Dunning Kruger Founder
Technical founder who has multiple startup failures due to dunning kruger keeps failing. How do I tell him he is failing because he is making bad decisions in other functions
The big advantage of co-founders are honest peer conversations of what worked, and what failed.
Ultimately to be a good founder requires that they are able to post-mortem well, and identify weaknesses.
Personally I would let the person know i had advice, but then keep the advice to myself until asked. Ultimately all decisions are compromises, and unsolicited advice on why a decision is "bad" without all the facts is seldom appreciated. My first goal would be to find out the constraints that lead to the decision in the first place.
What makes you certain that the technical decisions are bad? Any examples? There might also be economic, marketing or product fit reasons which are less obvious, depending on what information you have.
Try to understand his point of view, from his perspective. Why has he decided that way and not the other? All answers are valid except "'cause he's sh*t dunning his krugers at all occasions"