Playing to each other’s strengths: Conversations with Sisters

Last week, Courtney and Dana talked with another set of sister entrepreneurs—Jackie and Cassie Collier. This week, hear how Courtney and Dana grew to have different strengths and approaches to business, despite being raised together. Plus, find out what caused the sisters’ biggest fight ever and how they avoid fighting now.


Courtney Hopper: we were talking about celebrities and Liam, my eight-year-old asked me, he said, are you a celebrity? Asked me that, and I was like, no, he’s like, I feel like you’re kind of famous.

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: 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 sisters, Jackie and Cassie Collier, founders of the Bundle game, a unique personalized board game brand that is all about you. At Bundle, our mission is to bring people together for life’s most celebrated moments.

They create one of the kind custom board games encompass your favorite memory stories and inside jokes. 

Courtney: All right. Let’s get started. 

Dana: I always love interviewing sisters. It’s so fun. It helps me feel a little bit more like validated. Yeah, I know. And I’m not a crazy person. 

Courtney: And also it’s like, so refreshing and reassuring   like to see other people doing it.

Dana: I know. It’s very different having a conversation with sister partners and then just partners in general. Because the partners in general, like kind of dance around like the emotions of the other person where you’re just like, no, you’re being a fucking asshole. That’s the answer.

Courtney: I don’t know. Did you get the impression that that’s how Jackie and Cassie speak to each other? 

Dana:, I’m sure they’re pretty real with each other. I would assume so. They’re sisters, but I loved so, I think it was really neat, their journeys, or they’re very similar to us. One. They have a younger brother, like we do.

I know, just crazy. I love that they right off the gate, said they chose to share a room, which has always been our story. I know, I feel like they are very similar. So I would be curious, what do you think our biggest fight has ever been as kids? I mean, pre-business owner. 

Courtney: It was over the sweater vest. yeah, it was the sweater vest fight. Yes. That was a big, or was the time you called me a bitch on the way to baseball practice 

Dana: mm   either one. Yeah, those are bigger ones. You were being annoying.

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.

Amplify Your Expertise
About the Author
At Earfluence, we are proud to produce this podcast. We believe in sharing amazing stories, providing knowledge to the world, and celebrating diverse voices. Through podcasting, our clients are amplifying their expertise, expanding their networks, building a content engine, and growing their influence. If you're interested in podcasting, we'd love to hear from you! Schedule your free 15 minute podcast consult today.