Insights · Tax Smart From Math

Tax strategy in plain English.

This is my Tax Smart From Math series: 14 short, practical breakdowns of the moves that actually matter for high earners, business owners, and real estate investors. Real numbers, the code section behind each one, and zero jargon wall. Start at Day 1 or jump to what you need.

Planning Day 1: Why a big tax refund is a liability Stop treating the IRS like a savings account. The math on why you should aim to break even, and how to fix your withholding. Nov 25 · 4 minRead → Retirement Day 2: The only guaranteed 100% return You might be taking a voluntary pay cut. How to fix your 401(k) match, the front-loading trap, and the cash trap before December 31. Nov 26 · 4 minRead → HSA & Health Day 3: HSA, diet, and exercise The cash-price hack, the HSA triple tax advantage, and the shoebox strategy for handling medical receipts. Nov 26 · 6 minRead → Investing Day 4: How to turn a market loss into a tax win Tax loss harvesting, the wash sale rule, the ETF swap strategy, the crypto loophole, and 5 advanced moves most DIY investors miss. Nov 28 · 7 minRead → Investing Day 5: The reset trap You harvested the loss. Now don't mess up the recovery. The holding-period reset, the hierarchy of losses, and the 61-day window. Nov 28 · 6 minRead → Retirement Day 6: The gap year Roth strategy Taking a career break? Use the low income year to convert Traditional to Roth at a discount and save six figures in future taxes. Nov 30 · 7 minRead → S-Corp Day 7: The S-Corp trap (why high earners should think twice) Everyone says start an S-Corp. If you have a high W-2 job and a side business, the Social Security sunk cost can make it cost you money. Nov 30 · 7 minRead → S-Corp Day 8: The S-Corp sweet spot Inflation moved the goalpost. The new magic number, the QBI drag, the accountable plan, and the high-earner QBI unlock. Dec 2 · 7 minRead → Retirement Day 9: The mega backdoor strategy (why the SEP IRA is a trap) Your CPA probably put you in a SEP IRA. Why the Solo 401(k) and mega backdoor Roth shelter nearly double on the same salary. Dec 12 · 7 minRead → Retirement Day 10: The bank of you strategy How a Solo 401(k) loan under IRC 72(p) lets you access $50k of your own retirement cash tax-free, and pay the interest to yourself. Dec 12 · 7 minRead → Family Day 11: The Trump Account vs. the 529 The government wants to give your child $1,000. Take it. But be careful before you add your own money. Plus the business-owner angle. Dec 12 · 7 minRead → Strategy Day 12: The Mark Kohler trifecta A popular YouTube structure promises to audit-proof your life and slash your taxes. The logic is sound, the execution is dangerous. Dec 12 · 8 minRead → Strategy Day 13: Viral vs. vital (debunking TikTok tax advice) The Augusta Rule, the G-Wagon write-off, business meals, and travel. How to use the real strategies without going to jail. Dec 16 · 6 minRead → Real Estate Day 14: The holy grail (real estate professional status) Everyone thinks they qualify. Most don't. The actual math, the two tests, the grouping election, and the hidden cost of REPS. Dec 28 · 8 minRead →

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Articles are for general education only and are not tax advice. Originally published on Tax Smart From Math; figures reflect the tax year when each was written and change annually. Talk to a qualified professional about your situation.