Have you ever had this much of your portfolio in a single stock? If so, was it a company that had only been publicly traded for 8 years? Just curious.
Yes, and no, respectively.
My family never owns more than 20 stocks (you can't pay attention to more than that), so we tend to be highly concentrated. I've ended up with >33% in one stock, on three different occasions, due to that stock doing much better than the rest of the portfolio. (In each case I deconcentrated when the stock hit somewhere between 1/3 and 1/2 of the portfolio.) All three stocks had much, much longer track records. I'm not actually that concentrated in Tesla *stock* (under 30%), but Tesla is also *much* more volatile than any of those three, and I am that concentrated if I include the short puts.
The volatility normally wouldn't bother me except that I have substantial cash expenses coming up, which is the point at which volatility becomes an issue. I don't want to be forced to sell at a bad time due to needing the cash.
I probably have enough cash but it's backing cash-secured puts on TSLA, so I would strongly prefer that those expire. (Normally I'm fine if they execute.) They were in-the-money for a few weeks, but are now back out of the money again, thankfully. The Republican tax scam bill makes this problem worse, because normally in this situation I'd let them execute and sell the resulting stock as needed, but if they force FIFO on us then I'd have to sell my old lots instead and pay unnecessary taxes, which means I have to actually close the options positions before execution. :-( Which loses me time value and creates potential losses if there's a "one day drop" on expiration day when I try to close it.
One of my very short list of other investments right now is a merger arb which got delayed substantially; I was expecting it to cash out, or for the merger to be cancelled, months ago. It makes no sense to do anything but wait and see with it (it either merges or it doesn't, but it makes no sense to sell before it's determined one way or the other), but it has been cramping my cash flow planning. (Even if the merger *fails* and I have to sell it at a loss it would alleviate my cash flow issue, but it's tied up while I'm waiting.) For the curious, the delay is caused by the Trump administration, which has simply failed to staff the committees which would approve or disapprove the merger.
While I can certainly borrow the money to get me through this period, my family's allergic to debt, probably unreasonably so. We really don't like paying carrying costs; it keeps me up at night. So this cash flow situation has made me uncomfortable. To be clear, it's the potential for needing to borrow money (to avoid selling at the wrong time) which makes me uncomfortable, *not* the position concentration.
I'm more overextended than you I believe, but working with a much, much, much smaller amount of money.
However, you probably have income from a *job*. My primary source of income is investments, and nothing I'm invested in pays a dividend any more, so if I have expenses, it means I'm selling something or I'm borrowing to avoid selling something -- and the only way to deleverage is to sell something.
