Remove Math Remove Tax Planning Remove Valuation
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Should You Exercise Stock Options During a Pre-IPO Window?

Darrow Wealth Management

The upside of a well-timed exercise is clear: potential for significant tax savings and reducing the time you need to hold the stock to qualify for long-term capital gains tax rates. Unfortunately, for those tax savings to materialize, the post-IPO stock price at sale must be considerably more than the pre-IPO valuation at exercise.

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What Triggers an IRS Audit?

Harness Wealth

Math errors and typos Minor mathematical errors and typos can disrupt the IRS’s automated processing systems and can result in discrepancies that can flag your return for manual review. The IRS carefully scrutinizes these deductions to ensure compliance with strict valuation and documentation requirements.

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Transcript: Ted Seides

The Big Picture

It’s part of their own tax planning. RITHOLTZ: So hold the duration risk aside with those two, but just for an investor in treasuries, I know you’ve done the math before. What’s the valuation? RITHOLTZ: But some of these guys are sitting with a lot more than a billion dollars, and why not?

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The Long Game: Roth Conversions & Legacy Planning

Brown Advisory

Paying tax now instead of later goes against the grain of conventional tax planning. This option, available before the 2017 tax overhaul, was helpful if, for example, the market declined substantially after a conversion. The Roth account can grow tax-free until the owner’s death without making any distributions.

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The Long Game: Roth Conversions & Legacy Planning

Brown Advisory

Paying tax now instead of later goes against the grain of conventional tax planning. This option, available before the 2017 tax overhaul, was helpful if, for example, the market declined substantially after a conversion. The Roth account can grow tax-free until the owner’s death without making any distributions.