Ep #32 | Turning a Personal Challenge Into a Creative Outlet


Cara Thomas spent over 10 years inventing award-winning products for Fortune 100 companies. She found that adventure and playfulness led to breakthroughs. In need of that personally, she started Serenflipity as an experiment — and it ended up changing her life. It started with a one-way flight to Mumbai, and 90 challenges written by 90 friends, clients and strangers. Each day she flipped a card, followed its direction and blogged the tale. The results were surprising and serendipitous — and even included getting life-changing advice from Steven Tyler. Cara has launched Serenflipity to encourage that spirit of adventure into everyday life, anywhere in the world.



Shantel: Hi Cara. Welcome to the Imagine More Podcast.

Cara: Hi there. Thank you so much for having me. 

Shantel: Yes. We are excited to learn more about Serenflipity, and the backstory, and everything that inspired the company. So can you kick things off with telling our listeners a little bit about your entrepreneurial journey, and how the company came to be? 


Cara: Absolutely. So I am Cara, founder and CEO of Serenflipity, which is an adventure game that's designed to help people get out of their comfort zones and try new things. And it started with a deck of cards. And actually before it started as a deck of cards, it was a personal travel project that I did. So my entrepreneurial journey ... Actually I if I look back on it, I had quite a few entrepreneurial ideas when I was a kid, and was doing everything from coming up with different businesses to building a more formal career where I was a consultant for big corporations, helping them create new products and ideas. So I helped Fortune 100 companies become more entrepreneurial, and had this passion on the side that I wanted to turn into a business myself. So basically, Serenflipity started out of a little bit of a personal challenge. I was going through a breakup at the time, and I was feeling a little bit stuck and burnt out at work. So the best thing I knew to get myself unstuck was to travel. So I ended up booking a one way flight to India, and traveling by myself for six weeks. Or actually, no. It was 90 days. I was in India for six weeks, and then through Southeast Asia for the rest. And I convinced 90 people, some of whom were friends, some of whom were clients, others were complete strangers to write adventures for me to do while I traveled by myself. And every day I flipped a card and wrote a blog about it. And at the end of my trip, someone noticed that I was sort of a different person. I was feeling excited about life, I was feeling upbeat, and kind of looking forward to what each day would hold instead of feeling stressed out and anxious. And she challenged me to turn that project into a product, and that was the beginning of Serenflipity, and the beginning of our first deck of cards that we created. 

Shantel: Wow. So that is like your experience of the Eat Pray Love type of scenario a little bit. Do people always make that connection, and you're like, "Uh"?

Cara: Not my Eat Pray Love.

Shantel: Sorry. 

Cara: But it kind of is. I'm like, "I didn't go to Italy," but. But yeah, I mean I think in that sense, there was sort of the commonality of turning a personal challenge into a creative outlet, and into something that helped me to grow, and then helped other people to grow. 

Shantel: Absolutely. Will you share some of the initial adventures that were on the cards that your friends and loved ones put together for you?

Cara: Absolutely. Those cards, the ones that sort of impacted me the most on that trip are the ones that made it into the first stack of Serenflipity cards that we've published in December of last year. So one of them, which was one of the first ones I did, was to find the happiest couple around and ask them the secret to love. So that was a super sweet one. I was in India looking around for really happy couples, and I'm like sort of a little redhead, and this little redhead is going up to like, "Excuse me, you guys look really happy. What's the secret to your relationship?” It was actually one of my favorite flips to do. I love doing that in all sorts of situations. It really just, it sparks beautiful conversation, and it's amazing what you learn about people. And another one was to ask a stranger for a mantra, which started as a personal joke between a colleague and I. And I ended up, I was in Bangkok at the time during that adventure, and looking around for monks and people to ask for mantras. I was walking down the street with my backpack, and my greasy hair, and everything like that. You know how we are when we travel. And ended up running into Steven Tyler of Aerosmith of all people on that our paths crossed. So I had this card in my hand and an excuse to connect. I mean, I think that's the beautiful thing about the cards is that it's almost a social currency. It makes it possible to get out of your comfort zone and to speak to another person. So we ended up having this lovely moment, and he gave me great advice, which I continue to live by. 

Shantel: What was the mantra?

Cara: The mantra was the only way to get to the other shore, is to lose sight of the one you're on. 

Shantel: Wow. 

Cara: Yeah. 

Shantel: That is profound. I love that. 


Cara: And I was literally on another shore, and used that as inspiration to move from New York to Singapore after that trip. I'm like, "All right, new shores." And then I think as an entrepreneur, I don't know if you felt this way or other guests have felt this way, but I found for myself too it's like sometimes I feel like a little boat in the middle of the ocean. You're like losing sight of these sort of old ideas, or old structures, or things that you think you should be doing and moving towards this new shore that you don't quite know where it is, you don't quite know what it looks like, but you kind of just keep going. And you have those moments where you're like, "Okay, I'm in the middle of the ocean. I am not sure where I'm going, but there's something out there." 

Shantel: Yeah. And a little scary but exciting at the same time. I can definitely relate to that feeling. Those are some awesome adventures that your friends put together. So now we're going to dive into the product launch. So had you ever started or manufactured a product in the past?

Cara: I had manufactured. As a kid, I had created a fashion magazine. I would not call that manufacturing a product necessarily, but printer and putting things together. I think I had a very small circulation of maybe 10 friends and family members. But actually launching and scaling a mass product, I had never done that before. I'd always been on the side of strategy, and consulting, and helping companies come up with ideas. But the actual process of going from an idea scribbled on a napkin or a theoretical business plan to creating, manufacturing, developing, and retailing a product, it was definitely a new shore to use our friend Steven Tyler's words.

Shantel: Yeah. Well I mean, is there one thing that really stands out that you learned like okay, you definitely have to connect these types of people, or this is the best resource, or how did you navigate that new journey?

Cara: I did a lot of research, and I talked to a lot of people who had launched products that I respected. So one of the things that I learned early on probably in school even, and I grew up with a mother who was in the business world, was also an entrepreneur, she had always told me, "Reach out to anyone who you think is interesting no matter how senior they are because people always want to help other people." So I started looking at other products that I really respected, and I ended up doing a cold call to the founder of a deck of cards that had huge distribution, and is sort of all over the world, and has 20 different iterations. And just sent a cold email through LinkedIn, and started talking to her. So I started researching, and I started asking for help, and I eventually ended up going through a model with a publisher. So I did everything from going to trade shows, from talking to manufacturers, talking to distributors, and really getting a sense of what the landscape is like. And it's hard. It's a hard business to get scale in. So for me, I think the biggest thing that I decided to explore was partnership, and looking at what I can do well so I can create content well, I know the brand, I'm good at getting people out of their comfort zones and having new experiences, but I don't have roots in retailing, in distribution, in wholesaling, in dropshipping and all of those different things. So for me, what made the most sense to launch the first deck of cards was the find a partner who was expert in that where we could join forces, and they could bring the best of what they do, and I can bring the best of what I do. So it was almost a first test to get it out there in the world, verses doubling down. Because I think originally, when I was doing the beta test and crowdfunding it, I did manufacture it myself. I worked with a company to design it, to manufacture it, to do direct to consumer sales, but getting it into stores was really hard. Or figuring out what would pop on shelf that a mass retailer was something that others had expertise in that I didn't. So it was a lot of getting insight from other people, learning from different experts, asking for help, and ultimately choosing partnership with someone who could do the thing that I didn't do. I couldn't do better than I could.

Shantel: I think that's great advice. I mean, everyone is human and it doesn't need to be scary because they oftentimes do just want to share anything they've learned, and willing to because most people don't ask. So I think that's great advice. I saw you in Anthropologie, which is probably what you prefaced in kind of getting in stores. That's really exciting. 

Cara: So exciting. They were the first retailer to pick us up. And funny enough, when I started the company, when it was still scribbled out on Excel spreadsheets and I was kind of hacking the design on PowerPoint myself ... Like I should show you some of those designs. They were pretty ugly. Before actually going a professional designer route, my dream was to have it in Anthropologie. I was like, "I want these cards to be in Anthropologie. They're my dream retailer." And they were the first people to pick us up and put us in all of their stores. So that was really awesome. 

Shantel: Yeah. Huge win. So I also saw on the website a beta version of kind of making this a little bit more digital. Can you share a little bit about what prompted that decision, and a little bit more about that soft launch? 


Cara: Absolutely. It's interesting because I think from day one of starting Serenflipity and starting a deck of cards, I believe there's power in analog products, and I believe there's power in real products and tangible things. But I also believe there is power and growth in doing things digitally, and figuring out how to make something more accessible, and especially using technology and using our phones. So from day one, a lot of people would ask when we were going to do an app. And I've been a bit reticent on doing an app because I really wanted to make sure it was meeting a need, it was something that would be able to grow, and scale, and make money. So we've been testing a lot of things for awhile, and we actually stumbled upon this idea of a text message service. And the way that we stumbled upon that was we were testing out new additions of cards with a few friends. So one of the new additions coming out will be a sexy Serenflipity, which brings love, sex, and adventure to couples. And I wanted to get 10 friends to try out the new content to see if it was any good, and to get feedback on the actual cards. So like to test everything. And people said they wanted to receive the flips by text message. So I enlisted a friend of mine. I was basically like, "Will you pretend to be a robot?" 10 people. And what we ended up discovering was this whole new business model, and this whole new world of actually leveraging text, and leveraging real human connection through our phones to help us have more adventure, and kind of more in real life experiences using that technology. So basically, it started with a test of a really small beta test of wild users from the internet, and it's been amazing. Like every morning, I look forward to seeing what adventures they've been on, and hearing their stories, and getting the feedback, and hearing about how they're getting out of their comfort zone. And it's been interesting because it's been very organic, and very sort of soft, and a little bit hidden on our website. And we've tripled our users last week, and we have a waiting list that's growing now. So we're really figuring out how do we create something that's a really amazing digital experience that also brings in the power of human connection, and can really be a tool that helps people get out of their comfort zones, and almost use their phones to get off of their phones. 

Shantel: Mm-hmm. Have you found that a lot of people are then almost providing content back to you to share their experience? Like taking a picture of the adventure that they went on, maybe not for the sexy adventures, but for the others. Are they sharing like, "Hey, this is what I did today with it," and then now you have a catalog of how people actually utilized that adventure?

Cara: Absolutely. It's been amazing to hear the stories that people have. And we find that people share the stories pretty organically if they have something that they want to talk about. And one of the adventures that a lot of people end up really enjoying is to meditate on each sense as you go about the day, and to find something beautiful or unexpected that you would have otherwise overlooked. So we'll get these really cool pictures of everything from a tree, to like a crack on a sidewalk, to a flower, to a subway car that people are finding beauty in that they would have otherwise never seen. And again, this getting advice from a stranger is often one that we hear amazing things from people about, and kind of give them the opportunity to live by that advice for however long they choose. 

Shantel: That's amazing. Do you find so much inspiration just in these stories like when you're having a rough day, or you need to be inspired? Are they helpful in kind of reinvigorating some of that passion for what you've started? 

Cara: Absolutely. I would say when I wake up in the morning and I think about launching a business, or building Serenflipity, that's the thing that drives me is I'm driven by a desire to help people connect to real life, and to find magic for lack of a better word right in front of them. Because I think that oftentimes there's and if then mentality that we think that if I do this, then I can relax, or then I can have a relationship. Or once I'm done with work and then I go on vacation, then I'll be happy. But the real premise of Serenflipity, and I think what we're building with the tech service, is really easy simple tools to find the beauty in your partner, or find an adventurous new experience with the person you're dating, or connect with a coworker in a different way, or just take five minutes to de-stress and do something for yourself that can really shift your attitude and shift how you show up in a daily practice, versus having these longer term goals of like, "Once we go on vacation, then I'll be de-stressed.” So I think that's what really motivates me and excites me, and hearing those stories of, "I didn't think I could buy coffee for the person behind me in line, and it really was confronting because I was scared of being rejected by that person, but then I did it, and I feel great." That for me, I think, is probably the biggest motivator, and hearing those stories. And our next step, once we formalize this a bit more, we'll be building out a community platform where people can see each other's stories, and see what other people are doing, because I think to your point, that is really motivating. If you're confronted with a challenge that you might not want to do, but then you see 100 other people who've done the same thing or overcome that fear, even if you don't do it, it's a little bit of a nudge or just sort of a view into the possibility of what could happen if you get out of your comfort zone. 

Shantel: Mm-hmm. Absolutely. By the way, are you still in Singapore?

Cara: I'm in Los Angeles. 

Shantel: Okay. 

Cara: Santa Monica. 

Shantel: Okay, great. And your old blog page where you shared your 90-day adventure, can people still read through that, or is that something that you've taken down offline. 

Cara: theflipfiles.com

Shantel: Okay. 

Cara: Yeah. It is still up and about, so all the original adventures are up there. Throw them into our regular blog as throwback Thursdays sometimes. 

Shantel: Nice. Well I can't wait to take a look at that. What does your day look like now once you have an established company now, do you have a big team, and what's kind of on your day to day plate?

Cara: Yeah. We have about I'd say five people who ... What's so interesting in think about the way we're working these days is I was working with a team member who was doing our social media a few years ago who I didn't meet in person for a year and a half. 

Shantel: Oh, wow. 

Cara: It's fascinating. And there's something I think looking at the digital economy, and sort of how we're working these days, it's really easy to work across different boundaries, and to be able to collaborate across borders. So there are three of us in LA, there are two on the East Coast, and then a few others kind of in between freelancing and building. So that's been fantastic. And I would say from a daily perspective, it shifts. I try to sort of double down on my meetings on certain days for productivity. So today is a big meeting day where if I'm driving from one place to another, or it's sort of a more extroverted day of conversations, meeting with different partners, building out sort of the next interactions of the product. And then I try to have more of an introverted day where I might be working on pitch decks, I might be building content for example, because I find it hard to toggle between the two in the same day, or kind of in the same mindset. So I've been trying to carve out more concentrated meeting days, and more kind of I guess cave days to use a friend of mine's term. 

Shantel: I love that. We've actually had a couple guests on the show talk about how they stack these meetings. They only try to have meetings on certain days, and that really helps them compartmentalize and focus on the things the other days, which is great advice and something that I would like to try. I'm kind of diligent about it, but then someone says, "I can only meet at this time on this day." I'm like, "All right. I guess I can make that happen."

Cara: Yeah. 

Shantel: Which is tough. What have maybe one the biggest challenges in the business that you've had to overcome so far if you're open to sharing? 


Cara: There's so many. I would say I think when I started the company, I would say the biggest challenge was myself if I'm totally transparent and honest, which I don't know if other founders can relate to. But I think the biggest challenge that I thought I would have when I started the business was financial of like created PNLs, creating forecasts, financial things, tools, and projections and things like that. And I found that one of the biggest challenges, and one of the biggest areas that I've been focusing on over the past few years is actually internal resilience. In how I show up as a leader, in how I show up as sort of creator, and founder, and CEO, and colleague, and friend to people I'm working with, to customers, to partners and things like that. Because I think as an entrepreneur, you're inherently in an uncertain world, so it's really easy I think to feel down when the chips are down, or feeling like, "Oh my God. I don't know what I'm doing," and getting out of that, and getting back into that productivity, and getting back into that cycle, or easily when you have a really big win, getting excited and resting on your, I think I've learned to become more resilient, and just constantly move into more productivity. 

Shantel: I appreciate you being that open and honest there. I think being a leader, and a business owner, and a friend, and all of these other components, it does take a lot of compartmentalizing, and also just focus so that you can be present in those moments. So, no. I relate, and I appreciate you sharing that. 

Cara: Yeah. And I think one of the biggest things that's helped me do that is I think that question you were asking before of what am I creating, and who am I creating it for? As soon as I get back and connected to the customers, and the community, and what's being created for people's lives, I can get back into the. And once I get into ... I'll ask myself as a question, "What do I stand for?" And once I'm rooted in what I stand for, then all of the other details start to line up, verses focusing on smaller things. 

Shantel: Mm-hmm. No, I agree. Absolutely. Well, we have a few more questions for you, Cara. The first is are there any adventures or new travel on the horizon for you? And is that a big part of your life? 

Cara: Adventure. I mean, every day is an adventure. It's interesting. So I spent a lot of my time, I think, as a consultant, and living abroad, and traveling and working in different countries, finding adventure from external environments. And for me right now, a big adventure is more internal, and really rooting into my community in Santa Monica, and spending time in Los Angeles, and finding adventure here, which I think has been really, really fun. I always love to travel, I always love to go on adventures. In fact, last weekend I went on a spontaneous adventure where we got in the car and didn't know where we were staying that night. And we're like, "We're going to figure it out. It's great." So things like that. And then for 2018, I don't have my travel planned yet, but I'm always open. And for me, it's a lot about saying yes, and seeing what comes up. 

Shantel: Well, I can't wait to see where 2018 takes you and follow along there. Have you stayed in touch with Steven Tyler? 

Cara: I would love to. I actually keep that card in my wallet because I'm convinced that somewhere along the path, I'm going to run into him and be able to thank him for the advice, and for the wisdom that he shared that he probably has no idea what an impact it had. 

Shantel: Well, I'm sure you put it out there in the universe, yeah. One day you'll meet him again, or he'll follow along and reach out. That's exciting. 

Cara: Absolutely. 

Shantel: And how can people learn more about Serenflipity, and reach out, or get in touch if they have any additional questions?

Cara: So you can go to our website, which is serenflipity.com. S-E-R-E-N-F-L-I-P-I-T-Y.com. You totally could shoot me an email as well, cara@serenfliptiy.com. And that's probably the best way to get in touch and follow along. And we have our Instagram up kind of showcasing adventures, and some stories, and some flips that people can do if they don't have the deck of cards, or are not part of the beta yet. 

Shantel: Great. Well, thanks for carving out some time to connect, and we really appreciate it. 

Cara: So much fun. It was great to connect with you.