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Why You Should Always 1031 Exchange (And How to Do It Right)

Two people smiling with the Doctors Building Wealth podcast logo. Text reads: “Episode 176: Why You Should Always 1031 Exchange (And How to Do It Right) for mid-term rental cash flow.”.
 

What If Selling Your Rental the “Normal” Way Is Costing You a Fortune?


You bought a rental property years ago. It’s appreciated, you’ve paid down the loan, and now you’re thinking it might be time to sell. Maybe you want to upgrade to something bigger. Maybe the property isn’t performing the way it used to. Either way, the plan feels simple: list it, sell it, pay the taxes, move on.

We get it. That’s the path most people take, and it feels responsible.

But here’s what we’ve learned after years of building our portfolio: every time you sell a property and pay taxes, you’re not just losing money today. You’re losing decades of compounding. And the gap between selling the “normal” way and using a 1031 exchange isn’t small. It’s life-changing.

In this episode, we break down everything you need to know about 1031 exchanges, including the rules, the timelines, the mistakes most investors make, and the exact strategies we use in our own portfolio to make sure every exchange goes smoothly. We also share why we’re almost always 1031 exchanging and why we think you should be too.

BY THE TIME YOU FINISH LISTENING, YOU’LL DISCOVER:

      • The shocking difference in long-term wealth between selling with a 1031 and selling without one (this number alone is worth the listen)

      • Why anyone can use this strategy, no special tax status required

      • How 1031 exchanges can become one of the most powerful ways to pass wealth to your children, completely tax-free

      • The difference between a “lazy 1031” and the real thing, and why we never settle for the lazy version

      • The two deadlines you absolutely cannot miss, even by hours

      • Why most investors make the same critical mistake when they sell first and shop second, and the simple fix that protects you from it

      • Creative ways we’ve extended our timelines, including a lease-back trick that bought us months of breathing room

      • What to look for in a 1031 exchange intermediary so your money is safe and your deadlines are protected

      • How some investors in our community are using tenants in common structures to scale into much bigger deals together

    This isn’t about being overly aggressive with your taxes. It’s about understanding one of the most powerful tools the tax code gives real estate investors and learning how to use it the right way. Once you see what’s possible, you’ll never look at selling a property the same way again.

    Listen now and start planning your next move with the full picture in mind.

    RESOURCES WE MENTIONED IN THIS EPISODE
    Our 1031 Exchange Company Partners: [HERE]
    1031 Exchange Blog Article: [HERE]

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    Ready to Jumpstart Your Real Estate Portfolio and Achieve Freedom?

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    Do you want to learn how to creatively fund your real estate portfolio and achieve financial freedom? Join the conversation! Follow our Semi-Retired MD  Facebook page and join our Doctors or Professionals  group!

    Semi-Retired M.D. and its owners, presenters, and employees are not in the business of providing personal, financial, tax, legal or investment advice and specifically disclaims any liability, loss or risk, which is incurred as a consequence, either directly or indirectly, by the use of any of the information contained in this blog. Semi-Retired M.D., its website, this blog and any online tools, if any, do NOT provide ANY legal, accounting, securities, investment, tax or other professional services advice and are not intended to be a substitute for meeting with professional advisors. If legal advice or other expert assistance is required, the services of competent, licensed and certified professionals should be sought. In addition, Semi-Retired M.D. does not endorse ANY specific investments, investment strategies, advisors, or financial service firms.

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    Hi, we’re Kenji and Leti

    we provide coaching and mentorship
for doctors and high-income earners

    We’re former full-time hospitalists who achieved financial freedom in under five years through strategic real estate investing, generating six-figure rental cashflow while paying zero taxes. We run Semi-Retired MD, teaching thousands of physicians and high-income professionals how to build wealth through real estate with our 
”Fast FIRE System.”

    Two people smiling with the Doctors Building Wealth podcast logo. Text reads: “Episode 176: Why You Should Always 1031 Exchange (And How to Do It Right) for mid-term rental cash flow.”.

    Do you want to learn how to creatively fund your real estate portfolio and achieve financial freedom? Join the conversation! Follow our Semi-Retired MD  Facebook page and join our Doctors or Professionals  group!

    Semi-Retired M.D. and its owners, presenters, and employees are not in the business of providing personal, financial, tax, legal or investment advice and specifically disclaims any liability, loss or risk, which is incurred as a consequence, either directly or indirectly, by the use of any of the information contained in this blog. Semi-Retired M.D., its website, this blog and any online tools, if any, do NOT provide ANY legal, accounting, securities, investment, tax or other professional services advice and are not intended to be a substitute for meeting with professional advisors. If legal advice or other expert assistance is required, the services of competent, licensed and certified professionals should be sought. In addition, Semi-Retired M.D. does not endorse ANY specific investments, investment strategies, advisors, or financial service firms.

    Share

    Hi, we’re Kenji and Leti

    we provide coaching and mentorship for doctors and high-income earners

    Several years ago, we were newlyweds working as full-time hospitalists. On paper, it looked like we had everything: the prestigious careers, the happy marriage, the luxurious rental home, the cars, etc.

    But in reality? Despite having worked for several years, we had very little savings. Despite our high income, we had very little freedom in terms of time or money.

    One thing was clear: we had to do something.

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