Tax Strategy Blog for Business Owners

Tax compliance vs tax strategy is the difference between reporting what you owe and changing what you owe — legally — before the year is over. A business owner made $1.2 million last year. His CPA filed everything correctly. Every form. Every deadline. Every dollar reported. He still owed six figures he never saw coming. […]

HSA after death rules are very different from IRA and 401(k) rules. If your spouse is the beneficiary, the account can continue as that spouse’s HSA. If the beneficiary is someone else, the account generally stops being an HSA on the date of death, and the tax result can be much harsher. That matters because […]

A tax strategy for profitable business owners starts with a hard question: if your business did $1 million, $3 million, or $5 million last year, where did that money actually go? After payroll, overhead, and taxes, how much did you actually keep? And of what you kept, how much is working for you right now […]

If you're thinking about selling a property, you probably know capital gains tax may be coming. But depreciation recapture on a rental property sale is the second bill that catches a lot of sellers off guard. Most people are planning for one tax hit. Then they find out the federal tax math is doing something […]

Quick Answer Why do most tax strategies never get implemented? Based on my 20+ years implementing tax strategies for business owners, implementation fails because it requires coordination between multiple professionals (attorneys, CPAs, bookkeepers), state-specific compliance expertise, proper documentation, and ongoing maintenance. Most tax advisors specialize in strategy consultation but lack the systems, team, or liability […]

This is a strategy to offset the 28% gold collectibles tax using cost segregation and bonus depreciation. You bought gold years ago as financial insurance. Smart move. Now it's worth $4,888 per ounce—an all-time high. Your $500,000 investment is worth $1 million. Here's the problem: sell it, and the IRS wants $140,000 (28% collectibles tax). […]

If you own rental property and want to scale, a 1031 exchange for rental property is one of the cleanest ways to defer federal tax on the gain and keep more equity working. Important scope and eligibility note: Under current law, Section 1031 applies only to real property held for investment or for productive use […]

Can AI do my taxes? It is the question of the year. “Laura, with all this new AI, can’t a computer just do my taxes now?” The honest answer? Yes. If you have a single W-2, a standard deduction, and you don't plan on growing. Honestly? The AI will probably do a great job. It […]

Tax due diligence for alternative investments is the part that gets skipped when a deal is pitched as “safe” because a household-name firm approved it. Let’s talk about the “Big Firm” safety blanket. You might be sitting across from a financial advisor who has been in the game for 20 years. They are sharp. They […]