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Originally Posted by
SolipsismX 
I appreciate the detailed post but I can't say I understand it. In fact I'm quite confused on how debt looks like an asset and having cash on hand looks like a liability.
As used in "Enterprise Value", the word 'value' doesn't have the same meaning that us regular folks attach to it. I don't really understand the purpose of the number and I have an advanced degree in economics.
It's similar to Net Worth + Liabilities - Cash. (But you use market cap, the market's estimate of 'true' net worth, instead of accounting net worth, which is a suit's estimate of 'true' net worth.)
So EV is in effect similar to Assets-Cash. (Because Net Worth = Assets - Liabilities) Which is taken to be some measure of the value of the company's productive assets. But not 'value' as in how much it is worth to you and me but more like 'value in dollars' as a measure of quantity of productive assets.
But the "value of a company's productive assets" is not the same as the company's overall value, i.e. net worth.
And comparing the value of different companies' productive assets is useful only if you also know their profitability.
Exxon might have 'more' productive assets than Apple, but how much profit is Exxon drawing from those productive assets? Instead,
I would use EV/Profits and the lower is this ratio, the more 'efficient' is the company in employing its productive assets.
On the other hand, net worth by itself is a meaningful number and comparing net worth across companies is a meaningful exercise.
Furthermore with EV, you use market cap, not accounting net worth, so you're injecting even more uncertainty on your measure of the company's stock of productive assets.
Bottomline if you want to use EV to evaluate a company's performance, use EV over Profits, not plain old EV.
Notice, all other things equal, a lower EV is actually desirable! --Which answers the conundrum about EV: Why would larger debt raise the 'value' of a company? The answer is it doesn't, because a higher EV makes the company look less efficient, i.e. worse.
Have I muddied the waters sufficiently now?