The click-and-order, custom-lettered doughnut business, Letterbox Doughnuts, just opened its first storefront after two years of online ordering success.
When couple Jon and Priom Oliver started the business, they had zero experience in the food industry. Jon had been working in private equity and Priom, a passionate and skilled baker, worked professionally in tech, recruiting and D&I. When the pandemic hit, the duo had a little bit more time on their hands and they got to work experimenting with flavours and styles, guided by enduring optimism.

“With Letterbox, a major motivating factor was that with all the negativity the world was experiencing, we wanted to remind people to take some time to celebrate each other and the special moments in their lives,” says the pair. They set up an online shop and officially launched in August 2020, providing patrons with a unique – and delicious – way to share sweet messages for special moments.
According to Jon and Priom, the most common celebrations they prepare orders for tend to be birthdays, baby showers, promotions, bachelorettes and specific holidays like Eid, Father’s Day and Mother’s Day, with words and phrases varying widely. Naturally, bachelorettes tend to include cheekier, sometimes downright explicit, messaging.
“I don’t think you’d be able to publish the craziest phrase we’ve had to make,” Jon says with a laugh. “That said, we are constantly blown away by our baking team’s artistic abilities, some of the special characters they create are almost too pretty to eat…almost!”
The dough is handmade fresh daily and contains no artificial preservatives. The unique flavours and designs come from the glaze, which you can customize by colour and style – opting for unique patterns like the space-themed galaxy or ombre-esque marble. The doughnut itself is plain, but the glaze flavour options include classic chocolate, raspberry lemon or white chocolate with a rotating menu of seasonal, limited-edition flavours like caramel chocolate that you can top with sprinkles.
The brick-and-mortar bakery officially opened its doors in early June and, to celebrate, they launched two new products, filled donuts and the Grammar Box.

The filled doughnut is an Oreo cookie crumble and comes in a range of shapes like hearts or stars. The Grammar Box is a unique way to cut down on food waste and add even more delicious options to the menu. The bakers take the little leftover bits of dough from letter cut-outs, fry them and toss them in either Oreo crumble, cinnamon sugar or powdered sugar.
Know someone who could use a sweet message? Letterbox Doughnuts recently kicked off a partnership with Toronto-based clothing company, Spread Love. The initiative is called Love Letter and it’s all about celebrating and acknowledging amazing people within the community. Each month you can nominate someone who deserves a little pick-me-up and the two businesses will select three nominees to receive a care package. It’s Jon and Priom’s way of giving back to the community that has already shown them so much love.
“Without the amazing people of Toronto and the surrounding area we wouldn’t be where we are,” they say.
Letterbox Doughnut’s bakery is located at 235 Spadina Ave.



