Ep. 018 — Go Curry Cracker | Capital Gains, Losses and The Roth Conversion Ladder

Jeremy retired at 38 after saving 70% of his income for a decade — then figured out how to never pay federal income tax again. The blogger behind Go Curry Cracker walks through the mechanics of retiring early while traveling the world with a young family, paying zero in taxes, and spending far less than you'd expect. Jeremy and his wife Winnie achieved financial independence through a combination of aggressive savings, index fund investing, and what he calls "geo arbitrage" — living in low-cost countries while their investments grow. But the real revelation is how they've structured their withdrawals: by strategically harvesting capital gains and timing Roth conversions, they legally avoid federal taxes year after year while funding a life most people assume costs six figures.

Timestamps:

• 00:00:00 - Introduction to Jeremy and Go Curry Cracker
• 00:03:34 - Travel Rewards and Maximizing Travel
• 00:06:07 - High Savings Rates for Early Retirement
• 00:09:19 - The Importance of Eliminating Debt
• 00:38:57 - Tax Optimization Strategies
• 00:54:23 - The ChooseFI Hot Seat

Key Points:

• 70% Savings Rate: Jeremy and Winnie saved the majority of their income to reach financial independence in their thirties. 00:06:07 "Retiring in your thirties is simple, but not easy."
• Debt Elimination: Paying off debt is the starting point for financial freedom. 00:09:19 "Eliminating debt is key to financial freedom."
• Index Fund Investing: The couple invested their savings in index funds for long-term growth. 00:32:14 "Investing is essential for long-term wealth growth."
• Travel Rewards: They leverage credit card points and airline miles to drastically cut travel costs. 00:04:09
• Capital Gains Harvesting: By carefully timing the sale of investments, they minimize or eliminate federal tax liability. 01:05:05 "Strategically harvesting capital gains can minimize taxes."
• Geo Arbitrage: Living in countries with lower costs of living while earning or drawing income from U.S. sources. 00:02:29

Resources:

• Go Curry Cracker Blog 01:04:16
• JL Collins' Stock Series 00:56:14
• ChooseFI Episode 13 01:05:29
• ChooseFI Episode 17R 01:05:50