My Mom, the Cookie Queen

Food & Entertainment

My Mom, the Sweet Martha Cookie Queen – Wit & DelightAsk any Minnesotan. They know. Sweet Martha’s Cookie Jar is a cult classic.

Come every August, over the course of two weeks, hundreds of thousands of people flock to St. Paul daily for the Minnesota State Fair to send off summer. (Only Texas can boast a bigger state fair, though Minnesota’s runs for a shorter timespan and has a larger daily attendance.) It’s a big deal ‘round here. And so is Sweet Martha herself, Martha Rossini Olson.

Perhaps because she sells one thing and one thing only and one thing really well: fresh-from-the-oven chocolate chip cookies. Sweet Martha’s outsells every other vendor at the Fair and offers just two sizes. Either choose a paper cone, holding about a dozen cookies, or an overflowing plastic pail, which fair-goers carry with pride.

The woman with the brunette bob, big smile, and cookie sheet is beloved around these Midwestern parts. So, is she that sweet? She sure is, says her daughter Jen Olson, who is equally as lovely, a mini Martha in some ways, and not in others. Though Jen lives in New York City, working in fashion marketing (previously with Club Monaco, currently with J.Crew), she continues to contribute to her mother’s cookie legacy, coming home every summer for the State Fair.

We chatted with Jen to get the low-down on her sweet mother, affectionately known as Martie. What’s it like being the daughter of the Cookie Queen? Jen tells us.

My Mom, the Sweet Martha Cookie Queen – Wit & Delight

Your mom is a legend in Minnesota. Tell us about growing up with Sweet Martha as your mother.
Yes! Sweet Martha, Martha Rossini Olson, and my dad, Gary, raised my brother, David, and me in Highland Park, St. Paul. My parents still live in the house we grew up in. It was a lively household, always full of laughter and music. My dad could be found banging out classic rock songs on the piano and mom humming along. The sound of the screen door slamming was constant as the house was always brimming with neighborhood kids and cousins. We were always on the move – riding bikes, building ziplines across the yard, having crab-apple fights and making haunted houses (even outside of October) took up most days. Martie banned the word “bored” in our house, and when we complained that something “wasn’t fair,” she told us that the only Fair was on Snelling Avenue, referring to the Minnesota State Fair – ha! Sugar cereals were only allowed on Sundays (dubbed “Sunday Cereal”), as it was pretty apparent that our hyper personalities did not need any added sugar.

Having Sweet Martha as a mom was pretty convenient when it came to after-school snacks – we had a freezer in our basement that was always fully stocked with cookie dough. We’d stash some dough, sneak up to our secret fort in the garage and watch Sally Jesse Raphael or The Simpsons. (Both were not allowed in the Olson household.) During summer months, we’d open a makeshift cookie stand in our alley open to the neighborhood. I think it’s safe to say it wasn’t hard to make friends with Sweet Martha as our mom.

I was a pretty outgoing kid. I was really into performing – my cousin Rachel and I had a music group called “The Olson Twins.” (Pretty original.) We’d make up songs and sing them at recess, using our friends as backup dancers. We like to think we were a successful pop group in our grade school. A friend (who maybe had a lying problem) even promised us her uncle could get us onto MTV. I also was in a circus performing arts school called Circus Juventas from ages eight to eighteen. It started with a small group of 30 kids who would meet at the local community center after school. We quickly became family, learning to trust each other while performing acts like flying trapeze, high wire, and Spanish web.

My Mom, the Sweet Martha Cookie Queen – Wit & Delight

What was your role in the cookie stand as a kid, and how has that role evolved as you’ve gotten older?
It’s amazing to look back and see how my role has evolved at Sweet Martha’s. I started working the cookie booth at eight years old, cracking eggs and annoying all the older, cooler kids. At that age, 16-year-olds seemed so old and so cool. I just wanted to be like them! I loved serving the cookies and would stand on a milk crate to be able to reach over the counter.

By the time I got to high school, all of my friends were working at Sweet Martha’s alongside me. We’d work a shift, then head to the Fresh French Fries stand to congregate for the rest of the night. (I love that standing around was an activity.) As an adult, I now manage one of our three stands, where collectively we have close to 600 employees over the 12 days. It’s a bit like camp; you really get to know people when you spend two straight weeks together! TLC approached us at one point about making a reality show. My mom and I met with producers in New York City, but we failed to provide any juicy incidents that would create drama for the show. It’s true – we have a blast and it tends to stay drama-free! We love pumping up the music when we’re busy and having dance contests.

Since moving to New York, I’ve always let my employers know early on that I’ll be taking off two weeks at the end of August. As you can imagine, they don’t fully understand the concept of the Minnesota State Fair and tend to think it’s my mom and I behind a little lemonade-like stand selling cookies. I let them think that way because the idea of that is just too cute.

“They don’t call her Sweet Martha for nothing.”

Take away the cookies. Tell us about your mom.
They don’t call her Sweet Martha for nothing. Martie is so sweet. She is always thinking of how to make others around her more comfortable. She is strong and opinionated, yet doesn’t dominate a conversation. She is careful and considerate and an amazing listener.

As the eldest girl of eight kids in an Italian Catholic family, she definitely took on a motherly role early on. You don’t walk into a party hosted by Martha Olson without every detail taken meticulously into consideration. The most delicious food, fresh cut flowers atop gorgeous runners on every table and candy from Regina’s Candies in crystal dishes sprinkled around the house. (We make a joke that you can’t walk five feet around the house without running into a candy dish.) She takes hosting seriously, and our families thank her for that!

One of Martie’s true passions, aside from baking, is interior design. She and my dad have been flipping houses in and around St. Paul for the last 10 years. She has a knack for transforming ordinary spaces into serious works of art. Martie can enter a house and know exactly what walls to knock down, fixtures to put up and materials to use. I’d say her design style is traditional with a twist.

My Mom, the Sweet Martha Cookie Queen – Wit & Delight

You’re now in your early 30s, working in fashion marketing in New York. Now that you’re a full-fledged adult with your own career, living across the country, how would you describe your relationship with your mom?
My mom was my biggest supporter of me moving to New York City. There was never a hint of hesitation in chasing my dreams and moving to New York. She likes to compare me to her mother, Rose Rossini, who moved from the little town of Adrian, Minnesota, to the “big city” of St. Paul in the 1940s. That was a big deal back then! She knew how important it was to experience life outside the city you grew up in and I’m so appreciative.

Though I’m across the country, I talk to my mom most days, if even just a text. It also doesn’t hurt that she absolutely adores New York. Martie tries to get out here as often as possible, sometimes up to once a month! We love to go to Bergdorf Goodman for lunch (tip: request the table that overlooks Central Park), take long walks from my neighborhood of Greenpoint to the Brooklyn Bridge, scope out brownstones to buy and renovate (girls can dream, right?), see a Broadway show (musicals are her favorite), and of course, shop.

“My mom would also repeat an old quote my grandfather, Reno Rossini, liked to say: ‘When wealth is lost, nothing is lost. When health is lost, something is lost. When character is lost, all is lost.’”

What are some take-to-heart lessons your mother has taught you?
My mom would repeat an old quote my grandfather, Reno Rossini, liked to say: “When wealth is lost, nothing is lost. When health is lost, something is lost. When character is lost, all is lost.”

She has always taught me to be true to myself and follow my own path. To be accountable for my actions and do the best work I can. One of her favorite poems is “The Man in the Glass” by Peter Dale Wimbrow Sr., published in 1934, which essentially says that at the end of the day, it’s yourself that you have to answer to.

My Mom, the Sweet Martha Cookie Queen – Wit & Delight

Say you have an entire day, anywhere on the globe, for some mother + daughter time. Where would you go, what would you do, what trouble would you get into with your mother?
Martie and I would travel to Italy for some low-key mother/daughter time. My mom’s side of the family is from Lucca, Italy, and we love to celebrate our heritage. We’d probably go to Siena to see the Palio, a bi-annual horse race between the city’s neighborhoods. Then we’d cruise through Tuscany, getting lost and exploring the countryside. I think we’d probably get in trouble…shopping.

What’s one way you’re definitely your mother’s daughter? And one “she didn’t get that from me” way in which you two are different?
Everyone thinks my mom and I look identical. I definitely got the Rossini genes – dark hair and dark brown eyes. I think that might be where it ends. Martie is chiller whereas I have a pinch of ADD. I’m goofier and a bit of an entertainer. My mom is also insanely tidy (known for her cleaning spurts we call “white tornados”) while I’m known to be a little messy.

“I’m proud of my mom for being a badass woman leader in our world today. She has built a successful business through calculated risks, never cutting corners and by making the best product she can.”

What are you proud of your mother for?
I’m proud of my mom for being a badass woman leader in our world today. At the age of 25, she (along with my dad and their partners Neil and Brenda O’Leary) made a dream into reality through perseverance and hard work. She has built a successful business through calculated risks, never cutting corners and by making the best product she can.

And finally, do you still like cookies?
Hell yeah! How can you ever say no to a made-from-scratch, fresh-from-the-oven chocolate chip cookie?

BY Megan McCarty - May 23, 2017

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May 23, 2017 9:12 pm

As a Minnesotan also now living in New York, I know the challenge of trying to get people to understand the wonder that is the MN State Fair. I love Sweet Martha’s and it’s so great to learn more about the woman behind the cookies! I’ll be dreaming of a cookie pail for the next few months…thanks for sharing this interview!

I’ve actually never heard of this cookie place, probably because I live so far away. Everything sounds so delicious and it’s great to know more about the founders behind the business!

Charmaine Ng | Architecture & Lifestyle Blog

May 25, 2017 7:28 am

I LOVE these cookies at the fair (along with the rest of Minnesota)! Thanks for the interview <3

[…] True, it’s not even Memorial Day yet, but this one’s for my Fair folks out there – Wit & Delight […]

May 25, 2017 1:03 pm

I LOVE these cookies and especially the fair! I lived in Minnesota for 2 years and couldn’t get enough of either. Miss that place!

June 11, 2017 6:55 am

This is such a cute story. I want to go to the Minnesota state fair now – I live in England though so not sure that’s gonna happen wahhhh!

August 20, 2020 4:22 am

She is my third cousin. Why is she making such a big deal about being 25 percent Italian?

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