What percent hold past massive gains

I would have sold some. It’s individually. Depending on your other investments and current savings.

If my current job pays for expenses, I would ride since I don’t need it

For me it depends on how much an investment represents in the overall portfolio and total value of your nest egg.

For me I have a base foundation for retirement savings in index funds. And that amount in Index funds should provide a decent retirement. I feel comfortable making some strategic investments and would be willing to have Apple or other stocks I feel are strong companies up to 25% of my portfolio.

I think most financial advisors don’t recommend exceeding more than 10% of any one individual stock in your portfolio.

Speaking for us Bitcoin hodlrs, don’t know my true tolerance. I know it’s not a stock, but in January 2023 I Thought I’d bail between $80-$100k. I’m still in.

It's often the volatility that shakes people out. Any asset in the process of monetization that has only reached a tiny percentage of its total addressable market cap is more volatile than a 6 glasses deep Nancy Pelosi at a Trump dinner party. Amazon had a 90+% drawdown during dotcom and two 50+% drawdowns during the GFC.

I know several people who were into btc in 2011. I've asked them "so you guys all have pilots and chefs on the payroll now, right?"

"Naw man, we all sold at $1000, then bought back in later...". They're well off but not billionaires like they would be if they had just held for a dozen years. The same thing happens in equities or any investment. Having the conviction and the stones to ride that vol for years on end is rare. It happens, just not as often as you'd think given the benefit of hindsight.

My wife jokes that I sell all the companies that make us money to buy more of the companies that don’t. While I was once guilty of pulling the flowers and watering the weeds that’s not really the case.
There are a few examples of stuff that i made lots of money on and planned to get back in when the price was right but never did. I had lots of Microsoft at $38 at one point and Facebook at $16.

how does one take gains from something like that and minimize the tax effect?

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Talking with a doc at work the other day about what a $5k investment in AAPL in the 1980’s would be worth now. Someone asked yeah but who wouldve had the resolve to hold once they had 50k or a 100k profit, a million, 5 milliion. I wonder what percent of shareholders who get in early can afford the gamble to stay in forever as opposed to capturing life changing profits after a few years.

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This is why i have no regrets regarding never buying bitcoin when i learned about it in the high single low double digits, I never believed in it enough to hold it to where it would've been life changing money.

At this point in my life I am looking for the next AAPL type stock that i want to put money in and just let it ride.

I’ve often looked at Apple as an example for me when investing. The iPod changed the way we listen to music, the iPhone changed our society, the iPad made the computer less important. All these things were obvious to me that they were great. But it didn’t buy the stock.

I’ve been buying tsla since after covid because I believe they are a company that will change the way the world does things. I’ve bought some at 30 bucks and I’ve bought some at 275. Hopefully it pays off similar to how Apple would have if I would have bought.

I bought 1.1 BTC (and some worthless shitcoins) for $20k about 6 years ago. If it hits $120, I will sell 0.1. $175k another 0.1. But I would still run out in the (unlikely) went it went up to higher numbers