Family Portfolio: how to unload stocks into ETF's without losing $$$ to taxes

Hey all,

Need some advice here. I've been helping manage my family portfolio for a couple years, and we've had a pretty solid run of things. We invest mainly in large tech companies, and have held Netflix/Apple/Amazon/FB/Google/Alibaba for quite some time now, to the point where they are all up well over 300% each.

However, my dad's getting to almost retirement age, and definitely doesn't want the stress of having such a concentrated portfolio for the next 30 years, so we were considering moving everything into basic S&P/International ETF's.

Is there a way to do this without paying ridiculous capital gains taxes? Could he put the stocks in mine/my siblings name's as we just have internship salaries and the rate would be much lower?

Also- what would you do in this case? Is there an argument to just holding on for the ride? (For perspective, we do have 50% of the fund in ETF's already- these stocks represent 35-40%, and the other 10% is other large cap stocks)

 

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