AI: OpenAI's 'AOL Moment'. RTZ #970

As discussed in these pages, OpenAI had an extraordinary year in 2025, culminating in its third anniversary of ChatGPT on November 30 last year. This while its peers had a pretty good year for the most part too. Then of course came its internal ‘Code Red’ as Google took the current lap leadership in this AI Tech Wave with Google Gemini 3.

With over 900 million weekly users and a private market valuation of $500 billion+, OpenAI is still in the pole position in 2026.

But its current position is deja vu for a lot of tech anaysts like yours truly, who saw America Online, aka AOL, rule the Internet wave in the nineties. And that’s the Bigger Picture I’d like to unpack this Sunday.

The similarities are there, based on at least five key points.

1. Iconic Early Brand: For mainstream users, AOL was the Internet, just as ChatGPT is AI to early users today. From the dawn of the commercial Internet in 1995, AOL became the mainstream gateway to the internet through its walled garden subscription services. When regular folk paid their flat monthly subscription and went online via their AOL modem access, they assumed that everything they perused online was the internet. Much like today, when mainstream millions access AI via ChatGPT, they assume that’s the AI they’ve been inculcated with in the mainstream media for three years. Both AOL and ChatGPT became the ‘Kleenex’ of their respective tech waves. And that’s a great starting position in any wave.

   

2. Premium Valuation: At its peak in 2000, AOL was valued at over $220 billion, on the eve of its ill-fated merger with Time Warner, the biggest media company at the time. That is over $420 billion in today’s dollars. Not too far from OpenAI’s private market mark of half a trillion today. And OpenAI just signed an investment deal, although far smaller, with Disney, one of the biggest media companies around today. Again, a similarity worth noting for the extraordinary opportunities that offers to the perceived global market leader.

   

3. Rich Application Portfolio Aspirations: Just as AOL ruled the early internet in the nineties in applications ranging from messaging (AOL Instant Messenger, aka AIM), Finance, Healthcare, and more, OpenAI has similar ambitions in a portfolio of AI applications. Indeed, founder/CEO Sam Altman has appointed a ‘CEO of Applications’ in Fidji Simo, that I’ve discussed at length. And the company remains laser focused on its roadmap to AGI, with AI Reasoning and AI Agents the next key steps up that ladder to whatever AGI ends up being as the goal line.

   

4. Subscriptions and Ad Based Revenue model: ChatGPT pioneered the subscriptions model for mainstream chatbot AI, just like AOL pioneered flat, affordable pricing for ‘all you can eat Internet’. And OpenAI is focused on a ‘for profit’ model supplementing that major revenue stream with ads, just like AOL did back then. Of course today, OpenAI is also up against Google and Meta in particular, competing for those ad dollars. But the parallel holds, as well as OpenAI plans to make AI Ads work.

   

5. Mainstream growth via lower-priced subscriptions: AOL pioneered on making its subscriptions affordable relative to higher priced competitors like CompuServe, Prodigy and others. OpenAI this week announced a cheaper subscription ‘ChatGPT Go’ tier offering at $8 a month, a tier below its ‘plus’ offering at $20 per month and higher. Peers and competitors have been positioning for higher priced subscriptions of hundreds of dollars a month. This bid for mainstream AI affordability is smart move by OpenAI. Especially as its invests aggressively in a trillion dollar plus AI Compute Infrastructure portfolio to be able to serve billions of mainstream users.

   

These five are some of the key similarities between the two market leaders of their tech eras. And Open AI is leveraging them all in 2026 to expand the DISTRIBUTION of its AI services to mainstream users as fast as possible.

AOL of course, had a range of competitors, including MSN by Microsoft, CompuServe by H&R Block and others.

OpenAI’s competitors are far more formidable and relentless in their enormous resources and laser focus. Google, Meta, Elon’s Tesla/xAI, Apple, Amazon, Anthropic and others present a daunting competitive landscape indeed.

But OpenAI is in the frenetic fray on all cylinders.

And executing furiously against its ‘AOL Moment’.

Can’t wait to see how it goes this time. That is the ‘Bigger Picture’ indeed in this AI Tech Wave. Stay tuned.

(NOTE: The discussions here are for information purposes only, and not meant as investment advice at any time. Thanks for joining us here)