to learn, keep learning. I love learning. So for me, I just, in the next five, 10 years, I just envision helping people build better businesses, profitability, peace of mind. I’d love to stay fit and active. My kids both are graduated from high school now, so it’s really fun to just be able to sit around the dinner table with them and have awesome conversations. My husband and I love traveling, so I think just a simple, simple, quiet life leaning into the gifts that I’ve been given to help people that would make me happy.

Melinda Wittstock:

Wonderful. Well, I want to make sure people know how to find you and work with you. What’s the best way?

Ciara Stockeland:

Yeah. So the best way is probably just to go to my website, theboutiqueworkshop.com and then everything’s there. My podcast, there’s free profit first stuff, my blog, lots of amazing resources, my Instagram handles, all those things. That’d be the easiest way.

Melinda Wittstock:

That’s great. What’s your podcast?

Ciara Stockeland:

The Boutique Workshop Podcast. Surprise. Surprise.

Melinda Wittstock:

That’s fantastic.

Ciara Stockeland:

It’s awesome. Yeah. It’s like 10, 10 to 15 minutes once a week where we just break down all things number related. So profit first, cash flow, inventory management, and I promise the conversations are not scary or dull.

Ciara Stockeland:

I make 10, 15 minutes fly on by.

Melinda Wittstock:

Well, I’m going to follow it on Podopolo, my podcasting app that automatically and just 5 million podcasts with this really souped up recommendation engine that puts your podcast in front of the exact audience so you can really grow your reach, and engagement, and by extension revenue. So I invite you to join me there.

Ciara Stockeland:

Oh, I will.

Melinda Wittstock:

And also, especially because I can add you too as a guest when this episode airs and it’s interactive so we can keep the conversation going over there too.

Ciara Stockeland:

Oh, I love it. What a great app.

Melinda Wittstock:

Yeah, it’s super cool. So I will see you there, but Ciara, I really enjoyed our conversation. Thank you so much for putting on your wings and flying with us.

Ciara Stockeland:

Thank you.