Tax Planning & Compliance

I've been paying our family health premiums through the business for six years. My CPA never said anything, so I assumed it was handled. It wasn't. The premiums ran through the S corporation as a business expense, but they never appeared on his W-2. Under the rules, that means the plan wasn't established by the business, and the personal deduction is gone.

I sold a rental property last year and made $180K on the sale. Then tax season came and I found out I owed $80K, most of it from depreciation recapture. My CPA never mentioned it until the return was already done.

A healthcare practice owner recently told us: "I filed my taxes in April and found out I owed $45K. My accountant prepared the return but never mentioned anything I could have done differently.

June 15 is more than just another date on the calendar. For business owners, contractors, and self-employed professionals, it's the Q2 estimated tax deadline—and it catches most people unprepared.

Even if you’re confident you’ve done nothing wrong, seeing “Internal Revenue Service” at the top of an envelope can trigger stress, confusion, and a lot of unanswered questions. Is this serious? Did I make a mistake? Am I being audited? What happens if I ignore it?

As the year draws to a close, many investors focus on maximizing their returns — but the smartest ones also focus on minimizing their taxes. One of the most powerful (and often underused) tools for doing this is tax-loss harvesting.