psyklic parent
You can win economically, especially if it's a slam dunk case and hence get a lawyer on contingency. That said, it can take a long time to resolve which can prolong any stress surrounding it. And even if the other party is clearly, obviously at fault, they may spread falsehoods about you and the case. Especially if this is done in private, it's practically difficult to do anything about.
People talk about legal outcomes speculatively all the time. Talk about a real case from a real person that you know that went to court and the guy wins economically.
None of the most successful people I know are initiating lawsuitsx
They might be victims of lawsuits, they might be paying out settlements and suffering economically.
You likely don't know anyone because there is luck involved in success. Having to initiate a lawsuit would mean you are very unlucky.
For example, maybe your business partner fraudulently took most of the shares for himself despite a written equal equity split. Here, you can either sue or just walk away and give him your shares.
Keep in mind that "successful" people are incentivized to say all lawsuits against them are unfounded and they are merely the "victim". Why assume they are telling the truth? It's at least as likely that they had something to do with causing the lawsuit.