I think some people are over thinking this.
To me it seems like a guy has had business deals/investments go bad and this has resulted in financial stress in the context of not being able to work due to health issues - his mates have wanted to help out (fair enough) and Greg has reluctantly been roped into the idea.
We shouldn't be shaming people for losing money in business, afterall, society as a whole has benefited immeasurably from the technological advances that have been made possible by people taking a chance motivated by the desire to make money above and beyond the standard 80k a year government wage.
Of course, for every person that gets rich off a business idea, there are many more who end destitute and broken - we shouldn't shame these people.
People don't have to donate to Greg's fundraiser if they don't want to.
People who publicly ask for money should be shamed unless they desperately need it.