Stop Leaking Money to the IRS and Start Building Real Wealth with Brian Boyd

On Accredited Investors Only, host Peter Neill sits down with Brian Boyd, a tax attorney, real estate investor, and author, for a practical conversation about how accredited investors can think more strategically about taxes, entity structure, syndications, and wealth building.

Boyd is a partner at Thompson Burton in Franklin, Tennessee, where the vast majority of the firm’s work is tied to real estate. That includes syndications, 1031 exchanges, development, land use, litigation, and tax structuring. He also actively invests himself, which gives his perspective a useful combination of legal, tax, and operator-level experience.

The central idea running through the entire conversation is simple: wealth is built not just by earning more, but by keeping more, structuring better, and redeploying capital into income-producing assets.

Brian Boyd’s approach: reduce tax leakage, increase optionality

Boyd describes his legal practice in a way that will resonate with many investors. He does not see his role as simply helping clients comply with the rules. He sees it as helping them build wealth.

That starts with reducing what he calls tax leakage. In plain English, that means keeping money from unnecessarily flowing out to the IRS as ordinary income tax or capital gains tax when a better structure or better planning could preserve more of it.

The goal is not tax gimmicks. It is tax efficiency.

And the point of tax efficiency is not just to save money for the sake of saving money. It is to put that money back to work in assets that produce:

• Cash flow
• Appreciation
• Depreciation benefits
• Long-term wealth
• Asset protection and estate planning flexibility

That is the lens Boyd uses whether he is advising on a company sale, a partnership structure, a real estate syndication, or a personal portfolio decision.

Your CPA looks backward. Your attorney should look forward.

One of the most useful distinctions in the conversation is Boyd’s explanation of the different roles played by a CPA and a tax attorney.

Many investors assume their accountant is also their strategist. Sometimes that happens to a degree, but Boyd’s point is that those jobs are fundamentally different.

What a CPA typically does

A CPA generally works from historical numbers. Their job is to make sure the books are accurate, the returns are filed correctly, and everything balances. They are often looking backward at what already happened.

By the time tax season arrives, there may be only limited ability to change the outcome.

What a tax attorney should do

A tax attorney doing strategic work is looking ahead. The job is to:

• Analyze how things have been done historically
• Identify where money is being lost unnecessarily
• Restructure entities or transactions before the year ends
• Coordinate with the CPA so the plan gets carried out properly

Boyd compares it to coaching. The attorney is helping the client decide how to swing before the pitch comes, not just recording where the ball landed after the fact.

That distinction matters a lot for accredited investors, especially those participating in 506 syndications, private funds, or active real estate businesses. Structure decisions made early can have major implications later.

Why entity structure matters before you invest

When investors start allocating capital into syndications or direct real estate deals, one of the first questions is whether to invest personally or through an entity.

Boyd is clear on his preference: he does not want clients holding investment assets in their personal name if it can be avoided.

Why he prefers an LLC

For many real estate and syndication situations, Boyd typically encourages clients to invest through an LLC. His reasoning is practical:

• Liability protection through a legal shield
• Estate planning advantages
• Flexibility if the investor wants to bring in a partner later
• Cleaner planning opportunities compared with personal ownership

That flexibility point is especially important. If an investor enters a deal through an entity, there may be more room later to restructure ownership, add capital partners, or adjust planning without starting from scratch.

Why not just use any entity?

Boyd also makes an important warning here: not all entities are interchangeable.

He gives the example of investors wanting to hold real estate in an S corporation. In his view, that is generally not where you want real estate to live because of how disposition and other tax consequences can play out. He also cautions against taking an LLC and electing to tax it as an S corporation if the asset is real estate and partnership treatment would provide more flexibility.

The broader lesson is straightforward: the wrong entity can create unnecessary tax friction later.

The best time to talk to a tax attorney is early

Another recurring theme is timing.

Boyd prefers that clients come to him when the idea is still forming, not after the structure has already been set and documents are signed. In his words, the conversation should start while the idea is still “germinating.”

That early-stage planning might include questions like:

• Are you going to be a GP, an LP, or both?
• How much capital are you contributing?
• How much money must be raised?
• What does the capital stack look like?
• Are you using mezzanine debt?
• Is anyone contributing property instead of cash?
• What entities need to exist at the GP level, LP level, and asset-holding level?

He shares an example of a younger client who wanted to launch a syndication as a GP. Rather than rushing into setup, they started by talking through whether the client already had cash-flowing assets that could be contributed, how the fund might grow over time, and what the legal structure should look like once he was ready to move.

That process is part technical drafting, part strategic design, and part education.

Most investors need more education on how syndication money actually flows

One of the clearest insights from Boyd is that many people put money into deals without fully understanding what they are buying into.

That education gap matters.

Whether someone is investing $100,000 into a 506 offering or putting a larger check into a private fund, they should understand:

• Where their money is going
• What entity they are buying into
• Who controls the deal
• Whether there is a preferred return
• How the distribution waterfall works
• What the time horizon is
• What the exit strategy is
• What rights and responsibilities come with being a GP or LP

Boyd’s practice handles approximately one offering per month, so these are not edge-case questions for him. They are everyday issues.

His job, as he describes it, is often to draw the map. Show the money flow. Explain the tax flow. Clarify the entity flow. Once investors can see the structure, they can make a more informed decision.

Real estate is the core, but the opportunities are wider than most people think

Boyd’s world is heavily real estate-focused, but the types of opportunities he sees are broader than many investors expect.

In the same conversation, he references deals involving:

• RV parks
• Trash transfer stations
• Oil and gas leases
• Restoration companies
• Cross-border investment structures

That matters because the skills he is talking about are transferable. Investors need to understand structure, tax exposure, liability, management quality, and capital flow whether the asset is an apartment building or a niche operating business.

What a tax attorney actually works on inside a deal

Boyd gives a useful glimpse into the mechanics of larger transactions.

In a significant deal, his role can include:

• Drafting and reviewing structure documents
• Redlining transaction documents
• Designing or reviewing the tax distribution waterfall
• Making sure cash distributions align with the intended economics
• Coordinating with securities counsel on SEC-related issues
• Addressing cross-border investor questions

He mentions an active $55 million transaction where much of the work centers on making sure the cash distribution waterfall works properly for the client.

That is a good reminder for accredited investors: the legal work in a syndication is not just paperwork. It is where economics, tax, control, and investor rights get translated into enforceable structure.

Trusts, family offices, and multi-state investing

Boyd works with clients all over the country, and because tax law at the federal level reaches broadly, he is involved in transactions nationwide.

State choice, such as using a Delaware or Wyoming entity, does not automatically change the core economics of a deal. But once trusts or family office structures enter the picture, the conversations become more nuanced.

How irrevocable trust investing works

When an irrevocable trust invests in a deal, beneficiaries often want to know how the tax consequences reach them. Boyd explains that the income generally flows to the trust, and the beneficiary’s concern typically becomes relevant when distributions are made to them.

But tax treatment is only part of what these clients care about. They also want to understand:

• Whether the wealth is growing
• Whether gains are capital or ordinary
• How cash moves from the investment to the trust to the beneficiary

Again, the throughline is education. Whatever the ownership structure, investors need to understand what the arrangement means in practical terms.

The wealth team every serious investor should build

Boyd is emphatic about one thing: wealth building is a team sport.

He believes investors should intentionally build a professional team that includes:

• A lawyer
• A CPA
• A bookkeeper
• An insurance agent
• A financial planner

On the insurance side, he is not only talking about property and casualty coverage. He also brings up whole life insurance and the way some investors use infinite banking concepts to fund investments.

His point is not that every investor needs every product. It is that everyone on the team should know what the client is trying to accomplish. The free flow of communication between professionals helps align tax planning, accounting, estate planning, risk management, and investment strategy.

That kind of coordination becomes even more important for high-income professionals who are trying to escape the trap of trading more hours for more income.

The burnout that pushed Brian Boyd into real estate

One of the most compelling parts of the conversation is how Boyd got into investing himself.

It started years earlier when a client showed him a development model: build 10 townhomes, sell 7, keep 3, refinance the retained units, put tenants in them, and repeat.

Boyd began mapping the tax implications and saw how powerful strategic structuring could be. Conversations around 1031 exchanges, 721 UPREITs, Delaware Statutory Trusts, and related planning tools opened his eyes to what real estate could do.

But the real turning point came later.

In 2015, he says he worked around 50 Saturdays. He was exhausted, unhealthy, sleep-deprived, and miserable. He was not showing up well as a father, husband, or friend. During a turkey hunting trip, another client asked him a simple question: had he ever thought about owning a coin laundry?

He had not. But the idea stuck.

From coin laundry to rental portfolio

As they talked, Boyd began thinking through the depreciation on laundry equipment, how that depreciation could shelter income, and what the cash flow profile might look like.

The next year, he built a coin laundry because he needed another revenue stream that did not depend on him billing more hours.

After running it for a year and hiring help at the firm, he sold the coin laundry and used the proceeds to:

• Buy a short-term rental
• Pay off a student loan
• Buy his wife a new wedding ring
• Purchase a few shotguns

From there, the investing strategy accelerated.

He and his wife bought two long-term rentals. Then they sold the short-term rental and acquired 13 single-family homes. They improved the properties, increased value, built equity, and then borrowed against the portfolio to buy more.

The results were meaningful:

• Tax bills dropped sharply through depreciation
• Cash flow improved
• Equity built over time
• Multiple income streams reduced pressure on his law practice

He even mentions one year where the family got back roughly $140,000 in taxes, which was then applied toward debt reduction and further growth.

That is the core wealth-building loop he keeps coming back to: preserve capital, put it into assets, improve those assets, pull equity when appropriate, and repeat.

What Brian Boyd is focused on now: cash flow and retiring his wife

At this stage, Boyd says his own family’s tax picture is largely under control. His current investing priority is cash flow.

The reason is personal and clear. He wants to retire his wife so she can be the stay-at-home mom she wants to be.

That has him looking closely at investments that may produce stronger current income, including oil and gas leases and related funds. He notes that these can still fall within the broader real estate world and may even be eligible for 1031 exchange treatment in certain contexts.

For him, the next milestone is not just balance-sheet growth. It is lifestyle freedom for his family.

How he evaluates a deal: numbers first, then nuance

When Boyd walks through his due diligence process, it becomes obvious he is not relying on a single metric or a quick gut check.

The first layer: property and financials

He starts with the basics:

• Where is the property?
• What is the purchase price?
• How much additional capital is needed to improve it?
• How will it cash flow?
• What does the distribution waterfall look like?

He trusts numbers, but not blindly.

The second layer: qualitative reality

Sometimes a market looks great on paper, yet operators still cannot make deals work there. That is where he starts asking more nuanced questions:

• Is the area actually developing?
• Is it gentrifying?
• Why does this location make sense now?
• What local dynamics might explain the gap between theory and execution?

Good underwriting is necessary, but not sufficient.

The third layer: operator quality

Boyd also wants to know who is managing the deal and what their experience looks like. Lack of experience is not automatically disqualifying, but if someone is writing a six-figure check, they should understand whether the team has done anything similar before.

The fourth layer: tax impact

From there, Boyd overlays his tax lens:

• How is money moving through the entities?
• Who receives what payments?
• Can the structure be made more tax efficient?
• What are the state and local tax implications?

He gives the example of Tennessee’s franchise and excise tax, which is distinct from an income tax and can materially affect planning. Depending on the state, there may be exemptions or planning opportunities, but they need to be identified up front.

The fifth layer: the offering itself

Finally, he examines the securities side of the deal:

• What kind of 506 offering is it?
• Who can invest?
• What is the preferred return?
• What does cash-on-cash return look like?
• What is the IRR?
• What are the best-case and worst-case outcomes?
• What is the expected hold period?

His view is that every deal should be stress tested.

Why every deal needs a stress test

Boyd illustrates this with a painful but useful example.

In March 2020, he had two duplexes under contract in Tennessee and was approaching closing. Then the governor declared a statewide emergency and shut the state down. The deal died.

That is real investing.

Sometimes a deal fails because of something you missed. Other times it fails because circumstances changed in ways nobody could control. The lesson is not that stress testing predicts every black swan. It is that investors need to understand how much room for error they have before they commit capital.

That means evaluating downside scenarios honestly, not just hoping the base case plays out.

Sometimes the best opportunities are outside traditional real estate

Boyd shares another example that shows how he thinks about opportunities more broadly.

A client and friend of his launched a restoration company, the kind of business that handles water damage and storm-related repair work similar to what firms like Servpro do. Boyd invested because he trusted the operator, but he still stress tested the deal.

What he found was compelling: even under a weak scenario, he expected to get his money back in about three years.

The actual results were better. The business reportedly did around $2.4 million in revenue in one year, and Boyd says investors received back all of their original capital in roughly two years. At that point, future distributions were essentially profit.

He also points out the strategic appeal:

• Insurance companies often pay for the work
• The company may have opportunities to expand geographically
• Because it is veteran-owned, government contracting could become a meaningful path

It is not a retirement-by-itself investment in his telling, but it is a solid income stream. And that, again, fits his larger philosophy of stacking multiple streams of income over time.

How the book came together: from FAQ to published guide

Boyd’s book grew out of repetition.

Clients kept asking the same real estate questions over and over, so he began writing down answers in a simple FAQ document. That one-page FAQ eventually grew to about 10 pages. Then, after writing two articles per month for a podcast over the course of a year, he had a pile of written material that naturally started to organize itself into chapters.

The outline reached 55 pages. At that point, a book was the obvious next step.

The result is Replace Your Income: A Lawyer’s Guide to Finding, Funding, and Managing Your Real Estate.

What the book covers

According to Boyd, the book walks through topics such as:

• Short-term rentals
• Long-term rentals
• Single-family and multifamily real estate
• Cost segregation studies
• Bonus depreciation
• How depreciation offsets income
• Passive versus active activity
• Real estate professional status
• Finding and funding deals
• Managing real estate investments

It is intended to answer many of the foundational questions people ask before they ever need to book one-on-one time with an attorney.

Boyd even jokes that for someone who just wants to learn about real estate, buying the $20 book is a lot cheaper than booking an hour with him.

The bigger lesson for accredited investors

There are a few big takeaways from this conversation that apply well beyond any one asset class or structure.

• Tax planning is proactive. If you wait until year-end, many of your best options may already be gone.
• Structure matters. The right LLC or fund structure can preserve flexibility, improve protection, and reduce future friction.
• Education matters. Investors should know how money, control, and tax consequences actually flow through a deal.
• Stress testing matters. Good deals should survive more than a rosy underwriting model.
• Multiple income streams matter. The path away from burnout usually is not one giant win. It is a series of well-structured, compounding moves.

For accredited investors who are already participating in syndications, private funds, or active real estate projects, that combination of legal structure, tax efficiency, and disciplined due diligence can make a major difference over time.

The point is not simply to invest more. It is to invest in a way that gives your capital more durability, more protection, and more room to compound.

Where to find Brian Boyd

Brian Boyd can be found on Instagram, TikTok, Facebook, and YouTube under Brian T. Boyd or Brian Boyd Tax Lawyer. He is also available through Thompson Burton in Franklin, Tennessee.

His book, Replace Your Income: A Lawyer’s Guide to Finding, Funding, and Managing Your Real Estate, is available through Amazon and Barnes & Noble.