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How to not pay your taxes legally, apparently

(mrsteinberg.com)
113 points jimhi | 3 comments | 05 Jul 25 18:21 UTC | HN request time: 0.662s | source
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eli ◴[05 Jul 25 21:07 UTC] No.44475549[source]▶
The hard part is identifying a stock you acquire for cheap or free now but will be worth much more than $10 million in five years.
replies(2): >>44475656 #>>44476496 #
1. jimhi ◴[05 Jul 25 21:22 UTC] No.44475656[source]▶
If you read what I wrote, it doesn't even need to actually be 5 years if the person does some creative stuff with options which I have personally seen.
replies(2): >>44476281 #>>44476411 #
2. eli ◴[05 Jul 25 23:06 UTC] No.44476281[source]▶
Sure, to delay the "sale". A surefire way to go from minimal value to multiples of $10 million in fewer than 5 years is even rarer.
3. FreakLegion ◴[05 Jul 25 23:35 UTC] No.44476411[source]▶
There's no legal 'creative stuff with options' to get around the five-year holding requirement. QSBS can be rolled over into other QSBS without restarting the clock, or you can agree to delay the actual sale (including payment) until you've met the holding requirement. At the end of the day, though, you have to hold the stock for five years, and any early payment you take (e.g. for writing options) is taxed normally.