Wake Up to Wealth Podcast

Episode: Maximize Wealth: Inside Tips from Tax Attorney Brian Boyd

Host: Brandon Brittingham
Guest: Brian Boyd, Nashville-based Tax Attorney & Real Estate Investor
Date: January 30, 2026

Episode Overview

In this high-impact episode, host Brandon Brittingham sits down with tax attorney and seasoned real estate investor Brian Boyd to delve deep into practical tax strategies, wealth-building through real estate, and the legal loopholes that can fast-track your journey to generational wealth. Boyd, known for breaking down complex tax concepts into relatable, actionable insights, shares lesser-known tax advantages, stories from his personal investment journey, and highlights the importance of financial education. The conversation is packed with examples, analogies, and unique advice for both W2 employees and entrepreneurs, challenging listeners to reconsider how they approach taxes, business investments, and long-term wealth building.

Key Discussion Points & Insights

1. Brian Boyd’s Background

• [02:35] Brian shares his educational and professional journey:
  • East Tennessee native, law school at Samford and Georgetown (tax law).
  • Corporate tax work at Ernst & Young, 16 years running his own firm, and now partner at Thompson Burton.
  • Daily focus: tax efficiency in real estate deals, M&A, business disputes, and tax planning.
  • Also a passionate real estate investor with 20+ properties across TN and Montana.
  • “Every deal, just like every person, it's different. It's like a fingerprint. Just like our listeners, everybody's listening for a different reason.” – Brian Boyd [03:50]

2. Low-Hanging Real Estate Tax Strategies: The Short-Term Rental Loophole

• [07:38] Introducing Treasury Regulation 1.4691 TE3—the “short-term rental loophole”:
  • Only 100 hours of active participation unlocks significant deductions.
  • Especially valuable for W2 employees who cannot meet the 750-hour real estate professional test.
  • Combine with cost segregation and bonus depreciation to supercharge deductions.
  • Brian: “You may have a massive loss in your first year on paper, but you're going to see the cash flow increase because what you're not paying in taxes that year, you can then reinvest into another property and do it over and over again.” [09:08]

Brandon’s Example Calculation

• [11:21] Brandon walks through an example:
  • Buy $500k property.
  • Cost segregation: ~25% of price = $100k+ depreciation.
  • “You can actually take that depreciation and take that as a paper loss on your taxes. And that is freaking one of the biggest hacks in the world for you to get wealthy.” [12:22]

3. Why the Tax Code Is Built for Investors

• [13:37] Brian breaks down the real aim of the tax code:

  • The government incentivizes private investment in real estate because it doesn't build housing itself.
  • Multiple sections—bonus depreciation, business deductions, affordable housing credits—make real estate the most tax-advantaged investment.
  • Understanding credits vs. deductions: “A credit is like a dollar for dollar reduction of your liability... It changes your tax profile.” [15:31]

• On shifting your mindset:

  • “If people would look at the tax code as what opportunities are available as opposed to what penalties am I trying to avoid, I think the mindset changes the paradigm.” [16:40]

4. The Cost of Ignorance: Why Taxes Matter

• [18:10] Brandon underscores tax education as essential, not optional:
  • Taxes are likely your single largest expense as a business owner.
  • “There's two economies, the educated and the non-educated... I’m talking about being educated about money and understanding the tools like cost segregation, the different legal loopholes, defined benefits...that's how you become wealthy.” [31:25]

5. Entrepreneurship, Passive Income, and Recession-Proof Businesses

• [21:08] Brandon and Brian discuss alternative investments:
  • Laundromats as cash-flowing, depreciation-rich, recession-proof assets.
  • Brian started investing through a laundromat: “I ended up cashing out my retirement account... I built a laundromat. The deductions I got in the first year were incredible... I ended up selling it a year later for four times what I built it for.” [22:49]
  • Sectors with “no budget”: Pets and children (vet clinics, daycare, grooming).
  • “If people would look at businesses like that... being a passive investor in some of those businesses, it's a great plan.” [25:15]

6. Defined Benefit Plans & Advanced Retirement Strategies for Business Owners

• [26:22] For entrepreneurs, not just 401(k)s or SEPs, but defined benefit plans:
  • 3 components: profit sharing, 401k, actuarially-calculated annual funding.
  • Can contribute hundreds of thousands tax-deductible each year—major tax reduction tool.
  • “Imagine if you're making $500,000 a year, but you're grossing $1.2 million...you can actually take $200,000, put it into a defined benefit plan, bring your gross down so your taxability is also lower. So it's really a game changer.” [29:29]
  • Caution: More complex if you have employees—requires professional analysis.

7. Life Insurance as an Investment: Self-Banking, Family Wealth Transfer

• [32:13] Brian advocates for permanent life insurance, not as expense, but as a wealth-building, family-protecting asset:
  • Paid-up addition riders = “stacking cash,” self-banking.
  • Brandon uses these for “family banking” to fund investments, children’s future.
  • “You borrow against the policy. I'll go buy a house, I’ll refinance that house, pay myself back and I don't have to deal with the problems of having to go to a bank…” – Brian [33:24]
  • On generational strategies:
    • Buying whole life for his child, using 1035 exchanges, using accumulated value to pay for college, eventually gifting the policy.
    • “When he goes off to college, I have a 529 plan, but I can also borrow from that policy, pay for his tuition...and then when he graduates...I'm going to give it to him.” [36:36]

8. Tax Rule “Hacks” & Strategic Mindset

• [39:42] Boyd’s viral advice: If someone owes you money and won’t pay, use a 1099-C (Cancellation of Debt income) form:
  • “You're discharging it, you're getting the deduction for it. Now there are a lot of rules around it...but the idea is...utilize the tax code to take what is now a liability to you... to turning it into a deduction, which is a benefit to you.” [41:14]
  • “That's how tax lawyers, strategists, and tax practitioners think about the tax code. We don't think about it as punitive. It's not. It's just a set of rules.” [42:18]
  • Innovative tax pros ask: “The rule says this, but it doesn't say I can't do this.” [42:54]

Notable Quotes

• Brian Boyd:
  • “The world looks very different. You're not doing that nine to five every day, you're setting your own schedule, you're looking for deals, you're managing property, you're talking to like-minded people.” [10:40]
  • “If you know how to use that tool, much like you and I use it for self banking, it changes the game.” [38:59]
• Brandon Brittingham:
  • “There's two economies, the educated and the non educated... I didn't understand all these mechanisms of wealth that wealthy people used because I was just like, man, I'm making a shit ton of money, right?” [31:13]

Memorable Moments & Timestamps

| Moment | Timestamp | |---------------------------------------------------------|-------------| | Brian explains the short-term rental loophole | [07:38] | | Brandon’s vivid example of applying cost segregation | [11:21] | | Brian: “Money is just a tool” mindset anecdote | [37:04] | | Brian’s viral “1099-C for unpaid debts” strategy | [39:42] | | Brian’s story selling a laundromat for 4x cost | [22:49] | | How self-banking works with whole life insurance | [33:24] |

Resources & Where to Find Brian Boyd

• Instagram, Facebook, TikTok, YouTube: @Brian T. Boyd
• Long-form educational videos and course content on YouTube for deeper dives into specific tax strategies, including 1099-C processes.

Final Thoughts

This episode is a masterclass in seeing wealth-building not just as earning more but keeping more by smartly leveraging the tax code, deploying tax-advantaged investments, and approaching money as a tool, not just a necessity. Brian Boyd demonstrates how deep expertise (paired with a creative, rule-based approach) can turn everyday people into astute investors and protectors of generational wealth.

Brandon’s advice to listeners: don’t be intimidated by “boring” subjects like taxes—lean into them, and it’ll pay off exponentially. The episode is packed with practical, actionable insights for both beginners and seasoned entrepreneurs seeking to maximize wealth retention and financial freedom.

Listen, learn, and run with it!