And So, She Left: Wisdom from Women Beyond the Corporate World

Jackie and Cassie Collier on Fun, Business, and Board Games

Episode Summary

Cassie and Jackie Collier LOVE board games. Growing up in a small Pennsylvanian town, playing board games helped them to strengthen their bond as sisters and make new friends. Despite going in very different directions professionally, the Colliers eventually discovered that their shared passion for fun and games went far beyond the board. When they created a custom one-off board game for their family as a Christmas gift, they realized their potential to provide similar experiences for others. They realized the potential of Bundle. The Colliers talk to Katherin about learning the value of fun at an early age, and how working together as siblings has helped to strengthen their symbiotic personal and professional relationship. They also discuss the power of being both under and overestimated, the most bizarre customer prompt they’ve received when designing a game, a risky pitch meeting gone horribly wrong, and why having fun is such a key part of the entrepreneurial journey.

Episode Notes

Cassie and Jackie Collier LOVE board games. Growing up in a small Pennsylvanian town, playing board games helped them to strengthen their bond as sisters and make new friends. Despite going in very different directions professionally, the Colliers eventually discovered that their shared passion for fun and games went far beyond the board. When they created a custom one-off board game for their family as a Christmas gift, they realized their potential to provide similar experiences for others. They realized the potential of Bundle.  

The Colliers talk to Katherin about learning the value of fun at an early age, and how working together as siblings has helped to strengthen their symbiotic personal and professional relationship. They also discuss the power of being both under and overestimated, the most bizarre customer prompt they’ve received when designing a game, a risky pitch meeting gone horribly wrong, and why having fun is such a key part of the entrepreneurial journey.

 

Learn more about Bundle. Get 20% off any game with the code BUNDLE20. 

 

In this episode, we cover:

 

Quote of the Week:

"[By] surrounding  yourself with people who get you, you can be your full self."  - Cassie Collier

 

Hosted by Katherin Vasilopoulos. Made by Cansulta and Ethan Lee.

Music by © Chris Zabriskie, published by You've Been a Wonderful Laugh Track (ASCAP). 

Songs used in this episode include: "Air Hockey Saloon," "Virtues Inherited, Vices Passed On," "Short Song 020623," "Short Song 020923," "Your Skin's Not In the Carpet Anymore," "I Need to Start Writing Things Down."

Used under the Creative Commons 4.0 International License

Episode Transcription

[00:00:00] Katherin Vasilopoulos: Hi, I'm Katherin Vasilopoulos. Starting my own venture wasn't easy.

After a decade working in the corporate world, I realized that so many things were out of my control, like layoffs and changes and direction. I didn't like the instability. I didn't want that to define my whole career at professional story, and so I left. I started my own company and achieved more than I ever imagined.

Now I'm on a mission to share stories from extraordinary entrepreneurs who are changing the world and who never gave up on their vision.

[00:00:40] Ethan Lee: Hello, I'm Ethan Lee, the creator and producer of And So, She Left. Katherin's away on vacation this week, so I'm gonna handle the intro and outro for this one. She still conducted the interview you're about to hear, and she'll be back next week. But since I'm here, I wanted to thank you personally for your interest in the show.

So far, we've gotten a lot of great feedback from people who, honestly, I never thought would even be aware of what we're doing, and in many ways that's thanks to you. So thank you. With that out of the way, let's get into the episode. 

You probably don't think of leaving corporate as being fun, especially not at the start.

You might have even found yourself trying to blend in with the venture crowd, presenting as more buttoned up to attract funding. If so, you're probably not Cassie or Jackie Collier.

The Collier Sisters are the duo behind Bundle. You can say that the company creates custom one-off board games, but its real mission is to bring people closer together through the power of play. Realizing their passion for games at an early age, the Colliers seem to weave fun into every aspect of their lives.

They've used board games to bring their own family closer together, strengthen their bond with each other, develop friendships, and help others to do the same. Anyone who's lucky enough to sit down with them quickly realizes how essential the experience of having fun can be to the entrepreneurial journey. Despite claiming to be very different people, Cassie and Jackie are on the exact same page

creatively. They talk about some of their more chaotic experiences with Bundle so far, their deeper connection as siblings who share a profound appreciation for fun and games, and how they've been both under and overestimated as new entrepreneurs.

[00:02:37] Katherin Vasilopoulos: Hi Jackie and Cassie. Thank you so much for joining us today. So I'm gonna ask you to introduce yourselves and give me, give a bit of background about your personal and your professional journey so far. 

[00:02:49] Cassie Collier: Jackie, you're the older sister, so you can go first. 

[00:02:51] Jackie Collier: Well, I'm the older sister, but we like to say that I'm the big little sister because chronologically I was born first, but I definitely act like the little sister.

Uh, well, first of all, Katherin, thank you so much for having us.. We're just so excited to be here and you guys are just a joy and we love what you're doing, so we're honored to be a part of it. Um, yeah. So I am the big sister, uh, Cassie and I grew up in Mount Carmel, Pennsylvania, in the coal region. We were members of a sports family.

Um, my parents coach, Cassie and my brother Sean were star athletes. I didn't even make the starting lineup for the team that my parents coached. And they were like, you have other talents. So they found the community theater and that's where they put me. And I've been an actor ever since, which has been really, really great.

Um, then a few years ago, Cassie and I, you know, we're very different and, and she'll get into all of her talents and interests in a second. But one thing we have in common is definitely our sense of family, that's very important to us, um, our humor, and that we're both obsessed with games. So we created Bundle, our board game company and it's been really fun getting to work together in that, cuz I don't think we ever thought we'd get to work together in a professional capacity.

[00:04:08] Cassie Collier: No, I don't think so. It was a surprise for both of us. Um, and yeah, I'm Cassie Collier, Jackie's little sister by 16 months. And as Jackie noted, you know, we grew up in a really small town in the mountains of Pennsylvania and games were always what brought our family closer together and, and that definitely, as I grew up and I went to college, I met all of my friends my first year in my dorm playing games. That was what bonded us. 

[00:04:42] Jackie Collier: You know, I think for, for us, you know, we have very different skill sets and. I think growing up together and you know, sharing a bedroom our whole lives, not just a bedroom, but we shared a bed for our whole lives.

Not anymore. Not anymore. We've moved on from that since. But we did live together in New York for quite a while, but there was sort of a fluidity to who was gonna be responsible for what, and we're really communicative with each other. 

[00:05:13] Katherin Vasilopoulos: Um, did you collaborate in any form? Did you play nice together? How did that work out for you?

[00:05:19] Jackie Collier: I remember when we were. Very little. Um, we would put on shows together, which was really, really fun. Um, we would be dancing, we'd be singing. Our brother would sometimes play the drums and dance. And we also had the, like a radio show and a news show. And then we also played sports together, which, you know, as I noted earlier, I couldn't really keep up with.

But I think we, we were always, you know, the three of us, our brother is 16 months younger than Cassie, so we're all, we're like, Irish triplets. So we grew up just always being together. And I don't know if it's a thing that's just a thing now or, or if it just wasn't, when we were growing up, we didn't really have play dates with other people.

We had friends at school. But we pretty much just hung out with each other. 

[00:06:10] Cassie Collier: Yeah. Which, and I think such a credit to our parents, they allowed us to just be imaginative. And so if we decided we wanted to do a play, a murder mystery play about someone stealing family necklaces and a fancy hotel, which that was, it was called Masterpiece, and there's a video of it somewhere.

They would run with it and they would, you know, film the video and be our audience members. And so it was nice to have their support of sort of whatever sort of ideas you have, you can run with them. And that definitely was for me, really important just to know that, okay, you put your imagination out there and, and you can do- 

[00:06:53] Jackie Collier: And also, you can cut this if it's inappropriate, but just a testament to our parents that they could keep a straight face during our Masterpiece play when we kept referring to the family necklaces as the family jewels.

Over and over and over again. 

They didn't let us know We were very innocent kids. They didn't, they didn't fill us in so...

[00:07:23] Katherin Vasilopoulos: Well, tell me more about your, your playtime as children and how that shaped your adult versions and how you continue to play and have fun in this entrepreneurial, um. Endeavor that you've started? 

[00:07:36] Jackie Collier: Yeah, I think that's such a great question of how it's shaped it because something I love about our board game Bundle, you know, we make custom games that are personalized to your family members, to your friends, to your coworkers, and when I was growing up, I would say out of the three siblings I was the least competitive. I was the one who wanted to talk and hang out and connect the most. And I think Cassie and Sean, like they would always be competing about, you know, who wanted to sit shotgun in our parents' car, and they had a little bit more of a competitive spirit.

So something that is great about our game is that it lends itself to all sorts of types of people and everywhere in between or what you're feeling like that day. So with our game, it can be a vehicle and a tool to connect and for storytelling and to really get in the nitty gritty and talking about all your feelings.

Um, or it can be a really competitive environment where you're timing everybody. You're counting, you're going around the board, you're, you know, you're getting a prize if you win. It really lends itself to taking on the characteristics of the group that's playing. 

[00:08:49] Cassie Collier: We make custom games for any sort of group of people and, and yeah.

The way we do it is, um, a person fills out a list of questions about themself and then we create a one of a kind custom game for them, even including some of their photos on the cards. Um, and it's, uh, you know, we have a nice, cute board and you go around the board answering different questions. Doing different charades.

You might have a trivia question prompting you to name a specific memory from a fam, family vacation as one example. Another big aspect of our family, and I think of so many families out there, is every family has their own inside jokes, their own traditions, their own friendly stories that only make sense to all of you.

I know it's the same with our family. I mean, we have these stories, silly stuff. Um, I don't know about my dad's former coworker, like a nickname we gave him. And that name still sticks. And it's these little things that make families special. Um, and so that was an element that we wanted to bring into our game.

We have a customer, you know, they'll fill out a list of questions about their family. They'll tell us all their inside jokes and all their funny stories, and then we make a game all about them. So it's, that's an element that I find really cool is that all these little quirks that are unique to your family, they can be captured in. In the game. 

[00:10:23] Katherin Vasilopoulos: Yeah. Cuz family sayings or coined phrases happen at those moments. They're so spontaneous. You're playing, something comes out and then it stays for 20 years. You'll keep remembering that thing. Or someone gets a nickname. I dunno. When we were kids, we would play, um, blackjack with my dad and he didn't speak English super well, but we also didn't know what to call the joker because.

We didn't have the vocabulary for it, so we just called it the little kid. And there's a Greek word for that, "paidáki," and so we still use that today. We still get together and play blackjack and we still use that term to this day. 

[00:10:57] Jackie Collier: And I, I think it's kind of fun because you know, Katherin, when you were sharing that fun story about the Joker, people have different versions of stories in their families and you have.

Assume that everyone's version is the same as yours, but if someone in your family were to get a challenge card that was like, okay, tell the origin story of the name for the Joker card, and you started telling it. And then you have people in your family going like, wait, no, that's not it. Katherin, what are you talking about?

And I think that that's kind of fun. To get that going as well, or to have family members that maybe never knew the origin story at all to get introduced in a really organic, fun way. I think that surprises pop up all the time with that stuff, which is kind of fun. 

[00:11:39] Cassie Collier: Yeah, and I think that's a good point, Jackie, too, about the.

We like to think our game. It's multi-generational. And sometimes these stories get lost across generations. And you know, your grandparents may have a really funny story, but then by the time you know, it gets passed down to the grandchildren, it, it may have changed or evolved, or may have been forgotten, worst of all.

And so what we also like to do with our game is, you know, grandparents can play with grandkids and it's a way to keep your family's stories alive each, each and every time that you play the game. 

[00:12:15] Katherin Vasilopoulos: So this is ultra special because this is not just a off the shelf game that you'll purchase that's been shrink wrapped, and you bring it home and you played a couple of times and whatever.

This is really customized to your clients and whatever they've asked for. And now you're creating this magical centerpiece around a table where people are drinking and eating and having a good time, and you've created a whole other layer of, of, um, family bonding. 

[00:12:41] Jackie Collier: And we feel so lucky to get to do it too because, you know, for us it's so much more than a product.

It's so much more than a business. It's a passion and it's a calling and, you know, we get to hear these stories, like. Cassie and I are so privileged to get an insight into people's very intimate family stories and friendship stories, and it really is a great honor that people trust us with, with this stuff.

[00:13:09] Katherin Vasilopoulos: Can you share anything that's like, that was really funny, like a really funny story that you remember? You're both laughing, so I'm thinking it's, you both have something. 

[00:13:21] Cassie Collier: Okay. Uh, there's one that comes to mind, although Jackie, if it feels like we should cut it based on the story, you just will follow up and let you all know.

Um, but one funny story I remember is this daughter and her mother went to get spray tans together. And they were driving home from the spray tan place, and I don't know why, but the mother had to pull over and use the bathroom on the side of the road and she ended up going, and then she realized a few hours later that there was a, a, a streak down her leg, cuz the spray tan hadn't dried and she accidentally, you know, went to the bathroom in the wrong spot. Um, so the family joke now is always referencing this streak down the mother's leg.

[00:14:25] Katherin Vasilopoulos: And then, you know, you take that, you put on a board game and it's immortalized and everybody knows about it. 

[00:14:30] Jackie Collier: Yeah. We have pictures on our game too, but I doubt that they sent a photo of that one probably.

[00:14:43] Katherin Vasilopoulos: Do you remember when you were younger, um, did you ever think, I wanna be an entrepreneur? Did that ever cross your mind? Were you ever talking about that when you were children or it was always about, I wanna be an actress, I wanna be a teacher, I wanna be like, those kinds of things? 

[00:14:58] Jackie Collier: Um, yeah. When I was little, I always envisioned, I always would say I wanted to be an actress and a nun.

I guess Whoopi Goldberg inspired me. I didn't get that she was acting, I guess. I don't know what I, and I went, we went to Catholic school, so I was like, this is my calling. That didn't happen. Kind of glad it didn't. Um, but I think for, for me, you know, I always knew I wanted to live in New York and I don't know if this is something that Cassie and I hadn't talked about, but I always assumed I'd be the only person from my family living here and that like, I would go and have to, you know, see everyone back home.

And, to me, it's so exciting that Cassie and I not only lived, you know, a 20 minute walk from each other, but that we're in business together. It's like, that's not something, you know, I guess as, as a little girl who grew up wanting to be an actor, I always, like, imagined like getting to work with the people that, you know, I was watching on TV and all those things.

But I think I, it almost is like an even bigger dream for me to be in business with my sister and have her so close, cuz I never thought that I would get that. 

[00:16:06] Katherin Vasilopoulos: Aw, I love that. Yeah. 

[00:16:08] Cassie Collier: That's sweet. 

[00:16:09] Katherin Vasilopoulos: I'm gonna cry. 

[00:16:12] Jackie Collier: I've always had a lot of side hustles. Like I, I've babysat, I've been a personal assistant. Um, I've done so many random jobs in New York City and, you know, honestly, I've, I've enjoyed them all really.

And I love being an actor. I'm a kids acting coach. Like for me, having multiple income streams and multiple jobs is like, I can't imagine a life without it. But I did feel like I didn't really have anything to ground me in terms of like my professional life and having Bundle, which is this, even though it's entrepreneurship and it, it feels like it can be scary and not consistent.

For me, it's probably the most consistent thing in my life. And that consistency, but also balancing it with the fun and getting to do it with my sister, who's also my best friend, was really kind of like, oh yeah, of course I'm gonna do that. 

[00:17:14] Katherin Vasilopoulos: And Cassie, was it, uh, the same for you in terms of like describe what you did before?

[00:17:19] Cassie Collier: I think I always knew I wanted to start my own business. You know, it was always something I knew, but it, it, it felt so scary. I was working at a bank in spreadsheets all day. While there were a lot of pros to the job, you know, I was stable, I was learning good skills and how to do spreadsheets and financial analysis.

There was a part in me that felt such a void. Um, and so, a year or two into that job is when I thought, okay, now is the time to make the plunge. It feels right. I'm definitely more of that type of person. I wanna have all my ducks in a row. I wanna have a blueprint for how I need to do certain things. And being an entrepreneur, you, you're literally building the plane as you fly it. And flipping that script for myself I think took a lot of time. 

And I think the only way I was able to do it, frankly, was because of Jackie, who operates differently in the best way that it's sort of like, especially as an actor, it's like you put yourself out there all the time. Sometimes you book a, a role, other times you don't.

And it's simply being okay with putting yourself out there, being rejected and, and moving on. And as an entrepreneur, that happens so much. And so for me, I, I've learned a lot. So for me that, that partnership of having her alongside the journey was really key for me. 

[00:18:49] Katherin Vasilopoulos: Amazing. Jackie, what did you learn from your sister?

[00:18:52] Jackie Collier: You know, it's the exact opposite that in the sense that I learned from Cassie. What it's like to show up every day and be consistently working towards the same goal and the same vision, and essentially the same project. And I think it's so great to see how, for me, the instability in my career as an actor was actually something I always valued.

And rejection doesn't really bug me and I can kind of shrug it off, but something that is difficult for me is actually consistency and having a set schedule, Cassie and I working together, it's something that she's had a lot of grace and flexibility, but also we found a, a happy medium and a common ground of how we can actually get a consistent schedule and be grounded in that way.

So yeah, I've learned a lot from her. Uh, but some things I don't wanna learn, like how to do our taxes or spreadsheets or anything like that. And she's graciously continued to do that for us. 

[00:19:56] Katherin Vasilopoulos: Oh, she's so nice. 

[00:19:58] Jackie Collier: She is. 

[00:20:00] Katherin Vasilopoulos: Um, no, it's cool because I, I know that there's a saying that don't get into business with family.

And a lot of people swear by that, that's they're, like, I will never get into business with family. They don't wanna deal with it. They don't wanna muddy the relationship or even lose the relationship. So was that ever a concern for you? 

[00:20:20] Cassie Collier: Yeah, I mean, I think you're right, Katherin. The stakes are higher when you're running a business with your sibling.

If you're running it with a stranger, the business falls apart, even the business relationship falls apart. It's sort of like, it's okay if this one relationship is tarnished, but when you're running a business with a sibling, everything is on the line. Um, and so that, of course for me, it's how do we always maintain our sister relationship and our bond?

How do we draw boundaries? Um, if we're going away for, say, a weekend with our cousins? We're cognizant that this is family time and we're not constantly talking about work either. We're, we're also building and maintaining our relationship as sisters and, and for that, finding that balance and the cadence I think was really key for our, both our sister relationship, but also our relationship as business partners too.

[00:21:14] Jackie Collier: Actually, that's another thing that Cassie's taught me. I think anyone I've worked with, Cassie does a really great job of um, respecting and modeling how to set healthy boundaries. It's not something I was great at in my life and, and still continuing to work on, but Cassie is very good at it. It really gives me such a sense of comfort, cuz I think also in the acting industry and freelance life boundaries can get really messy and Cassie has really shown, like how you can get a lot of work done, but still be respectful of people's time. 

[00:21:52] Katherin Vasilopoulos: That's awesome. So tell me now about, you know, you found your sister and she's this perfect business partner. Um, how, how does that play in with creating an idea and then taking it off the ground and making it.

Turning it into something. How did that work for you guys? 

[00:22:08] Jackie Collier: We're really communicative with each other and I think in the beginning, you know, we had this sense, you know, we, we are really scrappy and we knew that we would do whatever it took to get this business off the ground. I think something that was really affirming for us and inspiring and I don't wanna say surprising, because we knew we had so much love from our family and friends in our, our hometown community. But I think the level at which people showed up for us was just overwhelming. Like our town supported us so much. Um, people that we hadn't talked to in quite a while were buying games from us. It was like this whole sort of effort to champion us, and it was really, really special.

Being from a small town that believed in us. 

[00:22:59] Cassie Collier: Absolutely. And some of my best memories from when we first started Bundle was, okay, we had this idea, we wanted to start a board game company. We had no idea how to design a game, how to do any of that. And so we started very small. Jackie and I, we created a paper prototype and then we invited a bunch of people over to our apartment to play the game and give us feedback in real time.

And we did this about three or four times. Uh, we'd get pizza, we'd get drinks, have people over. Have them give us feedback. And that for us was really instrumental. And you know, Jackie has a big social circle and so she would be able to bring all these people over to our place and, and it was market research, but it was also just a lot of fun getting to hang out people and see them.

Playing this idea that just a week ago had been solely in our head and now it was, you know, a physical product that we are getting people to, to play and give us feedback on. 

[00:24:04] Jackie Collier: I love the way Jackie has a big social circle is really a very nice way of saying Jackie has a lot of actor friends who are desperate for free food.

[00:24:14] Katherin Vasilopoulos: That's awesome.

What did you come up against? What were the bigger challenges and then how did you scale up? 

[00:24:31] Cassie Collier: Well, one right off the bat that we heard from people even very close was, you know, we said we wanted to start a board game business and immediately it was like, well, people don't play board games anymore. I mean, that was literally the first comment we got.

Um, and I think for Jackie and me, it was a good gut check because then we had to go and do our research and show, you know, look at the data, pull the numbers and see whether or not board game playing was going up or going down. And- 

[00:25:04] Katherin Vasilopoulos: That's so left brain, so left brain, eh? 

[00:25:06] Cassie Collier: Yeah, like digging into research papers and everything.

Um, and then we realized, okay, all the data is actually supporting this business because board games, we found this one article, I think from The Guardian, we're in the golden age of board games in a time where there's so much technology out there, people are craving really a hearkening back to the modern day campfire.

And, and board games are really a version of that. 

[00:25:36] Jackie Collier: I think for me, when we initially started off, it was a particularly busy and I would say chaotic time in my life in the sense that I was doing a play. I was auditioning for other things. I was babysitting. I just had a new boyfriend and, and we were starting Bundle.

And I remember like sitting like on the floor. In the, um, tutoring office where I had just taken the, the kid I was babysitting for cutting construction paper to like glue on our Bundle. And then I was like, okay. And then after I drop him off tonight, I have to go to rehearsal. And then after that I'm recording a podcast and that like, it was all these things of trying to juggle all this stuff and now, I'm still an actor.

You know, I coach kids, um, in acting, but my life is a little less chaotic. So when I sit down to work on Bundle, I can actually have the time and space not to be focusing on a bunch of other things, because that's a great way for my brain to be more creative and also just to be more task oriented and actually get stuff done.

Cassie. I mean, she's still good at making sure we keep all the balls in the air. Like she always sends a, an email at the beginning of the week that's like, here's what we have to accomplish for the week. And I think that, you know, she offered a lot of grace in the beginning when I was like a little bit scrambling all over the place.

[00:27:02] Cassie Collier: And then a second thing too, it's, you know, we're females working in a predominantly male dominated space, you know, a lot of the board game creators out there are males. And so, uh, right off the bat, again, it was Jackie and I having to really prove ourselves as female creators and inventers that, okay, we do know this space and we're tapping into.

Frankly some white space. Um, you know, there's a lot of females that want, want to connect through games, and they haven't felt like the games out there have been speaking to them. So we were able in some ways, to use our female status, I think as an advantage as well. 

[00:27:41] Katherin Vasilopoulos: This happens all the time when you start a business, but did you ever feel like, um, people underestimated you?

[00:27:51] Cassie Collier: Yeah, I mean, I think it's tough. Um, I mean, even now we're in the fundraising process looking for investors to really grow Bundle. And I think, yeah, it can be tough sometimes in in pitch meetings, studies show women often under promise and over-deliver. So even if you watch, watch Shark Tank for example, and they'll say, okay, what are your projected revenues for the next five years?

And female entrepreneurs typically will low ball their numbers, but they'll actually over-deliver when it comes to actually reaching their sales numbers and exceeding the sales numbers. Whereas, you know, male entrepreneurs, typically it's the opposite. And Kevin O'Leary, who's, you know, the famous Shark Tank judge, who's a tough critic in a lot of ways, he stands by this.

He says he is always very pleasantly surprised with the female entrepreneurs that he invests in. So I think that's something that we have to contend with. Jackie and I as we do these different pitch meetings with investors. Having to overcome, you know, perceptions that we won't hit our numbers and, you know, so I think that's definitely been tough, but I think sometimes being underestimated could be the best thing.

Then you can surprise people at the end of it all. 

[00:29:04] Katherin Vasilopoulos: I love it. I love it. You, you never know what people think about you when you walk into a room. They, they evaluate you based on some prejudice. Ultimately, it's only when you start working with a person that you really can find out what they're all about. You have to give them a shot.

And nothing against the, actually, I'm not gonna even go there. That's okay. Um, edit that out. 

[00:29:26] Jackie Collier: Oh, I'm intrigued though. I'm intrigued. 

[00:29:28] Katherin Vasilopoulos: What I was gonna say is, is nothing against working with men, but I've heard many times that if you want something done, give it to a, a busy woman, she'll get it done for you. And it's true.

[00:29:38] Jackie Collier: Yeah, I think that's very true. And I know I've found, as far as the underestimation thing, you mentioned, like how supportive our hometown is, but I, I feel like I've been blessed with so many people in my life that sometimes I'm like, they almost overestimate me. They're like, you could do anything. But I do think that there's been a certain type of...

It, sometimes it is a certain type of guy who's used to, say he's a VC or he is used to investing in the same sorts of things, or you know, Cassie and I have had a couple meetings recently where. You know, we've had a push back on someone and they're surprised because, you know, we do it in a really respectful way, but you know, we've been having fun. We, but it's like, no, also like, here is what we need from you and we're delivering this. You have to keep up your end of the bargain as well. 

I think sometimes in those interactions we end up leaving them with the person has more respect for us and if they're a confident person in themselves, like it actually ends up being a great interaction. 

[00:30:40] Katherin Vasilopoulos: But they were surprised that you set boundaries. 

[00:30:43] Jackie Collier: Yeah. 

[00:30:43] Katherin Vasilopoulos: They weren't expecting that. They were like, oh, okay, here we go. That's how you gained the respect. Yeah. But you were two people at the beginning. Then what happens? How do you go from two to, how many are you now? 

[00:30:54] Cassie Collier: Sure. Yeah. The very first person we worked with, we needed a logo, and Jackie and I are not graphic designers.

We have a lot of skill sets between the two of us, but graphic design was not one of them. My childhood best friend's sister was a graphic designer, and so we brought her on board to design our logo. Um, and then over time, you know, we've worked with different, um, you know, when we filmed our first commercial, we worked with, um, a production team, a director there to put that together.

Um, so we've worked with a host of different people, especially, I mean, Sarah Blakely. Again, one of the best pieces of advice she gives to entrepreneurs is hire your weaknesses. So figure out what you're not good at, and then find people to compliment that. And that's been Jackie and my mentality ever since.

What are we not good at? How can we find the right people to compliment our skillsets? And that's been really nice over the period of of time to have those people to support us. 

[00:31:58] Jackie Collier: Yeah, and it's been a real honor to be able to hire people and work with people that are women and people of color too. I think that's something that's really important to us, you know?

Cause we feel lucky to be a part of the space, but we also, you know, as white women have a lot of privilege as well. So how do we be cognizant? Of that when we're, um, looking for people to work with. But everyone we've worked with is fun and has a great sense of humor. So that is a non-negotiable for us. 

[00:32:26] Katherin Vasilopoulos: I like that. Only work with people who are fun. Only work with people that you're excited to see their name come through your inbox. That's right. You make entrepreneurship sound like fun, and I think that's maybe a message that people need to hear is that it's not just about suits and showing up in boardrooms and investors.

Tell me about your version of fun in this. 

[00:32:48] Cassie Collier: That's a good one because, so at the start of every year, Jackie and I, we make a vision board where we map out what are the goals, what, what's our vision for the future? And this year at the very start, we chose a word or a few words, um, and it was fun inducing, like what gets us excited, um, and those are the projects that we wanna pursue.

So that's been our North Star the last few months. Kicking off 2023 is what are those partnerships? What are those types of events? What are the, the types of board games that get us most excited? And that's what we want to pursue. I mean, this past weekend there in um, Connecticut, there was a 90's convention.

This big convening of all these 90's movie stars and TV stars. Jackie and I got to go and host a game live with some 90's celebrities. We played the game on stage, brought up audience members, and it was just a blast.

[00:33:50] Katherin Vasilopoulos: Who was there? Who was there? Tell me. 

[00:33:52] Cassie Collier: Oh my gosh. Buffy the Vampire Slayer, some cast members. Saved By The Bell was there. Full House was there, all these shows that we grew up watching. We got to see all these stars and it's like, oh my gosh, this is our life. Like, we're hanging out with all these people. Um, so it's situations like that where we feel so lucky to be doing the work we're doing. 

[00:34:12] Jackie Collier: In case you're wondering, Mario Lopez is aging like a fine wine, so things are all good in the world.

[00:34:19] Katherin Vasilopoulos: Love it. 

[00:34:20] Jackie Collier: You know, I thought Katherin, it was interesting what you were talking about, you know, saying like, it's not just all suits and everything like that. And Cassie and I have had some really amazing experiences and it's like finding the right people for you. Like when we met, um, Sarah Blakely and Jesse Itzler and, and you know, they're both these huge entrepreneurs, we've admired Sarah for so long in her work is the founder of SPANX and what she's done for women globally. 

And we met them, and Cassie came up with the brilliant idea to dress like them because she, we know that like, that's what they're into. Like they're into fun, quirky things. And to show up dress to the nines for them wouldn't work. So Cassie gets a blonde wig. She wears her SPANX, she gets her red backpack in honor of Sarah Blakely.

I dress like Jessie and we have, you know, a great meeting with them. But then conversely, and I just love this story, Cassie, I don't know if you know, the story I'm thinking of. But we are like, okay, we're on a roll with these kinds of, like, thinking outside the box pitches and we had a pitch with a dating website and Cassie and I were like, okay, great.

We'll be in the meeting. It's on Zoom. I will dress like, I had like a Saved By The Bell sweatshirt on and it was like off to the side and like I had my hair up and Cassie and I were doing like a mock date. And we're like in character, like flirting with each other, using the Bundle questions of how it would be great to have a first date bundle for this dating website.

There were jokes like, I was like, okay, we're nailing this. This is the performance of our lives. And at the end of the meeting, the guy, like, he didn't crack a smile. Once. 

[00:35:58] Katherin Vasilopoulos: Oh no.

[00:35:58] Jackie Collier: And like at the end he looked completely shell shocked. Like it just bombed so hard. And I've done standup before and bombed and this was like 10 times worse than that.

So like, you know, you win some, you lose some. 

[00:36:13] Katherin Vasilopoulos: Yes. But you have to try. 

[00:36:15] Cassie Collier: It's so true about Jackie mentioned too, knowing your people because yeah, with Sarah Blakely and Jesse, it was amazing. I mean, they're quirky, they're fun, they're. It was great, but with this guy, I think he was like the software engineer for the dating app and I love engineers, but like, you know, he was very by the book and so, yeah, he didn't even know what to do with it.

Jackie and I laugh about it now, but I think it's actually a really good lesson for surrounding yourself with people that get you, you can be your full self. So for us, that was a really interesting, um, juxtaposition to say the least. 

[00:36:53] Katherin Vasilopoulos: But that's so well said. Like, align yourself with people who get you, and there's all kinds of different business people out there.

We, we have to maybe reshape what we think about when we think business person. It's no longer this old fashioned, antiquated thing. It's a bunch of people who are just regular people living their lives and are solopreneurs or people who are working out of their home. 

[00:37:14] Jackie Collier: Yeah, especially now after the pandemic where people work and how they work and the spaces that they work in, like it's all changing and it's just so fascinating to watch that process and how it can really expand entrepreneurship for people, which I think is really important because we need so much more diversity in entrepreneurship.

[00:37:35] Katherin Vasilopoulos: No, it's true. I think that the pandemic has reshaped a lot of people's work lives, and it's given a, a view into you don't have to necessarily just be going into a workplace and working there. You can invent what you want. Yeah. You invent the future that you want. And I think that's what you girls did very beautifully too.

Like when you're younger and you're not even sure where life is gonna take you, and then you're, you're here now and you look back like, what, what have you seen? What's this evolution that you've seen for you guys? 

[00:38:03] Cassie Collier: Oh. It's a good question. 

[00:38:07] Katherin Vasilopoulos: Especially as sisters. Especially as sisters. Yes. Cuz you grew up together, you even shared a bed together.

[00:38:12] Cassie Collier: Well, I think for me it's occasionally those pinch me moments of like, oh my gosh, wait, how did we get here? An example of this is we, speaking of 90's TV shows, we grew up watching The Wonder Years. I adored Winnie Cooper. She was just everything. Um, and a few years back, yeah, Jackie and I did a partnership with the Hallmark Channel.

We worked at the CEO and the team there, and we created a custom game that was all about the Hallmark Channel movies. One day we were at Jackie's apartment, the actor who plays Winnie Cooper, Danica McKellar, called and asked about playing the Hallmark game and said she would post about it on our Instagram pa, on her Instagram page, and it was this moment where I thought, oh my goodness.

Like Winnie freaking Cooper is calling us to talk about a product. That we created. In what Universe did I think as a seven year old this would ever happen. Never. So life does take you in crazy directions and it's been a fun ride to see the different sorts of doors that it's opened. 

[00:39:25] Katherin Vasilopoulos: That is so amazing.

Thank you for really showing us the value of fun, not just in entrepreneurship, but in life, in sibling hood, in all things important in life because I think we really need this. As I said at the beginning, the world needs to have more fun. If we could just sit together with a board game, a sandwich, and people we love, everything will be wonderful.

[00:39:51] Cassie Collier: I love the sandwich element. We, we've never injected that. 

Who doesn't? Who doesn't love? Who doesn't love sandwiches? 

[00:39:56] Jackie Collier: I love sandwiches so much. I think I want one now.

[00:39:58] Ethan Lee: Many thanks to Cassie and Jackie Collier. You can learn more about Bundle in the episode notes and get 20% off any game with the Code BUNDLE20. If you like the show, please let us know. We would love to hear what you enjoyed in a review no matter what platform you use to listen. And So, She Left is made by Cansulta and me, Ethan Lee.

We'll be back next Wednesday with a new episode. Our music is by Chris Zabriskie, edited for your enjoyment. You can find a list of all the songs you heard here in the episode notes. For Katherin Vasilopoulos, I'm Ethan Lee, and thanks for listening.