Everyone eventually sells advertising online. It's one of those laws of the internet. Even if you despised it as vehemently as Sam Altman did. When you raise billions of dollars from investors, you will need to start paying the piper; otherwise, the capital will dry up.

But let's start by taking a step back.

It feels like ChatGPT has started testing ads on its platform, but compared to Facebook, Google, Walmart, Amazon, and eBay, it's clear that they are not the fastest to add ads. I know it's not apples-to-apples, but aside from eBay and Walmart, these are the juggernauts Sam Altman is competing against. Facebook (a part of Meta) offered low-cost ad slots two months after launch. Remember, it was “thefacebook” then, and ads were supposed to make it not cool, according to Zuck. We continuously forget that every company is a unique entity at a different lifecycle stage, unless you are Amazon, which seems to continually disrupt itself.

Advertising is the highest-margin business model any company can add to its revenue opportunities, but I believe it should be pursued only after all other opportunities have been exhausted. Why? Once you sell ads there is no going back. You are changing the customer experience - either making it worse (Amazon is the prime example of this) or raising questions over bias and accuracy of the results being generated by technology.

In other words, trust is paramount and cannot be regained after it is lost. We all learned during the Google advertising lawsuit that, as much as Google wants us all to believe, they operate a black box with no visible knobs in cases where executives had the opportunity to impact results.

It's yet another sign that shows the differences and access to capital at the times these companies were founded. So, can you really compare these companies to one another, or does this show investors' desperation to find a new opportunity that could generate significant revenue? I dunno.

It is increasingly clear that comparing companies like OpenAI, Anthropic, and others to incumbents is like Icarus flying close to the sun, hoping the sun will not melt his wings. These companies have raised capital at levels that make them borderline too big to fail, but it also requires Sam Altman to morph into Sam "Adman" to ensure that they can generate enough revenue amidst record capital burn. Imagine burning through $8-$12 billion in this current economy. Are there any analogs for entrepreneurs or executives to think of? Agentic, whatever that is, is not going away in 2026.

ChatGPT will test advertising with logged-in customers on the free or Go (a new option) plans. They claim to be doing this “thoughtfully,” but the company expects advertisers to commit $1 million on CPM ads during this test. Why would anyone feel the need to throw $1 million into an unknown advertising system?

Do you remember watching the classic movie: “Speed?” Keanu Reeves and Sandra Bullock on a bus heading into the city, being watched by a crook via video. Altman reminds me more and more of Reeves, and of the need for a third party to get him and others off the bus and into a place where they can get help.

Sam's sudden change of heart raises more questions about OpenAI's governance. Who precisely is driving this bus?

PayPal acquired Cymbio last week for an undisclosed sum, reportedly $150-200 million, to offer agentic services to merchants. This echoes PayPal's 2021 acquisition of Happy Returns ($275 million). Both startups received investment from PayPal Ventures. Cymbio, which raised $35 million in VC funding, was acquired four years after PayPal Ventures' investment.

Cymbio integrated merchant catalogs into LLMs prior to the acquisition and was not acquired for its original dropshipping solution. Notably, Cymbio customers used PayPal-enabled checkout for agentic commerce on platforms like Microsoft Copilot and Perplexity, not the most-adopted LLMs (ChatGPT and Google's Gemini).

PayPal is betting $200 million that the future of shopping isn't humans clicking "Add to Cart," but AI agents autonomously purchasing products via background data feeds. By owning this "agentic plumbing," PayPal transforms from a simple checkout button into the essential infrastructure for an AI-driven economy.

We are starting to get ready for earnings season. First, on Wednesday, Meta will report earnings. The questions that are top of mind: