How to find "original" principal invested (ignoring rolling amounts due to gains from original investment in subsequent investments) ?

I have a very important question which I could not figure out how Quicken can help answer regarding my investments.  I will appreciate if someone can provide the answer / point to the right resource for same.

I need to find out as to How much of my own money (principal if I can use that word) is invested into my portfolio ? It appeared very simple initially as the Net amount invested report gives the same but here is the catch. I need only my "original principal" and not the net amount invested across all the stocks / mutual funds (i.e. bought - sold). This is because I might have purchased first stock, made a gain out of the same by selling it partially and bought second stock from the gains of the first stock. Hence, the amount invested in the second stock does not really come from my original principal but rather gains from the first stock. Now, I will have two stocks in the portfolio and the above scenario will repeat itself tens of times over the years as the stocks will keep on rolling through buys and sells. Hence, it becomes very difficult to find the original sum invested. At the end, if this sum is positive, that means my money is in stocks and if this sum is negative, it means that I have recovered all my principal and my stock holdings is entirely from the returns from the market or dividend income etc.

I also understand that as per IRS, the cost basis of each stock has to be separately calculated. However, I do not want the above mentioned report for tax purposes. It is only for my understanding of amounts invested irrespective of  tax laws.


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Quicken has no way of knowing what stocks were purchased with capital gains and which were purchased with out of pocket investment capital.  This is an exercise you will have to do by hand.
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