A Canadian Holding Company Bet on Letterboxd. The New York Times May Pay 5x

In 2023, a holding company from Victoria, B.C. bought most of a quirky movie-logging site run by two developers in Auckland. Three years later, The New York Times Company is reportedly ready to pay roughly US$330 million for the whole thing. If it closes, it would be a rare big consumer internet exit for a Canadian investor.

The site is Letterboxd. The buyer is Tiny. And nothing is signed yet.

What exactly is on the table?

The Times Company is in exclusive talks to acquire Letterboxd in a deal valued at about US$330 million, according to CBC News, which cited the Times' own reporting on its parent company. That price would value Letterboxd at more than 20 times its projected 2026 earnings of about US$15 million. No agreement has been reached, the report said, and the talks could still fall apart.

The framework is already detailed, though. Founders Matthew Buchanan and Karl von Randow would stay in charge and report to a Times Company executive. Letterboxd would likely keep running as a standalone site, with the Times plugging in its advertising technology. Film studios A24 and Sony had been among the prospective buyers, but A24 dropped out as price expectations rose, CBC reported.

The number climbed all year. It was first reported at US$250 million as Netflix circled, then US$300 million in September, according to the New Zealand Herald.

Who is Tiny, and how much could it make?

Tiny is a Victoria-based holding company co-founded by Andrew Wilkinson, who serves as executive chairman, according to Tiny's own website. The company pitches itself as a long-term owner of internet businesses, which makes a sale this quick notable.

In 2023, Wilkinson took a 60% stake in Letterboxd through Tiny, the Herald reported. Buchanan and von Randow each made around US$15 million in that deal and kept 20% apiece, which the paper said it confirmed through New Zealand Companies Office records. Wilkinson and Buchanan had been friends since meeting on Tumblr in the 2000s.

The 2023 valuation depends on who you ask. IndieWire put it at US$50 million, while Deadline said US$60 million. Using that range, B2B News estimated a sale at US$330 million would hand Tiny "roughly a five- to six-fold return in three years." Treat that as press math, since neither Tiny nor the Times has disclosed terms. Still, 60% of US$330 million works out to about US$198 million on paper.

Deadline reported that Tiny hired investment bank LionTree to run the sale process.

Why is a movie diary worth this much?

Growth, mostly. Letterboxd went from 3 million users in January 2021 to 28 million by April 2026, with more than half under 35, according to B2B News. Membership reached 30.7 million in the second quarter, up 43% year over year. CBC described the platform as particularly popular among Gen Z film fans.

And it got there cheaply. LionTree senior managing director Alex Michael called Letterboxd "a phenomenon" at a Financial Times conference, Deadline reported. B2B News quoted him saying it draws 30 million monthly users "with zero paid marketing" and that its biggest cohort is 18 to 24. The marketing came from the users themselves, plus viral "Four Favorites" videos where celebrities name their top films.

That is the business of social cinephilia. Logging a film, rating it and writing a two-line joke review has become a form of identity for a generation that watches movies on phones and then argues about them online. A platform that owns that habit owns a direct line to the most engaged film audience on the internet, which is exactly what advertisers, studios and subscription publishers want.

Why would the Times want it?

It fits a pattern. The Times Company has spent years bundling things people use every day into its subscription, buying product-review site Wirecutter, sports site The Athletic and the game Wordle, CBC noted. It added 420,000 digital-only subscribers in the third quarter, bringing its total to 13.8 million.

Users are wary. IndieWire wrote that reaction online "generally peaked at resigned relief," with "the best case scenario" a common refrain, mostly because a studio did not win. It also flagged the precedent of The Athletic, which kept some independence before the Times dissolved its own sports department a year later.

What does it mean for Canadian founders and investors?

Canada produces plenty of consumer apps but few big consumer exits, and fewer still where a Canadian buyer gets in early and walks away with a multiple. This one came from a friendship, a majority stake in a product with a cult following and three years of patience. Letterboxd's roughly 40 employees include staff in Canada, according to the Herald.

The caveat is the same one that applies to every unsigned deal. Exclusive talks are not a closing. Until the Times or Tiny confirms terms, the US$330 million figure belongs to anonymous sources. If it does land, a Victoria holding company will have turned a bet on movie nerds into one of the cleaner returns in Canadian tech this decade.