Capital Gains
September 16, 2026
A private sale leaves no trail. No broker files a form. No title company mails a copy to the IRS. Cash or a wire transfer
In 2012, the IRS lost a case at the Supreme Court. It only took Congress three years to make sure the agency never lost that
The IRS did not get weaker when it lost roughly a quarter of its workforce. It got faster. That sentence sounds backwards, because fewer people
The bartender is refilling drinks. Someone is laughing too loudly by the charcuterie board. Behind me, two men are arguing about a watch. Not the
The IRS does not care how many hours you spend fixing a leaking water heater at midnight. It still calls your rental income “passive.” That
A computer in Kansas City decided my client owed $15,000. It never asked why. It just compared two numbers, found a mismatch, and mailed a
More than 46 million households in America paid rent to someone else last month. Every one of those checks landed in a landlord’s account. And
I have spent years telling business owners why an S-Corp usually beats the alternative. I still believe that, for most people, most of the time.
Picture a business owner in 2030 uploading a year of bank statements into a piece of software. Five minutes later, every transaction is reconciled. Expenses
On July 4th this year, while most of the country was watching fireworks, the Small Business Administration quietly doubled the amount of money it will
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