career memos

Reinventing the Puzzle Industry and Getting On Shark Tank with Kaylin Marcotte, Founder & CEO at Jiggy

September 15, 2021

EPISODE DESCRIPTION Jiggy is a DTC brand for beautiful puzzles featuring the designs of emerging female artists. Founder & CEO Kaylin Marcotte was inspired to launch Jiggy after enjoying the ritual of finishing a puzzle week after week, but finding the designs dated and ordinary. Self-care was heating up, and it was the ultimate way […]

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Jiggy is a DTC brand for beautiful puzzles featuring the designs of emerging female artists. Founder & CEO Kaylin Marcotte was inspired to launch Jiggy after enjoying the ritual of finishing a puzzle week after week, but finding the designs dated and ordinary. Self-care was heating up, and it was the ultimate way for her to find presence and unwind without the glare of screens and technology.

As the first employee for trending newsletter company theSkimm, Kaylin quickly caught the entrepreneurial bug, and after bootstrapping Jiggy for awhile, she landed an amazing opportunity to pitch the sharks on Shark Tank at the beginning of the pandemic. 

Kaylin shared the behind the scenes details of what it was like to be on the show during the beginning of the pandemic, how she prepared for the influx of attention, and what came out of it, along with the importance of taking bets on yourself. I know you’ll enjoy hearing her story today. Listen to Episode 41 of The Career Memos Podcast available on Apple PodcastsSpotifyGoogle Podcasts, and Stitcher.


From theSkimm to founding Jiggy

After a couple of years working in data management consulting, Kaylin joined female-founded newsletter company theSkimm as their first employee, crediting the small team environment as what initially sparked her entrepreneurial mindset. While the role fulfilled her and provided so much space for creativity, ownership, and responsibility, the days were long, and it wasn’t uncommon for Kaylin to spend an evening working on a puzzle as a way to escape and unplug from the constant stream of screens and technology.

At this moment in time, conversations around self-care, meditation, and burnout were common and the calming ritual of putting a puzzle together became Kaylin’s favorite way to be present and mindful. It got to the point where she was finishing a 1,000 piece puzzle every week, but the designs were often limited and dated. She wondered, “what if I could really connect to this? What if this was a really compelling piece of art?

It was there that the idea for Jiggy was formed. From the packaging to the puzzles themselves, they are stunning works of art that can be maintained and preserved afterwards using puzzle glue.

Kaylin’s golden opportunity to pitch Jiggy on ABC’s Shark Tank

While Kaylin was bootstrapping the business and the COVID-19 pandemic had just begun, the demand for her puzzles had gone through the roof. Inventory was selling out and she was considering a secondary supply chain until opportunity came knocking, in the form of Shark Tank!

Going into the trenches with the sharks and not only pitching Jiggy, but potentially walking away with capital and leveraging the platform of the show, was too good to pass up. Kaylin recalls that it was a wild, once in a lifetime experience, but she went in prepared, did her homework, and walked away with a deal from billionaire investor Mark Cuban.

As she reflects back on what it took to prepare, she stresses how important it is to know your key metrics, like your revenue, CAC, and lifetime value. But beyond that, share your vision. Your energy and confidence is contagious and the investment decision is just as much based on the founder as it is on your idea. You have to communicate in such a way that instills trust and a conviction that you are the one who has the best ability to bring this to life.

There were many other ripple effects from doing the show, including other partnerships, wholesale and retail collaborations, and additional investments. It’s a major lead generation opportunity.

Take a chance and bet on yourself

One of the best pieces of career advice Kaylin has ever received came at a time when she was continuing to evaluate new job offers while she was growing Jiggy. While in the throes of conversation at a mastermind group, a woman inspired her to rethink saying yes to that offer, and to bet on herself instead.

Kaylin was at a crossroads. She could say yes to the role and help another company build their vision, but was she ever going to feel any more ready to go all in on Jiggy than she felt now? 

There’s always that moment of second-guessing yourself before you take a leap or make a big decision. You might be wondering if you could be a little more prepared or ready, and maybe you’re not a typical risk taker. But if you take a calculated risk, just dive in and bet on yourself.

And while running Jiggy has its glamorous and not-so-glamorous moments, it’s being so deeply connected to the mission that helps Kaylin get through the more tedious moments.


“Being a part of such a small team, coming in at the ground floor is such a unique experience to just dive in. It really inspires that entrepreneurial mindset.”

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Your Podcast Host and Career Coach

Over the last 12+ years, I’ve done everything from work as a global human rights activist to lead marketing & partnerships initiatives at companies like Postmates and Apple. I’ve started businesses, lived in multiple cities around the world, pivoted careers more than once, and know what it takes to turn career goals into a reality. As a career coach & consultant, I’m passionate about sharing all that I’ve learned with you, helping you define tangible goals, and providing you with the tools and direct feedback you need to achieve them.

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