Where AIM Failed
When you think of the biggest company that failed to keep up with the times, you probably have Kodak, Blockbuster, Borders, Blackberry, and possibly Yahoo at the top of the list.
When I picked up The Third Wave by Steve Case, the founder of AOL, I couldn't help but think of how AOL failed to keep up with the market with AIM (AOL Instant Messenger). AOL essentially pivoted from being a prominent ISP to a media/ad network; this was a critical mistake.
There was no doubt that AIM was the dominant messenger in the 90s into the 2000s. AIM had profiles before Facebook even existed. It had file transfer which was the simplest method of sending larger files that e-mail couldn't handle (the limit was a couple mbs at the time). It had voice chat before Skype. AIM had bots, like SmarterChild, almost two decades before this bot obsessed craze we're in now. AIM had many features earlier than all of its competitors and I took advantage of all of them as a teenager. It was by far the best method of communicating digitally than anything else.
From this article about the history of AIM, it seemed that AOL had a very different vision of what AIM was to be than the AIM development team. AOL didn't see its potential and didn't put much resources in growing that part of the business.
The market cap of AOL was about $224 billion in 2000 and it is about $4.4 billion today. Skype was bought by Microsoft for $8.5 billion in 2011, WhatsApp was bought by Facebook for $19 billion in 2014, Slack was valued at $3.8 billion at its last investment round.
Maybe AIM was just too early for its time or new startups were necessary to transition to where we are now. But it's easy to imagine how AIM could have been a major player in today's messenger market with the proper effort put into it. But instead, AOL shifted in a more financially safe direction with ad media and abandoned messenging.