Month: December 2025

Christmas Eve Reflections:  3 shifts and 3 predictions…

Christmas Eve Reflections:  3 shifts and 3 predictions for 2026. 🎄❄️ Writing this on Christmas Eve as I look at the horizon for next year. The “AI Hype” is settling, and the real architectural shifts are beginning. The 3 Shifts: 1. RAG ➡️ Agents 🕵️‍♂️: Most chat solutions are stuck in 2024 architectures (Retrieval Augmented …

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You can build software over Zoom, but it doesn’t come…

You can build software over Zoom, but it doesn’t come close to the magic of in person meetings. For over a year, I’ve been working in the trenches remotely with the incredible teams at Victoria Beckham and Crocus. We’ve shared dashboards, Slack messages, emails, and strategy calls across time zones. But this week, we met …

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A lot of “classic” startup advice is about to age very…

A lot of “classic” startup advice is about to age very badly. đź‘€ For years, the default playbook was: focus on a narrow ICP, build a single wedge product that solves one acute pain (a painkiller, not a vitamin), and worry about your “second act” later. Then Rippling happened. Parker Conrad (I’m a big fan) …

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Just now The Information broke a story that a major…

Just now The Information broke a story that a major retailer’s newly launched chatbot was jailbroken into discussing off-limits topics after a guardrail misconfiguration This is a difficult problem and I understand how stressful it can be for the teams involved. Here is why most of Jailbreaks happen: If you ask a single LLM to …

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A global luxury brand asked me a blunt question today:…

A global luxury brand asked me a blunt question today: ‘Ashu, are these new AI browser assistants going to kill our brand equity?’ It’s a fair question. I’m in Silicon Valley, and the hype around browser-based AI (like Copilot, Gemini in Chrome, etc.) is deafening. But for premium brands like the one I spoke with, …

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