Hustle + Gather

Hosted ByDana Kadwell & Courtney Hopper

Sister entrepreneurs Dana Kadwell and Courtney Hopper talk about the ups and downs of the hustle, and the reward at the end of the journey. Life starts at the edge of our comfort zone, and that’s what running a business is about - it’s completely uncomfortable and yet thrilling at the same time. Hear Dana and Courtney talk about the hard parts of entrepreneurship with other business owners going through the struggle as well.

Conversations with Sisters: Entrepreneur Island, Culling Friend Groups, and Unpacking the Rachel Sheerin Episode

How do you manage relationships with friends and family who aren’t on entrepreneur island with you?  What if you’re in a job you know isn’t meant for you?  On Conversations with Sisters, Courtney and Dana unpack last week’s episode with Rachel Sheerin.

If you haven’t listened to the conversation with Rachel Sheerin, it’s the episode before this one, on Apple Podcasts, Spotify, or any other podcast app.

Hustle + Gather Conversations with Sisters Wide


Courtney Hopper: Welcome to Hustle and Gather. A podcast about inspiring the everyday entrepreneur to take the leap. I’m Courtney.

Dana Kadwell: And I’m Dana.

Courtney Hopper: And we’re two sisters who love business. On this show, we talk about the ups and downs of the hustle and the reward at the end of the journey.

Dana Kadwell: We know all of the challenges that come with starting a business. Between operating our wedding venue, doing speaking and consulting, and starting our luxury wedding planning company, we wake up and hustle every day. And today we’re talking, just the two of us, about last week’s episode with Rachel Sheerin; a motivational speaker, burnout expert, executive trainer, Ted Talk giver, podcaster, and future author. If you haven’t heard last week’s episode, you’ll give it a listen and come back to hear our thoughts.

Courtney Hopper: Dana, what was your, what was your first thought/takeaway after speaking to Rachel, besides like, she’s amazing, so much energy. I want to be Rachel when I grew up, even though I believe she’s younger than me.

Dana Kadwell: I feel like for me, it was– I think, always whenever I hear Rachel or speak with her, it’s confidence boosting. She is someone who can really inspire you to believe in yourself, even if there’s actually no reason to believe in yourself in your mind. But what really resonated with me a lot, and I mentioned, I think I said it in the podcast was, culling your friend group. And I feel like that’s something that I’ve done for years and I don’t, and I’ve always been not ashamed of it, but just more like, “Am I doing the right thing by not letting people in?”

I’m very protective of my feelings. Because I have big feelings. And I have a hard time processing those feelings with other people. And so, very few people actually get the full side of who I am. And I thought that was, it was really, almost affirming of saying like, surrounding yourself around people that feed you and tell you what you, not necessarily what you need to hear, but the truths about who you are.

And recognizing them as truths. It’s not just them being nice, or kind, or saying great things to like, pump you up, or whatever. It’s because it’s true. I really love that.

Courtney Hopper: I totally love that too. I mean, I, like, I’ve always been weird about friends. Like, I have a very small, small group of people that like, know my ins and outs and my everything. And if I’m going to be your friend, it means I’m going to be invested. So my number is always very, very small. So, there’s not really been a group to cull, I guess; necessarily. Like the, the biggest ancillary group that I feel like I’ve had has been since we’ve been in business, you know, like other industry friends. And there are some that are truly friends for sure.

But I think sometimes it’s hard in the industry, especially like owning a venue, like, are they saying these things to get on my venue list? Like, are they saying these things because they have an endgame? You know? Or are they saying these things because they’re true? Or am I discounting what they’re saying because of how I feel about myself? You know what I mean?

Dana Kadwell: Yeah.

Courtney Hopper: So I think it is definitely, like very different. Like, I wasn’t, Dana, we can speak to this. Like, was, like, college experience was very different. High school experience was very different. Like, I’ve always been a very, I don’t want to say guarded. I’m not like a guarded person, but very, I don’t know. I didn’t like, meet a lot of friends and people–

Dana Kadwell: Yeah.

Courtney Hopper: — And interaction. And the people that I did have fulfilled that in me. Yeah. Like I’m a, I’m a high-functioning introvert; is how I call it what I call myself. So, I need a lot of alone and downtime to recharge and be with my thoughts because I think my thoughts are important. And not everybody else does.

Dana Kadwell: That’s very accurate. Well, I was completely opposite. I like, did everything in high school and college and loved people. And I still love people. I mean, people fill me up. I am definitely an extrovert. So, I don’t have to go deep to have a good time with somebody.

Like I don’t have to, I can just have, I can just shoot the shit with anybody and have a wonderful time and laugh and have a great night. It just doesn’t have to be serious. And I only want to be serious, you know, with certain people who, and it’s not only because– I’m mulling something over. I’m trying to like, figure out how I should actually feel about something or how I should respond to something.

And I just need someone I trust to tell me–

Courtney Hopper: Yeah.

Dana Kadwell: –You know? How I feel is, how I feel is okay. It was just really powerful I feel like, for a lot of people to, to believe that it’s okay. That, to just have those few people that are feeding you and it doesn’t have to be this massive group of people.

Courtney Hopper: Yeah. I totally, I agree with that. Like, I, I think that kind of drowning out the riff raff and, like, the noise a lot of times. And I definitely resonated with, when she said that she didn’t want to tell her mom–

Dana Kadwell:  oh yeah.

Courtney Hopper: –Like, what she was doing. Like, kind of segwaying from friends and, you know, believing what people around you are saying. But also, being afraid to tell the people who, whose opinion that you value the most, how hard that can be when you’re trying something new and you’re doing something different. And you’re trying to tell the person that you care about the most. So you have the most meat in the game, right? Like, you have the most to lose. Like, if they disapprove, what are you going to do from here?

Dana Kadwell: Yeah. For me, it’s actually a little different. It’s not about how I think they’re going to feel about it. And I actually just listened to this podcast. Brené Brown was interviewing Glennon Doyle on her book, Untamed. And I haven’t read the book. It’s actually on my list to do, but she had this analogy. She talks about her “Island.” And this was when she told her parents that she was dissolving her marriage and she was going to be married–

Courtney Hopper:  With a lesbian.

Dana Kadwell:  Yeah, lesbian. Going to be marrying Abby. And she loved her parents. And her parents were supportive, but they were very fearful. Like, they’re very afraid of what it was going to do to the kids and all that stuff. And they were supposed to come down and she said, “You can’t come.” Like, “You can’t bring fear onto my Island. We just need happiness and peace because that’s what my family needs.

And I feel that. I felt that, I was driving to Charlotte when I was listening to the podcast. And I like, I remember I called Sam and I was like, “This is, this, is it.” Like, “This is what it feels like. This is why I’m trying to communicate to people who are my naysayers in my life.” And I don’t even want to say they’re naysayers.

They’re just, they’re fearful. And a lot of that is like, my extended family. Like, my in-laws. They have had corporate jobs their whole life, and they love me so unconditionally. They do. And I know that deeply. But their fear of entrepreneurship because they don’t understand it, like, sometimes seeps into how I feel about it.

And there’s times when I want to say you can’t come onto my “Entrepreneur Island” and give me that doubt and fear. Because it’s not what I need right now. And if you can’t give that to me, then I can’t interact with you in that way. And it’s hard. It causes riffs in our marriage and it caused, and I feel, I get hurt.

I get offended. I get emotional about it because I care deeply for them. And I love them a lot. And I know, I know that at the end of the day, they love me just like a daughter, but it’s still so damaging.

Courtney Hopper: Yeah. Continuing on with this therapy session that seems to be this, “Conversations with Sisters,” I am similar in a lot of ways. Because my people group that I care about is so small and so tight that I tend to care about their happiness. I tend to care about their opinion. I tend to care about what their thoughts are on what I’m doing, to the point where I have to, I have to be super careful. Because I will get lost as to what, how I feel.

Like, it’s, like, when she was talking about in therapy, what’s your dream? What’s your hope? Like, it’s very easy for me to get lost in what do I want? For worrying about what everybody else wants for me. Right? And I have to like, drown out those voices to get down to like, the meat of like, what do I want? Because it’s so easy for, for people like I’m easily influenced. I have to be really protective of X and I have to like, sort through it.

And I’m a very, like, I’m a deep thinker. I spend a lot of time in my own head. I spend a lot of time with my own thoughts and my own ideas kind of sorting through. And I think sometimes from the outside, like as a seven, it doesn’t look like that. Like, it feels like you’re very impulsive and not really thinking through things. But there’s a lot of time spent, even before presenting an idea or a thought or a life choice or whatever, for me. Like, that inherent, like people pleaser. “I want to make you happy” comes in and it can drown out how I really feel about something.

So, it’s super important for me to be cautious about what I’m sharing and what I’m divulging or whatever. Because I can get lost in it. And I can make choices that don’t reflect what I want. And I get stuck in them. And I’ve found this in many aspects of my life, where I’m in the middle of a life that I don’t want.

Like, this doesn’t look like anything like how I would want to be doing, or want to be treated, or wants to be acting. But I found myself here because I was following somebody else.

Dana Kadwell: Yeah. I mean, I think, I mean, obviously, I know that about you. Because we’ve had many deep conversations about this, but I personally feel like when you came to that realization and when you finally started saying basically, you know, I don’t know if I can, I can say like, “Fuck it.”

But like, “I’m important.” It’s about, not that it was selfish about me, but it was like, this is what I actually want. This is what I actually think. And I don’t care if what I think is going to upset you. But, because this is my truth. And I feel like that came out after many years of therapy for you.

Courtney Hopper: Yeah, totally.

Dana Kadwell: And kind of honed that in for what you actually were trying to communicate.

Courtney Hopper: Yeah, I totally, I agree with that. Because I, there was just like, how Rachel felt. Like, I totally resonated with that. Like, there was a point where you could have asked me what I wanted and I could not tell you. And it was a very like, stark moment for me. I mean, I can go back to that place and see how I was feeling. Where it was like, “I actually have no idea.”

But I literally, had no idea. And I think bringing it back to entrepreneurship or bringing it back into like, taking that big jump into like, something new and something scary, something that maybe you’re an imposter at. I think that moving out of that place of survival, like whatever you’re coming from, like, it doesn’t allow you for, to have dreams. That doesn’t allow you to have vision.

Like, when you’re like, in that survival mode, it doesn’t allow you to think as a way of survival about what could be better? What could be more? Do you know what I mean? And I think people feel like that a lot of times in their careers.

Like, I know like for, like when I was a teacher and you were a teacher, like, I knew that wasn’t my gig. Like, I knew it year two, I knew it year three, I knew it year four, you know? I knew all the years that it wasn’t my gig. And I remember someone telling me one time, like, “You would be a great administrator.” And I was like, “I am not committing any more time, education to this.” Like, I know that this is not me.

And God bless teachers who it is them. Like, my son has a teacher now that’s like, amazing. Like, she just was a natural-born teacher. Such an encourager, wonderful teacher, like that was never me. Right? It was a job for me. And I don’t think anybody wants their teacher of their child to say, “This is just a job.”

Like, I could be doing this, or I could be flipping burgers. Either one, this is what I’m doing now. But I remember at the time I was like, I didn’t have any vision for it. Right? I didn’t see any future. There wasn’t any hope or dream. There was nothing at the end of it for me. And I think sometimes when you know that you’re ready to like pivot and move on, it’s like that. Like, you don’t have a hope. You don’t have a dream. You can’t put your finger on it.

Dana Kadwell: So, Rachel kind of touched on this too. She said like, her dream was just to be happy. And I think that’s a great dream, just to be happy. But I, I sometimes find being an entrepreneur is sorting out what is going to make me happy. Because sometimes what I think will make me happy actually will not make me happy.

It will either add more stress or it’s something that I, I’m not ready to let go, or whatever. But, Rachel actually had a great– one of her podcasts episodes was the “F-It List.”.

Courtney Hopper: Yeah, I like that one.

Dana Kadwell: And my list was so long. And I remember going home to Sam and I was like, “I have more on my ‘F-It List’ than things I actually want to do this year. There’s more that I want to throw away and put in the garbage and pretend that never happened than things that I actually want to maintain in my life. And that should tell you something about my state of mental health right now; where I am at. But it was, it is hard because, and I think for me, I am not a dreamer.

I am not a visionary. I, I feel like I have good ideas. I feel like I can help brainstorm things, but it is not my natural inclination to, to forecast what I want to do.

Courtney Hopper: You’re like a pragmatic. You’re like, such a practical person.

Dana Kadwell: Yes. So, have a really hard time saying what I want and even knowing what I want, truly. Like, knowing what will make me happy, I actually don’t know that answer. And I can, I honestly could tell you, like, I know I said like my dream was to stop planning weddings, but it’s not because I don’t love weddings. Actually love it. And I love all the clients I have this year. Like, I adored all of them. They make me laugh. I enjoy getting drinks with them. I want to be friends with them.

I don’t want the responsibility of their wedding all the time. You know what I mean? Like, it’s hard when you’re trying to build a business, and grow a business, and be in the middle of your business. And so it’s not that I don’t love it. Because I do love it. I don’t love what it takes away from my overall job as a boss.

Courtney Hopper: Yeah, I totally agree. And I think that, to me, that the beauty of entrepreneurship. Like it’s not the negative, it’s like, the positive of entrepreneurship is where, okay, let me try this. I love it. And I can see where I can facilitate it, but don’t want to do it. I can build a team around it. And it allows you, like, running a small business, it allows you to like, shift and form into so many different roles. To try it on and to say that doesn’t work. And then to try on something else, right? And it also allows you to see where, what didn’t work for you is like a great fit for somebody else. And now you have this amazing team member that kind of completes your entrepreneurial vision.

And I totally love that. Like, I love the idea of trying on something, discarding it, giving it to somebody else. Like, you steam this, right? I’m not, I’m not steaming anymore. I’m not doing it. I don’t love it. It’s not my thing. But, I would like to pick out all the clothes that you’re going to steam. You know? Or, I would love to pick out the models that are going to wear the clothes that you’re going to steam.

Or I would like to like, direct this set. I’d like to be a creative visionary for whatever it is. And so, I think that’s like the joy in entrepreneurship; is to be able to try things on, find better fits than yourself. Like, I always tell people when I’m building a team that I want to be the weakest link on my team because I’m not building the best team if I’m the best person on it.

Everybody that I hire, I want them to have skills that are better than mine, because I want them to grow and move, move my team forward. Like, I’ve gotten my team as far. And I mean I buy we, have gotten our team as far as it’s going to go. We need other visions. We need other interests and ideas and enthusiasm for what we’re doing to take it to the next level. And that’s what I love about growing a team, and entrepreneurship, and whatnot.

Dana Kadwell: I know. I, and I think what I like, what I love about Rachel is, one, she’s like, so genuine. It’s just so genuine and authentic. And it’s funny because when you first meet her, talk to her, it doesn’t always come across that way. Because you’re like,” No one can be that happy. No one can love what they do that much.”

The more you talk to her, the more you realize that her why for what she does is so deeply rooted into who she is. And I think it’s why she’s so successful. Because it is a very authentic and genuine place, uh, for her for, to have to be this motivational speaker, because that’s just who she is. I can only imagine her as like, a 16-year-old best friend, right?

Courtney Hopper: Yeah.

Dana Kadwell: Who like–

Courtney Hopper: She probably got you in lots of trouble.

Dana Kadwell: Well, not even that, but she’s the one, like, your boyfriend just dumped you. And like, he started dating some other girl and she is like, “That girl is crap.” Like, “You are beautiful and wonderful.

And you have the best hair.” And, you know, you can have zits all over your face, but she’s like, “You are just so beautiful.” I mean, she is like, the one that’s going to pull every positive thing out of you and tell you to your face why you are amazing and why this, you know, jackass was a total stupid person for dumping you. Right?

Courtney Hopper: I felt like she was going to start a smear campaign against the guy too. I mean, I think–

Dana Kadwell: Yeah!

Courtney Hopper: — She would go all out at 16.

Dana Kadwell: Yeah. Like, she is like, your person. Like, she is going to–

Courtney Hopper: She’s like your hype-woman.

Dana Kadwell: Yeah. But like even just the person who, no matter what you do, even if you did the most shameful thing in the world, you could be like, “Rachel, I can’t believe I did this.” and she’d be like, “Girl, I would have done the same thing.” Like, no judgment, right?

Courtney Hopper: Oh, man. I could totally vouch for that. Like–

Dana Kadwell: Yeah.

Courtney Hopper: She’s totally that way

Dana Kadwell: Oh yeah. No, but I’m saying so like, I think for her, like her why is so deeply rooted into who she is. And I think for a lot of times, and I can honestly say for entrepreneurship, there is, some people who love the, the, like, the actual industry they’re going into, right? Like, maybe someone’s wise because they love weddings or they love cooking. So, they want to be a chef. Or they love SCO. So, they want to like, help other businesses. Like, there are people like, maybe like–

Courtney Hopper: Who are these people?

Dana Kadwell: I don’t know. I’m sure there’s people. But they love that part of it. And that, and that deeply feeds into who they are. And then there’s, I think another group of people who their why is purely about business. Like, they just love the ride of entrepreneurship. And so, when she’s talking and telling about this, you know, she took six months or whatever, and I’m like, I personally got like, drug into entrepreneurship by you. Right? You’re the one that–

Courtney Hopper: You’re welcome.

Dana Kadwell: –Convinced me to do this. And it wasn’t anything having to do with, because I was like, I one day wanted to own my own company. And, at all, like, planning just became this avenue to opening a venue. And then eventually, I actually really loved planning and I loved the design of it.

And I loved the connection with brides and, and whatnot. And now that’s evolved into something completely different where I just really love people. Like, I love talking to other entrepreneurs, other, just other people in the industry. You know? That’s what brings me joy more than what it originally was. And so I, I don’t know.

I just, I felt like it was one of those things where I was like, am I going to be in it for the long game? Because I could see someone like Rachel, who her why is so deeply rooted into who she is. Like, she’s in it for the long game. Like, that’s endgame for her.

Courtney Hopper: Yeah.

Dana Kadwell:  And for me, I’m like, I can’t say that right now this is my endgame because it’s not deeply rooted into who I am. Does that make sense?

Courtney Hopper: Yeah, it totally makes sense. I mean, I, well, you know, even more so, do not want to plan weddings. Like, I have slight ADD in general. And being pulled back into that, even though I only have a couple of this year that I’m finishing out from 2020, which was supposed to be my last one.

Like, it really distracts me from what I’m doing, right? Then I have to get refocused and it just feels like, it just feels like there’s a lot. And I think there is a point where it is, you can’t manage what you’re doing and do what you’re doing well. Right? Like, we’re managing this large team. And I love the girls.

So, I love being able to push other people towards their best. Like, I love being able to see our girls grow and succeed and hit their, you know, shatter that ceiling. And be able to make avenues for them to dream big. Like I, like when we talk about, and I don’t know if our luxury planning line is going to be launched when this comes out. I think not, but you know, we have a couple of girls who are, you know, launching a luxury planning line that, you know, we’re coming alongside of.

But it’s been so much fun. Even though I don’t actually want to do it, it’s been a whole lot of fun facilitating that dream dream and seeing them dream big. Right? Because it feels like, it feels a lot like the beginning of “C and D” to us.

Dana Kadwell: Right. And–

Courtney Hopper:  They love that.

Dana Kadwell: Yeah. The big difference is us coming alongside in a very supportive role.

Courtney Hopper:  Right.

Dana Kadwell: Like, where we’re they’re just bouncing ideas. Honestly, probably crushing some dreams when they send us a tagline we don’t like.

Courtney Hopper:  “Nah. That’s not good.”

Dana Kadwell: ” I don’t like that.” But I mean, it’s really just a supportive role. And a supportive role for the clients too. I mean, we’re there in some capacity, but we’re not the brains behind it. And it does feel really good and it feels really great to like, see, you know, these women excel in something and know that, that we had a hand in that in, in creating and making this space available for them to, to make their dreams bigger than what we, we, what we even thought for them.

Courtney Hopper: Right. Well, to know that, yes, they came to work for us as their employees, but they feel so empowered–

Dana Kadwell: Right.

Courtney Hopper: –To still dream and to still have vision. And to still feel and know that they’re able to go off and make, have these great ideas. And that we’re going to help facilitate them. Like, how amazing is that?

Dana Kadwell: Right.

Courtney Hopper: Like, that’s amazing. Like, you’re inspiring the next round of entrepreneurs right out of our own business. And now they have the backing and the, you know, finances of our business to help promote the next thing. And, I think that, yes, it’s about wedding planning and yes, I love our venue and I want it to be amazing.

And I want it to be the place to get married in North Carolina. But also, I want for our employees to know that there is no ceiling. Not even here in our company, there is no ceiling. Like, make it what you want it. You are empowered.

Dana Kadwell: I agree it’s what makes it unique to work for us. And I think it’s, that makes it great for our company. But I also think it’s our downfall sometimes. Because we inspire people so much that, you know, they go and do something else and walk away. And, and I don’t want to say downfall, because it’s not a bad thing. So I think we, like, I think it’s great that people want to open up their own company and whatnot, but it always is like a little, it’s a little tinge of hurt. You know? That obviously, we didn’t create an environment well enough for you.

Courtney Hopper: Really? All I think is, “Good luck!”

Dana Kadwell:  Yeah. I do think that’s too.

Courtney Hopper: You don’t know what you got until it’s gone!

Dana Kadwell: Two very different perspectives on this. Um, but yes. I definitely think so. I think that is some of the magic that we bring to the table.

Courtney Hopper: Well, let’s bring some levity to this conversation–

Dana Kadwell: Yeah.

Courtney Hopper:  And end it here. So I loved how Rachel, during her six months of just waiting around in the ethers, she drove for Uber and did some steaming on some sets and whatnot. I love that. So let’s say the pandemic got worse. Let’s say that, I don’t know, we just got sued and had no money. What would be your Uber job to get us through?

Dana Kadwell: I have no idea. I know that like, I feel like I should have an answer to that. But my backup always, always pre-pandemic, was that if I could not make it, I was going to go work in a dress shop. Because I like, love to say yes to the dress. I still love brides. I love the fashion.

I love making people feel beautiful and comfortable. Like, I always thought that. So obviously, the pandemic, bride shops probably wouldn’t be open. That probably wouldn’t be an option. Yeah. So, I mean more than likely, probably just go work in some like, corporate, managerial, something. Like, I got head hunted to be a Head Hunter at one point. So, I thought that, I don’t know. I really don’t know. I know that’s like, not a great answer.

Courtney Hopper: That’s a very boring answer..

Dana Kadwell: I know, but I like, don’t–

Courtney Hopper: I don’t approve.

Dana Kadwell: Maybe I would go Uber. I don’t know. It’s, I can’t imagine life outside of teaching in the industry. That’s like all  I know. And I only know hospitality. Because I only ever worked in a restaurant or I worked in Ann Taylor.

Or like, all I know is hospitality. I don’t know anything different. So, I can’t imagine the industry being so crumbled and dead that there was nothing available.

Courtney Hopper: All right. Well, you’re certainly not going to join a think tank anywhere.

Dana Kadwell: Let’s not do that.

Courtney Hopper: That’s not going to be a job for you. I was thinking that I would be some sort of like, mixologist. I remember when we went to yeah, like, NACE in Cincinnati. And there was this really cool, we did this whiskey tasting for lunch, which was yummy. And there was a mixologist. And I just remember feeling like, so like, enthused by her passion for it. Like, she knew so much about it and like, she was so passionate.

Like you could just feel it, right? And you know, like how, when you experience somebody who’s like super passionate and you like, get all the tingles? Like, you’re just experiencing their energy?

Dana Kadwell: Yeah.

Courtney Hopper:  Like, I felt like that, like maybe I could be equally as energetic about great cocktails.

Dana Kadwell: That would not be around in the pandemic.

Courtney Hopper: I would do it on Tik Tok. I would open a Tik Tok.

Dana Kadwell: Okay.

Courtney Hopper: Yes. I would be like, maybe I would be a cocktail influencer.

Dana Kadwell:  Okay.

Courtney Hopper: I don’t know how I feel about influencers. I feel very negatively about it. But maybe I would be that.

Dana Kadwell: Maybe.

To learn more about our hustles, visit,, and Or follow us on Instagram @CandDEvents, @TheBradfordNC, and @HustleandGather. And if you like the show, be sure to subscribe and leave us a rating and a review.

Courtney Hopper: This podcast is a production of Earfluence. I’m Courtney.

Dana Kadwell: And I’m Dana.

Courtney Hopper: And we’ll talk to you next time on Hustle and Gather.

Full Episode Transcript

Hustle and Gather is hosted by Courtney Hopper and Dana Kadwell, and is produced by Earfluence.  Courtney and Dana’s hustles include C&D Events, Hustle and Gather, and The Bradford Wedding Venue.

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