not unless the 'investment' he made was in actuality a loan - which doesn't sound like it's the case.
definitely not a good idea to go into business with friends or family, if i encouraged a friend to invest money into a business venture and it went bad i'd feel guilty even if he was made fully aware that the risk was the same as for any business, you can lose your investment - if i had the cash and the friend didn't have much i'd probably pay him back the investment he put in. that's if he acted decently towards me as the deal was going bad, if he was turning on me, being a dick because things weren't working out - no way.
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