Tax Planning to Extract Cash from existing Business Entities

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Effective tax planning can create meaningful benefits for businesses of all sizes.

You don’t need to be a multi-million-dollar operation to take advantage of smart tax strategies. In fact, smaller, closely held businesses often see significant gains simply by improving bookkeeping, restructuring entities, or implementing thoughtful long-term planning.

  • Good tax planning allows us to predict a tax return’s outcome before preparation.
  • It gives us some control over how much tax is due.
  • It addresses short-term needs, like reducing tax bills.
  • It covers intermediate goals, such as exploring capital gains treatment on business sales.
  • It looks ahead to long-term strategies, including:
    • Transferring the business to the next generation, or
    • Selling the business outright.

Financial Planning

  • We provide advice only—we do not sell financial products, ensuring no conflicts of interest from commissions or kickbacks.
  • Our goal is to understand and support your financial objectives.
  • Our expertise includes:
    • Retirement planning
    • Personal wealth management (ensuring you don’t outlive your resources)
    • Family wealth management (giving your children a financial boost)
    • Multigenerational wealth management

Multigenerational Wealth Management

  • As a relatively new area for our firm, we’ve invested in legal expertise and established relationships with major financial firms. We’re actively learning the intricacies of this domain, and the insights have been valuable.

Specifics

Entity Formation and Growth
When a new business is formed, making sound decisions upfront is important. Historically, this was uncommon, but recently, our expertise in long-term tax planning has gained traction, leading to our involvement in mergers and acquisitions — a sector we thoroughly enjoy.

In the last decade, we have honed a method for carving out goodwill tied to intellectual property (IP). At the time of entity formation, it’s simple:

  • Form an operating LLC to handle customers, revenue, and expenses.
  • Form a separate property LLC to hold assets and IP rights.

There are no downsides to having multiple entities to operate one business. In fact, it provides liability protection, improves insurability, and eases transferability. In certain cases, more LLCs may be required to manage family or multigenerational wealth.

Managing Multiple Entities
For example, in the transportation business, a property LLC would typically own trucks, trailers, and equipment, which the operating LLC would lease. The same principle applies to intellectual property, where the operating LLC would pay royalties to the property LLC, establishing a valuable property right.

Growth Phase Structuring
Recently, a client in a similar industry sought our advice regarding a multi-location operation. With the profitability they’ve maintained, we helped them project tax savings of $8 to $10 million over the next five years.

In another similar case, we expect to save a multi-partner client in Georgia $5 to $8 million in taxes over five years. Both cases involve expansion plans designed for high tax leverage.

Extracting Wealth from Mature Businesses

Not all tax planning starts at the expansion stage. For established businesses, restructuring can still unlock significant value. Most new businesses aren’t structured ideally from the start. Carving out intellectual property later allows us to unlock the tax savings I mentioned. Recently, we have done this for a mature business in the transportation sector with excellent results.

While the examples above involve businesses with significant profitability, you don’t need to be a multi-million-dollar operation to benefit from smart tax planning. In fact, many of the most impactful strategies—like entity structuring, IP separation, and long-term planning—are scalable and beneficial even for businesses with more modest revenues. The key is profitability, consistency, and clean financial records.

Factors for Success
To achieve these outcomes, several key factors are essential:

  • Taxpayer Integrity: This may seem obvious, but integrity is critical to long-term success.
  • Business Profitability: Profits must be substantial and predictable—tax planning only works if you’re paying taxes.
  • Quality of Books and Records: Your internal bookkeeping must be clean and understandable, with both management and outside parties, such as CPAs and the IRS, having confidence in your records.
  • Communication: Clear, consistent communication is the foundation of effective tax planning.

Long-Term Tax Planning

A good tax plan is rarely short-term. Typically, it takes 3 to 5 years, or even up to a decade, to develop a solid plan. Quick fixes—such as buying assets to claim depreciation—are often just temporary deferrals that can cause issues as the deferrals expire.

Our Approach to Tax Planning

Our firm has earned a reputation for solid, long-term tax and financial planning. We work with clients across 35 states and 25 foreign countries, staying connected through email, phone, and MS Teams.

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Charitable Giving Under the Big Beautiful Bill (OBBB)

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What’s changed, what hasn’t, and
what it means for your 2026–2027 tax planning.

The Big Beautiful Bill (OBBB) updated the charitable giving rules—but not in sweeping ways. Whether you give a little or give six figures, there’s something here for you. Below is a quick-scan guide by income level, with special notes on Donor-Advised Funds (DAFs) and Qualified Charitable Distributions (QCDs).

  1. Non-Itemizers

Starting in 2026, you can take a new above-the-line deduction for cash gifts to public charities—even if you don’t itemize:

  • $1,000 for single filers
  • $2,000 for married filing jointly

Doesn’t qualify: Gifts to Donor Advised Funds (DAFs), private foundations, or non-cash contributions. These limits are fixed and not indexed for inflation.

I will discuss Donor Advised Funds more in this newsletter.

Bottom line: Keep giving—now you can also shave up to $2,000 off taxable income.

  1. Moderate-Income Itemizers (AGI under $250,000)

AGI (Adjusted Gross Income) is the IRS’s version of income. It’s used for taxes, student aid, insurance, loans, and more—but it’s not always a full or accurate picture of your finances. The AGI acronym pops up everywhere.

Under OBBB, a new “floor” applies: the first 0.5% of your AGI in charitable giving gets ignored. Example: With $200,000 AGI, the first $1,000 of donations gets no deduction.

  • Cash gifts still deductible up to 60% of AGI
  • Appreciated assets deductible up to 30%

Strategy tip: If the floor or standard deduction wipes out your deduction, consider bunching two years of giving into one.

  1. Upper-Middle Itemizers (AGI $250,000–$750,000)

Same 0.5% AGI floor, just higher dollar impact. A $500,000 AGI household loses the first $2,500 of charitable deductions.

  • 60%/30% caps still apply
  • Phaseouts start to creep in
  • Timing large gifts around stock sales or business income can help recover lost deductions
  1. High-Income Donors (AGI over $750,000)

The rules get sharper as income climbs:

  • 0.5% floor still applies (AGI $1.2M → $6,000 ignored)
  • Cash and appreciated asset caps unchanged (60%/30%)
  • New wrinkle: deductions capped at 35% tax savings, even if you’re in the 37% bracket

A $100,000 gift saves $35,000 in tax, not $37,000.

Strategy tip: Accelerate large gifts into 2025 to lock in the full 37% benefit.

🏛 Donor-Advised Funds (DAFs): Still Useful—With Limits

Many clients use a DAF at the National Christian Foundation or similar. The core benefits haven’t changed:

  • Immediate deduction
  • Flexible grant timing
  • Easy record-keeping

What’s new under OBBB:

  • Above-the-line deduction doesn’t apply to DAF gifts
  • If you contribute to a DAF, you’re excluded from the $1,000/$2,000 deduction
  • Treasury has been instructed to propose new rules for large DAFs and big contributions (expected in 2026)

Takeaways:

  • Moderate donors can still use DAFs to bunch gifts into one year and spread grants out
  • Higher earners should time DAF contributions to high-income years
  • Stay flexible—we’ll revisit this as new rules emerge

🏆 Qualified Charitable Distributions (QCDs): Still the MVP

QCDs remain untouched—and still excellent:

  • Available at age 70½+
  • Annual limit: $105,000 in 2024 → $108,000 in 2025 (indexed going forward)
  • Counts toward your RMD, and bypasses AGI completely

Also available: a one-time QCD (up to $54,000 in 2025) into a charitable remainder trust or charitable gift annuity

QCDs are still unbeatable for retirees who don’t itemize or who want to keep AGI low to avoid Medicare surcharges and Social Security taxation.

The Big Picture

The tools you know—DAFs, QCDs, direct giving—are still here. But timing now matters more. The AGI floor, the 35% deduction cap, and upcoming DAF regulations all call for smarter planning.

Let’s map out your 2025–2026 giving plan before December 31.


Steve Richardson, CPA
stever@srcocpa.com

General information only. Not personalized tax advice. Let’s talk before acting.

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