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Why Having Fun in Business is Non-Negotiable (w/ Kaylin Marcotte, CEO & Founder - JIGGY)

Updated: Apr 2

Katherin Vasilopoulos [00:00:00]:

Entrepreneurship is serious business. That's the narrative we often hear during conversations with founders on this show especially. We're told that we need to be tough, resilient, and all the other adjectives that describe successful people who start their own ventures. But what if we weren't so serious all the time? How much fun can we have as entrepreneurs and still be successful? Kaylin Marcotte's early career wasn't particularly fun. In 2012, she was training as a management consultant at IBM and gearing up for law school in New York. But the following year, Kaylin discovered something that completely derailed her plans. 2 promising young female founders who wanted to start a media company. So she quit her job and became the first employee at a digital media company called theSkimm.


Katherin Vasilopoulos [00:00:51]:

Yes, that theSkimm, whose investors now include Google Ventures, RRE Ventures, Disney, and more. Throughout her time at theSkimm, Kaylin days were pretty demanding, and she often played with jigsaw puzzles at home to unwind. She loved them, and she got really into them, but she didn't always love the stock imagery she was putting together. There were lots of cottages, lakes, you know, the kinds of puzzles your grandmother might give you. So in 2019 she founded Jiggy. It's a direct to consumer company creating jigsaw puzzles that actually look pretty cool. But beyond the appealing aesthetic of its products, Jiggy's very existence is a reminder of how important it is to have fun throughout the entrepreneurial journey. This week, I spoke with Kaylin about how she went from getting hired as theSkimm's first employee to becoming the founder and CEO of Jiggy.


Katherin Vasilopoulos [00:01:45]:

What were her biggest learnings as she transitioned from working at a media company to manufacturing a physical product? What was it like to create a business out of her hobby? And how do we make fun a core part of the entrepreneurial experience? I'm Katherin Vasilopoulos, and this is And So She Left, the podcast about women entrepreneurs and the wisdom they gained beyond the corporate world. When she left college as a political science and economics major, Kaylin wasn't quite sure where she wanted to go. She was considering a career in law and soon found herself walking through the door at IBM. As Kaylin remembers, it was about as corporate as it gets.


Kaylin Marcotte [00:02:45]:

Management consulting was attractive to me in that I felt it was analytical, and I really liked the idea of working with clients and being on a project basis. And so I started in IBM's management consulting program, which was 2 years, and you rotate every 6 months to a different client, different project. So a really good kind of boot camp entry to, you know, thinking strategically and analytically. And so I ended up staying with IBM in their consulting program for a couple of years until I met 2, young cofounders and decided to make my first jump into the startup world.


Katherin Vasilopoulos [00:03:27]:

Okay. So you went from a very stiffer corporate structure to then going into a more of a startup environment, which we know is extremely different, and it's sometimes chaotic. So tell me more about that kind of environment.


Kaylin Marcotte [00:03:40]:

Yeah. That was definitely the biggest initial kind of culture shock of, the the lack of structure and I think also the never on, never off. Like, we're just work and life blend together so fluidly. And so I met 2 young female cofounders who were starting a media company called theSkimm. The daily email newsletter. The idea was to reconnect millennial women with current events and the news and serve everything you need to know about the top stories of the day in an email newsletter. And so I joined them when they raised a seed round of funding in the end of 2013. And being the 1st employee is such a unique experience to really see from the ground floor.


Kaylin Marcotte [00:04:31]:

You know, I remember my first day, they it was just the 2 of them, and they hadn't got an office yet. So it was, you know, great. Let's talk, you know, the highest level, biggest picture, our goals and strategy for the year, and then let's build office furniture together and get this place set up so that, you know, the the 3 of us can work together.


Katherin Vasilopoulos [00:04:52]:

You were literally building the company. Yeah. The furniture too. Completely. Do you remember what it was like to be that in that space where you have all these new ideas. Everything is just brand new. Like, what was your role exactly? How would you describe that?


Kaylin Marcotte [00:05:09]:

Yeah. That was another kind of adjustment to the talk about lack of structure. The I think the first 10 to 15 employees, like, we didn't even really have titles. It was like, you know, you're an editorial skimmer or you're a Marcotte skimmer. And so I guess my role on paper was around marketing. And so, you know, there was immediately a lot of traction and kind of grassroots community just growing around the brand organically. People felt very connected to this voice and tone and personality behind the newsletter. And so, kind of building out an ambassador program and doing a lot of content Marcotte.


Kaylin Marcotte [00:05:50]:

And we moved it to offline events, social media. And so all of that and then outside of my specific scope, but what ended up being on my plate just, I think, by virtue of being there first was a lot of kind of the internal stuff. So team building and, you know, welcoming each new employee, and so kind of onboarding and kind of almost chief of staff type role as well, just as the team was growing so quickly.


Katherin Vasilopoulos [00:06:20]:

Well, as you're talking, I'm listening to every single thing that you had to do that you learned. And to me, it's so obvious to me that you just got all the skills. You were getting ready for the next chapter. I mean, that's what it was.


Kaylin Marcotte [00:06:32]:

100%. I think working at a small you know, coming from such a corporate environment, I think taking the jump, you know, from IBM to being a founder would have been so drastic, but spending those few years at theSkimm working for 2 founders so closely, it kind of demystified, you know, what starting a company took and what those early days are like. And so I think that was such a pivotal stepping stone. I don't know where I would be if I if I hadn't seen that so intimately.


Katherin Vasilopoulos [00:07:08]:

I find it interesting because with all the guests that we've had on our show so far, many of them have said it's so important to get that corporate experience before becoming your own boss. But in your case, you have that added bonus of being in, like, not just corporate, but then moving to start up and then moving into entrepreneurial, which means that you're fully formed way before you're ready to start. And that's I find is you're lucky to have that experience. Tell me about your obsession or your interest in with puzzles. I wanna hear more about that.


Kaylin Marcotte [00:07:38]:

So it started very organically when I was at theSkimm in those early days that, you know, as I said, were amazing and also crazy. And, you know, I definitely at different times was reaching just that point of burnout and, you know, on one screen or another all day long from phone to computer. And then I come home and wanna unwind and so turn on the TV, and I was like, wait. This is more of the same. This doesn't actually feel relaxing. You know, everyone was talking to me, I think, headspace and calm and and just come out of our just talking about meditation, and I tried meditating and yoga. And I don't know. It didn't really stick.


Kaylin Marcotte [00:08:17]:

And I had done puzzles as a kid, but, you know, not really for my adult life. I kind of forgotten about them. But I had one lying around and I pulled it out, and it just clicked immediately for me that this was my ritual and it was relaxing and and meditative. But I still, you know, felt like I was working towards something and just that little dopamine hit every time I got the pieces to fit. And so I just fell in love with jigsaw puzzles, and I started doing about a 1,000 piece puzzle every week. Each night after dinner became my kind of just a habitual turn on music or an audiobook and make either, depending on the night, wine or tea, and sit down and just kind of unwind before bed with my puzzle.


Kaylin Marcotte [00:09:06]:

And so all the ones I could find, though, were, you know, I felt kind of outdated to kind of cheesy stock photography of animals or cottages or whatever it was. Uh-huh.


Katherin Vasilopoulos [00:09:17]:



Kaylin Marcotte [00:09:18]:

I just started thinking, what would my dream puzzle be? What would how could I improve this experience? And the first thing that came to me was, you know, the design itself, of course, the art. So how would this experience be different if this was, you know, a beautiful piece of an illustrative scene or photography or an abstract. And so I really wanted to kind of reinvent the classic puzzle in a much more elevated kind of design and art forward way.


Katherin Vasilopoulos [00:09:54]:

What did you learn from solving the mystery of the puzzle?


Kaylin Marcotte [00:09:58]:

You know, I I actually when I was launching the company, I wrote a, blog post of all of my life lessons that I felt I had you know, puzzling had taught me. And, you know, a couple of them, I think, especially in such an overly stimulated kind of instant gratification world, like, there are no shortcuts to a jigsaw puzzle and-


Katherin Vasilopoulos [00:10:22]:



Kaylin Marcotte [00:10:22]:

There's just that patience and, you know, delayed gratification and that, you know, you pour out these pieces and it looks like, you know, a mess on the table and you slowly start sorting through. And so really just, you know, I think it was so many things in life can be taken one piece at a time. And sometimes you you can look at the shape or look at the Katherin, and you can tell what fits where, and sometimes you just have to try a bunch of pieces and see what fits. And so, yeah, there were a lot of life lessons and just kind of slowing down, slowing down and focusing on the task in front of me.


Katherin Vasilopoulos [00:11:01]:

I remember during the pandemic, there are a lot of moments where I had to make a puzzle. There was nothing else to do. And I remember that the life lesson was, you know, you have to start with the foundation, the the freedom in the corners, and then there is always that one piece that you're convinced belongs somewhere, and you're trying, and you're trying to push it and it doesn't belong there. And you have to, like, maybe flip it 90 degrees or look at it differently at one point, and then you realize, oh, no. It goes in the other place.


Kaylin Marcotte [00:11:25]:



Katherin Vasilopoulos [00:11:26]:

In another part of the puzzle. And you're like, that's how life is. Sometimes you're really trying to make something fit somewhere, and it just doesn't. Tell me about your, what we call here at the show, your and so she left moment, which is the moment where you realized, I'm going to leave what I'm currently doing to start my own business. Tell me about that process.


Kaylin Marcotte [00:11:45]:

Yeah. That was kind of a slow role, I would say. You know, I had the idea. I actually started I found it the other day. I started a folder on my phone of photos, you know, called, like, potential puzzle art back in, like, 2016, and I didn't launch it until 2019. So-


Katherin Vasilopoulos [00:12:04]:



Kaylin Marcotte [00:12:04]:

There were, you know, years in there that I was still really enjoying my work at the skin. You know, this idea was in the back of my mind. It was like, I think there's something there. And then over that time, I was also just kind of paying attention to some trends I was seeing, and there was that adult coloring book fad. And I was like, okay. That's interesting. You know, maybe there's an appetite for something like this. And then, you know, Pinterest and DIY projects and crafting and-


Katherin Vasilopoulos [00:12:31]:

Right. Right.


Kaylin Marcotte [00:12:31]:

I just, you know, started I think getting more and more confidence that not only was this just my cute little hobby that I wanted to spend more time on, but that there might actually be some business potential here. And then finally, in 2018, I, you know, was coming up on 4 years at theSkimm, and the company had just changed, you know, so incredibly, seeing it from 0 employees to, like, 80. And, you know, we've done 2 more rounds of funding since I was there. So I just felt really good about the work that I put into this company, and I started really getting that itch. I was like, alright. You know, I could stay here forever and keep building these founders in a dream and vision, but I really this idea won't go away, and it keeps coming up. And I, along the way, had a different business idea and just, you know, never got around to it. And then I saw it on Instagram.


Kaylin Marcotte [00:13:28]:

Somebody else was doing it. And I just sat there and I was like, you know what? If 6 months from now, 12 months from now, I see an artsy, cool, elevated, beautiful puzzle company advertising on Instagram, I'm gonna freak out, and it has to be me to do this. And so I decided to leave and start navigating through the manufacturing world and figuring out how to make my dream puzzle.


Katherin Vasilopoulos [00:14:00]:

I like what you said there that you need some time to develop the confidence. And but along the way, you're seeing other people fill up that space on the market and you're like I need to hurry up and get in on this too. So you have an idea that's simmering, you know, like on the one hand you have your your folder on your phone but on the other hand time's going by. And so you have to make that decision and you know strike while the iron's hot.


Kaylin Marcotte [00:14:24]:



Katherin Vasilopoulos [00:14:25]:

What's your company's name?


Kaylin Marcotte [00:14:26]:

It is called Jiggy. Jiggy Puzzles. So I wanted, you know, some kind of fun play on Jiggy where once you knew what it was, it made total sense and connected, but was playful. I had a whole word doc of brainstorms and thesaurus sing different things. And finally, I was on a a walk with a friend, and I was like, I don't know. Something playful, fun, like a riff on jigsaw, jiggy, and it just came out. And I was like, wait. I think that was it.


Katherin Vasilopoulos [00:14:59]:

I wanna talk about the fun component of what you're doing right now. Why is it important for you to have fun in this job, and why is it important for you to develop this for people?


Kaylin Marcotte [00:15:09]:

I think about it a lot. On the one side, you know, it's the impact I wanna have and what I wanna bring to our community. And I think, again, just coming back to what puzzles did for me, you know, there's there's so much to be serious about and rightfully so, you know, things in the world and and, you know, impacting your career and work and building the family you wanted. There's just so much to be very intentional and thoughtful and serious about. But I think, you know, sometimes that can come at the expense of just keeping some lighthearted joy. And as we grow up, I think we lose play a lot. And my family, I'm always and now my husband and we have our first child, you know, just huge game night and board game family. And I think the idea of carving out time to just have such a different energy and just enjoy play is really important.


Kaylin Marcotte [00:16:12]:

And for me, personally, you know, it's hard. It's hard starting a business. It's hard bootstrapping it and being a female founder and a first time founder and all of these things, there are a lot of challenges that come with it. But I've had so many moments where I'm just like, you know what? I get to work with incredible artists and make puzzles. Like, if I'm not having fun with this, what's the point?


Katherin Vasilopoulos [00:16:36]:

I mean, that is probably the mission of your company. It's not just I make puzzles with nice art. It's the overarching theme of I help bring people together and and create playtime for people to build memories together. And completely. I'd love to hear more about you know, you already had a lot of experience coming into this because you were in a previous startup, but what were your own challenges in in building your brand and building a company from the ground up?


Kaylin Marcotte [00:17:02]:

1000000 challenges, but, I'd say, you know, a couple different categories or challenges maybe. So first, just starting the business. You know, once you have the name and getting the domain and setting up all the infrastructure and, you know, there's plenty of guides and lists and checklists to to get the business propped up. But then for me, what was brand new coming from the scam, which is all digital, is, you know, the physical product world. So I had a pretty clear idea of the product and what I wanted it to look like and some of the materials to use, but how to translate that vision into CAD ready print files for a factory, I was clueless on. And so, you know, getting you just each step of the way, just self teaching, having no ego about asking a million questions, and, you know, fine. I found a lot of just part time kind of project based contractor help getting the physical product made, imported, then having a I fulfilled out of my living room for a bit, but that was quickly unsustainable. So finding a-


Katherin Vasilopoulos [00:18:18]:



Kaylin Marcotte [00:18:18]:

Fulfillment center, you know, where housing and logistics and customer service issues. And so that whole side of the physical product world was brand new and a million, you know, lessons learned of of the first production run. Some of the dimensions were off and, like, the puzzle wouldn't fit in the jar.


Katherin Vasilopoulos [00:18:41]:

Oh, no.


Kaylin Marcotte [00:18:42]:

Yeah. I was so just learning the hard way on that, you know, not working with one of our vendors. Their email got hacked, and I wired the whole invoice to tie hackers, call the vendor when you're wiring, confirm over the phone. Of course, I didn't even think to do that. So, again, just raise your hand and find the people who do know the answers and have done it before, and don't be scared to ask for help.


Katherin Vasilopoulos [00:19:11]:

Yeah. And that goes back to your whole team building skill set is that you had to build your own team from scratch, as I could understand. So what was it like for you moving from a worker mentality to then a founder mentality? Tell me more about that.


Kaylin Marcotte [00:19:27]:

1, just, you know, the realities of the demands on your time and just the fact that in the beginning, certainly, you know, if I wasn't doing it, nobody was doing it. And so managing my energy when there was always more to do. You know, there was never sometimes as an employee, I think you get a task. You get a project. You have your to do list. You make your way through it, and you get to close your computer. And as a founder, you know, it's never done. And there's always more you could be doing.


Kaylin Marcotte [00:19:56]:

And even if that to do list is done, you know, what's next? How do I keep pushing forward, keep growing, get ahead of every predictable surprise, you know, that's gonna happen? So one, that kind of discipline to still carve out time, to still, have any kind of balance to protect my energy. That was really important. And to learn to delegate, you know, again, I think once everything has been on your plate, you're like, alright. Well, you know, I can just keep doing it this way. It's more time to explain it to somebody. But, it was actually theSkimm founders when I was working for them that said, your role as a founder when you're trying to scale is to replace and fire yourself from every task that is not the absolute highest best use of your time. So-


Katherin Vasilopoulos [00:20:48]:

Oh, I love that. Replace and fire yourself.


Kaylin Marcotte [00:20:50]:

Yes. Find the best person for the job, then fire yourself from that job. That's a big reframe on what will actually, you know, be in the best interest of of the company and growth, to to fire yourself continuously.


Katherin Vasilopoulos [00:21:08]:

Oh my god. That's hysterical. It's true. When you get to a point, we can't do everything. You have to absolutely tell someone else, okay. You need to take this on. Quickly, I would love to hear more about your experience on Shark Tank.


Kaylin Marcotte [00:21:22]:

Yeah. It turns out about a third of the companies that go on Shark Tank are scouted by the producers. So, they reached out, said they had found me on Instagram, I think. So that that only kind of gets you past the first open casting. You still have to do your pitch video and everything. So went through all the steps and ended up recording, and it aired in 2021. So it was still really much in the pandemic and they had built this whole bubble environment and recreated the set. But it was such a cool way to not only, you know, be able to share my story and the Jiggy story and for me to really think about some of the big questions that I knew they were gonna ask, I was about a year in business and had no investors, you know, no, no cofounders or employees.


Kaylin Marcotte [00:22:22]:

And so I was kind of just sprinting to keep up. And so the process of preparing for the show was actually really cool to, you know, kind of tie in the sky ideas. Like, what would I do with, you know, an investment and an infusion of capital? What is the 5 year vision? And so it was really fun to prepare and just to think big. And then, you know, the actual filming was really cool because what you don't see is you're in there for about an hour on average. And so you actually get into, you know, a real dialogue and you have a lot more time to discuss everything and and their whole kind of conversations and threads and questions. And so there's a lot more time you have to dig into everything. I ended up, getting an offer from Mark Cuban who was my dream shark going in. So I was so grateful for that.


Kaylin Marcotte [00:23:17]:

But whether you come out of it with a deal or not, to get the shark's input and advice and pushback and feedback and get that platform and that level of exposure is kind of once in a lifetime and has just catapulted so many brands to to a different level.


Katherin Vasilopoulos [00:23:37]:

Yes. How did it impact Jiggy's future?


Kaylin Marcotte [00:23:40]:

Oh, it was amazing. The Shark Tank audience is so supportive and really just rooting for you. You run on Shopify, so I was sitting on Shopify, you know, just refresh, refresh, and watching the immediate traffic and sales and all the nice notes and feedback and likes on social media and comments, and it got not only, you know, was the immediate impact from the airing, but then a lot of other people watched the show, like, you know, retail buyers for stores and potential partners. And so it actually not only helped with the direct to consumer business, but also the B2B wholesale and retail world as well.


Katherin Vasilopoulos [00:24:24]:

So what was your biggest learning from the experience? Because you said that you actually talk for an hour with them, but we only see about 10 minutes of it on on the air. Right? So what was that like?


Kaylin Marcotte [00:24:34]:

Yeah. I think, you know, they definitely were really interested in the kind of the growth model and how much I wanted to focus on direct to consumer or going into retail because in some ways, those are completely different businesses, you know. And the team you need, the personnel that you hire, the strategy around introducing new products and how many skews do you have, and pricing models is completely different if you're selling, you know, d to c on ecommerce or you're really going after, you know, the the Marcotte and Walmarts and big box retailers. And so we talked about that and kind of what the future strategy was. We talked about, you know, is this just a COVID fad? Is is this a real sustainable business? Or is this just kind of a inflated numbers because this is such a puzzle craze during the pandemic?


Katherin Vasilopoulos [00:25:31]:

That's a good question. You're right. People were locked in and had something they needed something to do. But then after, when people go back to normal lives, is this something that will continue to grow? And have the numbers gone in any direction that you didn't expect?


Kaylin Marcotte [00:25:45]:

No. So that was really something that, you know, because we were able to really get ahead of it and build that ritual with our customers. So a big thing that came out of it was actually our subscription. So, you know, we have a monthly puzzle club where you get a 500 piece puzzle every month. And so that was a way to build that ritual with our customers, which also was very organic to just me and, you know, my founding story of doing puzzles every night and getting through, you know, a a puzzle every single week. Acquisition is important, but vast majority of your business and revenue will end up being repeat and coming from your existing customers. And so I really wanted to make sure that we were still focusing on what our existing customers want and what will keep them engaged and coming back. And let's introduce new products.


Kaylin Marcotte [00:26:40]:

So we, you know, we, a big differentiator is that each of our puzzles is artwork by a female artist. And to that end, I thought, what if this was actually something you wanna keep and frame? And so we include puzzle glue with the puzzle so you can preserve it once it's done. And then we launched frame pairing so you can actually frame it and get it on the wall. And then we started hearing, I wanna do this with my family, but, you know, it's the pieces are a bit small or, you know, 800 is a lot for my kids. And so we introduced Jiggy Junior, which is our kids' line of puzzles. Okay. We started getting requests to do custom puzzles of I wanna turn my artwork or or even my kids' artwork or this family photo. Yeah.


Kaylin Marcotte [00:27:24]:

So we actually found a domestic printer who can print on demand. And so we started personalized custom puzzles between building the rituals and that habit and having the subscription model and then continuing to introduce new product and serve our customers in new ways, we were able to to get ahead of it and continue to grow.


Katherin Vasilopoulos [00:27:55]:

Tell me, what advice do you have for people who are thinking about jumping ship and starting their own business?


Kaylin Marcotte [00:28:03]:

Yeah. I think, you know, of course, it's so specific to everyone's circumstances and where they're at. But for me, I would definitely say start with what you can. Start where you are. There will come a moment that you have to make the leap, but I think especially if it's a brand or Cansulta facing business, there are ways to start building an audience. Launch a website and start collecting email addresses to build up your email list. Make sure you get that, the the Instagram and TikTok handles to start the social accounts, and start putting up content and seeing what the feedback is, and start building an audience, you know, even a year before launch day. And ultimately, you know, I bootstrapped, and I think that's much more viable path than it seems sometimes to be, you know, generating revenue pretty quickly and then run on cash flow and reinvest and, and build the business to a point where it's it's ready for, you know, a bigger infusion.


Kaylin Marcotte [00:29:09]:

And I think really on the brand building, I've, from my Skimm experience and brought it through to Jiggy. I'm such a fan of just really kind of transparent community building with your customers. As I mentioned with our product extensions, the Jiggy Junior line and frames, it all came from what our customers were asking for. So, really keeping that dialogue open and keeping close to your community and your customers.


Katherin Vasilopoulos [00:29:38]:

Thank you so much to Kaylin Marcotte. You can learn more about Jiggy through the link in the episode description. If you like the show, please rate, review, and subscribe to And So She Left wherever you listen. Your feedback helps us to better serve current listeners and reach new ones. Head over to for full episodes, transcripts, and application form to be on the show, a list of upcoming guests, and more. And So She Left is made by Cansulta and Ethan Lee. Cansulta connects entrepreneurs and leaders with a global roster of over 150 pre vetted consultants and experts like Ethan and I who can help organizations in any business area from HR to finance to sales and marketing and even innovation and product design. We'll be back next Wednesday with a new episode.


Katherin Vasilopoulos [00:30:24]:

Our music is by Correspondence and Chris Zabriskie, edited for your enjoyment. You can find a list of all the songs you heard here in the episode notes. I'm Katherin Vasilopoulos, and thanks for listening.

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