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I was just in Dallas, trying to remember other times when I was in Dallas, and then it hit me: I was inside Broadcast.com’s Dallas headquarters on the day in February 1999 when it tried to broadcast the Victoria’s Secret fashion show and melted the internet.

If you don’t remember Broadcast.com, that wouldn’t be surprising. But you probably do know of Mark Cuban, the large-personality owner of the Dallas Mavericks and Stars, host of the Shark Tank TV show, and backer of a whole host of fringe tech things like the secretive Dust chat app and Dogecoin cryptocurrency. He’s flirted with the idea of running for president.

Well, Broadcast.com was where all that started. Cuban co-founded the company in the 1990s with his fellow Indiana University alumnus Todd Wagner. This was back when the consumer internet was new and most people got online through dial-up modems. There was no video on the internet, barely any music. It could take a few minutes just to download one color photograph.

But Cuban and Wagner started their business with the idea that alumni of colleges who moved to some city far from campus might like to hear the radio play-by-play of their college’s sports events. If you went to Indiana and moved to Phoenix, you couldn’t do that – the game would only be on the local Bloomington station. Cuban and Wagner realized that if they could pump the audio – even at low quality – through the internet, anyone anywhere could listen. That was the initial concept of Broadcast.com – an aggregation of college sports radio broadcasts that anyone anywhere could access for free.

This was mind-blowing at the time. Broadcast.com broke radio free of geography. The concept seemed about as weird as a company saying it was building a teleportation machine.

Cuban and Wagner were ambitious, so once they got college sports up and running, they quickly moved on and added all sorts of radio stations and things like broadcasting company earnings calls. Then they took aim at the really big idea: TV over the internet.

That was before YouTube – and ages before Netflix or TikTok. The internet just wasn’t set up for video. Moving images needed too much bandwidth. Compression algorithms weren’t yet available to squeeze video down narrower pipes. Going into video seemed even more nuts than offering up radio over the internet.

The Victoria’s Secret show was intended to be the big bang that introduced the general public to the idea that we could watch TV online. Let me be clear that, unfortunately, I didn’t actually get to attend the fashion show and watch Victoria’s Secret angels strut down the runway in barely anything. I was in Broadcast.com’s data center looking at blinking lights on overwhelmed servers. As millions of people tried to watch (the show was hyped in a Super Bowl commercial just before), the video sputtered and often crashed for those who could log in. A huge part of the audience just couldn’t get in at all. As a publicity stunt for Victoria’s Secret, the show was a huge success. As an experience from Broadcast.com, it sucked.

And yet, as I wrote in my piece about this, the event gave us a glimpse of the future. “If homes start getting broadband internet connections and plugging them into set-top TV boxes, might people watch Broadcast.com instead of TV?” I wrote. “Could Broadcast.com become a kind of interactive, global cable firm?” (You know, like Netflix is today…)

Thinking back now on what happened to Broadcast.com, it’s an interesting twist on something called the adjacent possible. Innovations tend to really catch on when they land in a space that’s just beyond what was possible before, so the innovation seems new and amazing. Yet the innovation can’t be too far into the not-yet-possible where the technology doesn’t work well and the public isn’t ready for it. The adjacent possible, in other words, is the sweet spot between new and practical.

We talk about this with companies in our category design practice. Companies that position themselves too far beyond the adjacent possible risk putting out technology that doesn’t quite work yet while trying to win customers that aren’t ready for this new thing. Such companies often run out of money and time before getting traction. Many of them fail. Through that lens, in 1999 Broadcast.com was too far beyond the adjacent possible and was probably destined to tank.

Except…1999 was the peak of the crazy dot.com boom. Every company was afraid of missing out on something big. Established internet companies had wildly inflated stock prices, and so had lots of capital to play with. Yahoo took one look at Broadcast.com, understood that at some point video over the internet would be huge, and was determined not to whiff on that trend. So Yahoo paid $5.7 billion in stock to buy Broadcast.com in the fall of 1999.

Yep. $5.7 billion.

And THEN Broadcast.com tanked. The dot-com bubble burst in 2000. Internet stocks, including Yahoo’s, crashed. Video was indeed too far outside the adjacent possible and simply didn’t work. Within a couple of years, Yahoo shut down pretty much everything it got with Broadcast.com. The deal is today considered one of the dumbest tech acquisitions of all time, and helped Yahoo go into a long slow tailspin.

But Cuban got rich. He was smart enough to hedge against his Yahoo shares, and so held onto a large part of his fortune even as the dot-coms tumbled. He bought himself a $40 million Gulfstream jet before the end of 1999 and never looked back, buying sports teams and going on to do all the things Mark Cuban has done.

Wagner, who I met for lunch a few years ago in New York, also hedged and invested in some of Cuban’s subsequent ventures. He’s still in the billionaire’s club, but is spending much of his time on philanthropic work and is CEO of the Charity Network. He’s always kept a much lower profile than Cuban.

If there’s a lesson here – other than it’s nice to get lucky – it’s something like this: If you build a company way outside the adjacent possible, and someone wants to come along and prematurely buy you out before the technology really works, go for it.

And then hedge.

Below is the story I wrote after my 1999 visit to Broadcast.com. It’s not available online.

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