Navy & Air Force Cancelling $800M in Projects

Plus: GPT-5 will be OK; Perplexity‘s latest stunt

Joey Padgett
August 14, 2025

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.

A quick thank you to this week’s partners:

Photo by Conner Baker

What's up: OpenAI's GPT-5 launch has been turbulent, with users complaining about failed math problems, poor map drawing, and a "colder tone."
- The launch also initially blocked access to prior models (since reversed that for paid users); instead, GPT-5 would find the right model for the task.
So what: Most news coverage sees this as OpenAI losing a step (due to competition, departing talent, etc.), but I think they’re wrong. This is just OpenAI pivoting into monetization mode. They are already a household name with an incredible talent pool. Limiting model selection to paid users and sending cheaper models to do easier tasks are both signals they care about profitability. This isn’t losing a step, it’s a step forward. The other model co’s will follow suit.

What's up: The US Navy and Air Force are poised to cancel two nearly complete HR software projects that cost over $800 million over 12 years.
- Multiple factors seem to have contributed to this, including:
  - An executive order from President Trump demanding speed and risk-taking in defense-related spend
  - Re-prioritization of resources/funding from DOGE related cuts
  - Previously excluded vendors with more modern tech jockeying for a seat at the table
So what: Look, I understand wanting to modernize and move fast… but you hate to see wasted work! My heart goes out to all the vendors and consultants who have been grinding for years (through red tape, snow, uphill both ways…) to try to get these projects shipped. I hope the things that are actually ready get launched.

What's up: Perplexity AI made an unsolicited $34.5 billion offer to buy Google Chrome, framing it as an antitrust remedy.
- The startup, valued at $18 billion, pledged $3 billion over two years to upgrade Chrome's infrastructure.
- Analysts questioned whether this is a serious bid or a publicity stunt, given the offer is nearly double Perplexity's valuation.
So what: Call it what you want (publicity, ambitiousness, desperation)… I call it hilarious. And completely on-brand for Perplexity. This is the same company that hired an actor from HBO’s Silicon Valley show to be their “Chief Security Officer”, ran ads making fun of Google’s AI, and tried to buy TikTok. This Chrome deal will not happen. But eventually, one of these crazy stunts might actually work! Be on the lookout for the dog catching the car.

What's up: Google's Gemini will now automatically remember past conversations without prompting, personalizing future responses.
- The feature builds on last year's manual "remember" function and will be enabled by default in Gemini 2.5 Pro.
- Google is also introducing temporary chats that won't be saved or used for personalization, addressing privacy concerns.
So what: Compared to the swashbuckling Perplexity story above, this test and expand approach feels downright old-school. But Google’s gradual entry into memory functions is smart if you consider their scale. Sure, ChatGPT might have tons of random conversations with you, but Google has your Gmail, your calendar, your photos… If they want us to trust them to build Gemini experiences that connect that data as part of memory functions, they need to prove at every turn that they deserve that trust.