TC Tailwind

  • The Manifesto (aka About)
  • Optimizing Finances
  • Saving Money
  • Making Money
  • Contact
  • How to profit from the under-withholding of RSUs and bonuses

    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 pay can be profitable or costly. In this post, I explore the profitable things to do, and the costly mistakes to avoid. Read more

    May 21, 2024
  • The Complicated Math Behind the True Cost of Owning a Manhattan Co-op Apartment

    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 that my original annual cost of $50,183 is more like $31,010 after accounting for everything. Read more

    April 13, 2024
  • Finance Basics: The Investment and Savings Accounts I’ll Use This Year

    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 which ones I do and don’t use, and why. It also serves as a template for others with similar finances to me. Read more

    April 6, 2024
  • How I Negotiate for Free Money and Discounts

    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, or to pay less. This post covers my successes and lessons learned from negotiating. Read more

    March 30, 2024
  • The Profitable Intersection of Work and Personal Travel

    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. Read more

    March 16, 2024
  • Tax Mistakes Part 1: The Five Figure Tax Mistakes my Friends and I Have Made, and How to Avoid Them

    Tax Mistakes Part 1: 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 time. Read more

    March 11, 2024
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Optimize your finances, save more money, and make more money. Advice for those earning a high total compensation, based on my experiences as a high earner working in Tech.

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