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“Did You Read It?”
A little over a month ago I had a tough conversation with a young tech founder. Not a blow-up. Just one of those “here’s what I’m concerned about” conversations. I had a number of concerns and I wanted him to really think how he’d address these concerns as the company grew. Instead, the next morning, I awoke with an obviously AI-written 25-page report in my inbox addressing those concerns. I didn’t ask for a report. I am the LAST person to be anti-AI. I use AI all day every day. But this was not ‘thinking’. This was 100% outsourced thinking. I did skim it. It looked thorough. It sounded polished.…
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The Rise of the Chief AI Officer
Most companies are making the same mistake with artificial intelligence: they are treating it like software or as hype. That instinct is understandable. For the last two decades, business leaders have been trained to evaluate new technology in familiar ways. A product emerges, vendors make their case, the IT department reviews security and compatibility, finance negotiates pricing, and another software subscription is added to the stack. That model worked reasonably well in the SaaS era. It may prove inadequate in the AI era. The companies that solve this early may create years of advantage. Artificial intelligence is not simply another application layered onto existing workflows. It can replace certain repetitive…
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Are We in an AI Bubble? No, but Still be Wary.
9/25/2025 Super interesting article published in the Atlantic. In my 30ish years of startups i have NEVER seen anything like this current spate of AI companies. Part of it is technology: What used to take a team of at least nine or 10 employees, can now be accomplished by just one or two founders and it’s not because of the efficiency of AI Once you have the legal and financial underpinning of your company in place, the technology available to startups right now is unprecedented. Sites like bubble.io can help you to build a sophisticated website and user interface including login authentication and workflows. Stripe.com can do your billing. Hubspot can handle your landing…



