I know speculation can be subjective
Yes! What's speculative and what's not is a subjective thing....... One person's speculative bet is another's conservative investment!
and it’s probably not a good idea to carry too many speculative investments into retirement
That's strictly a function of how well funded your retirement is. As you say, " it's probably not a good idea to carry too many speculative investments into retirement." But, what is "too many?" Actually it's not a good idea to carry too much of anything into retirement, including ultra-conservative investments.
but I’m just curious if you have any.
Sure. And I find them very entertaining. Most of my stretch bets are in the energy sector right now but it has varied over the years. Having a little money in the game stimulates me to keep active with current events and economics (my undergrad major).
My biggest win was buying stock in a community bank years ago when the bank was a trailer parked on a gravel lot in a Chicago suburb. It was successful, split numerous times and when bought out by a regional bank turned into a very fortunate experience for me.
My biggest loss was an off shore driller that went belly up. Ouch!
Anyone remember ISM/OSM? One of our now mostly inactive members brought it to our attention. A wild, wild ride but very profitable. My final shares expire and cash-out mid January, 2018.
I'm ahead overall over the years but not by so much that I've become disinterested or complacent.
Of course, the vast majority of my FIRE portfolio is in broad-based domestic index funds and vanilla municipal bond funds. Oh, and an active fund or two (like pssssst Wellesley).