OWN WHAT THE PROS OWN
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Hold or sell? The question nobody owns.

Your CPA, your wealth guy, your attorney: none of them own this one. It's usually the most valuable question you're not asking.

Your CPA owns your tax return. Your wealth manager owns your portfolio. Your attorney owns the paperwork. Nobody owns the question of whether that specific building still belongs in your portfolio. That's often the most valuable question you're not asking.

Start with yield on equity, not yield on cost

The number that matters isn't what the building earns against what you paid years ago. It's what your equity earns today. If you could sell for a strong price, that equity is real money sitting in the deal. Ask what it's actually earning, and what it could earn somewhere else.

What pushes toward a sale

  • Trapped equity. A big gain sitting at a low yield on equity is capital that could work harder, often in something more passive.
  • Rollover and age risk. A lease winding down, an aging building, or a tenant you're unsure about are risks you carry for free while you hold.
  • The tax tool exists. A 1031 lets you trade up without the tax hit, so "I don't want the gain" isn't the wall people think it is.

The honest reasons to hold

  • Strong tenant, long term, real escalations. If the income is durable and growing, holding can be exactly right.
  • The replacement is worse. Selling only makes sense if the next use of the money beats this one after costs and taxes.

I run this for owners and tell them straight. If holding is right, I say hold. If a sale or a 1031 puts you in a better spot, I show you the math first.

Want to see this on real deals? Read the deal teardowns →