What Happens to Your Tax Bill When You Sell the Farm? DST Strategy & More. episode artwork

EPISODE · Jun 1, 2026 · 58 MIN

What Happens to Your Tax Bill When You Sell the Farm? DST Strategy & More.

from The National Land Podcast · host National Land Realty

Forty percent of the land in this country is expected to change hands by 2035. Most of the people holding it have no idea how much of that wealth they are about to hand to the IRS. Joe Michaletz and Mike O'Toole, CEO and principal at Discipline Advisors, have spent decades helping farmers, ranchers and land owners exit their real estate in the most tax-efficient way possible. In this conversation they break down the full toolkit, starting with 1031 exchanges and the most common mistakes people make going into them, including the debt replacement test that catches landowners off guard more than almost anything else. They walk through Delaware Statutory Trusts in real depth, how they differ from REITs, why diversification inside a DST portfolio matters as much as it does anywhere else, and what the 721 UPREIT path actually means and when it is and is not a good idea. The conversation also covers charitable remainder unitrusts, a tax elimination strategy for farm equipment, livestock and grain that most landowners have never heard of, and how one dairy farmer moved 6.5 million dollars of cattle and equipment into a CRUT, sold it with zero tax, and funded a lifetime income stream in the process. For anyone aging out of land ownership, planning a farm transition, or sitting on decades of appreciation with no exit plan, this episode is the conversation to have before you sign anything.   Visit Discipline Advisors! https://www.disciplineadvisors.com/   Visit National Land Realty to see our listings!  https://www.nationalland.com 

Episode metadata supplied by the publisher feed · Published Jun 1, 2026

Embed this episode

NOW PLAYING

What Happens to Your Tax Bill When You Sell the Farm? DST Strategy & More.

0:00 58:34

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

No similar episodes found.

No similar podcasts found.

Frequently Asked Questions

How long is this episode of The National Land Podcast?

This episode is 58 minutes long.

When was this The National Land Podcast episode published?

This episode was published on June 1, 2026.

Can I download this The National Land Podcast episode?

Yes. Use the download control on the episode player to save the publisher-provided media file.
URL copied to clipboard!