Dive deep into business, brand and strategy.
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Nobody is going to steal your ideas
♛ 18.08.2026 Nobody is stealing your ideas Read Time: 8 Minutes Hello Before we dive into this week’s Digest, I have to share two things. The first: I recently launched Kit.ceo Enterprise, which is essentially positioning-as-a-service that allows you to scale and sell strategy without the department or hire. This is…
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Ramp: The Best Experience Is the One You Don’t See
Ramp, Eric Glyman, and the position they built by accident and never named A note before we begin: I have been watching Ramp for a while now, and I think highly of what Eric Glyman and his co-founders have built. Getting a finance product to the point where customers describe…
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The One Room Where You Still Believe Words
Most of us learn a simple rule before we can read: when words and actions clash, children often take their cue from what adults do. You can say “be gentle” in your calmest voice while you slam the cupboard, but the slam is the stronger lesson. You can tell them…
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Where’s AI headed?
♛ 12.08.2026 AI in 2030 Read Time: 8 Minutes Hello I didn’t write a dedicated Digest newsletter this week. I’ve been heads down building Monopoly. Last week, I was travelling and spending time with a fascinating group of people. Between building and travelling, I didn’t have much time left to write.…
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The Next Moat Is the Learning Loop
Why the winners in AI will own the path from trusted context to better decisions—not merely the data or the answer Enterprise technology is approaching an uncomfortable moment. Companies have spent years centralizing data, connecting systems, building dashboards, and creating increasingly sophisticated models of their businesses. Now they are adding…
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When thinking costs nothing
♛ 04.08.2026 How to Own a Position When Thinking Costs Nothing Read Time: 7 Minutes Hello A quick announcement before we dive into this week’s Digest. For all Kit users, I’ve added two capabilities to Pablo (previously GNYS “Genius”) to audit or create offers and a funnel for any brand. All you…
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Simile’s $2 billion raise: The CERN of Saying Things
TLDR: I read the study behind Simile, the AI startup that just raised $200 million to simulate human beings. The founders interviewed 1,000 people for 2 hours each and built AI agents that fill out surveys the way those people would. Their own paper grades the copies against survey answers…
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Deeds speak
♛ 28.07.2026 Deeds Speak Read Time: 6 Minutes Hello Before we dive into this week’s Digest, I have something to share with you that I care about deeply. Nobody hands you a manual for your own head. You get one for a car, a mortgage, a phone. For the thing running…
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“We left about a billion dollars off the table.”
Patrice Louvet runs Ralph Lauren. That sentence is his, from a 44-minute interview about the brand, and he delivers it the way other CEOs report a record quarter. A billion dollars of real revenue, real customers holding real money, and the company walked away on purpose. Every positioning conversation happens…
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Everything I can prove about therapy
Therapy is a product. In the US alone, it sits inside a behavioural health market worth roughly $89 billion a year (Becker’s). It is sold by the hour, week after week, with no label on the box, no score at the end, and no receipt for whether it worked. I…
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Why therapy is a roll of the dice
Send 7 people to therapy, and about 1 of them gets better because of the therapy itself. The other 6 either improve for reasons that have nothing to do with the room, or they do not improve at all. That number comes straight from the field’s own research, once someone…
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Why Strangers Bet on You and the People Who Know You Won’t
A stranger will bet two million dollars on you after spending six hours with you. The people who’ve known you for twenty years won’t lend you ten grand. I wanted to know why. The answer took me through payroll records, grant reviews, a demoted scientist who ended up with a…
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