Ole's Cannoli's path to Minnesota State Fair has been thrilling, tedious, terrifying

Mother-daughter team Pam Olson and Marta Lindsey say being first-time vendors at fair is the fulfillment of a 10-year dream
Mother-daughter team Pam Olson and Marta Lindsey say being first-time vendors at fair is the fulfillment of a 10-year dream
Courtesy of Marta LIndsey

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The Minnesota State Fair begins today, and among its more than 300 food vendors and 450 edible snacks will be Ole's Cannoli, a brand-new food stand in Heritage Square run by the mother-daughter team of Pam Olson and Marta Lindsey, two self-described "fair nerds" who say that opening a food stand at Minnesota's epic Get-Together has been something they have dreamed about and worked toward for 10 years.

We talked with Lindsey about Ole's Cannoli's long journey to the fair, what it takes to score one of the rare and coveted food stands, their hectic preparation for the last three months, and what's going through her mind on the eve of her first day as a seller at the massive, 12-day event.

The idea for Ole's Cannoli, Lindsey says, was born 10 years ago when her mother came to visit her in Boston, where she was living at the time. Playing tourist, they stopped at a little shop that sold cannolis -- and they had an instant revelation.

"It happened very immediately, " Lindsey says. "It was like, Oh, my god, this cannoli is amazing! And this should be at the State Fair, because it's so good, and the fair is all about food, and people need to experience this."

Lindsey says the dessert they had was somehow different from a run-of-the-mill cannoli. "There's no way you can get a good cannoli in Minnesota," she says. The best ones tend to be in East Coast cities with large Italian populations.

The idea of re-creating that cannoli and selling it at the fair was a natural, she says, because she and her family are obsessed with the State Fair. "It has been a thing since I was literally a six-week-old baby. It's a tradition more important than Christmas to us." Though she has lived in San Francisco now for several years, she still flies home to Shoreview every year during fair time, "because there are certain things we must do, and my life doesn't make sense if I don't experience the fair."

Still, the idea of selling food at the State Fair was little more than an idea at the time. "We talked about it a lot," Lindsey says. "But you know how these things are. And then a few things happened where I was like, Oh, my god, we actually have to pursue this or stop talking about it. The next year at the fair I overheard this old man who was saying something about 'I've got an idea for a food stand at the fair, blah, blah, blah ...' And I'm like, what if I'm that guy in 30 years still talking about my cannoli idea? I can't be that guy. The next year I went to the fair and from a distance, I didn't have my glasses on, and I saw this sign, and I thought it was a picture of a cannoli, and my heart just starting pounding, and I was like, 'Somebody beat me to it!'

Spurred into action, she began researching how to apply to the fair. But after talking with a few people, it became clear that getting chosen as a vendor required more than a good idea - you also need experience as a concessionaire.

Ole's Cannolis with pistachios and chocolate chips
Ole's Cannolis with pistachios and chocolate chips
Courtesy of Marta LIndsey

After talking and daydreaming about the idea for a few years, "I started really doing the work in 2006, 2007," Lindsey says. " There was a phase where it was like, OK, what's everything I need to learn, what's everything I need to figure out. That was my hobby. That was my weekends." She took Small Business Administration classes and looked into selling their cannolis at street fairs at her home in San Francisco, which was an elaborate and tedious process of setting up a small business, applying for city permits, and health certification classes.

Lindsey and her mother sold their cannolis at San Francisco street fairs in 2008 and 2009, and they were a hit. "We had one Italian guy who said our cannoli were better than his mother's and literally begged us to open up a permanent shop! But the only place we want to be is the Minnesota State Fair."

Finally, Lindsey and her mother thought they were ready, and three years ago they formally applied to the State Fair. Their application was not just the simple required form - they submitted an eight-page, full-color, professionally designed brochure highlighting their experience and showing that "we understood the fair, we have our act together, we're not joking around," she says. "Really trying to make it a pitch, and a vision."

And they heard nothing for three years.

As the fair approached this year, Lindsey was resigned to the fact that her dream and years of hard work might not pay off. Applications to the fair are kept on file for three years, she says, "and I was like, well, I'm not going to reapply, because I think this is such a reach. What are the odds at this point?"

And then, just three months ago, she received an email from fair officials. "It was like, 'Hi, we know it's been a while, but we're wondering if you're still interested in bringing your cannolis to the State Fair.'" She called her mom, they screamed a little, and then realized they had to get to work.

The last three months, she says, have been a "whirlwind." Ole's Cannoli was assigned to a former cotton candy stand, a tiny 10-by-15-foot space inside the entrance to Heritage Square, that needed extensive upgrades to meet code. "You've got to have three sinks for washing stuff. You have to have a completely separate sink for hand washing. We have to tell the Department of Agriculture every single piece of equipment we're using. Every single container. It is meticulous. Like, what is the make of the commercial coffeemaker you're using. Specifically the model number."

Lindsey's mother has been rebuilding much of the stand herself and researching online for used equipment such as huge commercial refrigerators. Lindsey had to research employment law, get workers compensation insurance, and read the fair's 50-page manual for concessionaires.

One of the biggest concerns was how to physically fill so many cannolis. "I was chatting at a party with this guy and telling him about this, and he's like, "Have you ever thought about a sausage filler?' Which led us on this whole path of figuring out the perfect solution for being able to fill cannoli fast."

They also have to figure out how to transport the cannoli ingredients and supplies from offsite onto the fairgrounds during limited windows throughout the day, since their storage space at the fair is so tiny.

"I keep thinking of it all as a video game, where it's like, if you solve these five things then you get to the next level. And here we are finally at whatever the top level is. And holy cow, I'm so excited and terrified."

Today is D-Day for Ole's Cannoli. Lindsey says her credit card is maxed out, though many suppliers and their employees thankfully don't need to be paid till the end of the fair. They have hired six teenagers to help staff the booth in two shifts, and Lindsey's husband will be helping out, but Lindsey expects that she and her mom will be working at least 14 hours a day.

"My mom did buy a cot to put behind the stand, in part because I'm pregnant. This is just the year that things are happening in my life," she says.

The mother-daughter team will be selling two kinds of cannolis -- the traditional shell with a sweet ricotta cheese filling and another dipped in dark chocolate. The cannoli are filled and dusted with powdered sugar and can also be dipped in toppings -- traditional pistachios, mini chocolate chips, and even decidedly non-traditional sprinkles. Befitting the Ole's Cannoli name, they have given their Italian desserts a bit of a Scandinavian twist by also serving Swedish coffee, which Lindsey describes as a "very dark, intense, smooth roast. It's really good. And it's really strong." The cannolis are $4 for the plain and $5 for the chocolate-dipped, with toppings an extra 50 cents.

Lindsey says she has penciled out how many desserts they have to sell to break even. "It's a lot of cannolis," she says.

The Heritage Square site is a "challenging" location, Lindsey says, because it's in a corner of the fairgrounds and a bit off the beaten track.

"There's a lot of faith that goes into this whole thing," she says. "Since the beginning, we've felt we were really onto something that was really right for the fair. You hope it all works out. That's why it's so nerve-wracking right now. I'm like, 'Please, please come. You will love it. But please come!'

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