He had a tattoo that said "Call me a baby because dolphins make me cry." He also said he'd pour hot oil on a kitchen robot to keep his job. I met him because I turned down Dave Grohl to hold a sign in Washington Square. Here's what I learned.

The prompt before the prompt is noticing what deserves attention.

Reese Witherspoon asked her book club, "do you use AI?" Three million people watched. The internet split — and both sides were right, because they were arguing about the wrong word.

A real concern is not a valid conclusion. An EVP in finance emailed me last week about AI sycophancy. Most people raise that concern as an off-ramp. He made it the curriculum.

There are levels of AI augmentation: Some people use AI to draft emails. Josh used it to run 27 agents on a single problem, from his mobile on the road, with all the context of his laptop at home. Those are not the same thing.

AI can make you 100x more productive at work, and make being present at home feel 100x more expensive. That tension isn’t just personal weakness. It’s a new economic reality.

I almost moved a family trip for two business opportunities. That moment made me ask a question I think every AI power user needs to sit with: What if your biggest AI risk isn’t bad output, but a misallocated life?

I'd been stuck for weeks — not because the technology wasn't available, but because I hadn't thought to ask. I've started calling these 'wherewithal moments.' They're hard to manufacture. But they compound.

Most people treat AI like a better search engine. The few who've broken through treat it like a team that never sleeps. If you don't feel the pain of idle agents, you haven't grasped what's available to you.

Finance 101 says diversification — holding a broad range of investments from safe bonds to growth equities — is the best way to reduce your risk and maximize return. So why is your AI strategy all municipal bonds?

AI adoption is plateauing. I analyzed 5,000 anonymous survey responses looking for the culprit. I found it. And it's not what I expected.

A senior executive called to tell me my talk was "one of three ingredients in the best idea I've ever had." That almost never happens. Here's why it should.

If your board members haven't personally experienced what AI can do, they cannot exercise their fiduciary responsibility. Fiduciary duty used to mean financial oversight. Then it expanded to include strategy, risk, culture. Now it includes imagination.

Everyone's “exhausted” by AI talk, or at least, that’s what I’m hearing. But there’s a more nuanced undercurrent. When I asked a room full of executives to show me what they'd actually built, everybody froze. That's not fatigue. It's something else entirely.

Standing in my hallway surrounded by broken glass, I asked AI for 10 terrible ways to respond. What came back changed how I think about parenting—and about AI.

Here's what I've noticed over the past year. (And yes, I include myself in this.) Leaders are really good at telling their teams to embrace AI. They're much less good at embracing it themselves.

A generation ago, you had to be independently wealthy to have access to intelligent assistance. Not anymore. I’ve got a team of advisors at my fingertips. And so do you.

Your organization spent years building innovation capability. Now AI arrives, and folks ask: 'Should we keep investing in creativity, or redirect that budget to AI tools?' The answer will determine whether you dominate the next decade—or get left behind.

What if the most powerful AI leadership move isn't answering your team's questions, but asking them one simple question instead? Five words that build capacity, create permission, and get you out of the bottleneck.

There’s a dangerous double standard that's killing our AI collaboration: abrilliant friend makes an honest mistake? We easily overlooked it. But if AI had done the exactly same thing we’d be furious. We'd conclude AI is either incompetent or broken. Our loss.