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David Cummings on Startups

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Recently, I was talking to an entrepreneur who shared that one of his side projects was building a personal AI brain. The goal was to process information across every area he cared about, automate repetitive tasks, and deploy simple agents to monitor different parts of his life.

I was intrigued, so I asked him to show me how he had built it and what it looked like...


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One of the recurring debates I have encountered is around the role of founder-led sales.

Founder-led sales is the idea that, in the early days and even the early years of a startup, the founder should be the person selling the product on the front lines. By doing the actual work of selling, there is no telephone game about what prospects do or do not want. The fou...


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If you read the startup blogs and listen to the most popular startup podcasts, it is easy to think that the only way to raise money in the current climate is with an idea that can become worth tens of billions of dollars or more.

While those companies get the majority of the hype, as they should, they represent the biggest ideas, the biggest funding rounds, and th...


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I’ve always enjoyed learning about different business best practices, strategy documents, and ways of thinking through a company game plan. One example I’ve seen more frequently over the last year is the concept of “right to win.”

Right to win is the idea of understanding your competitive positioning and what makes your product distinct from competitors. It is oft...


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