Jessy Gilger

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.