Innovation in tech favors the naive and the stubborn. If you are too rational you won't tackle problems that others once failed at.

The chance of failure is almost always better than the guarantee of never knowing.

You want to find the really crazy but still somewhat reasonable outliers within the customer ecosystem.

That's already been tried before only means the first attempt got it wrong.

My co-founder Dylan Smith and I left our junior year of college to move to the Bay Area. To the horror of our friends' parents, we actually had two other friends drop out of college to work on the product. The four of us were just working non-stop growing Box.

You can look at the cost structure of an incumbent company and discover: where are they not going to be able to drop their prices... because that business model is fundamental to the existence of the company.

Your product should sell itself, but that does not mean you don't need salespeople.