Can you be both supermom and badass entrepreneur? Conversations with Sisters

On last week’s episode, Judy Pickett shared her struggles of building a business while being a mom – and eventually joining forces with her daughter Hilaire.  Today, Courtney and Dana unpack that conversation and wonder if it’s possible to truly be both supermom and badass entrepreneur.


Courtney: I love hearing other generational stories like that about women in those times. I think it’s very empowering. It’s very brave. 

Dana: Yeah, because she did have it all. She said, basically, fuck that. Like, I’m going to have it all. Like I’m not going to choose. I’m going to be a mom. I’m going to raise my kid in this world. I’m going to be a badass entrepreneur. That’s a long time to have a successful business that stayed relevant over 43 years.

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

Dana: And I’m Dana

Courtney: and we’re two sisters who have started multiple businesses together, and yes, it’s as messy as you think. We know that starting a business isn’t easy. 

Dana: I mean, we’ve done it four times. And on this show, we talk about the ups and downs of the hustle and the reward at the end of the journey. 

Courtney: And we love helping small businesses succeed, whether that is through our venue consulting, speaking, team training, we love to motivate others to take those big leaps. 

Dana: Or you can just use our misadventures to normalize the crazy that is being an entrepreneur, because every entrepreneur makes mistakes.

Courtney: And we like to call those unsuccessful attempts around here. 

Dana: And we know it’s just part of the process. And today we’re talking, just the two of us, about last week’s episode with Judy Picket and Hilaire Pickett-Martin, founders of Design Lines Signature, a Raleigh North Carolina based interior design firm. If you haven’t heard last week’s episode, go give it a listen and come back to hear our thoughts.

Courtney: All right. Let’s get started. I love talking to a mother daughter duo. That’s fun.

Dana: I hope I’m like that good of a friend as my daughter. 

Courtney: I know they seem very close. They didn’t have any like mom daughter drama. 

Dana: No. Yeah, I loved how she talked about, like she knew nothing different, how Hilaire talked about how she knew nothing different because she always grew up with entrepreneur and founder. And I really loved, you know, listening to Judy tell that story. And she was like, that was, there was no negative effect on that and probably how much she, Judy has carried that around and like how much guilt she had for this.

And I’m sure there’s other instances where, you know, she had mom guilt with and how that didn’t translate to Hilaire’s opinion of her mother, or opinion of the business at all. And it makes me think, what am I freaking out over that I’m doing that my kids aren’t going to give two shits about. 

Courtney: I think it’s funny that Hilaire has never heard that story. She just heard it today. 

Dana: Yeah. Maybe she was embarrassed by it or like just, maybe she still felt guilty about it. I mean, I’ve done, been in a very similar situation where my kids super sick and I chose work over being home with my sick kid. 

Courtney: I remember thinking when I was driving to a wedding in the middle of, I think it was hurricane Matthew, and there was like trees going across I 40. And I’m like trying to get to downtown Raleigh so I can facilitate this person’s wedding that we probably made like $2,000 on. And I remember thinking my children aren’t going to have a mother, raised just by their father because I’m driving to a wedding. Like at that moment, it just seems so like trite and trivial, like, what am I doing?

Why am I putting my life at risk for this right now? But then I didn’t see any other option. Like it was literally not an option.

Dana: Right. It’s so I, one of the things was like, do you have like one of your worst mom moments? And I just don’t even think I have a moment; I feel like I have years. 

Courtney: I have like weeks, days.

Dana: Like, but it’s not like I can look at it and say, okay, this was like, I brought my sick kid to work or whatever. I still to this day is probably like Henry’s first year of life. Like, I don’t remember anything.

I don’t remember a single solitary thing of it. Cause we were just so inundated with like getting the Bradford off the ground, and whereas like in the pre-process of it, we were like close, we got approved the day he was born and then we closed on the loan, he was two and a half weeks old for the land. And that whole year was just like, we did a bazillion weddings, help pay for it, to like create the down, down payment on like to approve for the loan or whatever. And then we were like going through all the process of that. So it was like one of our busiest years too. It was like the year we had like 35 weddings at that point, which seems crazy that that was busy for us, but yeah. And then like, and then his year two to three or yeah, two to three I don’t remember at all because we were building the Bradford 

Courtney: And I think that’s, for you, I think it’s sad for you that, you know, you don’t have those memories of whatnot, but at the same time, if there was any point in your child’s life that you are going to be MIA in some capacity, I think we could all agree that it would be better to have it younger because you’re so much present now.

Dana: I totally agree. I think for Henry he’s, he has no recollection of at all, but him being my last baby it’s it was very sad because I didn’t really get to like savor that, like, I didn’t really get to relish in that. And I knew that he was my last baby. Like I knew I wasn’t going to have another one.

And I, and I knew what I was getting into with Henry. So his baby life was actually a lot easier because I had the right expectations for what it should be like, you know, Ada my expectations were crazy high. 

Courtney: I mean, I think that we are like pretty kick ass moms at that point. Like we kept everybody alive. We had very minimal emergency room visits, very minimal. And we put out so much, the kids loved it. They had nothing but positive thoughts about, you know, rolling picnics and Lowes and like painting the house naked outside and like playing, like it was,

It was like magical for them, you know? And it was hard for us. So I don’t feel like it was bad momming or bad parenting. I think it’s more; mom guilt isn’t about the effects of the children or like how they feel about, or are they because like kids know what they know. You know what I mean? And I think that it’s about your expectations, what you’re going to look like as a mother. 

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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