‘At the end of the day, people connect with people’

Maddie Thompson was on a beach when she decided to drop out of school.

It was February 2022 and she was studying architecture at the University of Manitoba. While maintaining her spot on the dean’s honour list, Thompson was also running Mad Social Agency Ltd., the digital marketing firm she’d started two years earlier. She had enough business by that point she was hiring friends to help manage accounts.

Sitting on Locarno Beach in Vancouver, she realized it made sense to drop out and pursue the business full-time.

“My thought process was: I’m going to take a one-year leave of absence and see if I can make this work,” says Thompson, 23. “And I just never went back.”

Although Mad Social Agency is barely five years old, the Winnipeg company has already worked with more than 400 brands in three countries. The agency’s services include social media management, video production, targeted ad campaigns and coaching and consulting to help clients optimize their social media efforts.

At a time when there’s more content available online than ever before, Thompson and her staff want to ensure people see the videos and images they create.

Mad Social’s “deep understanding of the science of social media” and ability to tell unique stories that have emotional impact sets the company apart, says Blaise Lepine, head of social media strategy.

“With the volume that we post — around 2,000 videos a month — it allows us to have an obscene amount of data that backs our thought processes,” Lepine says.

The 31-year-old has worked at other digital marketing agencies in the past and marvels at what he calls Thompson’s “discovery-to-action time.” Often, he says, he’ll come across an interesting idea or technique, show it to Thompson, and she’ll have it implemented into a client’s account the next day.

In the ever-changing social media landscape, it is a smart approach.

I love just piecing together things and solving problems … and figuring out systems (for) how we can build the brand.”

“If you’re not adapting every single day, you’re falling behind every single day,” Lepine says.

Mad Social’s annual revenue is north of $1 million, Thompson says, and it’s set to double next year. The company has nine full-time staff and around 20 part-time and contract employees, with plans to fill three more full-time roles in the coming months.

“I enjoy that I get to be creative while also being able to build at the same time in a very tactical way,” Thompson says. “I love just piecing together things and solving problems … and figuring out systems (for) how we can build the brand.”

Raised 40 kilometres south of Winnipeg in Niverville, Thompson says she’s always loved being a creator. She started making videos and uploading them to YouTube when she was 10. As a teenager, Thompson says, she was extremely shy but loved attention.

“Making videos was my outlet for everything in my life,” she recalls.

At 13, Thompson wanted to be a fashion designer. Inspired by a social media post by American businessman and internet personality Gary Vaynerchuk, Thompson sent direct messages on social media to 150 clothing companies.

Triple Flip, a Canadian brand that at the time sold clothing to tween girls and had stores across the country, liked Thompson’s work and responded to her message. The brand produced numerous designs by Thompson, with her signature appearing on each item — Made by Maddie.

“The coolest experience (was) going out to a mall and seeing girls wearing the clothes I designed,” she recalls.

When she was 16, Thompson worked with a group of classmates to launch a line of streetwear called Social Clothing as part of their Visions and Ventures business class. The group eventually sold around $3,000 in clothing.

Thompson was working at a dollar store a few years later, when her manager asked her to run the store’s social media account.

The account started doing well and Thompson saw someone online talking about managing social media accounts from home. Working from anywhere, having freedom, building something on your own terms — it made social media management sound glamorous.

Thompson began offering social media management service to other businesses, starting at $80 a month (something for which Mad Social Agency now typically charges an average of $3,000 to $4,000).

The business has continued to grow from there.

While Mad Social previously offered web design and search engine optimization services, Thompson decided at the beginning of 2025 to focus on what the agency does best: social media management.

“I used to wear ‘full-service agency’ like a badge of honour, but I don’t think it’s a badge of honour anymore,” she says. “Often you end up spreading yourself too thin or outsourcing to freelancers. We do all our social media in-house, which I think is really important. It ensures quality control.”

“Brands still see social in a very corporate way and they’re not telling the story behind their brand.”

Staff members work remotely. About 75 per cent of them live in Winnipeg, and every two weeks they gather at Thompson’s St. George neighbourhood home to work together in person. The team is often showcased on the agency’s social media.

“Brands still see social in a very corporate way and they’re not telling the story behind their brand,” Thompson says. “At the end of the day, people connect with people. Us being able to do that on our own profiles definitely has allowed us to grow exponentially.”

Looking ahead, Thompson envisions a time when Mad Social enters into revenue-sharing agreements with clients. Starting additional companies also isn’t out of the question for Thompson.

Today, she describes dropping out of school three years ago as the best decision she’s made. It was scary, but she was determined to succeed.

“I think when you put yourself in those scary situations where you have to make it work, you just find a way to make it work,” she says.

She works on the business “14 hours a day on average” because aside from gardening, it’s the only thing she wants to do.

Thompson says that when she was growing up, her father would say, “Try harder than everyone else.”

“He said that consistently when I was young,” she says, “and I think it just stuck in my head.”

aaron.epp@freepress.mb.ca