Winning the
Tax Game
The Tax Strategy Workbook + Playbook
Most people learn how to make money. Very few are taught how to structure it, keep more of it, protect what they build, and transfer it intentionally. Winning the Tax Game is about understanding the rules that affect business owners, investors, families, and the assets they create.
You do not need every strategy in this book. You need the right strategies for your facts, installed in the right structure, documented the right way.
As you work through, flag:
Educational Disclaimer
This workbook is educational and illustrative. It is not individualized tax, legal, accounting, investment, or financial advice and does not create a professional relationship. Eligibility depends on your facts, entity structure, documentation, state, timing, and current law. Confirm implementation with qualified professionals.
Orientation
Follow the Workshop
Use the pages Rondi references live
Run Your Numbers
Use the WTTG Tax Calculator when prompted
Circle the Gaps
Note anything you are unsure about
Build a Shortlist
Pick the few moves worth deeper analysis
Implement
A strategy only works when structure, timing, and docs are correct
Part I
Understand the Game
Rules · Tax Snapshot · Follow the Money
"The return is the scoreboard. The decisions happen before the score is posted."
The Tax Code Is a Rulebook
Most people experience taxes as a bill. Owners have to learn to see taxes as the result of choices made throughout the year. The objective is not to hide income or invent deductions — it is to understand which legal choices are available before the year is over, and to document them correctly.
✗ The Default Game
✦ The Owner / Planning Game
"The goal is not to avoid tax. The goal is to stop volunteering for extra tax."
The PremiseYou Don't Have a Tax Problem. You Have a Structure Problem.
Tax is downstream from the decisions above it. If you only look at the bottom box in April, you are looking at the game after most of the moves have already been made.
Your Current Tax Snapshot
Estimates are fine. The goal is to get the real conversation onto the page.
What bothers you most?
Follow the Money
Draw every box your money passes through before it reaches you. List every entity, holding company, rental, trust, or asset company that changes the path. Where do you think the first leak happens?
The leak is most likely in:
Part II
Build the Structure
Entities · Ownership · Compensation · QBI
"Before you chase deductions, understand what owns what — and why."
Draw Your Current Corporate Structure
Put yourself and your family at the top. Add every business, entity, trust, rental, valuable asset, or holding company you currently use. Describe the ownership lines. Circle anything you are not sure belongs where it is.
Structure Principle — What Should Own What?
A useful structure separates operating risk from valuable assets. Does every box have a job? Is operating risk separated from valuable assets? Is tax treatment being confused with legal structure?
You / Family
Who ultimately owns or controls the plan
Holding / Ownership
Where ownership may be coordinated
Operating Business
Where day-to-day business risk lives
Real Estate / IP / Other
What may deserve separation from operations
LLC. S Corp. C Corp. Different Jobs. Different Conversations.
The trap: treating every entity label like it solves the same problem. Entity selection should follow the economics, risk, ownership, state law, and tax facts.
LLC
A legal entity structure. Tax treatment depends on elections and ownership.
S Corp
A tax election that can change how qualifying business income and owner compensation are treated.
C Corp
A separate taxpaying corporation with different planning opportunities and tradeoffs.
Strategy
S Corporation Planning
An S corporation can create planning opportunities around owner compensation and distributions. The value is not in the label alone — it is in the complete system around it.
System Checklist:
Strategy
Reasonable Compensation
The question is not "How low can I make my salary?" It is what the work would reasonably cost based on the owner's role, duties, time, experience, and the business itself.
A defensible number beats a cute number.
Rondi's Rule of Thumb
A defensible number is based on what the market would pay for the work, supported by documented analysis — not a number chosen primarily to minimize self-employment tax.
Strategy
QBI / Section 199A
What It Is
For qualifying business income, current tax law may provide a deduction tied to qualified business income. Whether it applies — and how much — depends on the facts.
Who May Benefit
Owners of qualifying pass-through businesses, subject to income, industry, wage/property, structure, and current-law rules.
Why It Matters
QBI can change the after-tax economics of compensation, entity choice, and income timing.
Guardrails
Do not assume everyone receives 20%. Income limitations, specified-service rules, wages, property, structure, and current law matter.
My Workbook Question
Was QBI intentionally modeled — or simply calculated after the fact?
Part III
Find the Strategies
Deductions · Credits · Reimbursements · Timing
"Some are foundational. Some are situational. Some are advanced. The point is to know they exist."
Strategy
Accountable Plan
What It Is
A written reimbursement arrangement that can allow a business to reimburse legitimate business use of personal resources — mileage, home office costs, phone, equipment, and other substantiated expenses.
Who May Benefit
Owners who regularly pay legitimate business expenses personally.
Why It Matters
It can turn expenses you are already paying into clean business reimbursements when the rules and records are followed.
Guardrails
Written plan, business purpose, timely substantiation, return of excess reimbursements where required, and consistent records matter.
My Workbook Question
What am I paying personally today that may belong in the business?
Strategy
The Augusta Rule
What It Is
A planning concept involving short-term rental of a personal residence for legitimate business use when the legal requirements are satisfied.
Who May Benefit
Owners who have real company meetings, planning days, or events and a residence that can legitimately host them.
Why It Matters
It may create a deductible business expense while qualifying rental income may receive different treatment under the applicable rules.
Guardrails
Business purpose, meeting records, fair market rental rate, payment, dates, and current tax rules all matter. This is not a magic "14-day write-off."
My Workbook Question
What legitimate company meetings or events do we already hold?
Strategy
Hiring Your Kids
What It Is
A business may hire a child for legitimate work and pay reasonable compensation for services actually performed.
Who May Benefit
Families with children who can genuinely perform age-appropriate business work.
Why It Matters
It can shift real business work into documented family employment and may create planning opportunities depending on the business and tax facts.
Guardrails
The work must be real. Pay must be reasonable. Duties, hours, records, payroll treatment, and entity type matter.
My Workbook Question
What real work could my child perform for the business?
Kids on Payroll: Make It Real
Do not start with the deduction. Start with the job. The facts must match the job.
| Child Name / Age | Job Title | Hours / Wk | Pay | How Documented? |
|---|---|---|---|---|
Strategy
Employing Your Spouse
What It Is
A spouse who performs bona fide work for the business may be employed and compensated like any other legitimate employee.
Who May Benefit
Owners whose spouse already performs real operational, administrative, marketing, bookkeeping, management, or other work.
Why It Matters
Proper employment can coordinate compensation, benefits, retirement, reimbursements, and family planning depending on the structure.
Guardrails
Real job, reasonable compensation, payroll treatment, duties, benefits, and records are required.
My Workbook Question
What work does my spouse already do that is not formally documented?
Strategy
Family Medical / HRA Planning
What It Is
Certain business structures may support employer reimbursement arrangements for qualifying medical expenses when the legal and employment requirements are met.
Who May Benefit
Some owners with bona fide employee-family arrangements and meaningful out-of-pocket medical expenses.
Why It Matters
When available, employer reimbursement can change the tax treatment of expenses the family already pays.
Guardrails
Eligibility is highly structure-dependent. Bona fide employment, entity type, plan documents, nondiscrimination rules, and current law matter.
My Workbook Question
Do we have significant medical costs that are currently paid personally?
Strategy
Home Office
What It Is
Tax rules may allow eligible business use of the home to be deducted or reimbursed depending on the owner's structure and facts.
Who May Benefit
Owners with a qualifying space used regularly and appropriately for business.
Why It Matters
It may move legitimate business-use costs from personal spending into a documented business expense or reimbursement.
Guardrails
Exclusive/regular-use concepts, business purpose, calculation method, entity structure, and records matter.
My Workbook Question
What portion of my home is truly used for business?
Strategy
Vehicle Planning
What It Is
Business vehicle costs may be handled using permitted methods based on business use, ownership, timing, and substantiation.
Who May Benefit
Owners who drive materially for legitimate business activity.
Why It Matters
Mileage, actual expenses, depreciation where appropriate, and ownership choices can materially change the treatment.
Guardrails
Business use must be documented. Depreciation has limits and recapture considerations. Buying something you do not need just to get a deduction is not a tax strategy.
My Workbook Question
How many business miles do I actually drive — and how are they documented?
Strategy
Business Travel
What It Is
Ordinary and necessary business travel may create deductible expenses when the trip has a real business purpose and the requirements are satisfied.
Who May Benefit
Owners who travel for customer work, conferences, meetings, training, or other legitimate business reasons.
Why It Matters
Proper planning can distinguish business travel from personal consumption and can improve documentation.
Guardrails
Mixed personal/business travel, family travel, meals, location, timing, and substantiation have special limits and rules.
My Workbook Question
Which trips this year have a real, documentable business purpose?
Strategy
Retirement Strategies
What It Is
Retirement plans can range from simple owner arrangements to 401(k), profit-sharing, and more advanced plan designs including cash balance and defined benefit plans.
Who May Benefit
Profitable owners who want to redirect current cash toward long-term retirement assets and may benefit from deductible or tax-advantaged contributions.
Why It Matters
The right plan can coordinate tax deferral, employee benefits, retention, and long-term wealth accumulation.
Guardrails
Contribution limits, employee coverage, testing, plan costs, timing, and future distributions all matter. No one plan fits every company.
My Workbook Question
Am I using the right retirement plan for the size and profitability of my business?
Strategy
Real Estate Depreciation & Cost Segregation
What It Is
Real estate may generate depreciation deductions; a cost segregation study can accelerate depreciation by identifying shorter-lived assets within a property.
Who May Benefit
Business or investment real estate owners, particularly those with higher-value properties or recent acquisitions and improvements.
Guardrails
Passive activity rules, at-risk rules, depreciation recapture, and professional study requirements apply.
My Notes
Strategies to Explore with Qualified Advisors
Seeing a strategy is not the same as qualifying for it. The goal is to know what questions exist. These are not recommendations — explore with qualified advisors.
Qualified Small Business Stock (QSBS)
Oil & Gas Incentives
Cash Balance Plans
R&D Tax Credits
Opportunity Zones
Charitable Planning
Business Succession
Exit / Liquidity Event Planning
Personal Goodwill / Advanced Estate
Part IV
Run Your Numbers
Calculator · Tax Rate · Cash Left
"Enough theory. Put your own information into the live Winning the Tax Game calculator."
Live Calculator
What Could You Actually Save?
The calculator identifies modeled opportunity based on the assumptions entered. Qualification and implementation still require analysis.
Open the Tax Calculator →Your Numbers
Where Are the Savings Hiding?
Record the modeled categories. Use "potential," "modeled," or "estimated" — not guaranteed savings.
| Category | Modeled Result ($) | Review? |
|---|---|---|
| W-2 Income | ||
| Augusta Rule Savings | ||
| Home Office Savings | ||
| Child Employee Savings | ||
| Business Trip Savings | ||
| Rental Property | ||
| Private Foundation | ||
| Standard Structures | ||
| Advanced Strategies | ||
| Additional Yearly Deduction |
Same Income. Different Structure.
Transfer the comparison that matters most from the live calculator. The number is not the strategy — eligibility, documentation, timing, and implementation still require analysis.
I will redirect retained cash toward:
What Did Your Numbers Reveal?
Part V
Protect More
Entities · Insurance · Titling · Trusts
"Tax savings do not matter much if everything you own can be reached through one bad event."
The Principle — Own Nothing. Control Everything.
The point is to separate valuable assets from operating risk and coordinate ownership, control, titling, insurance, and estate structure.
The Question: If I were sued tomorrow, what could they actually reach?
Build Your Fortress
A good structure has layers. Each layer has a different job. Describe your current setup for each layer.
Operating Business
Where risk happens
Real Estate / Assets / IP
What you may want separated
Holding Structure
Where ownership may live
Insurance
What transfers specific risks
Trust / Estate Layer
Succession and beneficiary planning
Family / Legacy
Who benefits and controls
Insurance + Structure
Insurance complements legal structure. It does not replace it.
Part VI
Give More
Estate · Succession · Family
"Legacy is not paperwork. It is clarity about who gets what, who controls it, and what happens when you are not there."
Estate Planning Is Not Just for Billionaires
| Element | My Status / Question |
|---|---|
| Will — Who receives assets and who handles the estate | |
| Trust — How certain assets may be managed and transferred | |
| Incapacity — Who can act if you cannot | |
| Succession — What happens to the business | |
| Beneficiaries — Are designations current and consistent? | |
| Guardianship — Who cares for minor children |
Who Gets What?
You do not need exact values today. You need clarity about intention, management, and risk.
| Person / Cause | Asset / Value | Who Manages It? | Concern |
|---|---|---|---|
If Something Happened to You Tonight...
What happens to the business Monday morning?
Part VII
Build Your Playbook
Scorecard · Shortlist · Top Three Moves
"The goal is not a stack of clever ideas. It is a short list of the right moves."
Your WTTG Strategy Scorecard
Mark the current status for each strategy. "Review" is not a failure — it is a question worth answering.
| Strategy | Doing It | Needs Review | New to Me | N/A |
|---|
Build Your Strategy Shortlist
Do not try to do everything. Sort the ideas by where they belong in your sequence.
Foundational — Structure, records, basics
High Impact — Moves worth modeling now
Advanced / Later — Explore when timing fits
Part VIII
Implement
90 Days · Annual Calendar · Advisor Questions
"Information is not the finish line. Put owners and deadlines on the next moves."
Turn Ideas Into Actions
One completed move beats ten saved ideas.
| Gap | Move | Owner | Deadline | Status |
|---|---|---|---|---|
Run Taxes on a Calendar — Not a Deadline
Q1 · Set the Year
Q2 · Document
Q3 · Project
Q4 · Harvest
Questions for Your CPA
The point is not to challenge your advisor. It is to make the planning conversation explicit.
"Are we doing compliance only — or proactive planning before year-end?"
"Which strategies have we intentionally reviewed for my business?"
"How was my entity selection determined?"
"How was my compensation determined?"
"What deductions or credits are we planning for before December 31?"
Questions for Your Attorney
Ask questions that test reachability, ownership, control, funding, and succession.
"If I am sued tomorrow, what can they reach?"
"Are valuable assets separated from operating risk?"
"Is my estate plan actually funded and coordinated?"
"What happens to my business if I die or become incapacitated?"
"Are ownership, control, and beneficiary designations consistent?"
Yours to Keep