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

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.

Design is more important than technology in most consumer applications.

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

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

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