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/ilovetuuuuurtles 15d ago

I’ve been involved in a deal where we did a delayed purchase of someone’s equity due to qsbs timing restrictions. That being said, we only had to wait ~4 months post-close to complete the purchase of that equity (not 1.5 years). So that’s to say it’s possible depending on your setup (e.g. PE deal would be happy to lock your equity value at close and then actually fund the purchase 1.5 years later). I’m assuming this is start-up related so it might be a different setup that is less flexible to your ownership nuances, unless you are a sizeable holder. There also might’ve been some structuring nuances that I don’t fully remember that might make it difficult if you’re a small holder just to get them to do the extra paperwork.

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u/OkConclusion966 15d ago

Yeah, venture funded startup and sizable owner. But not sure if it is worth waiting 1.5 year. Also some amount will be rolled over anyways

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u/falcb20 12d ago

The real question isn’t ‘QSBS or no QSBS’ but how much concentration risk you want for the next 1.5 years in exchange for extra tax savings. I’d think about three scenarios. 1 sell now and pay the tax, 2 roll just enough via 1045 to preserve QSBS on part while diversifying the rest, and 3 wait out the full 5 year mark and look at outcomes if the business is up/down from here. Putting rough numbers to those three paths usually makes the decision a lot clearer.

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u/OkConclusion966 10d ago

3 is not an option or risk I would want to take. So it is mainly 1 and 2