Back around the turn of the millennium, there was a company called AllAdvantage. They paid you to install spyware and watch you browse, and sold the analytics to corporations. They'd pay you for... I think it was 48 hours of spied browsing per month, and then stop paying you (but keep spying on you). There was also a pyramid aspect where you'd get something like 10% of all of the amount earned by your direct referrals, with no monthly cap. Also, 48 hours of browsing wasn't enough to hit their minimum threshold for AllAdvantage to mail you a cheque.

A /16 subnet was routed to our fraternity house, licensed to house up to 22 people. 65,536 (minus broadcast, gateway, and network address) IPv4 addresses for 22 people. My roommate bought 1 GB of RAM (about $4k at the time) and a VMWare student license for his Linux desktop. He cut down Win95 to be able to run in 32 MB of RAM (including his COM scripting bot, Internet Explorer, and the AllAdvantage spyware). I seem to remember him configuring the VMs to run 16-bit color to save memory footprint. He scripted the Win95 boot process to read a CSV file off of NFS, remove the top line, and write the file back. The CSV file contained fake name, fake address, etc. The VM would register itself with AllAdvantage, with my roommate as the referrer, and then randomly click on links in Internet Explorer until hitting the payout limit, and then shut down the VM. A Perl script (remember the late 90s?) on the Linux host would re-launch a clean VM every time an old VM shut down, and keep the CSV populated with fake account details.

30 VMs were browsing 24x7 for ALlAdvantage. My roommate set up a caching proxy on his Linux box, so he didn't hose the house's T1 connection. 10% of the payout (the referral fees) over something like 3 months paid for the whole desktop. AllAdvantage never got returned cheques from the fake addresses because they never paid out.

He ran his own DNS server that hopped randomly all over the /16 to reduce the probability of detection. He's pretty convinced AllAdvantage's fraud people noticed him as an extreme outlier. He suspects they ignored him because the data he was generating for them cost 1/11th as much as most of the other data they were selling to customers.

A few years later, our school kept the /16 allocated to us, but only routed the first /24 to the house. I'm sure my roommate wasn't the only one to get up to shenanigans with so many IP addresses.

Edit: He also found some online casinos that didn't explicitly forbid bots and he set up a poker bot that would keep track of its winning percentages against all other players. He set up some monitoring/control software for his feature phone (or was it a PDA) so he could watch his losses from class and shut it down if necessary.

He eventually dropped out of school and was living off of his poker bots until (without health insurance) his appendix burst and he was forced to get a day job to pay off his medical debt.

I hope he gets elected to Congress someday (though he's not very political) just to make a great epilogue to a biographical film.