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Aug 11
8m 37s

307: How to Reduce Taxes on Company Stoc...

Hilary Hendershott, CFP
About this episode
If you’re a high-income woman in tech and your company stock has grown into a large portion of your net worth, you may be facing a difficult reality: Diversifying feels smart… but the tax bill feels overwhelming. In this episode, I walk through why this happens — and how tax-aware strategies can help you reduce taxes on company stock while creating more fl ... Show More
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Aug 18
308: Am I Financially Stable? Signs You’re Doing Ok (Even If It Doesn’t Feel Like It)
On paper, everything looks good.You’re earning more. You’re saving. You’re investing.So why doesn’t it feel settled?In this episode, I walk through the subtle but powerful signs that your financial life is actually on track — even if it doesn’t feel that way yet.Because at higher ... Show More
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Aug 4
306: Should You Pay Off Your Mortgage Early — Or Invest Instead?
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Jul 28
305: How to Reduce Taxes on IPO Wealth (Before It’s Too Late)
If you’re holding startup equity and expecting a liquidity event, here’s what most people don’t realize:The biggest tax decisions are made before your equity becomes liquid.I walk through the most common tax mistakes I see with IPOs and startup equity — and what high-income profe ... Show More
7m 15s
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