On a long bet
In early 2012, at the Webstock conference in Wellington, New Zealand, my new friend Jeremy Keith was on stage talking about the impermanence of the web and the ephemeral nature of our work and over drinks afterwards together we came up with a quick challenge for a Long Bet (update: I misremembered the origin, Jeremy wrote about it a year before, mentioned it on stage, and I took him up on the offer as the opposing side afterwards). The original idea was that an arbitrary URL would still work far off into the future but when I read my justification today it feels hilariously short-sighted. I focused mostly on the stability of web tech in my argument while ignoring how many businesses, tiny blogs, and news desks disappear every few years. I still believed that the longbets URL would work in the future since I trusted the organization was stable and their tech stack was relatively mature, but I think there are flaws with how the bet was set up.
The way the bet was written and agreed upon isn't so much about the longevity of the web directly, instead it's more about the longevity of the Long Bets project and website, which kind of misses the mark in my mind all these years later.
In the 11 years since, I think I've come up with a better bet that hopefully gets closer to the heart of what Jeremy wanted to bet against. If I were to get a do-over on it today, I would pick the date the bet was created, February 22, 2011, and I'd say grab the front page of MetaFilter.com, which is here, with 35 posts on it that day. I think a more accurate bet would be whether or not more than 50% of the links mentioned in every post to outside pages still work (or don't work) 11 years into the future.
I would have taken the 50% or more links work side of the bet, and looking at the first handful of posts I'm frankly surprised I am only seeing a couple 404s and I even see a link to a publication's article from 2001 that still works(!!!). I would have guessed there'd be quite a bit more 404s so many years on, as it seems like every old post I stumble on at MetaFilter links to a 404'd site.
I'm stoked the bet is coming to a close and I guess I'm happy to win it for the Internet Archive, but I wish it sampled more from the general web, making it was more real-world and focused less on the long bets organization or website specifically.
By the way, this reminds me that I was once at a Stewart Brand talk at the SF City Club where he and other cofounders talked about the 10,000 year clock and sort of debuted the idea of the Long Bet website in 2001 or so, and the audience was asked to come up with some bets. I didn't have money to parlay back then but I really wanted to challenge my pal Jason on the spot that maybe 15 years into the future, we'd likely have legalized marijuana nationwide in the US. I'd seen early trends in the first medical uses and figured boomers would grow up and change the laws they flouted when they were younger by the time a few more presidents were in charge. I was hopelessly naïve.