When you work with start ups, you are dealing with a lot of risk. It just goes with the territory. That means accepting the possibility — indeed the probability — of failing. A lot of people don’t like this and it is easy to see why. They want “success experiences”.
I have had arguments about the relative value of success experiences and failure. My view is that people generally don’t understand the distinction. People who talk about needing success experiences often mean seeking comfort or reassurance. This may or may not be a success. It is often not when it is just reaffirmation of the status quo. People who talk about risk often think in terms of risking all. That is usually a very bad idea.
Good strategy means getting a better understanding of both.