Is There Any Way I Can Assure Financial Transactions Run Smoothly?

I am in a situation where I am attempting to set up a deal in which a friend of mine will invest money, expecting a substantial return on investment each month. I have done some due diligence on the individuals involved and generally feel good about the deal. However, I also get a nagging feeling in my chest about it. Could this be due to past programming where similar investments did not work out, or is it an intuitive warning sign I should heed? Is there any way I can assure that financial transactions run smoothly?

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