Advertorials: Building Trust Through Storytelling

Greg-Dubeau-The-North-End-Advertorials-Article-Jon-Hamm-01NOTE: This is a critique of the ”Money Diaries” series by Wealthsimple. In no way am I affiliated with Wealthsimple or any creative team or agency that produced this work.

When I was in College, I was introduced to the world of philosophy. It was the first time in my life that I actively took time to sit still and think about ideas and how I felt about them. In my pursuit of varying philosophical perspectives, I discovered the Penguin Great Ideas Series. I was immediately struck by how beautiful each booklet was adorned with illustrated and letterpress typography and decoration. Each 60-page booklet cost $10 at Chapters. I bought three; Seneca’s On The Shortness of Life, Henry David Thoreau’s Where I Lived, and What I Lived For, and Sir Francis Bacon’s Of Empire.

Of Empire was a particularly important read for me because it introduced me to the idea of communicating complex or abstract ideas through storytelling. Bacon wrote short opinionated essays on topics such as revenge, marriage, adversity, innovation, etc. It was wonderful to read because Bacon had a real knack for storytelling his way through fairly abstract concepts. I often think about how incredible a method storytelling is when trying to initiate the uninitiated to new, abstract or complex ideas. In advertising, this type of writing is called an ‘Advertorial’. The word is a neologism.

(Adver)tisement + Edi(torial) = Advertorial

I like to compare advertorials to the Penguin Great Ideas Series booklets because they both provide a long-form, yet approachable medium to communicate abstract, taboo, and often intimidating ideas. 

Why are advertorials important in advertising? Advertorials are the ultimate soft sell. They are the type of change of pace that advertisers need to compete in a saturated promotional marketplace. When the time is right, long-form advertising, like an advertorial, can be more effective than your run-of-the mill promotional ad. It’s a great way to zig when everyone else is zagging.

How do they work? Advertorials bridge the gap between a sales pitch and short story. They live in the grey area where they do not directly advertise a promotion or price point. Instead, advertorials rely on storytelling to provide insight into the subject matter and allows the audience to connect the dots and create their own interpretation of what they just read. Where a typical ad is brief, an advertorial takes time. Where a typical ad is direct, an advertorial is interpretive.

Why do they work? Advertorials combine hard data and soft data. Hard data is a conclusive variable that cannot be interpreted (e.g. statistics, facts, and measurable outcomes). Soft data is a qualitative variable that can be interpreted in multiple ways (e.g. art, editorials, comedy, poetry, and other emotion-driven mediums). The combination of hard data and soft data create a symbiotic relationship within the advertorial. Numbers feel less cold when combined with a plot and characters who have the capacity to display traits such as humility, honesty, bravery, and vulnerability. Characters and plots feel more real and relatable when accentuated by hard data that is familiar to the audience. All of a sudden, we have a yin and yang scenario, where hard data and soft data complement each other and are in perfect balance with one another. 

These are the ideal ingredients to create honest content. Honest content is the stuff that tries to show the full spectrum of human emotions, even the weak ones. It contradicts the predictable content and formulaic delivery that’s been beaten into the zeitgeist. Greg-Dubeau-The-North-End-Advertorials-Mobile-Elijah-Wood-01

August 29, 2017—I noticed a great digital ad campaign by Wealthsimple that used promoted posts on Instagram, Facebook, Twitter, and LinkedIn. They used a series of advertorials, and in my opinion, they knocked it out of the park. Money Diaries is an online series of advertorials by Wealthsimple featuring celebrity (and non-celebrity) spokespeople who speak candidly about their history and relationship with money.

Celebrity endorsement to hock product is nothing new, but Wealthsimple and their bullpen of spokespeople did something I didn’t expect—they were relatable. They provided honest content. It was genius. Wealthsimple tapped into the insight that money is a source of pride for a wide margin of their audience and is often a taboo topic of conversation. That kind of talk is private and opens us up to becoming all sorts of vulnerable. So how did Wealthsimple bypass the ‘pride factor’ and make the money subject more approachable? They built trust, one story at a time.

Wealthsimple found leaders and empowered them to be honest about their financial past. Some stories were gritty with drug use and crime, where others were nostalgic with lemonade stands and paper routes. Through all the stories, there was a unifying theme—“money is not everything”. In comparison to your health, family, happiness, future, passion or spirituality, it’s not the be-all and end-all. If you read between the lines of each advertorial in the series, it becomes quite clear what message they’re implying, “taking care of your finances is important, but there are way more important things in life to focus on than money.”

What is Wealthsimple doing? They’re building trust with their audience. They understand that finance can be intimidating and complex, so they provide relatable stories by seemingly unrelatable people.

How is Wealthsimple doing it? They’re telling stories and not giving a sales pitch. Nobody wants to live alone on an island. That’s also how many people feel about their finances. The purpose of each story is to let the audience know that they’re not alone and that there’s hope for them.


Imagine you are struggling to break into a competitive industry and you read that actor, Jon Hamm, spent just as much time being a waiter in Hollywood than he’s been a regular working actor. It’s an eye-opening story because you couldn’t imagine someone like Don Draper waiting tables.

Imagine you are a up-and-coming young professional and you read that Pro Bowl NFL cornerback, Nnamdi Asomugha, arrived to practice and games during his career driving the same car he drove to his prom, a ‘97 Nissan Maxima. He had a moment of clarity and realized that his football career would only be one small part of his life, so he decided to live for the future and not be swayed by a temporary lifestyle of excess.

Each story is familiar and relatable, whether it’s about Anthony Bourdain not having a chequing account until he was 40 years old or how Elijah Wood still has anxiety over making any purchase over $1,000. If this isn’t us, then we all know someone who this resembles.

Why is it working? There isn’t just one thing Wealthsimple is doing particularly well with their Money Diaries series; instead, they’re doing a combination of things really, really well.


1-Variety of spokespeople

Spike Lee (filmmaker), Maria Bamford (comedian), Kevin Bacon (actor), Amy Hereford (nun), Mario Batali (chef), Kylie Jenner (…entrepreneur?) and the list goes on. Wealthsimple has brought together a broad spectrum of pop-culture heroes, celebrities and non-celebrities from all different social and cultural backgrounds. Why is this important? Because the diversity of spokespeople appeals to multiple audiences. Collectively though, it shows that all of the spokespeople share similar financial situations, history, and shortcomings. These stories illustrate that these heroes are human and have the same problems we do.

Celebrity spokespeople have always been relied upon to promote strength, success, and exclusivity—it’s the predictable zig that’s been used forever. They’ve always dominated the consumer-provider power balance. Not this time, though. 


Providing honest accounts of their lives shifts the consumer-provider power balance. It shows that they are not all-powerful, when in fact, they are often weak. And that’s a feeling that most of us can relate to. Suddenly, we are empathetic to their stories. We begin to trust them. Not because they are telling us to, but because we are asking ourselves to. Now we have the power.

The truth is always engaging when the right person is telling the story. Whether it’s talking about your first job, growing up in a rough neighbourhood or how a generous tip made you feel love for all humanity.

Asking a celebrity to talk about their wedding isn’t an event most people can relate to, but Woody Harrelson made it work. His wedding cost $500. He traded in the ceremonial route for a simpler option—close friends, limited family, and low overhead. There’s real wisdom in his decision to bypass the excess trimmings and ceremonial lustre of a celebrity wedding. He seems more relatable. And by association, his story makes Wealthsimple more trustworthy.


3-Language and tone

Each story is conversational. Each storyteller is speaking up to the audience, instead of down to them. What does this do? It creates a non-confrontational bond between the storyteller and the reader. This type of relationship inspires familiarity and opens the audience up to being more perceptive to the storyteller’s ideas.

The language used in the Money Diaries series reads like a newspaper, but the tone reads like the transcript of a conversation between two friends. The situational familiarity of each story is the key to achieving the reader’s acceptance.

Simplicity of language and industry terms plays a huge role in the success of each story as well. A financial company like Wealthsimple could have written about things like 401k’s, ETF’s or GIC’s, but they chose not to.

After dropping out of film school, Boyhood Director, Richard Linklater, worked on an off-shore oil rig for two and half years to save up enough money to finance his first film.

When sword-swallower, Brent Loudermilk, was a 20 year old street performer in Los Angeles, he was only able to fill up his Ford Taurus with gas $5-$10 at a time.

Each story steers clear of professional financial services and jargon because that would have been boring and predictable. Instead, each storyteller writes candidly about their real wages and salaries, first jobs, financial struggles and self-discovery over the course of their careers. Some stories are longer and more detailed than others. Kylie Jenner’s story clocks out at 525 words, whereas Anthony Bourdain’s story clocks out at 2,500 words. Both stories, though very different, have an excellent economy of words and are entirely digestible with room for dessert.

4-Visual execution

Wealthsimple understands that the concept of money is a cold one, and is often viewed as intimidating and a taboo topic of conversation. Choosing to use illustrated portraits of the storytellers instead of photographed portraits makes a huge difference. Not only because it creates a unified look and feel, and reinforces the overall tone, but also because the loosely drawn style of illustration softens the subject matter and makes it more approachable. Behind the pastel colour palette and loosely-drawn portrait of beauty entrepreneur, Bobbi Brown, Wealthsimple approached the familiar, yet intimidating financial topic of credit card debt. Not only is there a human face representing the problem, there’s an accompanying story about how it happened and what steps were taken to solve the problem.

5-Wealthsimple is asking you for nothing, but giving you hope

The Money Diaries series is an extra-value component that Wealthsimple uses to strengthen its brand awareness. There are no sales points or promotional calls to action—just stories. The only thing that Wealthsimple requests of the reader is their time. It’s an incredible ask considering how much content is being thrown at people every day. But with the right people telling the story, advertorials can be an incredibly powerful communication and learning tool.

Finally, every story in the Money Diaries series ends with a concluding message of hope. No matter how deep a hole the storyteller found themselves in, they worked step-by-step towards finding a solution.

“For all the care you put into artistry, visual polish frequently doesn’t matter if you are not getting the story right.” — Ed Catmull

Storytelling is deeply seeded in human history. We all enjoy stories, but I believe most of us just don’t have the time to commit to them. So how does this affect the future of the advertorial? Will it survive and evolve in the digital era or will it become competed out of the media marketplace?

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