Understanding 1031 Exchanges: A Key Tax Strategy for Real Estate Investors with Jeremiah Boucher (Patriot Holdings CEO)
Finding Your Edge | Health, Growth, and Self-Mastery
Release Date: 05/30/2025
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The 22-Year-Old Investor who Built a Multi-Million-Dollar Business | Alexis Morgan
Finding Your Edge | Health, Growth, and Self-Mastery
🧑💼 WHO AM I
My name is Jeremiah Boucher. I build, buy, and operate niche commercial real estate, and teach investors like you how to think clearly, act intelligently, and build wealth without the hype.
🤝 WANT TO CONNECT ON LINKEDIN
https://www.linkedin.com/in/jeremiah-boucher
🙌 WANT TO CONNECT WITH ALEXIS
https://www.linkedin.com/in/alexismorgani
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It's not what you make, it's what you keep | The Power of Tax Planning
Finding Your Edge | Health, Growth, and Self-Mastery
Tax planning is one of the most underestimated and underutilized benefits of real estate investing.
In this episode of the Finding Your Edge podcast, author and investor Jeremiah Boucher breaks down the fundamentals of real estate tax that equip investors to ask the right questions of their advisory team and keep more of what they make.
Are you interested in investing
info_outlineJeremiah Boucher built a $400 Million portfolio of commercial assets (self-storage facilities, mobile home parks, industrial assets) from zero, through constant improvement, investing ahead of the curve, and hard work & execution.
In this episode:
- 1031 Exchanges Are a Tax Deferral Strategy, Not a Tax-Free Loophole: They allow investors to defer capital gains and depreciation recapture taxes when selling investment or business-use property, provided the proceeds are reinvested into like-kind property.
- Bonus Depreciation Benefits Are Shrinking: Recent reductions in bonus depreciation have made 1031 exchanges a much more attractive strategy for investors looking to manage capital gains and recapture taxes.
- Depreciation Recapture Can Have Major Tax Implications: Investors pay 25% tax on regular straight-line depreciation recapture, and up to 37% on accelerated ("bonus") depreciation recapture when selling—a potentially huge tax bill.
- When to Use a 1031 Exchange: Ideal scenarios include maxing out value or depreciation of a property, seeking less management-intensive investments, avoiding major capital expenditures, upgrading tenant stability, or finding better cash flow.
- Five Major Rules Must Be Followed: These include acquiring like-kind property, adhering to strict identification (45 days) and closing (180 days) timelines, and using a qualified intermediary to hold the sale proceeds.
- Qualified Intermediaries Play a Critical Role: The QI must hold your funds in a separate trust or escrow account with you as the beneficiary—failure to use a reputable QI could result in loss of your exchange funds.
- Not All Properties Qualify: Only investment or business-use properties are eligible; primary residences and most vacation homes do not qualify unless they've been used as rentals under specific rules.
- Passive 1031 Exchange Options: Investors can exchange into Delaware Statutory Trusts (DSTs), triple net (NNN) leased properties, or Tenant-in-Common (TIC) interests for more hands-off investments.
- Pitfalls and Mistakes to Avoid: Touching the proceeds before they go to the QI, missing deadlines, or failing to match or exceed the value of the replacement property can all disqualify the exchange.
- 1031 and Legacy Wealth :Continuously exchanging into higher-value properties lets investors avoid taxes during their lifetime, and heirs receive a step-up in basis upon death—making gains effectively tax-free generationally.
Are you interested in investing in Commercial Real Estate? Learn more at www.patriotholdings.com