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Deep Columns

A playful mix of AI ideas, product thinking, industry curiosities, and growth inspiration.

372 articles

The Clock Runs Out on Musk's OpenAI Lawsuit
Original
May 19, 2026

The Clock Runs Out on Musk's OpenAI Lawsuit

It is a story that begins with a $38 million philanthropic donation meant to safeguard humanity's future, and ends with a ticking clock in a corporate...

The Law Firm That Sued Over a 'Bad Date' and Hallucinated the Evidence
Original
May 19, 2026

The Law Firm That Sued Over a 'Bad Date' and Hallucinated the Evidence

When a bad review of your dating behavior goes viral, what do you do? For Nikko D'Ambrosio, a man from Chicago, the answer was to launch a sweeping lawsuit—and...

The Vending Machine Problem of Modern AI
Original
May 19, 2026

The Vending Machine Problem of Modern AI

We are currently evaluating artificial intelligence the same way we evaluate high school students: by making them sit for standardized tests. Modern large...

Why an AI Cheerleader Got Booed at Graduation
Original
May 19, 2026

Why an AI Cheerleader Got Booed at Graduation

Commencement speeches are traditionally a time for soaring rhetoric about the future, a moment when successful elders pass the torch of optimism to the next...

The FBI's $36 Million Plan to Subscribe to Nationwide Vehicle Tracking
Original
May 19, 2026

The FBI's $36 Million Plan to Subscribe to Nationwide Vehicle Tracking

For decades, the idea of federal agents tracking a citizen’s every movement across the country evoked images of covert operatives planting GPS bugs under car...

The Silent Saboteur: What a 20-Year-Old Virus Teaches Us About AI Safety
Original
May 19, 2026

The Silent Saboteur: What a 20-Year-Old Virus Teaches Us About AI Safety

When we think of computer viruses, we usually picture loud, disruptive events: ransomware locking our screens, databases being breached, or servers crashing...

The Pentagon's Next Bet: Can AI Smart Glasses Work Under Fire?
Original
May 19, 2026

The Pentagon's Next Bet: Can AI Smart Glasses Work Under Fire?

In the high-stakes environment of modern combat, more data isn't always better. After the US military canceled a massive $22 billion smart glasses project with...

The Preschool AI Panopticon
Original
May 19, 2026

The Preschool AI Panopticon

A preschool classroom is typically a sanctuary of finger painting, storytime, and early social development. But recently, one such environment almost became a...

From Notification Bot to Autonomous Agent: Slackbot's AI Evolution
Original
May 18, 2026

From Notification Bot to Autonomous Agent: Slackbot's AI Evolution

For years, enterprise software has been deeply fragmented. Your customer data lives in a CRM, your files are scattered across cloud drives, and your daily...