America Online

I remember the first time I heard that voice—"You've Got Mail"—and I understood instantly that something fundamental had shifted in American culture. This was 1995, maybe 1996, and I was visiting a friend in Silicon Valley who had one of those new Pentium machines, and the dial-up modem screamed its handshake noise, and then that disembodied voice announced that messages had arrived, and I thought: this is going to change everything. I was right about that, though not in the ways I expected. AOL didn't become the future of media; it became the training wheels that America used before throwing them away.

You have to understand what AOL was to understand the internet today. For millions of Americans—maybe most Americans—AOL *was* the internet. Not a portal to the internet, not a service that provided internet access, but the whole thing. The walled garden of AOL channels, chat rooms, Instant Messenger, email addresses that became identity markers (your first email was probably yourname@aol.com). The CDs that arrived in every mailbox, jammed into every magazine, handed out at every Best Buy—by some estimates AOL produced 50% of all CDs manufactured in the 90s. This was internet evangelism at industrial scale, and it worked.

The cultural impact is impossible to overstate. AOL chat rooms were where an entire generation learned to socialize online, for better and worse. A/S/L? became the universal opening line. AIM buddy lists were the first social graphs. Kids spent hours crafting away messages and choosing fonts that expressed their personalities. Before Facebook, before Twitter, before any of it, there were those yellow running men indicating that your friends were online and available to talk. I've interviewed rock stars and presidents, but I still remember the specific anxiety of waiting to see if a crush's screenname would appear on my buddy list.

The Time Warner merger in 2000—$164 billion, the largest merger in American history at the time—is remembered as perhaps the worst deal ever made, a case study in hubris that business schools will teach for centuries. Steve Case, AOL's CEO, essentially convinced old media that new media would eat them unless they partnered up, and convinced them at the absolute peak of the dot-com bubble, with AOL stock as the currency. When the bubble burst, Time Warner shareholders were left holding worthless paper while AOL's dial-up business collapsed under the weight of broadband. The synergies never materialized. The cultures clashed. The combined company wrote off nearly $100 billion in value. It was, as they say, a learning experience.

Today AOL exists as a weird appendage of Yahoo (itself an appendage of Apollo Global Management), still serving an aging customer base that never migrated to Gmail, still processing payments from people who somehow still have dial-up accounts in 2026. The brand survives as a news portal nobody asked for, serving content to people who accidentally made it their homepage in 1998 and never figured out how to change it. It's sad, but it's also a reminder: AOL brought more people online than any other company. For millions, AOL was their first glimpse of a connected world. That counts for something, even if the execution was ultimately fumbled.