Tax Planning & Compliance

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.

When you’re building a business, one of the most consequential decisions you’ll make is choosing its legal structure. On paper, it may seem like an administrative formality, but in reality, your choice between an LLC and an S-Corp could mean the difference between paying thousands more in taxes or keeping that money in your business to fund growth.