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Buy, Borrow, Die: The Wealth Strategy Checklist

Implement the same tax‑minimizing strategy used by billionaires to build lasting, tax‑free generational wealth.

Based on: Borrow Until You Die? The Strategy The IRS Doesn't Want You To Know by Sherman - My CPA Coach

Borrow Until You Die? The Strategy The IRS Doesn't Want You To Know▶ Watch the source video on YouTube

Why You Need This Checklist

What if the biggest financial mistake you're making isn't how much you earn — it's the moment you decide to sell? There are two tax systems operating in America right now. One for people who work, sell, and hand a chunk of every gain to the IRS. And one for people who buy, hold, and borrow — and legally never pay taxes at all. The question is: which system are you in?

Here's the painful reality most people face. You work hard, your investments grow, and the second you need access to that money, you sell — triggering a tax bill that can wipe out 20 to 50 percent of your gains before a single dollar reaches your pocket. That cycle repeats every time you need liquidity. Meanwhile, over $20 trillion in wealth is sitting in America completely untaxed, held by people who simply made a different decision about how to invest.

Imagine instead a future where your assets grow year over year, your net worth climbs, and you access cash through borrowing — not selling — so the IRS never gets involved. Imagine passing those same assets to your heirs with a stepped-up basis, meaning they can sell everything you built and owe zero capital gains tax. That's not a loophole. That's the Buy, Borrow, Die strategy — and it's completely legal by design.

Sherman from My CPA Coach is a practicing CPA who breaks down exactly how this works, referencing real-world examples like how Jeff Bezos offset over $46 million in income through interest expense deductions. This isn't theory — it's a documented strategy used by the wealthiest people in the world, explained in plain language by someone who helps real people implement it every day.

This checklist takes everything Sherman covers in the video and turns it into a clear, step-by-step action guide you can actually follow. You'll know exactly what types of assets to buy and hold, how to borrow against them tax-free using tools like HELOCs and securities-backed lines of credit, how to use interest expense as a deduction, and how to set up your estate so your heirs inherit your wealth without a tax bill attached. Stop handing your gains to the government one sale at a time. This checklist will help you build the foundation of a smarter, tax-efficient wealth strategy starting today.

What's Inside — Preview

Every checklist item comes with actionable notes to guide you — things like "Don't forget to do this before you start," "Avoid this common mistake," or "Set a reminder for 30 days out." Nothing vague, just clear next steps.

CHECK Identify which tax system you currently operate in — worker or owner
PLAN List every asset you currently own and note whether you intend to hold it long-term or sell it short-term
DECIDE Commit to a buy-and-hold investment philosophy as the core of your strategy
RESEARCH Research and select long-term asset categories that qualify as portfolio staples
AVOID Stop selling assets the moment you simply need liquidity — recognize the tax trigger

+ 15 more action items inside...

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