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The CakeSpy Brings Her Tour de Sweet to Angel Food Bakery

By Patty Wetli | Wednesday, November 16, 2011

Jessie Oleson is the CakeSpy, dedicated to seeking sweetness in everyday life. Credit: Image courtesy of cakespy.com

I’m pretty sure Jessie Oleson, aka the CakeSpy, is my soulmate. As a child, she snacked on butter dipped in sugar, I spooned Crisco out of the can; we separately came to the conclusion that the only way to improve upon the doughnut is to double fry it; and we share the opinion that crumb cakes should be more crumb than cake. We even had the same idea for a blog focused on our addiction to sweets, except hers actually exists and is so wildly popular, it beget a book deal (could the movie starring Amy Adams be far behind?). If we weren’t such total kindred spirits, I’d have to hate her, but it’s impossible to hold a grudge against the woman who invented Birthday Cake French Toast.

Currently in the midst of a round of promotional appearances for her cookbook, CakeSpy Presents Sweet Treats for a Sugar-Filled Life, Oleson brings her Tour de Sweet to Chicago this Friday, Nov. 18, with a stop at Angel Food Bakery, 1636 W. Montrose, 3:00 – 5:00 p.m.

When her publisher approved a tour that substituted bakeries for bookstores, “I felt like I had won the lottery,” Oleson says. “I can’t imagine [the book] being enough material for a reading. For me, I’m much more of a ‘let’s hang out and eat baked goods’ kind of person.”

Angel Food, with its Trailer Park trio, seemed the perfect fit for Oleson, who prefers full-bodied, nostalgia-tinged sweets as opposed to fancy pants pastries like macarons, which she likens to a Tiffany box. “I love the trend of more refined versions of childhood treats,” she says, though “refined” isn’t necessarily a word Oleson would apply to her own endeavors, which fall more into the category of adventure baking. CakeSpy Presents includes recipes for Grilled Cheesecake, S’moreos (a mash-up of S’mores and Oreos) and Blondie-Topped Brownies, because why choose between blondies and brownies when you can have both.

Oleson, a Seattle-based graphic artist and illustrator by training, is the first to admit her creations owe more to Hostess than Le Cordon Bleu. “I’m not a very scientific recipe developer,” she says. Many of her confections begin as puns: “I’m a pun fiend. If I come up with a good pun, I’ll develop a recipe around it.” She also draws inspiration from the cross-country road trips she embarks on every few years. Caramel cookie waffles were a revelation in Montana and Nanaimo Bars (chocolate crust, custard filling, chocolate topping), which Oleson would request for her last meal, hail from Canada. Oh, Canada, we now forgive you for Celine Dion.

Having seen what the entire U.S. of A. has to offer in the way of baked goods, it’s surprising that Oleson, an East Coast native, opted to settle not in South Dakota, home of her beloved Chocolate Peanut Butter Cereal Bars, but in Seattle, home of people who complain about the dearth of New Andean cuisine. “I came here for a visit just for the weekend,” Oleson says of a scouting trip to the Pacific Northwest to gauge its livability. “My mom said, ‘Jessie, before you do anything rash, make sure you find a good bakery,’” which easily trumps “wear clean underwear” as the best piece of motherly advice. Ever.

Though she admits Seattle’s foodies “can get a bit precious, there is plenty of that granola stuff,” Oleson discovered a thriving cupcake scene, which she attributes to the city’s gloomy weather. “People need to be cheered up.”

Cheer is the common ingredient in her favorite sweets: they, like Oleson, don’t take themselves too seriously. “Everything I do has a slightly subversive tone,” she says, pointing to the audacity of putting out a  recipe for Pop-Tart (er, toaster pastry) sandwiches at the same time the First Lady is waging an anti-obesity campaign.

“We need a reminder to lighten up and enjoy the sweet, unnecessary things in life,” says Oleson. “I’d rather eat a wonderful truffle than

Jessie Oleson, aka the CakeSpy, will be promoting her new cookbook, Friday, Nov. 18, at Angel Food Bakery.

one of those god-awful 100-calorie snack packs.” If there’s an underlying theme to CakeSpy, it’s that it’s OK to treat yourself. “I’m not a big fan of dieting and denying,” she says, though she has learned to restrain herself from eating every last bite of everything she bakes. “I think it’s interesting how people are interested in sweets without indulging in them. A lot of people tell me they read my blog for a virtual fix. I do fear for people not indulging themselves. I hope that people are embracing those appetites, I hope my book will enable them.”

If Oleson comes across at times like a Butter Belt evangelist, that’s only because she believes in following your passions. After graduating from art school, she worked for a string of greeting card companies (“That’s what you do after studying illustration”) and eventually landed as an art director for a refrigerator magnet manufacturer. “It was my job to find cool art and witty sayings,” she says.

Though fulfilled artistically, Oleson felt her other interests, which included writing and baked goods, lacked a creative outlet. “I had a little meeting with myself,” she says. A freelance gig for the Seattle version of Daily Candy gave her the idea for CakeSpy. “I was always pitching cake-related things,” Oleson recalls. “I thought, what if I start to post cake things in that ‘daily find’ format?” She took on the persona of a “dessert detective agency” dedicated to seeking out the sweetness in everyday life, creating whimsical illustrations of unicorns, robots and Cuppy, the CakeSpy mascot, to accompany her posts. Six months later she was ready to quit her job and devote herself to CakeSpy full time (though her bosses temporarily convinced her to hang on part-time).

Take note all you fellow bloggers with visions of sugar plums, or dollar signs, in your head: This sort of success makes Oleson one in a million. No, scratch that, one in 100 million. “I think that I am in the minority,” Oleson concedes. “I’m unique, I’ve been very fortunate. A lot of people when they start a blog think they’re going to make a living, but that’s not realistic. You have to start a blog you’re passionate about and your genuine enthusiasm will carry over. Focus on your content first and then becoming rich and famous.”

It doesn’t hurt that Oleson also had the ability and connections to parlay characters like Cuppy into a line of products that eventually enabled her to open the Cake Spy Shop, a retail gallery where prints, mugs, t-shirts and, you guessed it, greeting cards and refrigerator magnets feature her signature artwork. She even remembers her first sale: Thirty-five dollars for an illustration of a cupcake eating a turkey.

This off-center humor was initially lost on publishers. “About two years ago, I decided I should have a book deal,” Oleson says. She hired a literary agent, pitched her concept and received a tsunami of rejection letters in a single day. “A lot of them didn’t get it. A lot of people wanted me to make something that wasn’t quite as lighthearted or they just wanted a cake pop book.” Eventually Sasquatch Books came around to her way of thinking. “I’m glad I held out to do the book I wanted,” Oleson says.

Pick up a copy of CakeSpy Presents at Angel Food this Friday and Oleson promises to not only sign it, but draw a unicorn for you. In addition to hanging out and talking baked goods, she’ll be giving away items from her gallery, including notecards and cupcake-unicorn-robot socks. If that’s not incentive enough, here’s a teaser:

Jessie Oleson’s Doughnut Upside-Down Cake

1/2 cup (1 stick) butter
2/3 cup packed dark brown sugar
18 to 24 mini-doughnuts, plain or sugar coated
1 1/3 cups all-purpose flour
1 cup granulated sugar
1 1/2 teaspoons baking powder
1/2 teaspoon salt
1/3 cup butter, softened
3/4 cup heavy cream
1 large egg

Heat the oven to 325 degrees F.

In a 9-by-13-inch pan, melt the butter in the oven while it is preheating.
Remove the pan from the oven and sprinkle the brown sugar evenly over the
melted butter. Arrange the mini-doughnuts in rows on top of the brown sugar.
In the bowl of an electric mixer fitted with the paddle attachment, beat the
remaining ingredients on low speed for about 30 seconds. Scrape down the
sides of the bowl, then beat on high speed for about 3 minutes, scraping bowl
occasionally. Spoon the batter, which will be fairly thick, gently over the doughnuts
so as not to disturb their careful arrangement. The batter should cover the
doughnuts, but you will still see their shape underneath.

Bake for 50 to 55 minutes, or until a toothpick inserted in the center of the
cake comes out clean. Immediately place a large heatproof serving plate upside
down over the cake pan; carefully flip the plate and pan over. Leave the pan in
place for a few minutes so that the brown sugar mixture can drizzle over the
cake, then lift the pan off. This cake is best when served warm, or the same day
that it’s baked.

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