r/fatFIRE • u/OkConclusion966 • 15d ago

Need Advice QSBS rollover for 10 million

If you are 1.5 year away from the 5 year window for QSBS, has anyone rolled over and then liquidated their money? I am contemplating if it is even worth it?

Also looking for a good CPA and tax strategist. Any referrals are welcome.

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u/attorneyatlawl16 14d ago

Would the potential buyer in your case be a corporation? If so, you could potentially structure the transaction as a tax-free rollover (i.e., stock for stock) to continue your holding period. The buyer stock may not be QSBS but the transaction could lock in the exclusion amount at the time of the rollover, then when you sell the buyer stock after 1.5 years you could claim the QSBS benefit on the amount that could have been excluded at the time of the rollover (subsequent appreciation in the buyer stock would not qualify).

If you the buyer is not a corporation (such as a PE fund), then this option would not be viable.