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Form TR-0

THE TAX ROADMAP · STAGE STATEMENT

Stage 0: Organize

TAX YEAR2026

PART IYOUR PROFILE

1TYPICAL INCOMEAny income, first year with real moving parts

2HOW IT FEELSTax season feels like a shoebox, a scavenger hunt, and a surprise bill

3THE TEAM YOU NEEDA bookkeeper who closes your books monthly, plus a CPA who files on time

PART IIWHERE IT LEAKS, AND HOW YOU GRADUATE

4Business and entityLEAKSide income mixed into personal accountsFIXA separate bank account and card, books closed monthly

5Real estateLEAKFirst rental tracked in a spreadsheet, if at allFIXEvery rent payment, repair, and closing cost tied to the return

6W-2 and equity compLEAKWithholding set once and forgottenFIXW-4 updated so withholding plus estimates hit a safe harbor

7RetirementLEAKNot the focus yet; first get the cash flow visibleFIXKnow what you earn, spend, and owe

8Books and recordsLEAKReceipts in a shoebox, inbox, and three appsFIXMonthly close, receipts matched, records that hold up

9Giving and estateLEAKDonations made with no receipts keptFIXA written acknowledgment for every gift

10Your bottom line LEAKMessy records and the wrong withholding. GRADUATE BYGet organized before you get strategic.

Form TR-1

THE TAX ROADMAP · STAGE STATEMENT

Stage 1: Capture

TAX YEAR2026

PART IYOUR PROFILE

1TYPICAL INCOME$150K to $250K household income

2HOW IT FEELSYou earn good money, and somehow your tax bill keeps growing faster than your savings

3THE TEAM YOU NEEDA CPA who reviews your benefits and accounts every year, plus a bookkeeper if you have a side business

PART IIWHERE IT LEAKS, AND HOW YOU GRADUATE

4Business and entityLEAKSide business profit with no retirement plan attachedFIXSolo 401(k) or SEP opened; QBI deduction claimed and supported

5Real estateLEAKRental losses suspended as income rises; nobody tracking themFIXAbove $150K MAGI the $25K rental loss allowance is fully phased out, so suspended losses get tracked and used later

6W-2 and equity compLEAKCompany stock sales taxed twice because the 1099-B basis was wrongFIXBasis fixed on every sale; dependent care benefits elected at open enrollment

7RetirementLEAKContributing just enough to get the matchFIX401(k) and HSA maxed; backdoor Roth if you're over the income limits

8Books and recordsLEAKNo Form 8606; vest and sale statements scatteredFIXForm 8606 filed; equity statements saved; books still close monthly

9Giving and estateLEAKSmall cash gifts that never reduce your taxFIXNew non-itemizer deduction used; Trump account opened for eligible kids

10Your bottom line LEAKTax-advantaged accounts left unused. GRADUATE BYCapture every account you're already entitled to.

Form TR-2

THE TAX ROADMAP · STAGE STATEMENT

Stage 2: Structure

TAX YEAR2026

PART IYOUR PROFILE

1TYPICAL INCOME$250K to $500K, or your first real business profit or first rental

2HOW IT FEELSBusy, profitable, and paying more than your friends who earn the same

3THE TEAM YOU NEEDA proactive CPA (not just a preparer) and a bookkeeper

PART IIWHERE IT LEAKS, AND HOW YOU GRADUATE

4Business and entityLEAKSole prop or default LLC paying self-employment tax on every dollar of profitFIXS corp election when profit supports a reasonable salary, with state costs in the math

5Real estateLEAKProperties in your personal name; rental type decided by accidentFIXLLC or holding structure; long-term vs. short-term rental chosen on purpose

6W-2 and equity compLEAKSide income mixed in with W-2 life, no separate setupFIXMega backdoor Roth if your plan allows it; side business set up right from day one

7RetirementLEAKOnly the 401(k) from your day jobFIXSolo 401(k) or a plan run through your S corp

8Books and recordsLEAKBusiness costs paid personally and never reimbursedFIXAccountable plan, separate books per entity, reasonable compensation analysis on file

9Giving and estateLEAKBeneficiaries out of dateFIXBasic will in place, beneficiaries updated

10Your bottom line LEAKYou're paying more because of how you're set up, not what you earn. GRADUATE BYGet the structure right.

Form TR-3

THE TAX ROADMAP · STAGE STATEMENT

Stage 3: Shelter

TAX YEAR2026

PART IYOUR PROFILE

1TYPICAL INCOME$500K to $1M household income

2HOW IT FEELSYou do everything right and still write six-figure checks to the IRS

3THE TEAM YOU NEEDA proactive CPA who plans before you buy, plus a cost segregation firm

PART IIWHERE IT LEAKS, AND HOW YOU GRADUATE

4Business and entityLEAKProfit taxed at the top rate with no plan for asset purchasesFIXEquipment, vehicles, and R&D timed to your high-profit years

5Real estateLEAKRentals depreciated straight-line over 27.5 years; losses stuck as passiveFIXCost seg plus bonus depreciation; REPS or STR door chosen; grouping election decided

6W-2 and equity compLEAKWages with nothing offsetting themFIXShort-term rental strategy; DAF funded with appreciated stock

7RetirementLEAKAccounts maxed, nothing left to deferFIXKeep maxing; get ready for a cash balance plan in Stage 4

8Books and recordsLEAKHours never logged; no cost seg report; no mileage logFIXWeekly hour logs with proof, mileage log, Stage 3 records checklist complete

9Giving and estateLEAKGiving cash from your checking accountFIXGiving appreciated stock through a donor-advised fund

10Your bottom line LEAKActive income with nothing offsetting it. GRADUATE BYBuild a depreciation plan you can actually use.

Form TR-4

THE TAX ROADMAP · STAGE STATEMENT

Stage 4: Stack

TAX YEAR2026

PART IYOUR PROFILE

1TYPICAL INCOME$1M to $2M household income

2HOW IT FEELSEvery new dollar you earn, almost half of it disappears

3THE TEAM YOU NEEDCPA, retirement plan administrator and actuary, financial advisor

PART IIWHERE IT LEAKS, AND HOW YOU GRADUATE

4Business and entityLEAKState tax above the SALT cap isn't deductibleFIXPTET election; family on payroll for real work

5Real estateLEAKSelling properties and paying the gainFIX1031 exchanges; refinance instead of selling

6W-2 and equity compLEAKConcentrated company stock, no deferralFIXDeferred comp if offered; tax-loss harvesting; SALT cap planning

7RetirementLEAKOnly a 401(k)FIXCash balance plan stacked on top of the 401(k)

8Books and recordsLEAKFamily on payroll with no timesheetsFIXPlan documents, actuarial reports, timesheets, PTET payment records

9Giving and estateLEAKNo plan as net worth growsFIXStart estate basics before Stage 6

10Your bottom line LEAKThe top bracket eats every new dollar. GRADUATE BYDefer and stack.

YOUR TAX ROADMAP QUIZ

Takes under 60 seconds. No sales pitch, just your roadmap.

Nine stops between “just filing” and “building a legacy.” Answer a few quick questions and we’ll show you which stop you’re at, where you’re leaking money, and exactly how you graduate.

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