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Go Curry Cracker | Capital Gains, Losses and The Roth Conversion Ladder

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

Go Curry Cracker explains capital gains strategies and the Roth conversion ladder — advanced tax optimization for financial independence.

Brad Barrett, Jonathan Mendonsa · · Guests: Jeremy Jacobson · 75,094 plays
1h 6m 27s
  1. Introduction to Jeremy and Go Curry Cracker
  2. Travel Rewards and Maximizing Travel
  3. High Savings Rates for Early Retirement
  4. The Importance of Eliminating Debt
  5. Tax Optimization Strategies
  6. The ChooseFI Hot Seat

Choose FI has partnered with CardRatings for our coverage of credit card products. Choose FI and CardRatings may earn compensation from card issuers when a customer clicks on a link, when an application is approved, or when an account is opened. Opinions, reviews, analyses & recommendations are the author's alone, and have not been reviewed, endorsed or approved by any of these entities. American Express is a ChooseFI advertiser.

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. "Retiring in your thirties is simple, but not easy."
  • Debt Elimination: Paying off debt is the starting point for financial freedom. "Eliminating debt is key to financial freedom."
  • Index Fund Investing: The couple invested their savings in index funds for long-term growth. "Investing is essential for long-term wealth growth."
  • Travel Rewards: They leverage credit card points and airline miles to drastically cut travel costs.
  • Capital Gains Harvesting: By carefully timing the sale of investments, they minimize or eliminate federal tax liability. "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.

Resources:

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ChooseFI has partnered with CardRatings for our coverage of credit card products. ChooseFI and CardRatings may receive a commission from card issuers.

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