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Ask the Baker: Jessie Oleson of CakeSpy

JavaCupcake Note: This is the sixth post in the “Ask the Baker” series featuring interviews with bakers and bakery owners! Click here to see the complete list of bakers being interviewed.  This is the last interview until June! My husband is coming HOME and “Ask the Baker” will be taking a break!

From the CakeSpy website: is a Dessert Detective Agency dedicated to seeking sweetness (literally) in everyday life. We do this by writing about bakeries, conducting baking experiments, and picking the brains of bakers and food artists, and finding awesome products for lovers of baked goods.

The Cakespy crew is comprised of several Cake Gumshoes throughout the US, and is headed up by Head Spy Jessie Oleson. Jessie O is a freelance writer and illustrator, whose writing appears on, and has a weekly column on Serious Eats, and who has illustrated for various companies including Microsoft, iPop, All-Mighty, Taylored Expressions, and is a regular contributor to Taste of Home.

CakeSpy Headquarters is in Seattle, Washington.

Photo credit: Erica Daking, All-Mighty Clothing

You can find CakeSpy all over the web!

Recipe/Ingredients questions

What do I consider to be the perfect cupcake?

Vanilla buttery cake with pink buttercream. Basically, the cupcake character I draw all the time. I draw what I want to eat! Constantly!

How many times do you have to re-do a recipe?

I am guilty of being a little bit ADD with baking — I get bored. I like to mix it up, so I will rarely do a recipe more than 2x.

My favorite cupcake recipe?

I love the basic cupcake recipe from Magnolia Bakery’s cookbook – but I love to mix up the frostings.

Where do you purchase all those fun different sprinkles you use to decorate your cupcakes with?

The Home Cake Decorating Supply Company! And Bake it Pretty, online!

How do you get your cupcakes all the same size?

eh…They’re maybe not always all the same size, but I imagine that measuring out your batter carefully would be the key here.

Do you have a Vegan Chocolate cupcake recipe?

As a matter of fact I do! It’s the avocado cake that I found on Joy the Baker. It’s vegan but also the most decadent chocolate cake I’ve possibly ever come across. Here:

Do you have a delicious recipe for a trans-fat-free cupcake?

um…I don’t think so! Maybe that vegan one is though?

What is the best cocoa to use?

I know that some people get all fancy, but I actually like Hershey’s Special Dark.

I love buttercream… what’s your favorite recipe for it?

My favorite way to do it is usually sans recipe – start out with 2 sticks of butter at room temperature, creaming it until fluffy, and then adding confectioners’ sugar and a dot of vanilla (and whatever flavorings etc) until it’s reached a desired consistency.

How do you make the icing just the right sweetness?

I taste it as I add in the sugar – it is easy to add too much. I love sweetness but too much is too much!

How do you get great control of a pastry bag and make those mile high swirls of perfection on top of each cupcake?

Still working on that one!

Inspiration questions:

Did you always have a passion for baking?

I absolutely did–my mom says that my first real word (other than mama and dada) was “chocolate” after tasting frosting for the first time. Yeah!

What inspires you the most? Love of cupcakes or love of making things people enjoy?

What inspires me? Love of making things people enjoy. I like eating other people’s baked goods better than eating my own!

Where do you get new ideas for new cupcake and icing flavors?

The internet, silly! Isn’t that what it was made for?

How do you come up with new, creative ideas for decorating cupcakes?

Um, definitely Hello, Cupcake (the book) and their new follow up!

With the internet and easy availability of so many recipes and decorating ideas, how do you come up with new and unique recipes that someone else hasn’t already done?

I just don’t google it. Because if I have an idea and google it, someone has probably already done it. But if I don’t, I can at least pretend the idea was mine and have my own spin on it.

This and more original CakeSpy artwork can be found for sale at

Fun questions:

What’s your favorite part of cupcakes?

The part where the frosting and cake touch. Magical!

How can you be around all that yummy and not eat it all up?

I do eat it up though.

Would you bake me a cupcake that wouldn’t make me gain any weight please?

I can draw you one!

Do you ever get tired of the site or smell of cupcakes?

N.E.V.E.R. When I met a girl who made custom perfume once, I asked her if she could make me smell like a freshly baked birthday cake, so does that answer your question?

Can I live in your kitchen and be your personal taste tester?

OK! You have to clean the dishes though. Sorry.


Note from Betsy about Jessie:

Jessie recently bought the Bluebottle Art Gallery in Seattle and have transformed it into her very own CakeSpy Shop!!! This weekend is the GRAND OPENING of the shop and I couldn’t be happier for Jessie!  For more details of the opening, visit the event page on Facebook!

Photo Credit: Jessie Oleson of CakeSpy

I had the pleasure of meeting Jessie for the first time at Trophy Cupcakes when Rachel of Cupcakes Take the Cake came into town.  It was my first ever cupcake meet-up and it was a blast!! Jessie was as sweet in person as she is online and I was thrilled to be able to have an opportunity to chat with her.  My daughter, Emily, absolutely adores Jessie’s art and her famous Lil’ Cuppie!

Rachel from CTTC, Jennifer Shea owner of Trophy Cupcakes, Jessie Oleson of CakeSpy, Unknown, Betsy Eves of JavaCupcake

Jessie and my daughter at Cupcake Camp Seattle

Knowing Jessie has been such a pleasure.  I never realized what a blessing it would be to someway be involved in the cupcake community… And although I’m a newbie, Jessie has made me feel completely welcomed and appreciated for what I do.  Thank you Jessie for being a kind, welcoming, strong woman who inspires me to do better and be better! You are truly a rare gem in this world Jessie and I am proud to know you!