Websites in History takes a nostalgic look at the sites that shaped how people use the internet today. Each edition hands the mic to a Squarespace contributor, who revisits one site from the archives and unpacks what it got right, what it got wrong, and what it still teaches us about building for the web. This edition comes from Tyler, Director of Global Content at Squarespace.
I don’t remember exactly when I stopped using StumbleUpon. It was likely sometime around 2007 or 2008, when Digg and Reddit came on the scene and internet discovery came pre-loaded with visible peer reviews and voting, making StumbleUpon feel too unpredictable for my declining digital risk tolerance.
At that moment in time, freshly out of my parents’ basement and living with roommates in the Central District of Seattle, I didn’t realize how much I would miss Stumbling.
StumbleUpon began in 2001, founded by a small group of programmers who had a simple, yet untapped, idea: instead of searching for a topic the way you would on Google, what if a website could help you discover new, weird, and wonderful websites? By sharing your interests and clicking a button, StumbleUpon would take you from page to page across the vast nodes of the internet, uncovering the world’s creativity one stumble at a time.
Stumbling, as it was called, caught on fast. StumbleUpon reached 2.3 million users by 2007. That number looks small today, but it’s worth mentioning virtually no one had a computer in their pocket. Napster, a service seemingly everyone used, only reached about 26.4 million users at its peak, a figure that would be a rounding error for Facebook today. But in 2007, 2.3 million was a big number.
As StumbleUpon evolved, it became a toolbar, then a browser extension, and then an app. It launched StumbleVideo and pseudo-white label versions that made it possible for users to stumble across MySpace and Flickr accounts, too. In other words, it diversified and innovated in the hunt for revenue. But its core value stayed intact. I could click the Stumble button and land on a website that could change my entire afternoon.
Ask any StumbleUpon devotee about their Stumbling and they’ll immediately invoke a website they found in detail, as if it were yesterday. I vividly remember Stumbling onto a site that had a map overlaid with haunted locations across the United States. I pulled up my hometown and neighboring towns, reading the likely invented lore and letting my imagination run wild. One entry was for a school where my mom worked, noting that a young boy had been seen walking the hallways late at night . . . which is what I did when my mom worked late grading tests . . . (Am I the ghost?) I kept that site open for days, poring over ghost stories from every state I’d lived in, along with the cities and hometowns of extended family, so I’d have material for our next family reunion. Then I clicked Stumble again and forgot the name of that site forever, because Homestar Runner popped up on the screen.
At Squarespace, we love websites, design, and building something worth discovering. We talk about websites, look at websites, and even make ads featuring Adam Driver saying the word websites over and over.
As students of the website, we also recognize that the web, as it exists today, inherits the traits of the sites that came before it. By looking back at the websites of yore, we gain a better understanding of how the internet of today came to be. And while StumbleUpon wasn’t necessarily an exhibition of design virtuosity, its inner workings had significant implications for the current state of the web and how we exist within it.
Which brings me to surprise and delight.
I love talking about surprise and delight because a) I like being surprised and surprising (mostly) and b) being delighted and delighting (always). And surprise and delight, defined as something unexpected that gives a high degree of joy or satisfaction, is as much a part of successful website design as finding the right brand logo. Looking at StumbleUpon, the takeaway isn’t necessarily to develop a better algorithm for pairing user-generated content with customer data in an addictive format (although that’s StumbleUpon’s legacy), it’s about building a site that provides a genuinely human interaction, which, in a sea of impersonal sites, is delightful.
Many years ago, I audited a client’s website that looked like every other corporate site. Their weekly active users had dropped noticeably, and they were trying to understand why folks were interacting less with their site.
I dug in and noticed they’d removed a widget from their site a few days before engagement dropped off. The widget looped videos of extreme sports clips in the upper-left corner of the site. When I asked the company about it, they told me it felt unprofessional and antithetical to their (now) buttoned up brand. But when we interviewed their customers, it was clear people loved that video feed. It was entertaining, gave the brand a bit of an edge, and brought users back to the site because it reminded them the brand was more than a faceless entity.
For this brand’s audience, the video widget was a welcome surprise.
This isn’t to say everyone should add extreme sports clips to their site, but that little moment of surprise and delight endeared this brand to their users. When the widget returned, the usage rate returned with it.
What StumbleUpon delivered, and what its descendants still deliver today, is the promise of surprise and delight. I don’t scroll Reddit because I like content aggregators; I’m hunting for the feeling only a video of a kid relaying their love of turtles, corn, or some other equally cute thing can deliver.
Of course, StumbleUpon also helped give rise to the algorithmic content feed that shapes so much of how we browse today. StumbleUpon was addictive in a manner that’s familiar to any social media user, but it was slow and platformless, which meant content didn’t have to conform to any sort of algorithmic format or trend.
That’s not to say I didn’t spend an hour Stumbling from site to site. I absolutely did. But I had to actively engage with each one, evaluate its merits in juxtaposition of my interests and capacity for novelty (mileage varied), and then either spend the next 15 minutes smashing digital ants with a paperweight or learning about the physics of water or simply Stumbling on.
It was incredibly effective. Anyone who managed Google Analytics for a website in the early 2010s can attest that StumbleUpon surpassed Facebook in social media referral traffic. People pressed the stumble button over a billion times a month. People were Stumbling.
The state of the internet at the time had as much influence over my enjoyment of StumbleUpon as the site itself. When I say I miss StumbleUpon, I’m also saying I miss the internet as it used to be.
Back then (about when Mentos-and-Coke rocketed into the zeitgeist), the internet was a true world wide web of sites, owned and managed by people with diverse interests. People were weird and experimental online, mostly in a good way, and that made the internet endlessly interesting.
That’s something we still hold onto at Squarespace. We’re obsessive about the website and all the weirdness and interesting phenomena a website can convey. That’s our passion and we’re glad so many others feel the same way. And because we’re passionate about websites, we’re passionate about design.
That said, building and designing a website isn’t necessarily about being pixel-perfect. It can be, if that’s your passion, but good design is more akin to the adage that so many improv performers share with each other: “If you aren’t having fun, they aren’t having fun.”
If I can see your passion, your interest, or your personality on the page, that’s effective design.
One of my favorite zines is Cometbus, a zine about a Bay Area punk musician named Aaron Cometbus, who documented traveling across the United States on a Greyhound, seeing punk bands, and observing American life during the early ‘90s. The cover was often a black-and-white collage, his writing sometimes rough around the edges, and often he wrote about nothing in particular. But his passion came through every page. Despite an unpolished design aesthetic and penmanship, I and many others couldn’t wait to read and re-read Cometbus. Because Aaron was passionate about Cometbus, so were we.
Design, really, is about how much of yourself, in all your foible-ridden glory, you’re willing to put on the page. Yes, many of us have businesses and need to look professional online. We’re not all Bay Area punks traveling across Route 66 in the ‘80s and ‘90s, after all. But the quirks that surprise and delight our customers are what set us apart and make us accessible, whether that’s a button that opens a doorway into a new world, or a widget that streams BASE jumping.
Don’t delete the widget that sets you apart.
Stumble through Squarespace
Inspired by the button that started it all, we built a Squarespace version of Stumbling. Click through and discover real Squarespace websites you'd never find any other way.
Frequently asked questions
What is StumbleUpon?
StumbleUpon was a web discovery tool that let users click a button to jump to random websites based on their interests. It launched in 2001 and became one of the most popular ways people found new content online before social media feeds took over.
What happened to StumbleUpon?
StumbleUpon shut down in 2018. Its founders relaunched a similar concept called Mix, which focused on curated content discovery rather than the original's random, button-click browsing experience.
What are some StumbleUpon alternatives?
A few tools carry on StumbleUpon's spirit of random discovery, including Mix, the direct successor built by StumbleUpon's original founders. If you’re looking for a new adventure, other random website buttons exist today like theuselessweb.com, boredbutton.com, and clicktheredbutton.com.
Tyler Huggins is Director of Global Content at Squarespace. He previously led growth at Acuity Scheduling. His work sits at the intersection of writing, design, and the future of content.