Jennifer Olson may have devoted the last eight years of her career to Dôen, where she serves as the label’s head of community and brand engagement, but her allegiance to another business goes even further back. In 1979, Olson’s parents launched Sweet Martha’s Cookie Jar, which has since become a mainstay of the Minnesota State Fair—and for 12 hectic days each summer, Olson surrenders her life in Los Angeles to sell some cookies.
Here, Olson pulls back the curtain on a typical day working the fair. Vogue: What’s the story behind Sweet Martha’s Cookie Jar? Jennifer Olson: Sweet Martha’s Cookie Jar was born in 1979, dreamt up by my mom, Martha Rossini; my dad, Gary Olson; and their best friend, Neil O’Leary. My mom grew up in St. Paul, close enough to the fairgrounds that the Minnesota State Fair was a summer tradition for her family every year.
She also spent her childhood baking alongside my grandma, Rose Rossini, making desserts for their family of 10. After college, Martha, a.k.a. Martie, became an elementary art teacher—a career she loved for over 30 years. But she also had an entrepreneurial streak. In the 1970s, that itch turned into Sweet Martha’s Yogurt Shop, a side venture in downtown Minneapolis. That’s actually where the cookie story begins.
She and her partners applied to the Minnesota
She and her partners applied to the Minnesota State Fair to sell yogurt and cookies, and were shocked when the fair said yes to the cookies but not the yogurt. So my mom, dad, and Neil got to work, combining each of their mothers’ cherished recipes until they landed on the chocolate chip cookie Minnesotans know today. This year marks Sweet Martha’s 47th at the Minnesota State Fair; what began as a 9′ x 11′ plywood booth built in the backyard has grown into three permanent locations across the Fairgrounds.
How far in advance does the Rossini/Olson family start prepping for the Minnesota State Fair? We usually start preparing for the Minnesota State Fair in February so we’re ready to open by the end of August, which includes hiring over 750 staff members. That’s no small feat, especially since many of the people we hire are students just getting ready to head back to high school or off to college.
Katie Atlas, my childhood neighbor and babysitter, is our master scheduler and keeps everything running smoothly. From there, we prep each of our three permanent stands—cleaning them top to bottom and stocking up on everything we need to feed the hungry fairgoers. Since we mix and bake our cookies from scratch and sell them straight from the oven, our ingredients aren’t delivered early—they come in fresh each night of the fair.
Many of our incredible crew come back
Many of our incredible crew come back to help year after year, and with more than 40 years of Minnesota State Fairs under our belt, we’ve got it down to a science. What does a day in your life look like for you during the week of the state fair? I usually get to the Fair by 7 a.m. to join my cookie family and get the booth ready to open by 8. (More people want breakfast cookies than you’d think!) We like to start the morning with what we call “Classical Hour”: a calm, quiet stretch where we play classical music and soak in the cool early morning before the madness kicks in.
Then production starts. Each batch of dough begins in a mixing bowl, and one bowl makes 5,000 cookies. Our walk-in ovens bake 2,000 cookies at a time, and with 22 ovens across our three locations, we have the capacity to bake 44,000 cookies in 12 minutes. On an average day, we make about one million cookies, and on our busiest days, as many as three million. Over the 12 days of the fair, we go through about 197,000 pounds of sugar, 143,000 pounds of flour, 125,000 pounds of chocolate chips, and 58,000 pounds of eggs.
Tell us a little about the family members who join you for the week-long affair. I come from a big family—my mom is one of eight siblings, my dad is one of seven—so there’s no shortage of aunts, uncles, and cousins who come in to help crank out cookies during the fair. We usually have at least 20 family members working each year, which basically makes it our annual family reunion.
It doesn’t stop with us: our partner Neil,
And it doesn’t stop with us: our partner Neil, his wife Brenda, and their son Charlie have loads of relatives who pitch in each year too! I have one sibling, an older brother named David, who I’ve always been close with—people used to think we were twins. We’re in lockstep when it comes to our working styles, and some days we might have too much fun together. His wife, my sister-in-law Erica, handles all of our PR.
There are cousins aplenty. Cousin Lucia runs the clipboard and makes every day fun for the employees. She’s the one making our TikToks, getting everyone to dance, and encouraging our theme days, like Crazy Hat Day and Crazy Sock Day. My cousin Will is an engineer, and he runs the baking at one of our booths—he’s actually built a mathematical system to track how many racks of cookies should be in the ovens based on the size of the crowds.
My cousin Mikey takes time off from his job at Apple and flies in from San Francisco to join in the festivities. It’s been so much fun watching all my cousins grow up and become such a vital part of the family business. I’m so lucky to have my husband, Aidan, who stepped right into the family business alongside me. We met six years ago, and it’s no small ask to sign up for these crazy 12 days every year—but he’s embraced it completely.
He’s my rock and my emotional support system,
He’s my rock and my emotional support system, and I honestly couldn’t get through the fair without him. Even Aidan’s parents come in for a few shifts each year! How do you dress for the fair? Do you lean into being a fashion girl or just sport the brand merchandise? Comfort is key. I’ve got a uniform: our bright yellow Sweet Martha’s employee tee paired with vintage fatigue pants, old Dickies, or Patagonia Baggies when it’s hot.
This year I ordered some yellow Human by Nature shorts to go with our color theme. We also have an array of Sweet Martha’s merch—hats, sweatshirts, shorts—so I’m usually decked out in some kind of SMCJ gear. I also swear by New Balance sneakers for comfort and style. Tell us a little about the Sweet Martha’s merchandise that always sells out! How did it come to be and who designs it?
Before we ever had an official merch line, we did a one-off T-shirt with Vampire Weekend—the collaboration came about after Ezra Koenig and Jake Longstreth had my mom on their podcast, Time Crisis, which was adorable. We sold the tee when they toured through Minneapolis in 2019, with proceeds going to the St. Paul Public Library, which my mom is passionate about supporting as a former educator.
They even brought Martie out onstage during
They even brought Martie out onstage during the show to say hello to the crowd and played “Martha My Dear” by The Beatles as she walked off. Then in the summer of 2020, when COVID canceled the Minnesota State Fair and we suddenly had some extra time on our hands, we officially started making Sweet Martha’s merch. We began by tie-dyeing tees with our logo on them, and customers loved it.
After such an overwhelming response, we decided to grow the line the following year, with guidance from my dear friend Aaron Levine, who I worked closely with back in the day at Club Monaco. We’ve also done some incredible collaborations since then, including the embroidered cookie shorts we made with Petrified Good—a nod to the Grateful Dead’s dancing bears. And we’ve continued collaborating with bands that come through town, like The Black Keys and, most recently, LCD Soundsystem, with proceeds always benefiting the St.
Paul Public Library. It’s been so much fun being able to combine my love for the family business with some of my favorite bands. What will you miss most about the Minnesota State Fair? Our employees! When you hire over 700 people, you get so many different personalities. The majority of our staff are between 16 and 21, and it’s so much fun getting to hang out with them and learn what’s trending and popular these days (FYI, “bet” is still a thing).
Everyone brings such different, interesting skills
Everyone brings such different, interesting skills to the table. Our senior staff are just as essential—many take time off from their regular day jobs or come in after work just to help us run the ship. For example, my aunt Mary is a public school teacher by day and comes in to help at nights! Not all heroes wear capes—some wear aprons dusted in flour. Relative or not, these people are my cookie family, and we couldn’t do it without them.
This interview has been edited and condensed for length. See pictures from a typical day at the Minnesota State Fair for Olson and the rest of the Sweet Martha’s team below. I spend most of my time at our newest location on Machinery Hill. Screenshot Oven hot, baked on the spot! My mom, Martha, and our employee Nick, serving customers at the fair. My brother Dave and I in front of our observation window!
We serve our cookies in two sizes—a cup (pictured here), and by the bucket. I have over 20 family members that work every year. These are my cousins on the Rossini side—Lucia, Tony, Will, and I. The SkyGlider is a must at the Minnesota State Fair. One of my favorite new vendors is the Turkey Jive. They sell southern comfort food from North Carolina. This is Cayden, Cheri, and Michael Neal.
Crazy hat day at the booth
Crazy hat day at the booth! Sneaking a smooch from my husband, Aidan Klimenko. My cousins Michael and Lucia Anderson with our classic bucket of cookies. Screenshot Blue shorts day! My friends Theo Chapman and Romeo Okara came from LA and NYC to check out the fair madness. Working at Sweet Martha’s feels like camp… we have the best kids, with many returning year after year. We make sure to grab Polaroids of everyone to keep for the mems!
Mama Martie and I getting loose in the merch closet. My friends Peter Bian and Linda Cao are new vendors this year with their Chinese street food. The ube cheesecake wontons are INSANE! Selfies in the back of the booth! Our location near the Grandstand is our busiest location. It’s at the intersection of one of the fair’s entrances and the Midway. Star employee Idile works at both Sweet Martha’s and the All You Can Drink Milk Stand.
Talk about the ultimate combo. Minnesota’s own Tre Jones (of the Chicago Bulls) and Tyus Jones (of the Denver Nuggets) try to make it to the fair every year to visit Martha. One of my favorite stands, the Palestinian-American vendor Baba’s, is conveniently located right across the street from our booth. Pickles on a stick, daily! My sister-in-law Erica Dao and I keeping the vibes high.
Pickle pizza. Period
Pickle pizza. Period. We use our mixers and ovens at a much higher capacity than they are made for. My husband Aidan and brother Dave are always fixing something! Cousin Lucia winning a stuffed bear, her pride and joy. My mom and mother-in-law, Mary Karen Lynn-Klimenko. So nice of my in-laws to help out! Walking out from another great day at the fair with cousin Rose and uncle Bill!
Me and my bud chef Andrew Zimmern early one morning before the madness begins. AZ had an extensive collection of Sweet Martha’s merch.
Source: www.vogue.com
