Bitcoin Taxes, Inheritance & Knowing When You Have Enough | Jessy Gilger

— Bitcoin financial planning focused on concentrated Bitcoiners, treating Bitcoin as a pristine first-class asset rather than dismissing it like traditional advisors do.

— Tax efficiency through lot selection, basis management, Roth IRA accounts, and loss harvesting; the IRS will not refund overpayment, so intentional tax strategy matters.

— Inheritance and succession planning must connect legal documents, financial plans, and private keys to avoid probate complexity, public record exposure, and leaving loved ones with a "treasure hunt."

— Cash flow and short-term volatility management to balance long-term conviction with present-day family needs, home improvements, and life enjoyment without guilt over selling sats.

— Bitcoin Scholars Fund leveraging school-choice tax credits ($3,400 individual / $3,400 married under the new Big Beautiful Bill) to fund education rather than taxes.

— Plan B optionality: holding keys and understanding jurisdictional flexibility (El Salvador, tax-free states, expatriate strategies) while hoping for and building toward a free America.

— Review your tax returns with fresh eyes: most Bitcoiners have never had an advisor examine their actual tax situation, leaving hundreds of thousands in recoverable gains or basis management on the table.

— Align your legal structures (will, trust, keys, custody solution) before an emergency forces your family into probate and public record exposure; this is one of the highest ROI preventive actions a Bitcoiner can take.

— Name different chunks of your Bitcoin stack for different goals (retirement, family gifting, short-term purchases) and practice reversing your dollar-cost averaging in bear seasons rather than waiting for perfect price timing.