I had a similar problem during an IPO lockup and couldn't sell when the stock was at a high point. If you buy protective puts (for the collar), it would reset the long term capital gains clock on your long position. I would love to be wrong so I can regret/cry about it!
> If you buy protective puts (for the collar), it would reset the long term capital gains clock on your long position.
Yes, this is true.
However, it doesn't force you to pay taxes at the higher rate, only to wait longer before the lower rate applies. Once you dispose of the put, the clock resets. But if you continue holding the stock for greater than a year, then the only issue is that your dividends may be taxed more.
On a large-cap name, one thing that some people do is to use a well-correlated index or competitor for the hedge.
In your lockup, I'm betting there were some restrictions on hedging anyway, which may have prevented you from buying puts at all.
I had a similar problem during an IPO lockup and couldn't sell when the stock was at a high point. If you buy protective puts (for the collar), it would reset the long term capital gains clock on your long position. I would love to be wrong so I can regret/cry about it!