Here Is What I Would Tell a Tech Founder Heading Into a Tax-Free Decade of Early Retirement

"The 0% long-term capital gains bracket is the engine here. For 2026, a married couple pays 0% federal tax on long-term gains as long as taxable income stays at or below $96,700. Stack the $32,200 standard deduction on top, and the gross income that fits inside the 0% band is meaningfully higher."

"Combined with HSA reimbursements (tax-free) and Roth contribution-basis withdrawals (tax-free under Roth ordering rules, even before 59.5), a household pulling $180,000 a year can owe under $1,500 in combined federal tax."

"The instinct is to start drawing from the 401(k) because it is the biggest pile. That instinct is expensive. Many arrive at their fifties with most of their wealth in tax-deferred accounts and appreciated stock."

A 56-year-old former tech founder has $4.2 million in various accounts and plans to withdraw $180,000 annually until age 65. The challenge is to minimize taxes during this drawdown period. Many professionals face similar situations, often instinctively withdrawing from their largest tax-deferred accounts, which can be costly. Utilizing the 0% long-term capital gains bracket allows for tax-efficient withdrawals, enabling a household to potentially owe under $1,500 in federal tax while accessing funds from taxable brokerage accounts, HSAs, and Roth accounts.

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