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What Great Dealmakers Know and Do that You Should Too

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How do the best dealmakers and investors make go / no decisions? How do they handicap the probability of a company or project’s return projections actually coming to pass?

And once they do, how do they determine fair terms and pricing upon which to do a deal?

It is upon these “Due Diligence” matters where the real - as opposed to the theoretical - money on deals is made.

Now, due diligence - as it is done by serious, professional dealmakers and investors - is an enormous undertaking.

It often requires hundreds and sometimes thousands of hours of accounting, legal and background reviews and checks, along with third party validation and research as to claims regarding market opportunity, competitive landscape and customer pipeline, traction, and satisfaction.

It can be as time and energy intense as any business process or project one could possibly imagine.

And because it is so, for those without very significant analytical resources and expertise, it is often also unrealistic to do it thoroughly and right.

Luckily, there are some shortcuts that can yield impressive similar insight and results.

I call them the “Who, Why, and When” 15 minute Modern Due Diligence Checklist.

Who. Easily the most important question to ask of any endeavor of importance: Who is involved? What are their personal and professional histories and backgrounds? Of leadership, business, investment and life success? Who are the professional partners (Law, Accounting, Banking, etc.)? Who is on the Board? (Is there a Board at all)? Who are the Customers? The Partners? The Employees?

When it comes to whether a deal is good or not, the answers to these “Who” questions is as often as not all you need to know.

Why. Why is a deal happening? Why are who are involved in fact…involved? Why is the deal being offered to youStart with Why.

When. The old adage that “Time kills all deals” is also a great harbinger into the likelihood of a successful investment outcome.

How long has the deal been shopped? How urgent/desperate are those involved to get the deal done?

Now, these question cuts both ways. I as much want to see principals that need to get a deal get done versus those that perhaps just want it to be so.

Need, in its best sense, drives urgency and action.

Want is often lighter, less substantial, and thus more prone to delays and “almosts” versus results and return.

Who. Why. When.

Mediocre answers to any of these and almost certainly the deal is not right.

But as they are all spot on, well then the next question to ask is often “What are you waiting for?”


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