🕶️ Google vs. the DOJ: The AI Chapter

Ten bullets of updates

1. 🇺🇸 Tech CEOs met behind closed doors with lawmakers in DC, warning that beating China in AI means betting on them.

2. ⚖️ Firms like Paul Weiss and DLA Piper use AI for research and drafting, calling it a “super associate” that never sleeps.

3. 📚 A judge questioned Meta’s use of copyrighted books to train AI, signaling that fair use may not cover mass scraping of protected texts.

4. 🧑‍💻 Burned-out devs are pivoting to roles like prompt engineer, AI ethicist, and no-code consultant — trading code sprints for saner, still tech-adjacent gigs. 

5. 🍕 Giordano’s CEO is modernizing the iconic pizza brand with AI tools, delivery tech, and a push to expand beyond Chicago’s deep-dish legacy.

6. 🤖 A DOGE recruiter claims AI agents could replace 70,000 federal jobs, sparking backlash from Palantir alumni who responded with clown emojis and skepticism.

7. 🔄 Fivetran acquires Census to offer an end-to-end data movement platform, aiming to simplify how companies sync, store, and activate their data.

8. 🍏 A new ruling in the Apple vs. Epic case forces Apple to loosen App Store rules — but stops short of calling it a monopoly, keeping both sides unhappy.

9. 🗣️ OpenAI pledges updates to reduce ChatGPT’s “sycophantic” answers, aiming to make the model more honest, nuanced, and less eager to agree with users.

10. 🇪🇺 TikTok pauses its new app in the EU after regulators raised concerns over data transfers to China, reigniting scrutiny over its ties to Beijing.

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🧠 Google’s AI Advantage Faces a Legal Test

The biggest antitrust case in over a decade just put AI front and center. According to DOJ testimony, Google didn’t just dominate search — it used billion-dollar deals with Apple and others to stay dominant, locking out competitors like Neeva and other AI-powered challengers before they had a shot.

Internal emails show execs were worried about emerging threats to the “Google habit,” especially as AI started changing how people search. 

Now, as Google rolls out its own AI Overviews, the trial raises a bigger question: is the future of AI-powered search already captured by the same gatekeepers we’ve had for 20 years?

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Panama Took Back the Canal—Then Sold the City

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These companies just raised money

1. 🌱 Ara Partners raises $800M to decarbonize old industrial assets, betting that cleaning up dirty infrastructure is the next big climate opportunity.

2. 💥 Defense tech startup Mach Industries is raising $100M to scale its hydrogen-powered weapons, drawing serious interest from VCs and the Pentagon alike.

3.  📈 Buzzy investing app Dub lands $30M Series A to gamify stock trading for Gen Z, blending social features with real-time portfolio tracking.

4. 📊 GenAI adtech startup Paramark raises $6M with a deck promising more personalized, efficient media buying — and fewer wasted ad dollars.

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💸 The Quiet Desperation of Fintech Startups

Canadian fintech startup Bench just laid off 10% of its staff — not because it's folding, but because it's been operating “month to month” for over a year. The company hasn’t raised funding since 2018, and while it’s not bankrupt, it’s also not thriving — stuck in a holding pattern with no clear way out. And it’s not alone.

Across the startup landscape, many companies are quietly doing the same: trimming teams, freezing raises, and trying to extend runway without admitting they’re out of options. It’s a side of the downturn we don’t talk about as much — not the dramatic collapses, but the slow fadeouts.

In a post-ZIRP world, the startup graveyard isn’t filled with explosions. It’s filled with silence.

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Startup Events and Deadlines

1. Smash it like a Founder l May 3 l Bengaluru

2. Builders' Evening with Andreessen Horowitz l May 5 l NYC

3. Chicago Coffee Club | Early-Stage B2B SaaS Founders & Funders l May 6 l Chicago

4. Slidebean’s Crash Course in Financial Modeling l May 8 l Online

5. Crash Course on Startup Fundraising with Caya (Slidebean CEO) l May 20 l Online

6. Startup Battlefield 200 | Deadline: June 9 | Global

7. Entrepreneur First London - Summer | Deadline: July 1 | UK

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