This Multimillion-Dollar Puzzler Shares How She Turned Her Hobby Into a Seven-Figure Startup

Puzzles and the pandemic go together like peanut butter and jelly. The early days of hunkering down were filled with jigsaws and sourdough starter. But what makes Kaylin Marcotte unique is that she was a puzzler before it was trendy. When brands launched pandemic-related businesses, Kaylin was already far ahead of them. She formed Jiggy Puzzles in 2019 and has always eschewed traditional business advice for a more intuitive model – following her gut.

Kaylin worked 14-hour days as the first employee of a successful startup. The company was in a period of hypergrowth, and Kaylin was in the driver’s seat. She used her social media prowess to help launch new initiatives and build a community. But it wasn’t all roses. 

The long hours in front of a computer screen caused fatigue and the beginning stages of burnout. Kaylin was grateful for the experience, but she felt her quality of life diminish. Thankfully, she found a release. “Puzzles became my form of therapy. I did a thousand-piece puzzle every week for about three years. And these were like your grandma’s puzzles with cheesy stock photography.”

As Kaylin finished puzzle after puzzle, she wondered if there was a way to elevate the game. As she looked at the finished pieces, she didn’t understand why something so difficult to put together had to be so displeasing to the eye. Finished puzzles should be aesthetically pleasing, but her finished puzzles were not worthy of being framed.

“The idea was planted right then to reinvent puzzles and modernize them. I wanted to work with emerging and established female artists. I grew up in Los Angeles and my Mom started an art nonprofit. I was always surrounded by the art community. Right away, I knew that this was an amazing chance to marry the two worlds. Because what is a puzzle? It’s a vehicle for a design with a unique image on it.”

Don’t Move Fast and Break Things

Kaylin didn’t subscribe to the “move fast, break things” business model. Instead, much like doing a puzzle, Kaylin slowed her roll. She stayed at her day job while gathering ideas about how a puzzle should look and feel. She had no background in product design, but she wanted a product that would be unlike anything on the marketplace – something that drew eyes on a store shelf and in the buyer’s home. 

“Because this was a physical product, I felt like I only had one chance out of the gate to hook people into the brand. I wanted to get it right. So I took my time with all of the packaging and the overall design. I wanted to include puzzle glue to encourage framing at the end. I wanted people to be struck by the thoughtfulness when they unboxed and completed each puzzle.”

Kaylin began to curate her aesthetic vision by saving anything that caught her eye on social media, be it a gallery exhibition or an artist sketch. She was always mindful that it wasn’t just about the image, but the act of puzzling itself. “I wasn’t just thinking of the finished piece, but also about detail, color, saturation, and layers. It all matters.” She compiled information on each artist and built relationships with them through social media.

Four years later, Kaylin was ready to jump to solo entrepreneurship. How did she know that it was time? “I just got more and more conviction that this was the right time to do something. My skills from the startup were transferable – I knew how to write content and how to build a community around a brand. The physical product was brand new. It wasn’t just the actual production, but it was also getting it from point A to point B, freight logistics, and manufacturing. It was a very steep learning curve.”

Don’t Keep Things Close to the Vest

Many people in business subscribe to this motto: “Keep things close to the vest.” This mid-19th century phrase has its origins in poker and other card gambling games. It’s not a part of Kaylin’s playbook. “I never listened to that advice, to be in stealth mode and worry about trade secrets or stealing IP. No, I was a solo founder and I needed other people to help me. I relied on my network for support, connections, and introductions.

“I talked to anybody who would listen. I got factory introductions. I hired a product designer from the School of Visual Arts in NY through a LinkedIn connection. I met everyone. I compared samples from different vendors – from actual puzzle pieces to packaging. This was important because all of the details mattered. Everything I asked for was custom, and I wanted to work with a manufacturer who believed in my vision. At the time, pre-launch, I was completely unproven and I needed to find partners who would be willing to work with me.”

Kaylin used her social media knowledge from the startup days to build up the excitement around the brand. She teased the puzzles on Instagram and built relationships with fans online. She began to reach out to artists she had been admiring from afar. Everyone wanted in. Prospective customers signed up for the mailing list. Artists enthusiastically agreed to participate for a percentage of profits. Kaylin settled on unique glass vessels to store the puzzles. This made Jiggy look and feel different from everything else in the marketplace. 

A Modern Approach to Puzzling

Don’t Be Afraid to Launch Out of Your Apartment

Jiggy Puzzles launched in Kaylin’s apartment in Brooklyn in November 2019. She spent $25,000 to get the company off the ground. There were two different-sized puzzles (it would eventually grow to several sizes) with a price point of around $40. “I’d been thinking about launching for four or five years, and then launch finally happened a few months before Covid.” She started selling off her first run of inventory and her company of one was moving in the right direction. In the early days, Kaylin shipped everything herself. 

When everyone was sent home in March 2020, Jiggy’s sales soared 500 percent, blowing through all its inventory in that first month alone. “At the beginning of March, everyone was looking for activities. They found us and we sold out immediately. It’s a good problem to have, but I was riddled with anxiety. This is the moment, this is the window – and I’m missing it. But there were all of these supply chain issues. I couldn’t restock quickly enough.”

Kaylin needed to think differently to maneuver through this mess. Unlike before, she didn’t have the luxury of time. She contacted her manufacturer and asked what they could provide her with and the answer was blank puzzles. Maybe she could find a workaround? 

Helping Artists While Maintaining Momentum

Kaylin realized she could solve her problem while helping local artists. She’d take the blank puzzles and ask creatives to produce what she later named Jiggy Originals.

“Jiggy Originals didn’t just help us. At the same time that Jiggy was sold out, the artists that we were building our community with had nothing. All of their exhibits and gallery shows were canceled overnight. No one was commissioning artists. So we distributed blank puzzles to artists and they created one-of-a-kind originals. We then hosted an auction (puzzles sold for thousands of dollars) and the proceeds went to the artist and Covid relief efforts. This carried us through the next few weeks and we were eventually able to restock.”

Experiencing art at the micro-level gave puzzlers a chance to get intimate with every thoughtful detail. Puzzlers flocked to each artist’s site and even bought prints directly from them. The Jiggy community was growing far beyond the brand. 

In business, people often talk about needing to adapt to unforeseen problems. But for Kaylin, it’s more than that. It’s about assessing the bigger picture and figuring out how to help everyone involved. “You have to be adaptable. Startups are always a moving target but especially during a pandemic. It’s important to be adaptable and to stay humble. It’s a learning curve and it wasn’t just about me.”

Designs are fun and often irreverent.

Operationally, Jiggy Puzzles remained a one-woman show for the first two years. She didn’t hire her first employee until only recently. “It’s not scalable if I’m doing it all on my own. The direct relationship with the customer is something I feel so protective over. Every social post, every email campaign, it’s me.”

In addition to selling individual puzzles, she has created a subscription model so that customers can experience a new puzzle every single month or even quarterly. For $29 a month, customers receive a 500-piece puzzle and membership in a club that includes exclusive content and opportunities to meet Jiggy’s artists. Kaylin is also exploring more non-profit opportunities and collaborations.

Kaylin sees that many people “don’t risk entrepreneurship unless they think that they have novel technology or a new invention. They think that they have to create something that no one has ever seen before. But, sometimes, the opportunity is right in front of you. It’s about putting your unique spin and different angle on an existing product for a new market.”

Jiggy Puzzles’ Instagram gallery always includes links to the artist’s page

As a female founder, Kaylin encourages other women to think big. “I’ve heard that women don’t apply for a job unless they can fulfill a large percentage of the job requirements, while men apply anyway. Entrepreneurship is the same way. If you wait until you learn one more thing or have one more year of experience, you may miss your opportunity. At a certain point, you have to bet on yourself.” Kaylin took the chance and it’s paying off in dividends. At the time of publication, Kaylin expects investment from Marc Cuban after a successful pitch on Shark Tank.

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Andrew Gazdecki
Andrew Gazdecki
Andrew is an award-winning serial entrepreneur with three exits. He’s the founder and CEO of MicroAcquire, the world’s most founder-friendly startup marketplace, and its rebellious child, Bootstrappers, which gives voice to the entrepreneurial underdog. When not building businesses, he writes for Forbes, Entrepreneur, and now, Bootstrappers.

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