[zinglersen]

What.. they are taking a lot of risk...

But I guess we first have to agree on "who" we are taking about - is it the company itself or the owner / shareholders ?

Back to your question, yes that could happen in several different cases. But of course the risk/benefit is not split 50/50 (nor 0 risk, 100 upside, as you said), in reality the future outcome depends on both internal and external events.

Even the richest(?) man in the world was relatively close to loosing it all;

Musk, who had $200 million in cash at one point, invested “his last cent in his businesses” and said in a 2010 divorce proceeding, “About four months ago, I ran out of cash.” Musk told the New York Times https://www.cnbc.com/2017/04/27/the-crucial-decision-teslas-... https://archive.nytimes.com/dealbook.nytimes.com/2010/06/22/...