If you want to hit on a touchy subject with an entrepreneur ask them about their personal health insurance situation. 

Most probably pay for their own individual plan with a high monthly premium and shitty benefits. 

A close second will be those that forgo health insurance because they are going to live forever or something. 

Then there are those rare few geniuses that have hacked the system. The guys that get great health insurance benefits for free through their spouses' plan. 

America has the greatest healthcare system in the history of the universe. 

So great that a grown man needs to choose between being healthy, founding a startup or getting married.