S1E405 - Building an AI Chief of Staff

What if you had an AI that not only assisted you, but acted as a highly trained source of strategic support in your day-to-day work? Dennis and Tom explore the idea of creating an AI Chief of Staff that could function in an organizational or advisory role. They share their experimental approach, walk through their methods for developing and training the AI to work for them, and discuss the challenges they’ve encountered along the way.

Later, they shift to a common pitfall: buying technology to solve law firm pain points, only to discover it isn’t the...