Alex Lieberman(@businessbarista):Being at a legacy company must feel like a clusterf*ck of emotions right now. Optimism: collection of moats earned over time (brand/trust, proprietary data, network effects) that disruptors haven't yet accumulated. it's a huge unfair advantage. Frustration: roll out of AI tools feels sluggish, turning a cruise ship on a dime feels painful, and there's not nearly enough urgency to become AI-native before disruptors eat our lunch. Fear: it feels like AI transformation will take us 5-10 years, but do we have the luxury of that much time before we lose our market position?

2026.09.24 18:45

Being at a legacy company must feel like a clusterf*ck of emotions right now. Optimism: collection of moats earned over time (brand/trust, proprietary data, network effects) that disruptors haven't yet accumulated. it's a huge unfair advantage. Frustration: roll out of AI tools feels sluggish, turning a cruise ship on a dime feels painful, and there's not nearly enough urgency to become AI-native before disruptors eat our lunch. Fear: it feels like AI transformation will take us 5-10 years, but do we have the luxury of that much time before we lose our market position?

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