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 in Commercial Real Estate?
Keep listening for the training and motivation you need to Find Your Edge.

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Jeremiah Boucher, Founder & CEO of Patriot Holdings
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This podcast is designed solely for educational purposes and does not constitute an offer or solicitation of an offer to buy or sell securities. patriotholdings.com/disclosures

Financial freedom is powerful, but it's not the only kind of freedom that matters.

In this episode of the Finding Your Edge podcast, entrepreneur and investor Jeremiah Boucher gives his definition of true freedom, the kind that leads to fulfillment, and offers practical tips for listeners to find it for themselves.

Are you interested in investing in Commercial Real Estate?
Like and subscribe for the training and motivation you need to Find Your Edge.

Want more from your host?
Jeremiah Boucher, Founder & CEO of Patriot Holdings
Follow on LinkedIn

Are you interested in investing in commercial real estate?
Learn more at PatriotHoldings.com

This podcast is designed solely for educational purposes and does not constitute an offer or solicitation of an offer to buy or sell securities. patriotholdings.com/disclosures

What's the story behind Patriot Holdings? How does a private equity firm like ours maintain consistent, durable returns, through the market ups and downs? And who is Rick Cherry?

In this episode of the Finding Your Edge podcast, Patriot Holdings CEO Jeremiah Boucher sits down with newly appointed CGO Rick Cherry to explain the Patriot blueprint for alternative commercial real estate investing. They explore Patriot's investing philosophy and its utility in the current market.

Are you interested in investing in Commercial Real Estate?
Like and subscribe for the training and motivation you need to Find Your Edge.

Want more from your host?
Jeremiah Boucher, Founder & CEO of Patriot Holdings
Follow on LinkedIn

Are you interested in investing in commercial real estate?
Learn more at PatriotHoldings.com

This podcast is designed solely for educational purposes and does not constitute an offer or solicitation of an offer to buy or sell securities. patriotholdings.com/disclosures

Jeremiah 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

Jeremiah 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:

• Trust Your Intuition: Jeremiah emphasizes the importance of trusting your gut and intuition when making big decisions—whether in real estate, partnerships, or life.

• Fear Is a Message: Fear and pain shouldn’t be ignored; they're messages from your mind or body. Instead of avoiding them, learn to explore and understand what they’re trying to tell you.

• Preparation Eases Fear: When fear arises, it’s often reminding you to be more prepared. Doing your homework and properly researching before major decisions builds confidence.

• Understand Your Mind’s Role: Our minds are wired for survival and tend to focus on potential dangers and negatives, even when threats are minimal in modern life.

• Confidence Is Contagious: People around you can sense both your confidence and your fear. A leader’s conviction and certainty can stabilize and reassure a team.

• Calculated Instincts Over Impulsive Bets: Trusting your gut doesn’t mean acting on a whim. Make sure your instincts are backed by research, preparation, and experience rather than impulse.

• Alignment and Motivation Matter: When partnering or negotiating, look for genuine motivation and alignment of goals. Forced or one-sided engagements rarely work out in the long term.

• Intentions Are Felt, Not Hidden: True intentions, whether aligned or not, tend to come through in interactions. Operating with honest, positive intent is essential for building lasting relationships and deals.

• Detachment from Outcomes: Don’t become emotionally attached to a particular deal, person, or outcome. The ability to walk away provides power in negotiations and protects you from poor decisions.

• Continuous Growth and Self-Trust: Decision-making is a muscle that develops with experience. Combining intuition with logic, reflection, and learning from both success and failure leads to better, more confident choices over time.

Are you interested in investing in Commercial Real Estate?
Learn more at www.patriotholdings.com

Jeremiah 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:

• Evolution of an Investor: Jeremiah talks about the journey of being an investor and how evolution in business revolves around mastering your craft over time.
• Mentorship and Learning: He highlights the influence of his mentor, Matthew Ferry, and the importance of understanding language and communication skills in sales and real estate.
• Formulation Stage: This is where you start with an idea, explore the basics, and feel excitement despite not knowing everything. Jeremiah recalls his start in real estate with no money down deals as exciting but full of unknowns.
• Concentration Phase: A challenging phase where hard work might yield minimal immediate returns. Jeremiah references his cold calling efforts during tough financial times and the importance of dedication.
• Networking Value: Emphasis on the importance of human networks, compared to Metcalfe's Law, explaining that as networks grow, their value becomes exponential due to increased connections and intelligence.
• Momentum Phase: Once skills are honed, success begins to flow more naturally, offering more opportunities and a deeper, more valuable network.
• Avoiding the Pride Trap: Jeremiah warns against the dangers of pride during success, stressing continuous hard work and vigilance to prevent falling into complacency.
• Stabilization Phase: This involves building systems and having the right people to maintain business continuity. Jeremiah learns this through personal experience with employee challenges.
• Breakthrough Opportunities: Once stability is achieved, new opportunities can be explored. Jeremiah talks about rising above current operations to spot new initiatives and possibilities.
• Embracing Challenges: Jeremiah encourages embracing discomfort and persistence, learning from failures, and experimenting, rather than viewing challenges as a constant grind. He emphasizes the enjoyment and growth found in this journey.

Are you interested in investing in Commercial Real Estate?
Learn more at www.patriotholdings.com

Jeremiah 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:

• Realistic Expectations: Making money in real estate involves more than the often-touted "easy" paths. It's important to understand the realities and challenges involved in different asset classes.

• Finding Your Edge: Find a competitive edge in real estate investing by seeking out less crowded asset classes or markets. It's about being a first mover to drive higher returns.

• Active vs. Passive Investing: Differentiate between being an active investor who manages properties and a passive investor who invests in general partnerships or funds. Each approach has its own set of challenges and requirements.

• Importance of Timing: Beyond location, timing plays a crucial role in real estate success. Market cycles can affect investments significantly, and understanding when to enter or exit is key.

• Long-term Perspective: Have a long-term horizon, typically at least ten years, for accruing substantial wealth through real estate. Patience and timing are crucial to success.

• Leveraging Debt Carefully: Real estate often involves leveraging properties with debt, which can be risky if cash flow is not managed properly. Adequate reserves are essential to weather downturns.

• Choosing the Right Partner: For passive investors, selecting a trustworthy partner or sponsor with skin in the game is crucial. The focus should be on the partner's expertise and commitment.

• Tax Advantages: Real estate offers tax-deferred benefits, especially through methods like the BRRR strategy, allowing reinvestment without immediate tax burdens.

• The Role of Teams: Real estate is a team sport, requiring collaborative efforts to manage, market, and maintain properties effectively.

• Communication and Integrity: Ongoing communication with partners or sponsors and understanding their history, including past failures, is vital for building trust and ensuring a successful investment relationship.

Are you interested in investing in Commercial Real Estate?
Learn more at www.patriotholdings.com

Jeremiah 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:

• Introduction: Jeremiah Boucher introduces Jared Elmar, owner of the Geneva Group, who is launching his book "Built from Nothing." Jared has experience across multiple real estate sectors except self-storage and mobile home parks.
• Jared's Background: Jared initially had a radio show focused on financial services like life insurance and wealth transfer, which got affected during the global financial crisis of 2008. He reinvented himself by focusing on real estate investment.
• Transition to Real Estate: Jared began investing in residential properties and sold most of them before the financial crash. He then transitioned to commercial real estate, starting with multifamily units.
• Challenges and Growth: Jared's first multifamily deal was a challenging one, with significant issues like crime and accidents, but was successful in generating returns for investors. This deal sparked his interest in syndication.
• Strategic Adaptation: Jared shifted from multifamily to industrial and retail spaces due to scalability issues with multifamily. His approach involves adapting to different asset classes and market conditions.
• Importance of Intuition and Vision: Emphasize the role of a visionary in identifying deals that others may overlook, focusing on intangibles like market conditions and potential property improvements.
• Current Market Strategy: Prepare for future opportunities by enhancing his acquisitions efforts and anticipating foreclosures, believing that capital flow changes cap rates rather than interest rates.
• Negotiation Skills: Value authenticity and emotional intelligence in negotiation, stressing the importance of understanding the seller's motivations and conditions beyond just the numbers.
• Leadership and Culture: Jared fosters a culture of philanthropy within his company, encouraging his team to engage in charitable activities, which has contributed to the company's positive work environment.
• Fitness and Mental Clarity: Fitness is a crucial aspect of Jared's life, providing mental clarity and discipline, which supports his resilience and leadership capabilities.

Are you interested in investing in Commercial Real Estate?
Learn more at www.patriotholdings.com