Something Awful isn't exactly a "weird asset", it's a literal one that has now been driven into the ground.
Ebaums world (a site that basically just steals content) was sold in
2007 for nearly 70 million dollars/stock options.
4chan was sold in
2015 for an undisclosed amount, but likely for a decent stack of cash.
Reddit, a shit website launched in 2005, is now allegedly worth $2.5+ billion
Twitter, a shit website launched in 2006, is now allegedly worth $4.4+ billion
Minecraft, a videogame started by a single asshole on 4chan in ~2007, was sold for $2.5 billion cash.
Something Awful in 2000-2010 was likely worth a lot of money for larger companies trying to break into social media and try and be the next myspace/facebook/whatever and Something Awful checked all of the right boxes (content creation, currently profitable, large footprint, attractive to new users) and
@Lowtax probably received several really good offers on it, I wouldn't be surprised to hear an offer of 30 million being thrown around, considering some offers made to Ebaums world.
The problem with Something Awful as an asset is
@Lowtax - he doesn't want to do
anything but thought without any intervention that SA would be a Twitter/Facebook tier site, that he would be the CEO of a 3 billion dollar company so
of course he wouldn't sell the site. That would be like asking Zuckerberg to sell facebook in 2011 - it's only going up from here!
Most internet sites (like Something Awful) start small, but grow large as needed - YouTube started as just two friends wondering why it was so fucking hard to share videos, 4chan was just SA's ADRTW off-site, and reddit was just two guys trying to come up with ideas. Something Awful never grew large as needed,
@Lowtax never had more than 2 employees (+a few per article writers, not getting paid much) - he never seemed to entertain the idea of letting anyone help with SA, or giving up any of the control for investment capitol. He also never seemed willing to pay real money to people producing content for him, something that would have tons of content creators walking away from him (Yahtzee of the Escapist being the most obvious).
When companies expand, they need a lot of cash to do so. They will put out funding calls (using company shares) sometimes to the tune of tens or hundreds of milliions of dollars - and it's usually needed. Massive amounts of hardware, bandwidth, a professional IT team (with a real CIO/CTO), and a whole slew of employees that are invested in the company.
@Lowtax only ever got Radium and Shmorky and can't even scrape together $30,000 to move onto real forums software (like Xenforo).
Something Awful, from an investment standpoint, is dead. The site is profitable, but not substantially so. They are no longer content generators (except for Kiwi Farms) and the existing content generators have all left for greener pastures. They no longer have a draw for new users and have been supplanted by every other website in existance in some way, as they are all free. The much larger trend in profit in the social media space, User Data, has no value as SA doesn't have the capacity to collect any data on it's users - even if they did, SA's userbase is regardeded as the least friendly to marketing and marketers.
TL;DR -
@Lowtax thought that SA would just magically grow to Reddit/Twitter size with 0 effort on his part and that selling SA would be dumb, because some websites can be worth literal billions. We know that SA did not magically grow and instead shrunk into a garbage cesspool and that it is in no way worth anything in 2019, but it was probably worth quite a bit in the 2000s.
