Skip to main content

Money Diaries

Errol Morris Says He Doesn't Deserve His Money. Neither Do You.

The Oscar-winning filmmaker, and director of our new “Investing for Humans” ads, tells his financial life story in our first video edition of Money Diaries.

Wealthsimple makes powerful financial tools to help you grow and manage your money. Learn more

Wealthsimple is a whole new kind of investing service. This is the latest installment of our recurring series “Money Diaries” where we ask interesting people to open up about the role money has played in their lives.

Errol Morris has a core belief about money: he doesn't deserve the money he has. And, furthermore, neither do you. If you have money, he says, you're lucky. Errol Morris, is probably the world's preeminent documentary filmmaker. He has won an Academy Award for his film Fog of War, as well as the MacArthur “Genius Grant” and a Guggenheim fellowship and his film Gates of Heaven was named one of Roger Ebert's “Ten Best Films Ever Made.” So it's not surprising that he has lots of beliefs. And you'll learn about them, and hear many interesting stories like how he used to get evicted from his apartments all the time (before he rather quickly became a millionaire) if you watch our very first Money Diaries video.

Why is Errol Morris the first person to do a video Money Diary?

Our “Money Diaries” series is meant to tell human stories. You know, interesting people opening up about how money has affected their lives. (See, it's right up there in the fine print above!) Why do we care? Because, whether they admit it or not, everyone cares. Everyone's curious about other people's money, everyone's voyeuristic, everyone's worried, and ashamed, and proud, and avaricious. So yes, the stories are fun. And money is also a nifty prism through which to tell your life story — successes, failures, brushes with disaster. But that's not really why we do it, either.

We really do “Money Diaries” because we believe people should talk more openly about money. We'd all be smarter, more informed, less anxious, and less prone to make the same mistakes over and over if we did that. It was the idea of our first unscripted ad campaign, “Investing for Humans.” And when we had that idea, we had a wish list of one director who would have unparalleled skill at getting regular people to open up and talk about money: Errol Morris. We also thought he'd make a fantastic subject himself. So we got Errol's son Hamilton — himself the host of a documentary-style show on Vice — to ask him all the personal money questions we would have been too chicken to ask ourselves.

We're happy to report the apple doesn't fall far from the tree.

Wealthsimple's education team is made up of writers and financial experts dedicated to making the world of finance easy to understand and not-at-all boring to read.

Related articles

Money Diaries

Less than 5% of Canada’s truckers are women. I’m one of them

One Toronto driver on how long-haul truckers can easily make $100,000 in a good year, and why the money doesn’t fully justify the dangerous lifestyle.

Money Diaries

How I Lost $1.6 Million in Bitcoin in 8 Minutes

And how I am staying sane now that it’s all gone.

Money Diaries

Salary Confessions: 14 Canadians Get Candid About Their Wages

We asked a bunch of Canadians (with neat jobs!) how much money they make … and their answers revealed way more than just a number.

Money Diaries

To Win Four Oscars, Sean Baker Had to Go Broke Again and Again

Baker has made a career of spending his own money to tell stories Hollywood wouldn’t. It paid off at the 97th Academy Awards.

Money Diaries

Money Diaries: Pride Edition

For the last five years, our “Money Diaries” series has been all about telling truths. In honour of Pride Month, we share some of the greatest conversations we’ve had with LGBTQ+ icons.

Money Diaries

Roxane Gay on Financial Independence: 'The Most Important Thing a Woman Can Do for Herself'

She's the best-selling author of 'Bad Feminist' and 'Hunger.' And until five years ago she'd never saved a penny. The author on her complicated relationship with money.

Money Diaries

How I was Conned by the “Fake German Heiress”

Rachel DeLoache Williams’ relationship with Anna Delvey began over drinks and infrared saunas, but it ended with a $60,000 bill, a grand jury, and a new understanding of friendship and financial crime.

Money Diaries

The World Wouldn't Make a Place for Angelica Ross. So She Made One for Herself

Before she was cast on 'Pose,' she worked at Arby's and Apple. Got kicked out of the Navy and Applebee's. The winding money journey of a new type of TV star.

Money Diaries

Emily Ratajkowski Is Not a Commodity

The actress, model and now writer tells us her money story, and all the intense contradictions about objectification it entails.

Money Diaries

Shangela Would Like to Remind You to Tip Your Drag Queen

The perennial crowd favorite on 'RuPaul's Drag Race' talks wig economics and why resourcefulness is a vocational imperative.

Money Diaries

Love and Crypto: The Hackatao Story

Just before their show at Christie's, the crypto-artist duo talk to us about money, marriage, and the blockchain.

Money Diaries

Karen Russell: A Brutally Honest Accounting of Writing, Money, and Motherhood

The novelist didn’t realize how fervently society wants to turn us into calculators — every action has a payment or a fee — until she had her first child. Here she reckons with motherhood’s ticking meter: every minute with her kids is work lost, and each minute writing subtracts from precious, un-price-able joy.

  • Money Diaries

    Joel Kim Booster Was in Massive Student Debt Until Two Years Ago

    Before he was cast in Sunnyside or had a Comedy Central special or wrote for Billy on the Street, he was raised working class in Illinois, saddled with huge student debt, and worked marathon hours doing customer service for Groupon. Joel Kim Booster shares his money story.

  • Money Diaries

    Stories From Our New Economy: Bullish on Bidets Edition

    Our new Money Diaries series tells stories of humans whose lives have been upended by this crisis. In this edition we meet four businesses (the owner of a bunker company, a bespoke distiller, a day-trading celebrity, and a bidet magnate) that took unexpected turns.

  • Wealthsimple

    Grow your money

    Smart investing tools and personalized advice designed to build long term wealth.

  • Money Diaries

    Alison Roman Is the Patron Saint of Home Cooking and Everyone’s at Home

    She always wanted to cook and never thought much about money. But life gets strange when everyone’s wondering what to do with half a pound of broccoli and some dry kidney beans and you know the answer. The chef and cookbook author on her pandemic money story.

  • Money Diaries

    Pandemic Money Diaries — Panic at Trader Joe’s Edition

    Our virus-era Money Diaries series tells stories of humans whose lives, financial and otherwise, have been upended. In our first edition: a grocery clerk, a weed dealer, the author Jon Mooallem, a restaurant manager, and a male escort.

Wealthsimple

Grow your money

Smart investing tools and personalized advice designed to build long term wealth.

Get started