When WIRED first launched in 1994 it hit me so hard that I bought 10 copies and gave them out to customers and friends. By 1998 they were the arbiters of Tech Cool and riding the wave of the Internet Bubble - you could see the ad pages growing every issue and year. For some reason I still remember their subscription phone number 1-800-SO WIRED, and of course I still have every issue from at least the first 20 years.

Before ROBLOX and Minecraft there was Club Penguin, a cozy, snow-covered, kid-safe online world where players roamed around as penguins throwing snowballs and solving puzzles. It launched in 2005 and was purchased by Disney in 2007 for $350 million+, and rose to over 200 million registered users at its peak around 2013.

Before the iPhone ruled the world, there was the BlackBerry, and it was truly the device of choice for anyone serious about sending email and messaging on a mobile device. It had a fantastic physical keyboard, and its own secure Blackberry Network (BBN). The unlikely story of this small Canadian tech company that turned into a communications giant is so wild it was made into a comedy movie in 2023.

The initial Web proposal by Sir Tim Berners-Lee to his managers at CERN is one of the founding documents of our online world. Like the Magna Carta, it's as notable for what was breached as for what was observed. We got the viral, easy-to-use version of hypertext that let us surf a devil’s brew of incompatible computers with just a click of a mouse – while drawing haughty contempt from most early makers of "serious" hypertext. We did NOT get the combined browser-editor and universal authoring that Berners-Lee had made fundamental to his proposal, nor the seamless, scalable multimedia that could have let the early Web dance and sing even on slow connections.

Most features of our online world were predicted back when cars had fins. But which features get deployed – and whom they benefit, and what they lead to – is determined by business model. The lack of central control for either the Web or Internet scuppered the traditional pay-per-unit models that supported connectivity since telegraph days, creating an enormous vacuum as the Web grew with no obvious way to make money. The Google Search Appliance was one try at monetizing search. It targeted the internal “intranet” search market, where the company’s Web crawlers could not reach. Companies would buy the units with a mandatory fixed-term support contract, so that employees could use them to navigate internal data.

Yet the GSA proved a niche product for the search giant. It was released soon after a brilliant Google team had refined the contextual advertising invented by GoTo.com into the juggernaut that funds most of the online world today, incubating the development of modern generative AI along the way. It would be Web-scale “big data” that turned data-hungry machine learning – both statistical and later neural – from specialized research into the foundation of large-scale Internet business.

In the early 1960s, J.C.R. Licklider and his cohort of timesharing and networking pioneers at MIT and ARPA imagined much of the online world we live in today, and even beyond. Their vision of "computer utilities" delivered to home terminals included online banking, news, email, shopping, books, and search, and soon AI agents and personal intelligent assistants. Libraries was Licklider's attempt to summarize their thoughts for the future of books and navigating knowledge. Once everything was digitized, which they predicted could be as soon as the year 2000, specialized AI would help humans categorize and make sense of the full body of written human knowledge – a foreshadowing of the dreams for the Semantic Web and LLM-based efforts like Parallel.ai today.

Before startup culture became performative and commodified, Facebook codified its worldview in the Little Red Book. I was struck at the time, as I am now, by a young company investing thoughtfully in a physical artifact, shaped by an internal analog lab, to define how it thought and built. Still one of the clearest examples of culture as a designed object.

I was a kid living in Florida, far from tech and Silicon Valley, when Pets.com was everywhere and so was their sock puppet. The ads were loud, opinionated, and straight to the point: buy pet supplies online. Unfortunately, margins were low and demand wasn’t there in the late 90s. While the company didn’t last (bankrupt just months after IPO!) and is mostly forgotten among the dot-com wreckage, the sock puppet endures…. As a reminder that the idea itself was sound (as Chewy later showed), just too early. Timing matters.

While it feels common today, Google Street View was a revelation: see your street and nearly anywhere on the planet from the comfort of your browser. An enormous undertaking: cars, cameras, and teams mapping nearly every country and continent. Google turned this technical feat into something familiar and human: a simple figure you drag into the world, turning the planet into something intuitive and playful. I worked on Street View at Google and contributed to Pegman along the way.

Juicero was peak ZIRP: a company that raised $120 million to sell a $700 internet-connected juicer for proprietary fruit packets. It captured a moment when venture money was so cheap and abundant that even the most overbuilt, unnecessary ideas could attract serious investors… until Bloomberg posted a 30-second video of the packets being squeezed by hand.

xkcd was, and still is, a shibboleth for a certain kind of proud nerd. xkcd comics were posted everywhere: office doors, dorm rooms, lab walls, and on programmer’s desks. Recognizing one, quoting one, or sending the right one at the right moment (there is an xkcd for every situation) signaled membership in a shared culture.

Growing up in the ’90s and early 2000s, we all communicated with our friends by hiding our computer screens from our parents and messaging on AIM. Gone were the days of curling up with the landline; now you had an AIM username that defined basically your whole personality, and if you had to – God forbid – step away, you set a pithy status to remind your friends that you were funny even if you were momentarily missing. AIM was absolutely ubiquitous. It was the internet’s place for tween romance and sharing the new hot pop punk song.

This is the only item in the museum that I actually own. Beanie Babies were my first true collecting obsession, which eventually turned into baseball cards, and then into art. Every time I walk by flowers for sale, I’m immediately transported back to Ace Florist in Syosset, New York, which also happened to sell Beanie Babies in the late ’90s. After school, I would religiously call from the landline in our house to see if they had any new ones in stock. The day they had the Princess Diana Beanie Baby was the purest rush of dopamine that only true collectors understand. The fact that I still have it, tags and all, nearly 20 years later speaks to the type of hoarder collector I am.

Nothing has shaped my career quite like playing The Sims (and Survivor: Ultimate) on PC as a kid. Growing up, my best friend Tucker and I would disappear into those games, and into the characters we created. Crypto: The Game, the online reality show I created before TBPN, was the game I always wanted to play. Ever since those days at the PC, I dreamed of a real-time, online version of The Sims or Survivor: Ultimate with my friends. I’ve never operated with more conviction than I did building it, because I was the kid playing those games. I knew exactly what challenges would excite me, what twists would shock me, and what hidden immunity idols would be the most fun to find.

HQ Trivia was the second act of Vine co-founders Rus Yusupov and Colin Kroll, and working with them on HQ Trivia, from launch to millions of live concurrents, was the highlight of my career. It deeply shaped everything I’ve done since, from CTG to TBPN. Some of my closest friends are people I met while working on HQ, and there would be no HQ without Vine.