Wealthsimple

May 25, 2026

In This Issue

8 min read

Juicy AI melodrama

Dad books in decline

Victoria’s new secret

Have we seen the last of new skyscraping condo towers in Toronto? That’ll do, pig. That’ll do. | Babe: Pig in the City | Universal Pictures

The Week in Markets

Mega-IPOs and the Roaring 2020s

Now that word is out that OpenAI plans to go public as soon as September, it’s official: 2026 will be the year of the mega-IPO. And the valuations being thrown around are stirring up a whole range of emotions from market watchers: joy, envy, FOMO … but also just the “F” part (as in fear).

Why? All that heat can swiftly turn into overheat, hence last week’s spate of pump-the-brakes headlines about a Roaring ’20s redux. A broader look at market history, though, suggests a complicated story. In the year following the 25 largest IPOs ever, the S&P was positive roughly two-thirds of the time. Now that is slightly below the long-run base rate of 74% positive years, but only slightly. Meanwhile, just as there’s risk in jumping in, there’s risk in sitting out: stocks average +21% in up years but only -13% in down years. Time to decide just how much risk you’re willing to tolerate.

TSX:	1.2% (+8.4% YTD)

S&P 500:	0.4% (+8.7% YTD)

📈 What’s Up: Enbridge (+5.3% 5D), the Canadian oil-and-gas giant, extended its yearlong rally amid news that it will supply Meta’s Wyoming data centre with clean energy.

📉 What’s Down: Walmart (-10% 5D) reported so-so earnings, in part since shoppers are trying to avoid filling up at its pumps as gas prices remain high.

One Chart That Explains Everything

What Happened Last Week

Important

Alberta loves the Alberta-to-B.C. pipeline. B.C. does not. The Carney government scored a few Alberta Points™ this month with its blessing of a proposed oil pipeline — very aggressively scheduled to break ground in late 2027 — that would stretch from Alberta to B.C.’s western coast. Slight problem: the project needs buy-in from B.C. too, and the province’s governing NDP is a hard no (as are some First Nations), largely on environmental grounds. But Carney doesn’t seem to be in a negotiating mood: he’s warned that the Feds will take their business elsewhere if B.C. holds things up.

The AI wars are turning into a soap opera. On last week’s episode of As the Artificial World Turns, we had a verdict in the Musk/Altman trial! Elon lost on a technicality. But! Thanks to a pointless trial, we got days of soapy melodrama starring two filthy-rich tech tycoons, featuring a baffling inheritance subplot, cringey diary entries, a near-punching, and a baby-mama-turned-informant. And that was all before OpenAI co-founder Andrej Karpathy defected to rival Anthropic later in the week. Welcome to the palace-intrigue phase of the AI boom!

Interesting

CEOs are getting anxious … so they’re cracking the whip. Toronto-based Hudson Labs ran an ingenious little experiment to gauge the stress levels of CEOs by using AI to assess their language and tone during earnings calls, and … it turns out they’re pretty stressed! The CEO of Miracle-Gro lamented that the economy “just sucks,” while the head of a Texas minerals company declared that they’ve “gone back to the drawing board” on everything. No coincidence, perhaps, that Bloomberg just dropped this story about corporate leaders dispensing with the post-pandemic kid-gloves approach to employee morale and dialing up the pressure to perform.

“Dad books” are getting killed by podcast bros. Bad news for the Malcolm Gladwells of the publishing world: serious nonfiction — think historical narratives, sports books, doorstop biographies — has taken a serious nosedive, with sales this year down 8%. Why? Men are reading less and listening more: according to a Wall Street Journal survey, 62% had listened to a podcast the previous month, up 16% since 2023. Here’s a cruel irony: one of the few remaining ways to sell a dad book … is by scoring a major podcast shoutout. So as Father’s Day approaches, spare a thought for the TLDR staff, which just so happens to be well stocked with dad-book authors!

—Jenna Benchetrit

From Our Sponsor

The FOMO Index

by Stacey Woods

Important

Experiment shows mean bosses can turn AI bots into Marxists. So go easy on Claude and Grok for breaking the Xerox machine with their manifesto.
Source

New vape pen helps you earn Bitcoin while you get high. No thanks, we’ll just top ourselves up with the ketamine/RRSP shot.
Source

Victoria’s Secret is changing its stock ticker symbol to “VSXY.” It’s NSFS&P 500.
Source

Celebrating Habs fans triggered microearthquakes around the Bell Centre. It’s a shame — that area is still rebuilding from the ’24 Swiftquake.
Source

Crash & Burn

To the Moon

The Zuckerbergs are hiring a lifeguard they’re calling a “Beach Water Person.” Should get along well with their “Empty Desks Person.”
Source

Schlitz beer has brewed its final batch. Please spare a thought for the grizzled 58-year-old in your life and his roommate.
Source

Tribunal denies woman compensation for the stress of returning jeans to Holt Renfrew. Trigger warning: article details having to print a shipping label.
Source

Timmins councillor is looking into penalties for trespassing by farm animals. And the worst offenders will be held without bale.
Source

Who Cares?

The Big Important Story

Is This the End of Canada’s Condo-Tower Era?

Canada’s condo market is spiralling. Nationally, prices have tumbled by about 20% since their peak in 2022 — and prospective buyers are still struggling to afford the available inventory. Meanwhile, in the first quarter of the year, just 246 new condos were sold in the Greater Toronto and Hamilton Area — the ground zero of the downturn — bringing sales volume to a 35-year low. No new project launches were announced during the quarter, either, a first in at least 30 years. Jake Cohen, president of The Daniels Corporation, one of the GTHA’s biggest developers, explained to us how the market came to a standstill and why he thinks the era of building giant condo towers is over in Toronto. The highlights:

The Cause of the Crash

This is one of the toughest times I’ve seen in the industry. Back in 2020 and 2021, everybody wanted in: first-time buyers, young professionals, newcomers, downsizers, investors. Then in May of 2023, it felt like the tap got turned off.

What happened is that almost every pressure point intensified at once. A condo price includes land, labour, and materials — but also financing costs, municipal fees, taxes, and so on. In Toronto, government charges can represent [as much as 36%] of the purchase price. These costs, coupled with high interest rates, became so astronomical that buyers just couldn’t afford new homes. And developers couldn’t slash prices much further, since their margins are often so tight.

So now we have this weird situation where people desperately need housing, but fewer buildings are getting built.

The Fallout

Gone are the days of 80-story condo towers, I think. That size and scale are just not financially viable under the current conditions. We’re now seeing a push toward smaller homes and developments — projects that are maybe 14 to 18 months to finish instead of monster builds that take 60-plus months and bleed a lot of money. That scale is less risky.

I’ll say the government has made some good moves recently. On April 1, the Ontario government announced a 13% tax reduction for anyone who buys a new condo unit, which significantly drops a home’s purchase price. Since then, our company has sold 45 new homes, when in 2025, we sold just 56 homes total. Mind you, during the boom years, we were selling 500 to 600 condos annually. Still, in a short amount of time, the government rebate has already stimulated sales.

Now What?

The construction slowdown is going to affect housing availability for years to come. There are simply not enough new projects underway to meet future demand. The government will provide funds for not-for-profits to deliver affordable housing, but developers will need to help meet demand. The biggest challenge will be figuring out how to make math work for us.

The conversation around affordability can’t only be about lowering home prices; it must also be about lowering the cost and risk of building housing in the first place.

—As told to Marin Cogan. Interview edited for length and clarity.

The Big Listen

💸 Jack Bogle, the Birth of Index Funds, and the Rise of Vanguard

Acquired, aka the finance world’s favourite deep-dive podcast, just dropped a 3.5-hour episode chronicling the history of mega-investment manager Vanguard. The 10-second version: it’s the largest equity owner in most S&P 500 companies — and yet it’s always been run more like a hippie co-op than a titan of capitalism. | Acquired

Post of Wisdom

canadians be like did you get $48.11 from the bread settlement

Thoughts on Today’s Issue?

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This week’s newsletter contributors: Brennan Doherty (writer), Devin Gordon (writer), Stacey Woods (writer), Jenna Benchetrit (writer), Ambrose Martos (fact checker), Ciara Rickard (copy editor), Maude Campbell (copy editor), Sara Black McCulloch (fact checker), Eva Grace Clement Cruz (specialist, product engagement), Lauren Edwards (production coordinator), Matthew Karasz (markets editor), Jared Sullivan (senior editor), Peter Martin (senior editor), and Devin Friedman (editor-in-chief).

TWIM: Total returns shown in local currency, via TradingView.

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🛢️ Carney’s pipeline problem