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Retiring at 55 can sound simple, especially if you’ve saved well and built meaningful wealth.
But early retirement is not just about having enough money. It is about whether your money can support your life for decades, through changing markets, taxes, healthcare costs, and unexpected life events.
Hilary Hendershott explains what really needs to be considered befo...
A large IRA can feel like proof that you did everything right.
You saved, invested, deferred taxes, and built wealth over time. But once required minimum distributions begin, that same IRA can start forcing large taxable withdrawals whether you need the money or not.
Hilary Hendershott explains the RMD trap and why large IRAs can create bigger tax problems in reti...
One of the most common questions people ask in their 40s is: Have I saved enough for retirement?
And often, that question is not coming from someone who ignored saving or investing. It is coming from someone who has been working hard for years, building a career, raising a family, making smart decisions, and suddenly wondering, “How am I actually doing?”
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...