Tax Planning Services

Keep More of What You Earn

Strategic tax planning for business owners and high-income individuals. Entity selection, §199A optimization, retirement stacking, real estate, and family wealth strategies.

Tax Planning for Business Owners and High-Income Individuals

Most people only think about taxes once a year, when their CPA hands them a return to sign. By then, the tax bill is already set. Nothing you do in April changes what you owe for the year that just ended.

Real tax planning happens before December 31. It happens when you choose your entity structure, when you decide how much salary to take, when you fund retirement plans, when you buy or sell real estate, when you make charitable contributions. Every one of those decisions has a tax outcome. Most of them are reversible if you catch them in time. Almost none of them are reversible after the year closes.

After more than three decades of working in federal tax law, I have seen what separates the business owners who keep more of what they earn from the ones who do not. It is not income level. It is whether they treat tax planning as a year-round discipline or an April panic.

Here is what real tax planning for business owners and high-income individuals actually looks like.

Entity Structure: The Decision That Locks In Everything Else

The entity structure you choose for your business determines what tax strategies are available to you for as long as that entity exists. Get it wrong and you lock yourself out of significant savings. Get it right and you create the foundation for every other planning move.

Sole Proprietorship (Schedule C)

The default for a single owner with no entity. Simple but tax-inefficient. All net business income is subject to self-employment tax (15.3% on the first $168,600 in 2024, plus 2.9% Medicare above that). No employer-employee distinction. No qualified retirement plan options at the same scale as other structures.

Single-Member LLC

Same tax treatment as sole proprietorship by default (disregarded entity). Provides legal liability protection but no automatic tax benefits. Can elect S-corp taxation if it makes sense.

S Corporation (or LLC taxed as S-corp)

The most common choice for established small business owners. Allows owner-employees to split income between salary (subject to payroll tax) and distributions (not subject to self-employment tax). This single feature can save thousands per year for owners netting $80,000 and up. Requires running formal payroll and paying yourself a "reasonable compensation" salary under IRS guidelines.

Partnership

For multi-owner businesses without S-corp election. Different distribution rules. Can be more flexible than S-corp on allocations but less tax-efficient on self-employment.

C Corporation

Generally not optimal for closely-held businesses because of double taxation, but specific situations (Section 1202 Qualified Small Business Stock, certain industries, multinational operations) can favor C-corp.

The entity choice is not "set it and forget it." Reviewing entity structure every 3-5 years, especially when income materially changes, often surfaces meaningful tax savings.

S Corporation Reasonable Compensation: The IRS Audit Target

If you elect S-corp taxation, you have to pay yourself a "reasonable" salary as an owner-employee under Internal Revenue Code Section 1366. Too low and the IRS reclassifies your distributions as wages, triggering back payroll tax, penalties, and interest. Too high and you defeat the purpose of the election.

The IRS does not publish specific salary tables for S-corp reasonable compensation. They look at:

  • •What comparable W-2 employees earn in your industry and region
  • •Your role and time commitment in the business
  • •The profitability of the business
  • •Industry standards from RCReports, BizComps, and similar databases

A well-structured S-corp owner draws a defensible salary, documents the basis for the salary determination, and takes the rest as distribution. The savings can be substantial. A business netting $200,000 with a $90,000 salary saves approximately $13,500 in self-employment tax compared to taking the full $200,000 as Schedule C income.

The IRS audits S-corp reasonable compensation aggressively. Documentation is everything.

§199A Qualified Business Income Deduction

The 2017 Tax Cuts and Jobs Act created the Section 199A deduction, allowing pass-through business owners (sole proprietors, partners, S-corp shareholders, LLC members) to deduct up to 20% of qualified business income.

The mechanics are complex. The deduction has income thresholds (currently around $383,900 for joint filers, around $191,950 for single filers as of 2024, adjusted annually). Above the thresholds, "specified service trade or business" (SSTB) limitations kick in, and the W-2 wages / unadjusted basis in qualified property tests apply.

For owners near the income thresholds, planning specifically to preserve the §199A deduction matters. Strategies include:

  • •Timing income recognition (deferring or accelerating)
  • •Increasing W-2 wages paid by the business
  • •Investing in qualified property that adds to UBIA basis
  • •Strategic retirement contributions to reduce taxable income below thresholds
  • •Entity election changes if the business is in an SSTB category

The §199A deduction is scheduled to sunset at the end of 2025 under current law, though political pressure to extend it is significant. Planning that assumes §199A continues should be hedged against the possibility it does not.

Retirement Plan Stacking for High-Income Earners

Most business owners use a Solo 401(k) or SEP-IRA without realizing they can stack multiple plans for dramatically higher contribution limits.

Solo 401(k)

Available to owners with no employees. Allows employee contributions (up to $23,000 in 2024, $30,500 if age 50+) plus employer contributions (up to 25% of compensation), capped at total $69,000 ($76,500 if age 50+).

SEP-IRA

Simpler but lower limits than Solo 401(k) for most owners. Calculations differ.

Defined Benefit Plan

For high-income owners who can commit to consistent contributions, defined benefit plans allow contributions in the $200,000+ range annually. Best suited for owners over age 50 with stable, high income.

Cash Balance Plan

A hybrid that combines defined benefit features with individual account balances. Can be paired with a 401(k) for stacked contributions exceeding $300,000 annually for older high-income owners.

For business owners with net income above $250,000 and over age 50, the combination of a 401(k) plus cash balance plan often allows total contributions of $250,000-$400,000+ per year. The current-year tax deduction at marginal rates of 37% federal plus state taxes can save $100,000+ in current taxes while building substantial retirement assets.

This stacked-plan strategy is one of the highest-leverage tax planning moves available to high-income business owners. It also requires careful actuarial design and ongoing compliance with ERISA and IRS rules. Not DIY.

Real Estate Strategies for Active Business Owners

Real estate ownership creates specific tax planning opportunities that pure W-2 earners do not have.

Cost Segregation Studies

For commercial property or larger investment properties, a cost segregation study reclassifies portions of the property from 27.5-year or 39-year depreciation into shorter schedules (5, 7, or 15-year). This accelerates depreciation deductions significantly, especially in the first year if combined with bonus depreciation under Section 168(k).

Real Estate Professional Status

Under Internal Revenue Code Section 469(c)(7), taxpayers who qualify as real estate professionals can deduct rental real estate losses against ordinary income without the $25,000 passive loss limitation. The qualification requires more than 750 hours per year in real property trades and more than half of personal services time in real property activities. Documentation is critical.

1031 Like-Kind Exchanges

Under Section 1031, real estate investors can defer capital gains tax by exchanging one investment property for another. The mechanics (45-day identification, 180-day closing, qualified intermediary requirements) are strict but the deferral is powerful.

Augusta Rule (Section 280A(g))

Allows business owners to rent their personal residence to their business for up to 14 days per year without recognizing the rental income, while the business deducts the rent as an ordinary business expense. Requires fair-market rent documentation and genuine business use.

Short-Term Rental Loophole

Properties with average rental periods of 7 days or less are not subject to passive activity rules, allowing material participation losses to offset ordinary income for many active business owners.

Charitable Strategies for High Earners

For taxpayers with substantial charitable inclinations, planning structure matters more than the gift amount.

Donor-Advised Funds (DAFs)

Allow you to take an immediate charitable deduction in a high-income year while distributing the actual grants to charities over time. Useful for bunching contributions in years with unusually high income.

Qualified Charitable Distributions (QCDs)

For taxpayers age 70½ or older, direct transfers from IRAs to qualified charities (up to $105,000 in 2024) satisfy required minimum distributions without including the amount in taxable income.

Charitable Remainder Trusts (CRTs)

Provide an income stream to the taxpayer (or beneficiaries) for a term of years or lifetime, with the remainder passing to a charity. Generates a current-year charitable deduction and defers capital gains on appreciated assets contributed to the trust.

Charitable Lead Trusts (CLTs)

The mirror image of CRTs. Income goes to charity for a term, remainder to family. Useful for transferring wealth to heirs with reduced gift/estate tax.

Appreciated Securities

Donating appreciated stock directly to charity (rather than selling and donating cash) avoids capital gains tax on the appreciation while generating a full fair-market-value deduction.

The right charitable structure depends on income level, charitable intent, family situation, and time horizon.

§1202 Qualified Small Business Stock

For founders and early investors in C-corporations meeting specific requirements, Internal Revenue Code Section 1202 allows exclusion of up to $10 million (or 10x basis, whichever is greater) of gain on the sale of Qualified Small Business Stock (QSBS) held for more than five years.

The requirements are detailed. The corporation must be a domestic C-corporation. Total gross assets at the time of stock issuance must not exceed $50 million. The corporation must be engaged in a qualified trade or business (excluding certain service businesses, real estate, hotels, and similar activities). The stock must have been issued directly by the corporation, not purchased on a secondary market.

For founders considering entity structure at startup, the QSBS opportunity is one of the most significant reasons to consider C-corp despite double taxation drawbacks. The 5-year holding period and complex eligibility rules make this a planning topic that has to be addressed at formation, not after the fact.

Roth Conversion Timing

Traditional retirement accounts (401(k), traditional IRA) provide upfront tax deductions but require taxable distributions in retirement. Roth accounts work in reverse: no upfront deduction, tax-free distributions in retirement.

Strategic Roth conversions involve voluntarily converting traditional retirement balances to Roth during years when your marginal tax rate is unusually low. Common triggers:

  • •The gap year between retirement and Social Security / required minimum distributions
  • •Years with business losses
  • •Years with extraordinary itemized deductions
  • •Years before tax rate increases (such as the scheduled TCJA sunset)

Conversions are taxable in the year converted. The right amount to convert depends on filling up lower tax brackets without triggering higher brackets, the Medicare IRMAA surcharge, or higher capital gains rate thresholds.

For taxpayers age 60-70 with substantial traditional retirement balances, multi-year Roth conversion ladders often save six figures over a retirement lifetime.

The Estate Planning Intersection

Tax planning during life and estate planning at death are deeply connected. Decisions made now affect what happens later.

The federal estate tax exemption is currently around $13.6 million per person ($27.2 million per married couple) as of 2024, scheduled to revert to roughly $7 million per person at the end of 2025 unless Congress acts. Taxpayers with potential estates near or above the post-sunset thresholds have a planning window now.

Coordinating tax planning with estate planning involves:

  • •Gifting strategies that use the annual exclusion ($18,000 per recipient in 2024) and lifetime exemption
  • •Family Limited Partnerships and other discount valuation structures
  • •Spousal Lifetime Access Trusts (SLATs) to lock in the current exemption
  • •Grantor Retained Annuity Trusts (GRATs) for transferring appreciation
  • •Charitable strategies that combine income tax savings with estate tax planning

Estate planning attorneys handle the documents. Tax attorneys handle the tax positions those documents create. The two have to be coordinated.

How Our Tax Planning Engagements Work

For high-income individuals and business owners, tax planning typically follows a structured process.

1

Assessment

Review of current entity structure, recent tax returns, retirement plan structures, asset holdings, business operations, and family situation. Identify the planning opportunities most relevant to your specific situation.

2

Strategy Development

Build a specific planning plan addressing the identified opportunities. Quantify the expected tax savings and the costs of implementation.

3

Implementation

Execute the strategies. This often involves coordinating with your existing CPA, financial advisor, estate planning attorney, and other professionals.

4

Annual Review

Tax law changes. Your situation changes. Annual review ensures the planning continues to fit.

Tax planning is not a one-time product. It is a year-round discipline that compounds over time. The business owner who started planning ten years ago is in a meaningfully different financial position than one who started this year, even with similar incomes.

Why Tax Planning Is Different From Tax Preparation

Most tax professionals are tax preparers. They take last year's transactions and put them on the right forms. That work is necessary but it is not tax planning.

Tax planning is forward-looking. It asks: given what we know about your situation now, what should you do this year and the next five years to minimize total lifetime tax burden while achieving your other financial goals?

A good tax planner works closely with your CPA. A good CPA prepares returns that reflect the planning decisions. They are different roles requiring different skills. Some firms do both. Many do not.

The Law Offices of Darrin T. Mish focuses on tax controversy and tax planning. We do not prepare tax returns. We coordinate with your existing CPA to ensure that the strategies we develop get implemented correctly on the returns they file.

Is tax planning worth it for me?

If you are a business owner or high-income individual and you are not actively planning your taxes year-round, you are leaving money on the table. Sometimes a little. Often a lot. The first conversation is free. We can assess your current situation, identify the highest-leverage opportunities specific to you, and tell you honestly whether the engagement makes financial sense.

Related Videos

What the IRS Will Scrutinize in 2026 (Business Owners Must Prepare Now)

5:13

Read the transcript

Most small business owners don't get in trouble with the IRS because they're bad people. They get into trouble because they only think about taxes once a year, and that's usually just a few days before the [music] deadline. Today, I'm going to show you exactly how to stay ahead of the IRS in 2026 with year- round tax planning strategies that my most successful business clients follow. Because when you get this right, you don't just reduce your taxes, you protect your business, your cash flow, and your peace of mind.

Why do small business owners face the biggest IRS risks? Well, it's because business owners frankly juggle dozens of responsibilities and taxes often fall to the bottom of the list. They often operate with incomplete records, rough estimates, or do-it-yourself bookkeeping. IRS returns [music] have to tell a story that makes sense, and messy books trigger scrutiny. IRS audit rates for business owners are higher because their revenue fluctuates. Deductions are larger.

Expenses can look estimated. Cash flow practices aren't always documented, and often entity selection is unsophisticated. [music] Most business owners are great at what they do, but terrible at keeping up with the IRS. The truth is, year- round tax planning keeps you out of crisis mode. Most owners do taxes backwards. They deal with everything in April, but real tax planning happens monthly and quarterly. Fixing tax problems later is always more expensive than preventing them.

Let me pro provide you a few examples of year- round habits. You need to keep expenses documented monthly. You need to avoid round number estimates. You need to keep business and personal accounts separate, so no co-mingling. You can tell that's a hot button with me. You need to track your business miles, your meals, your subcontractors, and equipment purchases. And really, you should be reviewing your taxes on a quarterly basis. [music] The IRS has become much more data driven lately.

They already know more about you than you think. They have your W2s, your 1099s, your mortgage interest, and records from your payment platforms such as Zel, Venmo, and PayPal. In 2026, with new AI tools being ruled out internally, they're going to match this data even faster. Now, if the thought of keeping up with IRS rules all year long already feels overwhelming, I get it. And that's exactly why I created something called the IRS Battle Guide.

It's a long- form, do-it-yourself breakdown of the real IRS processes, the traps that business owners fall into, and the exact mistakes that turn a small issue into a six-figure tax problem. Most people download it and instantly realize two things. It's a lot more complicated than they thought, and they probably shouldn't try fighting the IRS alone. You can grab it for free. I'll leave the link below. Let's talk about key strategies to stay ahead for 2026.

You need to know the difference between an allowable deduction and a deduction that you shouldn't take. Many businesses pay more because they leave legitimate deductions on the table because they're afraid to take them. The key to winning the deduction battle should it come down to an audit is the quality of your documentation. So, keep your records in a manner that you can easily store and track them.

No more round number expenses. When I'm reviewing a tax return and I see your tools expenditure is exactly $15,000, I know that that's an estimate. If I know it's an estimate, what are the odds that the IRS doesn't know it's an estimate? You need to keep receipts and paid invoices even when you pay online. Just print out the receipt and store it so you can find it in the future if you need to.

You need to use one bookkeeping software or accountant, not five. I want to help you get ahead of the new 2026 tax law changes. The one big beautiful bill goes into effect in 2026, and we're still finding good stuff in this new law. The state and local tax limit, also known as salt, increased from 10,000 to $40,000. Purchases of Americanmade automobiles will have an interest deduction. Opportunity funds have been made permanent, and all taxpayers can use them to kill capital gains.

There's no taxes on tips and there's other changes to deduction limits for business owners such as retirement and healthcare related. Once the IRS technology upgrades finally hit, then there's going to be faster matching and faster enforcement of tax liabilities. There's going to be a smaller margin for bookkeeper [music] mistakes, late filings, or sloppy records. Changes are coming and business owners who prepare early save the most. If you thought the IRS has been bad in the past, now they have fewer employees who have much less training experience, [music] who will be empowered with AI and other software tools to collect.

That doesn't sound like a fun recipe to me. You need to act early before the IRS contacts you. The earlier a business owner gets help, the more options they have. Waiting removes leverage. Once a garnishment, levy, lean, or audit hits, it becomes 10 times harder to negotiate. Now, all of this gives you a clear picture of how to stay ahead of the IRS in 2026. But there's another issue just as important that most business owners overlook, who you rely on when something actually goes wrong.

Because a CPA and a tax attorney solve completely different problems, and choosing the wrong one can cost you thousands. [music] So, before you file another return or respond to an IRS letter, make sure to watch this next video. [music] It'll show you exactly who to call, when to call them, and how to protect yourself before things escalate.

The Real Cost of Waiting Until April To Think About Taxes

4:50

Read the transcript

Tax planning isn't just about saving money. It's about control. If your accountant only talks to you once a year, you're not really doing tax planning. You're just reporting what's already happened. I call that recording history. I like to say that tax planners create history. And here's what's what most people miss about a time you're filing a return. Most of your real options are already gone. Most business owners think that tax planning happens in April because that's when the pressure shows up.

Deadlines hit, people start scrambling, digging through bank statements, texting their bookkeeper, hoping they can clean it up fast enough to file. But April is when the planning window has already closed. In this video, I want to explain why. Now. Not April, not later, not earlier, but now is when tax planning actually matters and why waiting quietly cost you money you'll never get back. The difference between tax prep and tax planning is that tax preparation is reporting the past.

You gather your documents, you add up the numbers, and you tell us what happened last year. By definition, it's a backward looking tax. Planning is shaping what happens next. It's making decisions now that change your tax outcome before the year closes. These are fundamentally different activities, but most people experience them as if they're the same thing because they only talked to their accountant once a year at filing time when it's too late to do anything but report.

By the time you're sitting down to file, most meaningful decisions have already been made or missed. And to do structure that needed to be addressed before the tax year started. S-corp election. There's a deadline and it's not an April. Retirement contributions. Some have cut offs well before filing. Timing of income and expenses. You can't move revenue you've already collected into next year. The tax code rewards planning.

It doesn't reward scrambling, and the people who pay the most aren't necessarily earning the most. They're the ones who made decisions by default instead of by design. What I hear from business owners all the time is I CPA said we'd figure it out at tax time. I didn't know I could have done anything differently. I just paid whatever they said I owed. These aren't bad business owners.

They're busy people who assume someone was looking out for them. But reactive accounting isn't the same as proactive planning. And most accountants are set up to prepare returns, not to advise in advance. The quiet cost of waiting is when you wait until filing season. You lose leverage not with the IRS, but with your own finances. You lose flexibility on entity elections. You lose timing options on income and deductions.

You lose the ability to fund retirement accounts at optimal levels. You lose the chance to restructure compensation in ways that reduce self-employment tax. None of this is dramatic. It's just quietly adds up year after year until you realize you've been overpaying for a decade or more. What is tax planning actually look like? From my perspective as a tax attorney, planning isn't about chasing deductions or finding loopholes.

It's about understanding your full financial picture and making intentional decisions before the tax year closes. That means looking at your entity structure and asking whether it still makes sense. It means reviewing how you pay yourself and whether that structure is tax efficient. It means timing, major purchases, retirement contributions, and income recognition strategically. It also means increasing compliance, getting your books clean, your records organized, and your filings accurate.

Good planning doesn't create problems down the road. It prevents them. So who should be thinking about this now? I would say business owners with revenue that fluctuates. Higher income individuals with multiple income streams, and anyone whose financial situation has changed significantly this year. New business. Sale of assets. Major growth. Anyone who's never had a real tax planning conversation is just had a filing appointment. If you've been filing a returns but never actually planning, you're likely leaving money on the table.

Not because you're doing anything wrong, but because no one showed you what else is possible. This isn't about tricks or gimmicks. Tax planning isn't about being aggressive. It's not about audit risk or gray areas. It's about using the tax code the way it was designed with foresight, not hindsight. The people who benefit most aren't in claiming the system. They're just making decisions early enough that they still have choices.

Why now? Not January, not April? Now? Because the window closes quietly. No one sends you a reminder that your S Corp election deadline passed. No one tells you that you missed the optimal time to fund your step, IRA. The opportunities just expire, and you don't find out until you're sitting with your accountant looking at a number you don't like. If you've been meaning to get serious about tax planning but haven't started.

The goal isn't panic. It's clarity. You can call my office toll free at 888. Get Mish to book a call. That's (888) 438-6474. That conversation is about understanding where you stand. What options are still available this year and whether working together makes sense for your situation?

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