We have a stacked edition today
+ Shopify's new parent perk, A Rogers' padel play, BMO's GLP-1 summit, WestJet's tiny seats, and more.
Good afternoon everyone.
I thought we’d be able to slowly ease back into the 2026 news cycle together—but no. In fact I’m already so exhausted by some of the headlines coming out of (specifically) the U.S. that it feels like a good time to redirect our attention to what’s happening at home, in Canada, with Milk Bag’s first edition of 2026.
I’ve missed writing this newsletter and I hope you’ve missed reading it (at least a little). Over the last couple of weeks, I’ve been focused on figuring out how to take it to a new level this year… and let’s just say if you saw what was on my mental vision board you’d probably send a psychiatrist to my house.
In today’s edition: Edward Rogers makes a play into pro padel, another Matty Matheson-backed restaurant closes, Shopify’s new perk for parents, BMO is hosting a GLP-1 conference, looking into WestJet’s very small seats, and more.
Edward Rogers bought a minority stake in Canada’s only pro padel team. The executive chairman of Rogers Communications, which now holds ownership in every major sports team in Toronto, has secured a stake in the growing sport of padel. More than 3,200 clubs opened last year, and there’s new speculation over whether the sport will make a showing at the 2032 Olympics in Brisbane. The Toronto Polar Bears are one of 10 teams currently in the Pro Padel League, which claims to reach 300 million viewers worldwide and last year raised US$10 million in seed funding from NYC-based Left Lane Capital, Gary Vaynerchuk, and others.
Last year I wrote about the growing investor interest in pickleball as well, but didn’t mention that Canada’s pro league has attracted money from private equity, athletes, influencers, DJs, and restaurant owners.
Seems like a lot of companies missed the note about Ontario’s pay transparency laws. Can’t even name names because there are so many.
Alexis von Hoensbroech told the Canadian Press he “personally felt OK” in the new WestJet seating configuration that sparked online backlash. I don’t think it’s possible to have this conversation without knowing more about the build of this particular airline executive. A source tells me that he’s just under 6’ and that “a breeze could take him away.” So there’s that.
CI Global Asset Management signed a deal to manage Invesco Canada’s products. A reminder that CI Financial is now wholly owned by Mubadala Capital, an asset management arm of Abu Dhabi’s sovereign wealth fund.
Are you comfortable with the prospect of 20 million new Meta smart glasses on the market in 2026? I still need to review mine.
The Matty Matheson-backed Cà Phê Rang is closing later this month. Which goes to show that not even a Michelin Guide listing can keep your favourite restaurant open. Toronto Life published an article this morning by David Schwartz on why seemingly successful restaurants are closing left and right. He points to the growing gap between what diners expect to pay and the costs of business, using a pastrami sandwich at Linny’s Luncheonnette (he says he makes $1.60 on each one) as an example. For months he has been calling on governments for financial support, and says that without it we’ll be left with “nothing but Tim Hortons and A&W.”
A new study from Dalhousie University estimates that about 4,000 restaurants will close in Canada this year (7,000 closed last year).
To his point McDonald’s Canada did today announce price freezes on small coffees and value meals by finding “savings from high volumes.”
The SSENSE co-founders have won a bid to buy back their company. Brothers Rami Atallah, Bassel Atallah, and Firas Atallah teamed up with an unknown family office to regain control of the struggling online retailer after lenders forced the company to sell itself to repay its debts. The deal is expected to close in the next month. SSENSE has owed $93 million to hundreds of vendors since filing for creditor protection in August 2025.
BMO is hosting its third conference on the weight loss drug market in March. Surely a main topic of conversation will be the introduction of generic GLP-1 drugs in Canada, as names like Felix, Raven (I’m seeing these ads everywhere), Phoenix, and Him & Hers are gearing up for it.
The Logic found that Shopify has replaced its $1,000 child benefit with a children’s book about entrepreneurship by Harley Finkelstein.
Vinoteca Pompette will re-open as an apertivo bar called Bar Allegro later this winter. About a year ago, Martine Bauer shut down Pompette, a French Restaurant to add an Italian twist with Vinoteca Pompette. Given the other restaurant news in this edition, I think she deserves credit for a quick pivot as the math around opening a $100+ a head restaurant grows more complicated. There’s also a bigger conversation here about the need to constantly re-invent yourself in the age of RestaurantTok. Down the street, Oma says it will change concepts every year, presumably to keep up with all the people who outsource their decision-making to TikTok.
And because nothing is real on TikTok, I almost don’t believe that an LA-based influencer just decided to fly home with 144 Gryfe’s bagels. Don’t get me wrong, I want this to be true. But it’s so good it seems suspicious.
It’s worth listening to this Canadaland interview with The New York Times Canada bureau chief Matina Stevis-Gridneff. It’s worth learning about her approach to coverage (more Canadians pay for the Times than any Canadian media outlet), but her perspective as a newcomer is also refreshing: a main takeaway for me was that if you think it’s so bad here (as many Canadians do), you should see how everyone else is living.
C’mon Shopify💀