Fostering Human Connection in a Digital World

Dana Clark never set out to create a card game company -- she set out to spark better conversations. What began as a side project to enhance her podcast evolved into Cool To Connect, a Toronto-based brand now known for its sleek decks of conversation starters designed to foster authentic human connection. Clark’s mission is deceptively simple: make connection feel modern, stylish, and accessible in an increasingly digital world. In this interview, she reflects on the art of designing for vulnerability, the challenges of innovating in a timeless space, and why making connection “cool” is a goal worth pursuing.

Tell us your name and walk us through your journey from your podcast to creating Cool To Connect. What sparked your transition to tangible connection products?

My name is Dana Clark, and I'm the founder and owner of Cool To Connect. Cool To Connect is a Toronto-based lifestyle brand that really focuses on experiences – making connection cool in different experiences for people. Card games are kind of our bread and butter. Never thought I would say I own a card game company, but that's where we are, and they're essentially decks of conversation starters that help people engage in more meaningful and thought-provoking conversations and connections.

I really wanted to make a deck of cards to use on my podcast, the podcast I had before Cool To Connect. It was such a long process – I made a deck under the podcast name, my manufacturers didn't work out, they fired each other, it was dramatic, this whole thing and everything kind of went kaput. I was like, okay, I need to start this again. If I really love this, I need to give it another stab. And I was saying to myself, I just need to make connection cool. I want it to be cool to connect. I want connection to be sexy and fun and just the coolest thing. And I was like, Cool To Connect. Oh my god. Hello.

So Cool To Connect was born, and what started with one deck of cards as conversation starters has now evolved to seven or eight custom products. I think they do go hand in hand though, having that type of social impact mentality and then creating something for social impact. These cards enforce and encourage connection, which therefore amplifies and helps and encourages us to come together and create social impact. So it's kind of like a full circle moment.

1. What does innovation mean to you when your goal is fostering human relationships? How do you innovate in a space that's fundamentally about timeless human needs?

I think innovation in the space of Cool To Connect is creating modern and innovative ways for people to do something that we do day to day, naturally – like connect – but make it innovative in a sense that it's not an experience you've had before. Make it easy to use. Make it perfect for your favorite event. Make it perfectly packaged for your coffee table. Make it the right size to take with you on your trip.

To innovate connection, to make it mainstream and applicable for you to use in your day-to-day life. I think that's been a major goal of mine – to make this product that is really just conversation feel really innovative and really cool and really different, that people want to integrate it into their lives.

2. Your question cards need to feel both fresh and authentic. How do you and your team generate ideas for prompts that spark genuine dialogue without feeling forced or artificial?

It's crazy. If you looked at the note section in my phone, it's just questions sparking off in my mind all day long, and I'm like, "Oh, that would be a good question." For the most part, it's just me. I make all the questions by myself, unless I have a collaborator who's working on the deck with me. For instance, the kids deck and the intimates deck, I had an expert work on both of the decks with me. For the intimates deck, it was a confidence facilitator and coach. And for the kids deck, it was a mom of four who helped make the questions.

There's certain areas where I feel like more than one opinion is needed for some of the more specialty categories. And then, of course, for the collaborative products like Sage Natural Wellness and Jillian Harris for the Jilly Box and Smash and Tess, those were collaborative efforts from their team along with myself to make sure the questions reflected their brand and ethos. But for the most part, it's me.

3. Designing products that facilitate vulnerable conversations requires a particular mindset. What rituals or practices help you tap into the creative intelligence needed for this work?

I don't think I have specific rituals. I think my practice, just in general, of owning this company, is trying to stay really open-minded, and to immerse myself into as many in-person experiences and situations as possible, within boundary and within reason – I am a person – but to be able to experience different things, which then gives you greater insight and experience to form questions that are really intelligent, really intellectual, that get people thinking, and that are outside the box.

I think it was at Indigo or something, and I pulled out this deck of cards, and it was a similar product to mine, but it was like, "If you could be a fabric, what fabric would you be?" I was like, okay, this is not elevating the human experience whatsoever. This is not it. So I really do make an effort to make them intelligent and innovative.

4. You're essentially tracking shifts in how people connect and communicate. How do you identify emerging patterns in relationship dynamics and conversation needs? What signals do you watch for?

I feel like a trend right now that I'm tapping into that I feel is coinciding with me is the trend of creating dinner experiences for people. That's been something that I feel like all over the city, people are creating in-person, meaningful dinners. And I love it. I think it's beautiful for people to come together.

Where I'm finding that I can be a part of this trend, but make it Cool To Connect, is that I actually have the products. I have the cards, I have the conversation starters. I have five years of that business under my belt. But then I've also been in facilitating and hosting, in communications and the people business for the last 10-12 years. So those two things coming together have been able to play a really neat role in being a part of that people trend and to stay current with what people are enjoying consuming in the areas around you too – what your customers are having fun engaging with.

5. Creating something as seemingly simple as conversation cards likely presents unique challenges. What's the biggest obstacle you face when innovating in this deceptively complex space?

I think a lot of what I'm attracted to right now is brands that are not seen as sexy, right? When I say easy, nothing's easy to sell, but things that are a bit easier to sell are clothes, athleisure, makeup, beauty – people want them to better themselves and their appearances. And it's kind of a sexy thing to sell. Like you see a gorgeous athletic wear set on someone you think is beautiful, you're like, I want that. I want to look like that.

Connection, not so sexy to sell. How do you make this sexy? And I think there's a lot of brands who sell really cool things in really niche markets, and they've had this approach to making it seem really sexy and really cool. That's something that I pay a lot of attention to, because I feel like out-of-pocket, chaotic marketing is kind of hot right now, and it's kind of cool, and it resonates with me, because I'm in a niche where I'm promoting something that isn't standard cool, but I'm making it cool.

6. Has another industry or unexpected source ever influenced how you approach connection products? Where do you find inspiration outside the relationship and wellness space?

Mid Day Squares has a lot of really out-of-pocket marketing and advertising. I have friends from a company called Mintier, and they're a mouth tape company – that's not sexy, but they make it sexy and cool. So how to take your product and how to take your messaging and your ethos and make them with the trends, and make it a little out of pocket that people remember what you're talking about, whether it's been seen before or not.

I'm launching some apparel to go with Cool To Connect, and you've seen some of those signs that people hold on the street, right? That was a part of my campaign. I was myself, the founder of this company, made this sign and walking up and down the street, and it says, "I have mixed feelings," and everyone was going crazy. And it was so fun, and it was so unexpected. It was so real.

I've been doing a lot of showing more of my personality in my brand, and it's so much cooler – unboxing videos of certain things, and right now I'm doing this ASMR with the martini glass, and showing sneak peeks of new products that I have coming. It's so random, but it works, and it's so fun. Connecting with your audience in a way that's so you as the founder of a brand is just so much cooler than pretending that you have nothing to do with it.

7. Your work bridges business innovation with social impact. How do you create an innovative culture that serves both commercial success and your deeper mission of connection?

I wanted Cool To Connect to appear and to feel luxury and modern and sexy in your hands and in your life. I want you to feel proud of this product and proud of this deck. Everything from the iPhone suction on the box when you open the box, to the velvety feel to the gold foil, to the matte hand feel – everything is just so intentional, because I wanted it to be so luxury.

You don't think of a deck of cards to be a luxury item that you have in your house, but that's where I wanted Cool To Connect to fill that gap, and to be something you're proud to gift or to own or to buy and display and not have to hide it, because we should all be having conversations. Might as well make them something we're proud of having out in the open.

8. What do you think the connection and conversation space gets wrong? What gap are you addressing?

I think when I try and express through a lot of my events and dinners that I do with these cards is that sure, although I'm prompting vulnerable conversation and meaningful topics and kind of out-of-pocket questions, literally, you can still have a boundary with these things. You don't have to talk about everything with anyone, actually, if you don't want to.
Whereas I think in this whole world of this type of brand, it's very much like everyone needs to be open all the time, and talking and being vulnerable, but you can actually choose if that's not right for you in that moment. I'm the first one to be like, I respect that. That's totally fine. You don't have to answer that question, or you don't have to be part of that or you can pass.

Not feeling like answering a question is kind of your answer to the question. And I think it's important to not push the envelope. There's a difference between feeling encouraged and safe to maybe share something that you wouldn't typically versus, I'm actually really uncomfortable disclosing this right now, and it might do more harm than good. There's a difference, and I think to encourage people to be able to make that decision is what's important.

9. Looking to the future, how will Cool To Connect continue to evolve its approach to innovation while expanding your mission of fostering genuine human connection?

I've toyed with creating a virtual, digital alternative to Cool To Connect the physical cards, whether that's an app. I think staying current with a lot of media is important and trends and stuff like that. But honestly, the more digital we get, I think the more we need to prioritize in-person experiences and in-person connection for people. We can't just all follow suit and go digital – what's going to happen to the world? That's very scary.

So I think we do need to prioritize – I will be prioritizing more and more in-person, interactive experiences for people, no matter how digital our world feels.