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You could pay more in taxes and still end up with more money.
That sounds wrong at first, because most people assume the goal is always to pay as little tax as possible. But for high earners with appreciated assets, that instinct can actually cost millions over time.
Hilary Hendershott explains why the timing of taxes can matter just as much as the amount of taxes...
If you’re a high-income earner — especially in tech leadership or business ownership — there’s something quietly shaping your financial future:
Taxes.
In this episode, I explain what’s known as tax drag — the slow, often invisible erosion of your wealth over time.
Because for many high earners, the biggest financial cost isn’t fees or investmen...
Divorce is one of the most financially complex transitions many people will ever navigate.
And the decisions you make during this process can affect your financial stability for decades.
In this episode, I'll walk you through 7 guiding principles to help you protect your finances during divorce and avoid costly mistakes, including:
Why you shouldn’t rush major ...If you’re a woman working in tech, your compensation may be changing faster than you expected.
Equity grants are larger.
RSUs are vesting.
Stock options are becoming real money.
And what’s coming in 2026 may not just be another wave of wealth — it could be a major liquidity event.
In this episode, I explain:
Why tech wealth cycles are compressin...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 levels of income and wealth, progress doesn’t always feel obvi...