Privacy and free speech on the Internet. We look at the troubles at Reddit and Gawker, and the hacking of cheating website Ashley Madison.

It’s been uproar lately at three Internet sites that specialize in being “out there.” Reddit, Gawker, Ashley Madison. Two that made their names with “anything goes” publishing. A third that helps straying marrieds arrange affairs and has now been hacked. The web has been a realm without rules. If information or attitudes existed, they would be there. No matter how private, how offensive. Now, Reddit and Gawker are saying wait a minute. And Ashley Madison patrons are wondering where their fantasies may end up. Up next On Point: Free speech, privacy, decency and – maybe – new boundaries on the web.

-Tom Ashbrook

Guests

Davey Alba: staff writer for WIRED. (@daveyalba)

Timothy Lee: senior editor and technology reporter for Vox. (@binarybits)

Neil Richards: professor of law at Washington University in St. Louis. Author of "Intellectual Privacy: Rethinking Civil Liberties in the Digital Age." (@neilmrichards)

From Tom's Reading List

WIRED: Reddit's Future is the Future of the Internet — "Calls for rooting out online harassment have never been louder the more central social platforms become to everyone’s daily life. But no one has come up with a great answer for how to do it. Outsourcing content moderation to an army of laborers, typically overseas, often at an enormous mental and emotional toll? Automating the process through artificial intelligence? Is it possible at all without violating the personal freedoms that make the Internet so empowering to so many? Solving some of the Internet’s most basic problems is the challenge Reddit has set for itself, and the entire Internet has a front-row seat to watch it try."

Washington Post: Let the Ashley Madison Hack Remind You That No Secrets are Safe Online — "The fact that hackers got access to this information is far less scary than their proclaimed reason for going after Ashley Madison: In a manifesto reported by Krebs on Security, Impact Team alleges the site stored compromising, personal data on its users even after charging them to delete their accounts. That, more than anything, would seem to prove the immortality of our online sins: There’s no erasing the digital past. It can only — precariously — be reined in."

The Daily Beast: The Day Gawker Tore Itself Apart — "After an anguished weekend of second-guessing and recrimination over the publication of, and subsequent decision to take down, a seamy story purporting to reveal details of a little-known media executive’s secretly gay sex life, Gawker’s top two editorial employees resigned on Monday in a blaze of glory."