@tctailwind.bsky.social
Tax Mistakes Part 2: How I messed up the Foreign Tax Credit and overpaid $893 (and how I’ll recover it)
This post explains how a quirky TurboTax UI led me to miss out on $893 in foreign tax credits from my international ETFs, and how I'll recover it.
tctailwind.com/2025/04/04/t...
This post explains how a quirky TurboTax UI led me to miss out on $893 in foreign tax credits from my international ETFs, and how I'll recover it.
tctailwind.com/2025/04/04/t...
Tax Mistakes Part 2: How I messed up the Foreign Tax Credit and overpaid $893 (and how I’ll recover it)
In Part 2 of my tax mistakes series, I explain how quirks of the TurboTax UI led me to miss out on $893 in foreign tax credits from my international stock ETFs. I also explain how I fixed the mista…
tctailwind.com
April 4, 2025 at 2:27 PM
Tax Mistakes Part 2: How I messed up the Foreign Tax Credit and overpaid $893 (and how I’ll recover it)
This post explains how a quirky TurboTax UI led me to miss out on $893 in foreign tax credits from my international ETFs, and how I'll recover it.
tctailwind.com/2025/04/04/t...
This post explains how a quirky TurboTax UI led me to miss out on $893 in foreign tax credits from my international ETFs, and how I'll recover it.
tctailwind.com/2025/04/04/t...
My Optimizing Failures and Lessons
I love optimizing all things personal finance. Usually that habit pays off, but sometimes it burns me instead. Here are a few examples of my failed attempts to optimize, and the lessons I learned from them.
tctailwind.com/2025/01/19/m...
I love optimizing all things personal finance. Usually that habit pays off, but sometimes it burns me instead. Here are a few examples of my failed attempts to optimize, and the lessons I learned from them.
tctailwind.com/2025/01/19/m...
My Optimizing Failures and Lessons
I love optimizing all things personal finance. Overall, I think this habit has paid off for me in many ways. Sometimes, however, it burns me instead. Here are a few examples of the ways in which I’…
tctailwind.com
February 17, 2025 at 2:26 PM
My Optimizing Failures and Lessons
I love optimizing all things personal finance. Usually that habit pays off, but sometimes it burns me instead. Here are a few examples of my failed attempts to optimize, and the lessons I learned from them.
tctailwind.com/2025/01/19/m...
I love optimizing all things personal finance. Usually that habit pays off, but sometimes it burns me instead. Here are a few examples of my failed attempts to optimize, and the lessons I learned from them.
tctailwind.com/2025/01/19/m...
Quantifying the Value of Personal Finance Optimizations (or: How to Make $43,608 in an Hour)
I calculated the dollar value of common (eg. 401ks) and uncommon (eg. Mega Backdoor Roth, credit cards) optimizations to show you which are most valuable.
tctailwind.com/2025/01/04/q...
I calculated the dollar value of common (eg. 401ks) and uncommon (eg. Mega Backdoor Roth, credit cards) optimizations to show you which are most valuable.
tctailwind.com/2025/01/04/q...
Quantifying the Value of Personal Finance Optimizations (or: How to Make $43,608 in Under an Hour)
Ever wondered about the actual value —in dollars— of all the personal finance optimizations you’ve heard of? I went through and calculated the dollar value of common (eg. investing, 401ks) an…
tctailwind.com
February 16, 2025 at 3:56 PM
Quantifying the Value of Personal Finance Optimizations (or: How to Make $43,608 in an Hour)
I calculated the dollar value of common (eg. 401ks) and uncommon (eg. Mega Backdoor Roth, credit cards) optimizations to show you which are most valuable.
tctailwind.com/2025/01/04/q...
I calculated the dollar value of common (eg. 401ks) and uncommon (eg. Mega Backdoor Roth, credit cards) optimizations to show you which are most valuable.
tctailwind.com/2025/01/04/q...
Emergency Funds Part 3: Modeling Expected and Worst Case Scenarios
This post calculates just how much money I stand to make and lose in my expected and worst case emergency scenarios, and it comes with a spreadsheet you can use to do your own modeling.
tctailwind.com/2024/08/17/e...
This post calculates just how much money I stand to make and lose in my expected and worst case emergency scenarios, and it comes with a spreadsheet you can use to do your own modeling.
tctailwind.com/2024/08/17/e...
Emergency Funds Part 3: Modeling Expected and Worst Case Scenarios
In Part 3 of the Emergency Funds series, we look at the hard numbers. I model out just how much money I stand to make and lose in my expected and worst case scenarios, and I share a spreadsheet you…
tctailwind.com
February 15, 2025 at 2:23 PM
Emergency Funds Part 3: Modeling Expected and Worst Case Scenarios
This post calculates just how much money I stand to make and lose in my expected and worst case emergency scenarios, and it comes with a spreadsheet you can use to do your own modeling.
tctailwind.com/2024/08/17/e...
This post calculates just how much money I stand to make and lose in my expected and worst case emergency scenarios, and it comes with a spreadsheet you can use to do your own modeling.
tctailwind.com/2024/08/17/e...
How to Pay Large Tax Bills with a Credit Card, and Profit Doing It ($115k Tax Bill = $4,382 Profit)
This post explains the logistics of profitably paying 10's or 100's of thousands of dollars in taxes on your credit card.
tctailwind.com/2025/02/13/h...
This post explains the logistics of profitably paying 10's or 100's of thousands of dollars in taxes on your credit card.
tctailwind.com/2025/02/13/h...
How to Pay Large Tax Bills with a Credit Card, and Profit Doing It ($115k Tax Bill = $4,382 Profit)
There’s plenty of great advice on the internet on how to pay your taxes with credit cards, and why it’s profitable (cash back and sign up bonuses!). In this post, I go beyond those basi…
tctailwind.com
February 14, 2025 at 1:53 AM
How to Pay Large Tax Bills with a Credit Card, and Profit Doing It ($115k Tax Bill = $4,382 Profit)
This post explains the logistics of profitably paying 10's or 100's of thousands of dollars in taxes on your credit card.
tctailwind.com/2025/02/13/h...
This post explains the logistics of profitably paying 10's or 100's of thousands of dollars in taxes on your credit card.
tctailwind.com/2025/02/13/h...
Emergency Funds Part 2: Improvements, Criticisms, and Misconceptions about not Having One
In Part 2, we discuss: reasons to have an emergency fund, concurrent market crashes and employment loss, which assets to sell, interest rates, and other feedback.
tctailwind.com/2024/08/04/e...
In Part 2, we discuss: reasons to have an emergency fund, concurrent market crashes and employment loss, which assets to sell, interest rates, and other feedback.
tctailwind.com/2024/08/04/e...
Emergency Funds Part 2: Improvements, Criticisms, and Misconceptions about not Having One
In Part 2 of the Emergency Funds series, we discuss: additional reasons to have an emergency fund, dealing with market crashes and employment loss concurrently, which assets to sell, current intere…
tctailwind.com
February 12, 2025 at 3:41 AM
Emergency Funds Part 2: Improvements, Criticisms, and Misconceptions about not Having One
In Part 2, we discuss: reasons to have an emergency fund, concurrent market crashes and employment loss, which assets to sell, interest rates, and other feedback.
tctailwind.com/2024/08/04/e...
In Part 2, we discuss: reasons to have an emergency fund, concurrent market crashes and employment loss, which assets to sell, interest rates, and other feedback.
tctailwind.com/2024/08/04/e...
How to profit from the under-withholding of RSUs and bonuses
Supplemental income can be under-withheld at a 22% federally. While you ultimately have to pay the government full income taxes on that income, HOW and WHEN you pay can be profitable or costly.
tctailwind.com/2024/05/21/h...
Supplemental income can be under-withheld at a 22% federally. While you ultimately have to pay the government full income taxes on that income, HOW and WHEN you pay can be profitable or costly.
tctailwind.com/2024/05/21/h...
How to profit from the under-withholding of RSUs and bonuses
Supplemental income such as RSUs and bonuses are sometimes under-withheld at a 22% federal rate. While you ultimately have to pay the government full income taxes on that income, HOW and WHEN you p…
tctailwind.com
February 10, 2025 at 11:57 PM
How to profit from the under-withholding of RSUs and bonuses
Supplemental income can be under-withheld at a 22% federally. While you ultimately have to pay the government full income taxes on that income, HOW and WHEN you pay can be profitable or costly.
tctailwind.com/2024/05/21/h...
Supplemental income can be under-withheld at a 22% federally. While you ultimately have to pay the government full income taxes on that income, HOW and WHEN you pay can be profitable or costly.
tctailwind.com/2024/05/21/h...
The Complicated Math Behind the True Cost of Owning a Manhattan Co-op Apartment
The mess of federal, state, and city tax beaks mean that my original annual cost of $50,183 is more like $31,010 after accounting for everything.
tctailwind.com/2024/04/13/t...
The mess of federal, state, and city tax beaks mean that my original annual cost of $50,183 is more like $31,010 after accounting for everything.
tctailwind.com/2024/04/13/t...
The Complicated Math Behind the True Cost of Owning a Manhattan Co-op Apartment
The mess of federal, state, and city tax laws make calculating the cost of ownership of a Manhattan co-op very complicated. This post goes through the math with my own personal example, showing tha…
tctailwind.com
February 9, 2025 at 2:53 PM
The Complicated Math Behind the True Cost of Owning a Manhattan Co-op Apartment
The mess of federal, state, and city tax beaks mean that my original annual cost of $50,183 is more like $31,010 after accounting for everything.
tctailwind.com/2024/04/13/t...
The mess of federal, state, and city tax beaks mean that my original annual cost of $50,183 is more like $31,010 after accounting for everything.
tctailwind.com/2024/04/13/t...
Finance Basics: The Investment and Savings Accounts I’ll Use This Year
There are so many financial tools to choose from: 401ks, IRAs, FSAs, HSAs, DCFSAs, 529s, Whole Life Policies, and Emergency Funds. Here's which ones I do and don’t use, and why.
tctailwind.com/2024/04/06/f...
There are so many financial tools to choose from: 401ks, IRAs, FSAs, HSAs, DCFSAs, 529s, Whole Life Policies, and Emergency Funds. Here's which ones I do and don’t use, and why.
tctailwind.com/2024/04/06/f...
Finance Basics: The Investment and Savings Accounts I’ll Use This Year
There are plenty of accounts I’ve seen recommended for tax advantages or other benefits, such as: 401ks, IRAs, FSAs, HSAs, DCFSAs, 529s, Whole Life Policies, and Emergency Funds. This post covers w…
tctailwind.com
February 8, 2025 at 10:49 PM
Finance Basics: The Investment and Savings Accounts I’ll Use This Year
There are so many financial tools to choose from: 401ks, IRAs, FSAs, HSAs, DCFSAs, 529s, Whole Life Policies, and Emergency Funds. Here's which ones I do and don’t use, and why.
tctailwind.com/2024/04/06/f...
There are so many financial tools to choose from: 401ks, IRAs, FSAs, HSAs, DCFSAs, 529s, Whole Life Policies, and Emergency Funds. Here's which ones I do and don’t use, and why.
tctailwind.com/2024/04/06/f...
How I Negotiate for Free Money and Discounts
Many people just accept the initial dollar value they are given, be it an item’s cost, a loan’s rate, or a salary. The reality is, you can often ask to be given more money, or to pay less.
tctailwind.com/2024/03/30/h...
Many people just accept the initial dollar value they are given, be it an item’s cost, a loan’s rate, or a salary. The reality is, you can often ask to be given more money, or to pay less.
tctailwind.com/2024/03/30/h...
How I Negotiate for Free Money and Discounts
Many people just accept the initial dollar value they are given when making a transaction, be it an item’s cost, a loan’s rate, or a salary. The reality is, you can often ask to be given more money…
tctailwind.com
February 6, 2025 at 2:49 AM
How I Negotiate for Free Money and Discounts
Many people just accept the initial dollar value they are given, be it an item’s cost, a loan’s rate, or a salary. The reality is, you can often ask to be given more money, or to pay less.
tctailwind.com/2024/03/30/h...
Many people just accept the initial dollar value they are given, be it an item’s cost, a loan’s rate, or a salary. The reality is, you can often ask to be given more money, or to pay less.
tctailwind.com/2024/03/30/h...
The Profitable Intersection of Work and Personal Travel
Travelling for work offers ample opportunities to earn a little profit for oneself (within policy!). Many workplaces also have benefits for personal travel. Here's how I take advantage of both.
tctailwind.com/2024/03/16/t...
Travelling for work offers ample opportunities to earn a little profit for oneself (within policy!). Many workplaces also have benefits for personal travel. Here's how I take advantage of both.
tctailwind.com/2024/03/16/t...
The Profitable Intersection of Work and Personal Travel
Travelling for work offers ample opportunities to earn a little profit for oneself (within policy!). Many workplaces also have benefits for personal travel. Here’s how I take advantage of bot…
tctailwind.com
February 5, 2025 at 2:13 AM
The Profitable Intersection of Work and Personal Travel
Travelling for work offers ample opportunities to earn a little profit for oneself (within policy!). Many workplaces also have benefits for personal travel. Here's how I take advantage of both.
tctailwind.com/2024/03/16/t...
Travelling for work offers ample opportunities to earn a little profit for oneself (within policy!). Many workplaces also have benefits for personal travel. Here's how I take advantage of both.
tctailwind.com/2024/03/16/t...
The Five Figure Tax Mistakes my Friends and I Have Made, and How to Avoid Them
Tax mistakes can be expensive, and this post will help you avoid them. It summarizes real examples of common filing-time and year-round mistakes.
tctailwind.com/2024/03/11/t...
Tax mistakes can be expensive, and this post will help you avoid them. It summarizes real examples of common filing-time and year-round mistakes.
tctailwind.com/2024/03/11/t...
The Five Figure Tax Mistakes my Friends and I Have Made, and How to Avoid Them
Tax mistakes can be expensive, and the goal of this post is to help you avoid them. It summarizes real examples of common filing time mistakes, as well as year-round mistakes that show up at filing…
tctailwind.com
February 2, 2025 at 9:40 PM
The Five Figure Tax Mistakes my Friends and I Have Made, and How to Avoid Them
Tax mistakes can be expensive, and this post will help you avoid them. It summarizes real examples of common filing-time and year-round mistakes.
tctailwind.com/2024/03/11/t...
Tax mistakes can be expensive, and this post will help you avoid them. It summarizes real examples of common filing-time and year-round mistakes.
tctailwind.com/2024/03/11/t...
Emergency Funds Part 1: Why I Don't Have One
Emergency funds are an important safety net for many people, but they also have an opportunity cost of missed investment gains. Here's how I plan for an emergency, while avoiding those costs.
tctailwind.com/2024/03/01/w...
Emergency funds are an important safety net for many people, but they also have an opportunity cost of missed investment gains. Here's how I plan for an emergency, while avoiding those costs.
tctailwind.com/2024/03/01/w...
Emergency Funds Part 1: Why I Don’t Have One
Emergency funds are an important safety net for many people, but they also have an opportunity cost of missed investment gains. This post covers my alternative setup that gives me access to money i…
tctailwind.com
January 31, 2025 at 2:30 PM
Emergency Funds Part 1: Why I Don't Have One
Emergency funds are an important safety net for many people, but they also have an opportunity cost of missed investment gains. Here's how I plan for an emergency, while avoiding those costs.
tctailwind.com/2024/03/01/w...
Emergency funds are an important safety net for many people, but they also have an opportunity cost of missed investment gains. Here's how I plan for an emergency, while avoiding those costs.
tctailwind.com/2024/03/01/w...
How to Make and Save Money when Changing Employers
Changing jobs creates a series of unique opportunities to both double dip on many benefits, as well as save money on expenses that might be associated with the transition.
tctailwind.com/2024/02/24/h...
Changing jobs creates a series of unique opportunities to both double dip on many benefits, as well as save money on expenses that might be associated with the transition.
tctailwind.com/2024/02/24/h...
How to Make and Save Money when Changing Employers
Changing jobs creates a series of unique opportunities to both double dip on many benefits, as well as save money on expenses that might be associated with the transition.
tctailwind.com
January 31, 2025 at 12:50 AM
How to Make and Save Money when Changing Employers
Changing jobs creates a series of unique opportunities to both double dip on many benefits, as well as save money on expenses that might be associated with the transition.
tctailwind.com/2024/02/24/h...
Changing jobs creates a series of unique opportunities to both double dip on many benefits, as well as save money on expenses that might be associated with the transition.
tctailwind.com/2024/02/24/h...
How I Earned $7,085 in 2023 by Churning Credit Cards While Paying My Regular Expenses tctailwind.com/2024/02/12/h...
How I Earned $7,085 in 2023 by Churning Credit Cards While Paying My Regular Expenses
New credit card sign up bonuses are a lucrative way to turn money you already had to spend into points and cash back. This post covers how I opened 9 credit cards this year to earn $7,085.
tctailwind.com
January 29, 2025 at 6:42 PM
How I Earned $7,085 in 2023 by Churning Credit Cards While Paying My Regular Expenses tctailwind.com/2024/02/12/h...
You can use a Fidelity account to automatically invest all your cash in money market funds. It's a great way to constantly have access to some of the best rates for short term cash, without having to keep hopping between banks for promotional rates.
tctailwind.com/2024/02/06/h...
tctailwind.com/2024/02/06/h...
How I Maximize Interest on my Short Term Cash, Without Chasing Rates Across Banks
This post covers how you can use a Fidelity Investment account like a checking account, while automatically investing all your cash in money market funds. It is a great way to constantly have acces…
tctailwind.com
January 29, 2025 at 2:16 AM
You can use a Fidelity account to automatically invest all your cash in money market funds. It's a great way to constantly have access to some of the best rates for short term cash, without having to keep hopping between banks for promotional rates.
tctailwind.com/2024/02/06/h...
tctailwind.com/2024/02/06/h...
Buying a home is the single biggest purchase most people will make in their lives, so it's worth spending some time to optimize it. Here's how I optimized the financial side of buying my apartment.
How I Saved $99,724 When Buying My Apartment
Buying a home is the single biggest purchase most people will make in their lives, so it’s worth spending some time to optimize it. Here’s how I optimized the financial side of buying m…
tctailwind.com
January 28, 2025 at 2:52 AM
Buying a home is the single biggest purchase most people will make in their lives, so it's worth spending some time to optimize it. Here's how I optimized the financial side of buying my apartment.