Capital Gains & Losses

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

Introducing Capital Gains Harvesting

In Today’s Podcast we cover:

  • Our guest: Jeremy from Go Curry Cracker
  • Jeremy and Winnie are living the geo-arbitrage life: currently in Taipei, Taiwan and then on to a four month trip to Europe
  • They are using travel rewards points to get nearly free business class flights from Taipei to Europe.
  • “Retiring in your 30s is simple but not necessarily easy”
  • The biggest contributing factor is saving a high percentage of your income
  • It’s easier to save a high percentage of your income when you have a larger income
  • Make unconventional choices to save a high percentage
  • 2nd Generation FIRE and how college costs can be lowered
  • Jeremy had $40,000 in debt when he came out of college
  • They have already opened a Roth-IRA for their son and used the income he earned from ‘modeling services’ for Go Curry Cracker
  • He used the 80/20 rule to look at where 80% of their spending was going
  • Sold his car and rode a bicycle
  • Winnie made it so her cooking was the best food in town and they never wanted to go out to eat
  • They spend approximately $2 per person per meal for delicious gourmet home cooked meals
  • Most of their entertainment was community based with friends where they weren’t spending money
  • How did he get started on his FI journey? He took the first 6 years to pay down his $40,000 in debt.  Didn’t take vacation, worked overtime to earn more money.
  • On his first vacation he realized he didn’t want to work forever and started formulating his plan
  • He set a 10 year plan and retired in 10 years plus 1 day from when he started!
  • What was it like when he actually quit his job?
  • The power of FU money and not needing to work plus how much more power it gives you while you are actually working
  • How is he investing his money? 100% of his money is in 2 index funds
  • Wait for compound interest to take hold so you can benefit over decades
  • Unpacking his article ‘Never Pay Taxes Again’
  • Harvesting Capital Gains and how it enables you to get up to $90,000 in tax free income each year and increase the basis in those funds so you are never paying taxes on the gains
  • Wash sale rules aren’t relevant to harvesting capital gains, only capital losses
  • Harvesting capital gains actually makes it easier to harvest capital losses in the future
  • They also do the Roth-IRA conversion ladder to effectively make their regular 401k tax free
  • Harvesting capital losses to offset other income
  • Avoiding the wash sale rules: Need to buy back another fund (example: Sell Total Stock Market Index fund and buy S&P 500 Index fund)
  • Hot Seat questions
  • Favorite blog:
  • Favorite life hack: credit card rewards points

Links from the show:

Books Mentioned in the Show:

Your Financial Resilience Toolkit

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7 thoughts on “018 | Go Curry Cracker | Capital Gains, Losses and The Roth Conversion Ladder”

  1. I love this show. I really like how you guys focus on simple guides to all the aspects relevant to Fi. I really appreciate that you guys focus on actionable items.

  2. Tax discussions hurt my brain.

    So basically, I should sell all my shares once a year, then the next day buy them all back in the same fund. This is a wash sale, so I won’t be taxed on it, but it increases the cost basis of the shares. The purpose is just so that when I do sell the shares for real I won’t have a huge capital gain to be taxed on, correct? And then the 2nd reason is so that I can realize a capital loss if the price goes down?

    • almost- you would be taxed on the gain from when you purchased. however if you are in the 10-15% marginal tax bracket (up to 100K for a married couple) the federal government chooses not to tax you. ( note that some states do tax capital gains). this allows you to realize your gains without paying a tax. and then from there you nailed it 🙂

      The underlying implication is that if you had 78K of income you could realize up to 22K in capital gains without paying any federal tax

  3. How are you saying that non taxed income is upto $100,000. When i look into tax brackets it showing just 20,000 exemption and then I get taxed based on the brackets that i am earning money?

  4. Hey guys, I absolutelty love this podcast! Trying to catch up to the recent episodes (I have a long way to go 😅), but I decided to write a small comment just in case it was read.

    Duel enrollment is amazing just like AP courses because those are credits that help in college. However, some problems with these courses is the fact that you have to know which college you’re going into (and if you get accepted) because not all schools accept these. I did both but then the college I got into would only take some of these credits. In the long run you don’t lose much for taking these courses but it’s extremely time consuming and it may affect your GPA in high school which in turn affects if the college wants higher GPA’s to be accepted.

    Thank you so much again for sharing amazing content and I hope this bit of information helps!

  5. Yo! This podcast is filling me with so much FIRE! It makes something I always ignored because they bored and/or intimidated me – i.e. finances- exciting and limitless.

    I have a question on this one:
    I am a really good saver and really good at not making lots of money – like, less than 15k for the last 3 years (grad student, farmer, herbalist… not lots of high paying stuff!) – so I am in the bottom of the tax bracket. I do have money in stocks and after listening to your podcast, I have a diversified portfolio with most in Vanguard’s Total US Market fund. Can you clarify something for me: when and how do we go about claiming those dividends? Is this something we can only do once a year? And am I eligible for ~75k dividend withdrawal tax free because of my low income?


  6. Hi Guys,

    Love the show but have a question – note that I have not yet listened to ALL of the episodes, so maybe this is addressed in another podcast – but here is my question / comment.

    I like taxes, I like that in Australia where I live and in the US where I was born, the taxes that we pay provide (for the most part), great infrastructure, education, safety / security, healthcare (in AU – US is a different story here), and a bit of a helping hand to those who need it sometimes (especially now). Given that everyone who benefits from these services, dont you think there is a moral responsibility to contribute to the provision of these services?

    Don’t get me wrong, I am not against deductions and tax optimisation, however, if everyone were to optimise to an extent that they no longer paid taxes, the government would either collapse or they would work to close the loopholes so that the revenue was able to sustainably support the costs.

    I am pursuing FI with my family, but want to be sure that I do so in a way that is not detrimental to those around me (for example I like the school that my girls go to and believe that the teachers there should be paid fairly so I am happy that part of my taxes go to support that). I have found that the majority of the FI principals and ideas align well with my outlook on life, but this is one area where I feel there could be some line crossing (a bit like Brad’s story at the very beginning where he had a website but didnt feel right about the way the money would come in, despite it being ‘legit’).


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