That Jessie Oleson is a woman of many talents—baker, writer, illustrator, businesswoman—is impressive. That this Seattle resident manages to make a full-time living by harnessing all those talents under an umbrella enterprise called CakeSpy is damned improbable. Under the CakeSpy flag, she blogs at; sells cute, anime-esque illustrations and merchandise; shares recipes for gloriously-bad-for-you sweets such as Cookie Cake Pie; and writes books—her first, CakeSpy Presents Sweet Treats for a Sugar-Filled Life, is due to pop in October via Sasquatch Books. We caught up with the sugary muse to find out more about her book and how she brought all her talents together so successfully.

Who were you before CakeSpy? And how did you become CakeSpy, anyway? It all seems like a lot to sort out.
It all started in 2007. My only real job out of college had been at stationery companies as a designer. I was getting married, and I was like: “Gosh, I kind of want to do something different.” I sat down and I came up with this: “What I really love is writing, illustration, and cake. So, how can I put those together?”

The timing was excellent, because I was going around trying wedding cakes, and I kind of felt like a little cake spy. I thought: “I don’t know what I’m going to do with this idea, so maybe in the meantime I’ll start a blog; I guess that’s what people do.”

I started, based on requests, selling prints and postcards from artwork featured on the site, and that has become my bread and butter. After six months, I was able cut down to part time at my job, and after about nine months, I was able to quit entirely. Then a year ago, I took over a retail space. It’s a gift shop, focused on food-based art.

Was that kind of a scary leap, moving from the Internet to a real physical space?
I kind of feel like everything that’s happened with the site has been both scary and a natural progression. I’m paving this path kind of on my own—I don’t know anyone who has done quite what I do, with baking and writing and illustration. I hope that people keep on responding to it, because I want to keep doing it.

Tell me about your upcoming book CakeSpy Presents Sweet Treats for a Sugar-Filled Life.
About two years ago I decided I wanted to do a book without any real knowledge of how one did this. But I learned. I put together a book proposal, got an agent, and put it out there to a lot of publishers. I got rejected by every single one.

After that I was like: “I hate publishing.”

Around the holidays, Sasquatch Books came back to me and they said: “Gosh, we can’t get you out of our minds—would you come back and meet with us again?” So I dusted off my book proposal, and they gave me an offer the same day. It’s a lot of things that had already been featured on my site, so it was a matter of reworking and presenting them in a way that would really feature the artwork. It’s between 60 and 70 recipes, and there are illustrations on every page—kind of New Yorker–like drawings, but baked goods.

What are your favorite recipes in the book?
Cadbury Creme Eggs Benedict—that one is like a crowning achievement for me. One that is simple is the Red Velvet Cake Shake—that’s a beloved classic. Oh, and certainly Birthday Cake French Toast.

Let’s talk baking trends for a moment—what’s going on out there?
My little pet project to bring to the masses is the Nanaimo bar. It’s a Canadian specialty; a no-bake bar with a chocolate graham cracker crust, a custard middle section, and chocolate topping. Those are just insanely delicious.

In general, a return to no-bake treats is going to emerge. I also see an overarching trend of return to all sort of home art, from knitting to DIY projects and especially pie.

As a food writer, I sometimes have doubts about what I’m doing, what with all the crazy stuff going on in the world—like, maybe I should be practicing law, or fighting fires, or something. Are you ever gripped by existential doubt about your profession?
Yes. There was this children’s book that I had where it said basically your job in life is to go out, see the world, experience things, and ultimately make it a better place—so, I’ll have moments where I’ll ask, “Am I doing something that really matters and makes the world a better place?”

But I was at my store not too long ago and this customer came in, wearing hospital scrubs. And I said: “Oh man, you’re a doctor.” She said: “Yep, I’m an emergency room surgeon.” And I said: “You’re saving lives!” And she said: “Well, you are too, because on my break, I like to go to your website and read it and feel like the world is still a good place.”

Talk about Scrooge and his heart growing 10 sizes or whatever. OK, I’m not doing brain surgery, but I do have an impact. If I can offer that little sugar coating that makes many people’s day a little bit nice, I do think it matters.

In that way, you and I are agents of delight for people.

Here’s an easy (some might say insane in the best way) recipe sneak-peek from Oleson’s upcoming book to take you a little further into her world.

Glazed Cinnamon Rolls Stuffed with Chocolate Chip Cookie Dough
From CakeSpy Presents Sweet Treats for a Sugar-Filled Life by Jessie Oleson

It’s true: stuffing cinnamon rolls with chocolate chip cookie dough really does make them more delicious. I know this, because one serendipitous morning, I happened to be making cinnamon rolls while concurrently preparing some cookie dough for a Cookie Cake Pie. I suspected that there was a sweet possibility for recipe fusion here, and I was right: the resulting rolls were gooey, high-fat, high-carb heaven. While I use the pop-and-bake variety of cinnamon rolls, feel totally free to use your favorite homemade version.

1 package pop-and-bake cinnamon rolls with glaze
8 heaping tablespoons chocolate chip cookie dough, homemade or store-bought

Preheat the oven as directed on the cinnamon roll package.

Pull the paper tab on the package of cinnamon rolls until you get that festive “pop” that means the feast has been unleashed. Separate the rolls and gently unroll one of them.

On a separate work surface, roll a tablespoon of cookie dough into a thin log (using floured hands if the dough is sticky); it should be slightly narrower than the width of the cinnamon roll. Place the log of dough on top of the uncoiled dough, and gently re-roll. Repeat with the rest of the rolls.

Place the rolls on a lightly greased pie plate or 8-by-8-inch baking pan and bake according to the package directions.

Warm the packaged glaze in the microwave for about 10 seconds, or until pourable. Liberally glaze the cinnamon rolls and serve immediately.

Images courtesy of CakeSpy

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