I think you want to show a level of transparency that breeds trust. You don't want to show a level of desperation that breeds concern.

I figured maybe I had some talent as an investor… since it seemed like I was only a half-assed entrepreneur.

Design is more important than technology in most consumer applications.

For the most effective pitch, focus 80% on the problem, 20% on the solution.

The path to the mountain ahead of you? is not the path you took to the mountain you stand on.

Wait until companies have an initial prototype, have shown that they have the potential to be profitable and have the ability to scale. That's the best time to invest.

Entrepreneurs usually don't listen to people. Trust them to do their job. Remember, you invested with the understanding the project was likely to fail.