Oracle Fires CEO Amidst Best Year Ever

Plus: Ad-Free AI is Ending; YouTube Hides Pop-Ups

Joey Padgett
September 25, 2025

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Hey people!

Welcome back to Forests Over Trees, your tech strategy newsletter. It’s time to zoom-out, connect dots, and (try to) predict the future.

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And as a housekeeping note, we’ll be off for the next 2 weeks for some very exciting and eagerly-awaited vacation. Talk to you after!

Photo by Faris Mohammed

What's up: OpenAI posted a job for a Growth Paid Marketing Platform Engineer to build internal ad campaign management and attribution tools.
- The role is part of a new "ChatGPT Growth team" tasked with building technical infrastructure for OpenAI's paid marketing platform.
- ChatGPT usage has grown to 700 million weekly active users, up fourfold from a year earlier.
So what: Oh dear… the ads are coming. It’s been nice to use AI to our hearts’ content (or our daily maximum allowed tokens) without feeling like we are being sold to, but it was inevitable that the ads would come. The silver lining, if there is one, is that monetizing should strengthen OpenAI and the competitors that will undoubtedly follow suit. We’ll need them to get stronger and more grounded in business reality if we want to avoid the “AI bubble” pop some analysts have been predicting.

What's up: YouTube added a "hide" button to dismiss end screen recommendations that often cover video content.
- Testing showed the feature resulted in a 1.5% decrease in views from end screen clickthroughs.
So what: This grabbed my attention for a few reasons. First, as a user, this is great. I love YouTube, but the pop-ups, autoplays, and other features designed to boost views can be infuriating. But second, putting myself into the shoes of creators, this has to be frustrating. Every percentage point counts! Pop-ups help drive viewers deeper into creators’ archives, building more trust and better monetizing in the long term. This move by YouTube is another reminder to all my fellow creators out there… if you are beholden to a single platform to reach your audience — then it’s not your audience. It’s the platform’s.

What's up: Oracle appointed cloud executives Clay Magouyrk and Mike Sicilia as co-CEOs, replacing 11-year veteran Safra Catz.
- Magouyrk (39) handles cloud infrastructure while Sicilia (54) oversees cloud applications and AI products.
- Oracle stock is up 85% this year amid AI boom, with a reported $300 billion OpenAI cloud deal over five years.
So what: This timing feels all wrong. You don’t change coaches when you’re winning championships. For the last year or so, Oracle has been all over the news (for the right reasons). They’re included in the TikTok deal that will (allegedly) be signed this week. They signed a $300B deal to sell compute to OpenAI for Stargate. They had a record-breaking financial quarter and raised cloud infra revenue by 55%… It’s against human nature to walk away from being CEO when you’re having the best year of your corporate life. So why now? Maybe Catz is just a class act thinking of what’s best for Oracle long term (the way the press release implies). Or maybe she’s concerned about the pace of change and the risks being taken. Or maybe the board is recognizing the leaders who are most contributing to the upswing. I can’t wait to find out what’s actually going on here.

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