Always take measures to protect the downside. This applies to all areas of your life, and has been most relevant to me with my startups.
Entrepreneurs are typically portrayed as reckless risk takers… the fact is entrepreneurs are some of the best people at taking calculated risk while protecting their downside. The best entrepreneurs don’t dive headfirst without looking… they prepare for multiple scenarios and get creative in ways to protect the downside of what they are doing. You can do this with financial investments,

Said another way: Hope for the best, plan for the worst.