No extension after restricted property transfer
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Tax Intelligence · U.S. planning deskKeep more of
Keep more of
what you build.
A decision system for founders, investors, executives and owners navigating equity, liquidity, gains, giving, estates and the deadlines that decide the outcome.
Basic exclusion amount per individual
Per recipient for 2026
2026 elective deferral limit
2026 traditional + Roth combined
2026 self-only / family coverage
2026 federal markers
Limits are not eligibility determinations. Confirm contribution, income, plan, age, filing-status and transaction-specific rules before acting.
Primary sourcesFounder tax flight plan
Equity creates clocks.
Most expensive founder tax mistakes are sequencing mistakes: a missed election, incomplete QSBS record, unmodeled AMT bill or deal structure reviewed after leverage is gone.
83(b): decide, file, prove
Restricted founder stock can start an unforgiving 30-day election window. Confirm whether an election fits, use the current filing method, and retain the election plus proof with your permanent equity records.
Build the QSBS file now
Section 1202 is a fact pattern, not a cap-table badge. Preserve original issuance, C-corp status, asset levels, active-business evidence, redemptions, reorganizations and holding history before people and records disappear.
Treat exercise as a tax trade
Before exercising ISOs or NSOs, model ordinary income, withholding, AMT, liquidity, holding periods and a severe price decline. Separate a tax decision from a conviction decision.
Model every exit structure
Stock sale, asset sale, rollover equity, earnout, escrow, installment payments and transaction expenses can produce very different after-tax proceeds. Run the model before the LOI hardens.
Know the rollover windows
Eligible QSBS held more than six months may qualify for a Section 1045 rollover when replacement QSBS is purchased within the statutory window. Do not discover the deadline after cash has been redeployed.
Coordinate company + founder
Payroll, cap table, legal documents, 409A work, state nexus and the founder’s return must tell the same story. Assign one person to reconcile the data before filing season.
Investor tax system
Manage tax like another portfolio risk.
Good tax management does not let the tail wag the portfolio. It creates visibility, avoids preventable collisions and lets you compare decisions on after-tax terms.
Open Portfolio OSGain budget
Maintain a year-to-date view by tax lot, holding period, character and jurisdiction. Reforecast before rebalancing, a tender, fund distribution or concentrated-stock sale.
Output: realized-gain ledger + tax reserveHousehold wash-sale control
Coordinate taxable accounts, IRAs, a spouse’s accounts and controlled entities. Replacement exposure can invalidate a loss even when it sits at a different custodian.
Output: restricted replacement listAsset location
Evaluate which assets belong in taxable, tax-deferred and tax-free accounts based on expected return, turnover, income character, liquidity and withdrawal horizon—not a one-size rule.
Output: account-location policyEstimated-tax system
Monitor withholding and quarterly payments against current-year projections and safe harbors. Consider the annualized-income method when a gain arrives unevenly during the year.
Output: payment schedule + ownerCharitable asset routing
Compare cash with appreciated stock, direct gifts, donor-advised funds and other vehicles before selling. Confirm valuation, substantiation, deduction limits and charity acceptance first.
Output: gift memo before transferReal-estate tax map
Model depreciation, passive losses, debt, recapture, state tax and eventual exit. Section 1031 generally applies only to qualifying real property held for business or investment.
Output: hold / sell / exchange cases2026 deadline deck
Put the dates in the operating system.
These are selected federal individual markers for calendar-year planning—not a complete filing calendar. Entities, payroll, trusts, estates, states and international reporting have their own clocks.
DateDecision / filingWhy it mattersOwner
Any equity transfer83(b) review
30 calendar days from transfer
Founder + counselApril 15, 2026Q1 estimated tax
Federal individual estimate
Tax teamJune 15, 2026Q2 estimated tax
Federal individual estimate
Tax teamSeptember 15, 2026Q3 estimated tax
Federal individual estimate
Tax teamOctober 15, 2026Extended individual return
Filing extension—not payment extension
PreparerDecember 31, 2026Most calendar-year actions
Gifts, gains/losses, conversions, deductions
Full teamJanuary 15, 2027Q4 estimated tax
2026 federal individual estimate
Tax teamAn extension to file generally does not extend the time to pay. Always confirm the date for your facts and jurisdiction.
Wealth transferEstate size Control Basis Liquidity Governance Administration
Model the family balance sheet—not one tax.
Estate, gift, generation-skipping, income, capital-gains and state tax can pull in different directions. Start with goals and cash flow, then compare structures.
What is the estate today—and after five, ten and twenty years of plausible growth?
Which assets can leave the estate without compromising lifestyle, voting power or business control?
Would a transfer-tax strategy create a worse income-tax basis result for the family?
Where will cash come from for tax, debt, equalization and operating needs?
Who makes decisions when the founder cannot, and are documents and beneficiary designations aligned?
Who will value assets, file returns, send notices and maintain trust/entity records every year?
Risk control
Walk away from magic.
Tax-smart is legal, documented and explainable. Aggressive marketing language is not authority.
A promoter says a structure is “IRS approved” or guarantees audit-free savings.
Someone proposes backdating a document, inventing a residency fact or omitting income.
A charitable gift is planned only after the sale is effectively locked in.
A loss-harvesting plan ignores IRAs, a spouse, managed accounts or controlled entities.
An advisor quotes tax saved but will not show fees, risk, exit cost and annual administration.
A preparer will not sign the return, provide a PTIN or explain the reporting position in writing.
Advisor + firm referral desk
Build the right room.
A complex tax life usually needs a coordinator plus specialists. Verify credentials, relevant transaction experience, capacity, conflicts, fees and who will actually do the work.
Structure, privilege, legal opinions, controversy and transactions
Projection, compliance, elections, estimates and record reconciliation
Deal model, diligence, purchase price, rollover and multistate issues
Wills, trusts, gifts, governance, succession and transfer-tax design
Residency, sourcing, nexus, withholding and cross-border reporting
Credentialed return preparers
IRS preparer directory
Search by ZIP code and credential for CPAs, attorneys, enrolled agents and other listed qualifications.
CPA / specialist verification
AICPA & CIMA directories
Locate or verify members and credentials, then confirm active state licensure separately.
Enrolled agents
NAEA tax expert directory
Find federally licensed tax practitioners who may represent taxpayers before the IRS.
Trusts + estates counsel
ACTEC fellow search
Search experienced probate, trust and estate-planning lawyers by location.
Andersen
Private wealth, individual tax, wealth transfer, cross-border and family office
EisnerAmper
Private-client tax, accounting and reporting for individuals, families and closely held businesses
BDO
Private-client tax, estate, wealth and succession planning for complex individuals and businesses
Armanino
Private-wealth tax, equity compensation, AMT, charitable, estate, gift and trust planning
Withum
Venture-capital accounting, tax, compliance and investment-valuation work
Take this to every first call
Seven questions before you hire.
- 01How many clients with my exact equity, transaction and state profile did you advise last year?
- 02Who owns proactive planning, and how often will you update my projection?
- 03Which work is performed by the person I am meeting versus delegated?
- 04How do you coordinate with company counsel, payroll, investment and estate teams?
- 05What assumptions, authorities and reporting positions will you document in writing?
- 06What are fees for planning, compliance, amended work, notices and special projects?
- 07What deadlines or decisions would you prioritize in my first 30 days?
Primary-source chart room
Read the rule behind the strategy.
Official sources can still be technical and incomplete for a specific situation, but they are a better starting point than a viral tax hack.
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2026 inflation adjustments
Estate and gift limits, AMT and other indexed federal provisions.
83(b) election guide
IRS Publication 5992 on eligibility, the 30-day deadline and filing steps.
QSBS changes + business provisions
IRS 2026 discussion of expanded Section 1202 treatment and other current business provisions.
Investment income + wash sales
IRS Publication 550 on investment income, capital transactions, wash sales and QSBS context.
ISO alternative minimum tax
IRS Form 6251 instructions, including the general AMT treatment of ISO exercise spread.
2026 estimated tax
Form 1040-ES rules, safe harbors, due dates and annualized-income method.
Like-kind exchanges
IRS guidance on Section 1031 treatment for qualifying real property.
2026 retirement limits
IRS announcement for 401(k), IRA and catch-up contribution limits.
2026 HSA limits
IRS Revenue Procedure 2025-19 for health savings account limits.
Important tax + legal notice
Shark Money provides general educational information, not tax, legal, accounting or investment advice. This page does not know your income, basis, entities, documents, elections, residency, citizenship, goals or jurisdictions and cannot determine eligibility or calculate liability. Do not delay a filing, payment or professional consultation while using it. Engage qualified advisors before acting.