Second Quest
In a normal culture, a company as gray-haired as MapQuest would not be having a straight-on cultural revival in 2026. But our culture is not normal.
Last year, I wrote about MapQuest, and presented the company’s story as one that was fundamentally changed by a poor decision—AOL’s purchase of the company, which only completed after the tech IPO bubble burst.
AOL, like its merger partner Time Warner, was a frequent target for acquisition. But unlike the modern day Warner Bros. Discovery, it lost cachet every time an acquirer swooped in to pick it up. And that left companies like MapQuest to languish in a culture that simply was too big to understand what was actually going on.
But MapQuest, as I noted at the end of that piece, seemed to land in the perfect situation: In 2019, it was acquired by a company that actually made sense for it, the StartPage owner System1. Verizon essentially gave them the company for free, and System1 responded by actually making the company something of a viable player. It just needed something to put a little gas in its engine.
Last year, the Trump administration gave them a prime PR opportunity by renaming the Gulf of Mexico to the “Gulf of America,” which MapQuest handled by letting you rename the gulf yourself. And last week, as the president tried the same trick on Lake Ontario, MapQuest repeated the trick—which stood out all the more because Google, and later Apple, chose to acquiesce.
Those companies have something to lose if they make Trump mad. System1, and by extension MapQuest, does not. And audiences responded by making MapQuest the hottest app in the App Store for the first time ever.
It sure feels like MapQuest was ready for its close-up.
I’ve covered a lot of companies in my time, and I can name on one hand the number of times a stodgy technology firm was effectively at the brink of obsolescence only to pull off a complete cultural comeback. (Apple is, famously, one. Thank you, Dr. Gil Amelio.)
MapQuest wasn’t on my bingo card. But it reflects an inherent flexibility that companies who aren’t on the top of the tech world have, especially if they don’t sell physical products. Companies like Mozilla and DuckDuckGo simply have more room to get savvy as tech giants find themselves at the mercy of a transactional presidency. But that extends beyond political; for example, Mozilla earned plaudits for publicly stating that it would continue to support the popular ad-blocking extension uBlock Origin, which Google seemingly upgraded its extension platform to disable. It’s a great time for easy wins if you lead a mature tech company.
That said, the hard part for MapQuest will be sticking the landing. While the app is ready for prime time, it lacks certain features that many users take for granted. For example, if you want to take the bus, MapQuest doesn’t have in-depth mass transit integration like Google or Apple’s offerings do. And good luck using it to book an Uber.
But if this sudden moment at the top of the news cycle turns into something lasting, it might just give the legacy map provider an opportunity to fill those gaps while building a lane for itself. (The company has already pledged to add Android Auto support.)
At a broader level, MapQuest’s story offers a template for other legacy tech companies to make a modern-day comeback. MySpace’s current owners, Tim and Chris Vanderhook, have already made a recent case for a social media “antidote” play. And at least some players, like Flickr, have found ways to stick around, even with declining relevance.
But there’s a real risk that the revival might end up being like what is currently happening to Digg. That company, relaunched with much fanfare by Kevin Rose and Alexis Ohanian, had to pivot just months after its relaunch, as it became clear the domain was too easy a target for spammers. The website is now best described as a Techmeme for AI bros. That feels like a pretty easy-to-ignore model.
It won’t work for every old company with a dusty server, but the play is clear: Position yourself as an antidote to the negative parts of modern tech culture, and then position your marketing to exploit that position. That requires smart planning and a willingness to meet the moment, even if it means being divisive or stepping on toes to reach that moment.
It also probably requires a brass stomach, because it can go bad pretty easily. But I guess I’m optimistic that MapQuest is going to start a trend where mid-sized tech companies suddenly discover the backbone that was there all along.
Directionless Links
The first issue of Boxed News, my new mini PC newsletter, landed yesterday without a hitch, and things are off to a good start. Wanna support a new newsletter built from the ground up? Sign up here.
There’s no reason whatsoever to give the NES a CD add-on. Especially in 2026. But I ain’t gonna lie, seeing this project gave me a certain sense of joy, especially as it uses the previously vestigial NES expansion port. (We love vestigial features around these parts.) Word of warning that the video is meandering as all get-out but the result makes it worth the dig.
We actually have multiple videos in the subgenre of “video game consoles doing things they shouldn’t be able to do” this week. Apparently it is possible to run Mac OS X Tiger on an Xbox 360, whose processor is effectively a PowerPC G5 minus a couple of features. If you feel like following in this dude’s footsteps, here’s the GitHub project.
New social network alert: One of the more interesting pitches that landed in my inbox this week was for Innie, a MySpace-esque social platform that focuses on design, avoids profile pictures, and promises feeds that don’t go on forever.
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