"Windy City" - An Interview with Courtney Cohen, owner of Da Shayna Punims

Ever felt the tug to make something you can’t find on the shelf? We sit down with attorney and mom-creator Courtney Cohen, whose Florida-to-Chicago journey led her to build a joyful Jewish lifestyle brand from a single sticker into a growing catalog of hats, tees, totes, and more. The throughline is Jewish joy—captured in weekly challah, kids who treat stickers like art supplies, and designs that turn bagels and Yiddish into everyday style.Courtney walks us through her unconventional path: eight years in PR, a leap to law, then the itch to create fun, modern Judaica, Da Shayna Punims, that isn’t only for holidays or display cases. She shares how starting without a formal business plan forced fast learning, why bringing embroidery and printing in-house changed quality and timelines, and how she prototypes obsessively—auditioning fonts, testing placements, and refining until the piece feels right. We talk candidly about marketing in the age of algorithms, from TikTok’s vibrant Jewish corners to the bizarre reality of bots dropping geopolitics into soup videos, and why focusing on real community beats chasing viral spikes.The conversation widens into representation and culture: the promise and pitfalls of Hanukkah movies, choosing Jewish actors for Jewish stories, and the simple rituals that anchor identity when the world feels loud. Courtney’s big dream? Thoughtful expansion—dishware with a Kate Spade vibe, espresso cups with bagel wit, and traveling to markets like Jewish Joy Con to meet the people who wear and gift her work. Along the way, you’ll hear lightning-round favorites, from beloved Yiddish words to the holiday that makes everything feel cozy.If you care about creative entrepreneurship, Jewish small business, and the craft behind products that make daily life brighter, this one’s for you. Listen, share with a friend who loves bagels and good fonts, and tell us: what does Jewish joy look like in your home? Subscribe, rate, and leave a review to help more curious listeners find the show.TopDogToursTopDogTours is your walking tour company. Available in New York, Philly, Boston, & Toronto!Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.Support the show