Understand Your Client so you can Better Understand the Deal

Many brokers, especially in the M&A space, are focused on so many things that they completely miss the boat on what or "Who" they are about to put something together with. Sure you always know "Who" the investment company is investing in but brokers seems to just want to close the deal and make money instead of really understanding the principal(s) in the company that will receive the capital and that is the first mistake. Rule #1, ALWAYS protect investors money, again, problem is the broker just wants to close the deal and make money looking away at probably the most important factor, the principal of the receiving company.
You could have an amazing deal or product and everything looks fantastic for this amazing deal to happen but as you are going thru conversations with all the principals in the deal you have to pay special attention to the principal of the company that will receive the capital. Again I am mainly referring to a merger or acquisition, investing money into a company.

If the principal of the receiving company keeps talking on and on and on and on... and is MOSTLY focused on the fact that they have heard so many stories of this one not working out or another one not working out and they get OCD on a paragraph one point whatever or paragraph two in the merger or acquisition docs which are pristine but they "Feel" if this or that happens or IF, IF, IF, IF then you need to step in and reevaluate completing this deal because this principal ONLY has themselves in mind and not the investing company OR the MOST important person or entity in the scenario which is.... THE INVESTOR and THEIR capital.

How do you know if you should kill the deal? These are a few steps, certainly not all steps but just a few. 1), Bring in a 3rd party that is not familiar with the deal and ask that person to start being on phone calls and attend meetings and get their feedback, 2) Hand the deal off entirely to someone else on your team and let them vet it out, 3) If the target company is REALLY great then apply both 1 and 2 and then as a team work on educating the principal on how the investor and investment recipient works (Although this probably is a waste of time in most cases but...) once you have done all these things you can go to #4), Tell them you will buy them out and that after a transitional period or even sooner and that they will not be needed any more or #5) Don't waste time and move on.

Don't waste time, TIME is something we all know that you can never get back. Look, there is a balance of not wasting time and wasting time because there are thousands of other great people and companies right behind this target company.  As i said #1 rule is always the #1 rule, ALWAYS protect the investors capital, ALWAYS and as a friend once told me "The key is to make a call right away and then act on it right away..." and unfortunately in most cases going right to #5, moving on, will most likely be your best option. Good luck!