How Wealthsimple Got Oscar-Winning Director Errol Morris To Talk About Money Problems

The brand’s new campaign, with Morris-directed ads, features everyday people talking money. But then they got the director to answer some questions.

How Wealthsimple Got Oscar-Winning Director Errol Morris To Talk About Money Problems

Who wouldn’t want money advice from Woody Harrelson? Or Anthony Bourdain, Rachel Bloom, Mario Batali, or Kevin Bacon? Okay, maybe not advice per se, but engaging and interesting conversations about dealing with money that actually makes the lives and decisions of these well-known people relatable to the rest of us. This is what Wealthsimple’s “Money Diaries” series has been doing for the last few years, using celebrity names to get people talking about money and money management in a different, more open, way.


In its newest ad campaign, the investment tech brand has taken the Money Diaries concept to video, capturing real conversations with real people talking about real money issues–all directed by Oscar-winning filmmaker Errol Morris.

Not just that, but Morris himself steps out from behind the camera for a chat with his son Hamilton (host of Hamilton’s Pharmacopeia on Vice) about the days before the sports cars, when he was collecting eviction notices and learning the dangers of adhesive tape on pant cuffs. It’s an interesting chat and one that will hopefully lead to more video versions of the long-running written series.

Wealthsimple chief product officer Rudy Adler and executive creative director Mike Giepert tell me that Morris didn’t exactly know he was going to feature so prominently.

“We were trying to be a bit sneaky about it,” says Giepert. “We had a plan, but he didn’t. When it first hatched was when he suggested his son might be a good person to interview. Hamilton Morris is a really interesting dude with a dry sense of humor and delivery, so we were really interested in Errol interviewing him because it had the potential for a really cool dynamic of a father and son talking about money. As we got more excited about that, we thought maybe that would be a good way to get Hamilton to interview Errol.”

Related: Wealthsimple Is Aiming For U.S. Millennial Investors With Creativity And No BS

Morris was cool to the idea initially, but after interviewing the 20 everyday people about money, hearing their various stories and circumstances over many hours, that process softened him up to the idea of getting on camera himself.


But Morris didn’t just work in front of the camera. With a diverse group of 20 people lined up to interview, Giepert and Adler were hoping it would result in maybe eight to 10 ads.

“We asked Errol how many of the 20 people to talk on camera he thought would be usable in the campaign, and he said, ‘With me? All of them.'” laughs Adler.

They ended up with 56 different spots. “It was incredible,” says Giepert. “We just had to put a lot of trust into the process.”

The result is a consistent step forward in an already engaging marketing strategy, unique among financial brands for its personality and laid back vibe.

“We’re trying to build this environment where people can really, openly talk about money,” says Giepert. “Whether that’s a celebrity or a regular person, it’s about sharing experiences, hopes, and fears about money.”

About the author

Jeff Beer is a staff editor at Fast Company, covering advertising, marketing, and brand creativity. He lives in Toronto.