This issue does not end with an answer. That is deliberate. For more than thirteen years I have arrived in your inbox with a position. Something I had already worked out, tested, and was prepared to defend. This week I am arriving with a decision that is wide open, and tomorrow afternoon I am going to work it in front of a room of people with AI arguing against me the entire way. Start with what I told you last...

AI will agree with you. Ask it for feedback, a second opinion, a pressure test on your best idea, and the first thing back is some version of yes. Good thinking. Strong point. You are on the right track. That is not the AI being honest. It is the AI being built. Standard models learn from human feedback, and human feedback rewards the answer that pleases. Agreement scores well. Disagreement feels like friction, so training optimizes it out. There is...

Two members of the AI Insider Lab came in from different backgrounds, different skill levels, different expertise. They ran the same process and walked out with results that had almost nothing in common. One left with a metaphor that changed how he thinks about leverage. The other left claiming a tenfold jump in impact against effort. Neither outcome was promised. Neither was an accident. Together they prove something most people miss when they judge whether an AI program works. The...

In recent AI Insider Lab sessions, the same realization has surfaced from completely different directions, in completely different industries. One member named four decades of accumulated knowledge that had never been written down. Another named an entire career of pricing intellectual property that lived only in their head. A third described years of thinking scattered across notebooks and folders with no structure connecting any of it. A fourth named a career spent distilling judgment that only they could access. Different...

I started creating content. Then I hit a wall I didn’t see coming. Last week I wrote about my commitment to raise my visibility. I shared that commitment publicly, with full agreement from the toughest critic I know: myself. I then built my content rhythm calendar to hold me to it. There was no more hiding behind busy weeks, many client projects, or even better timing. The pressure was real. The September 4 launch of the second AI Insider Lab...

The Fourteen-Year Blind Spot Fourteen years. That’s how long I’ve been publishing remarkable thinking into inboxes every Wednesday without fail. Clients knew me. My network knew me. But the market, the consultants, advisors, and thought leaders actually struggling with invisibility, had no idea I existed. Here is what makes this worse. For years, I’ve helped my clients do exactly what I’m describing: create vast amounts of remarkable content, publish across platforms, build digital presence that compounds. I built the system....

Eight months ago, I made a decision that had nothing to do with my business. Or so I thought. I had spent several years studying AI. Hundreds of hours of reading, testing, and experimenting. And I kept arriving at the same conclusion: the real advantage was not in using AI tools. It was in learning to work with AI as my thinking partner. But a conclusion is not proof, and I was not going to bring this to a single...

Seven sessions into the AI Insider Lab, I was confident I understood what was happening in the room. I had been present for every minute of every call. I use Glasp.co to transcribe each recorded Zoom session and run it through Claude’s analysis, which gives me a detailed read on what was covered, what questions surfaced, and where members are in their thinking. After every session, I review those notes carefully. I thought I had a clear and accurate picture...

The week before I facilitated a structured AI interview exercise live with my AI Insider Lab participant, I ran it on myself first. I do this with everything I teach, but this particular run changed something. AI asked me one question. Then another. It refused to let me summarize early, refused the easy answer, kept pushing until something I had been doing instinctively for decades finally got named back to me, out loud, for the first time. That exercise is...

I am spending this week on the streets of New York, in a street photography workshop with Peter Turnley and a dozen other photographers. On the subway back from Coney Island, a young woman sat down across from me with her eyes closed, listening to music, somewhere far inside her own world. When she opened her eyes for a moment, I waved and told her I would be honored to capture a few photographs of her. She smiled and nodded....