Selling a highly appreciated business, property, or investment usually means writing a big check to the IRS — but the tax code offers legitimate ways to reduce or eliminate that bill. Most people either don't know these strategies exist, or assume they're only for the ultra-wealthy.
In this episode, Michael Haslam and Nathan Croxford break down six legal levers for reducing your taxes — from structuring a sale so it's never a taxable event, to deferring gains for decades, to shifting income to family members in a lower bracket. They cover who each strategy actually helps (business owners selling to family, real estate investors, high income earners, anyone sitting on an appreciated asset), why a properly structured trust can turn a taxable sale into a non-event, and why any strategy — no matter how good it sounds — needs to be vetted by a real tax attorney before you use it.
Key Takeaways:
- The Non-Taxable Sale: How selling a business to a properly structured trust for your kids — instead of directly to them — can eliminate the taxable event entirely.
- The 1031 Exchange: How real estate investors defer capital gains taxes indefinitely by swapping properties, and why holding until death can erase the deferred gain for good through stepped-up basis.
- Deductions vs. Credits: Why a tax credit saves you a dollar-for-dollar amount while a deduction only saves you your tax rate — and how a cost segregation study can turn a $1M building purchase into a $300,000 deduction.
- Changing Your Tax Category: Why capital gains rates beat ordinary income rates for high earners, and how an S Corp structure eliminates self-employment tax on profit distributions.
Michael Haslam and Nathan Croxford are practicing attorneys at Voyant Legal in Utah. This episode is for educational purposes only and does not constitute legal advice. Visit voyantlegal.com or call 801.951.0500.

