Private Wealth Tax Planning
Cut through the noise. Stay up to date on IRS changes and tax planning questions for equity awards, business sales, settlements, lottery prizes, and other large financial events.
Selling Your Business: Which Deal Terms Change the Tax Result?
Selling a business tax planning starts with deal structure, allocation, recapture, seller financing, and the cash needed for taxes.
Charitable Giving Before a Share Sale: Review the Gift Before the Deal Is Finished
Review charitable giving before a share sale, 2026 deduction limits, assignment-of-income risk, appraisals, and Form 8283 before transferring stock.
Choosing a Tax Adviser After Sudden Wealth: The First-Year Plan
Choose a tax adviser after sudden wealth by the work the first-year plan requires: documented tax analysis, payment planning, and reporting review.
Do You Need an IRS Ruling or a Written Tax Analysis?
An IRS ruling and a written tax analysis serve different purposes. Sheepdog Tax reviews the question, available procedure, and transaction timing.
Selling Structured Settlement Payments: Tax Review Before the Transfer
Selling structured settlement payments raises separate questions about your income tax, the buyer’s excise tax, and the payments you retain.
Won the Lottery? Tax Questions Before Choosing the Payout
Lottery payout tax planning compares the cash option, annual payments, withholding, and tax reserves before you commit to a payout choice.
Moving Before an Equity Payout: Which States Can Still Tax It?
Moving before a stock payout does not erase earlier work. Review residency, award types, California and New York sourcing, and possible tax credits.
Selling Qualified Small Business Stock Early: Can Section 1045 Defer the Gain?
A section 1045 rollover review tests the 60-day purchase window, replacement stock, recognized gain, basis, and cash available after an early sale.
Restricted Stock and the 83(b) Election: What Must Happen Within 30 Days?
A restricted stock 83(b) election has a 30-day deadline. Sheepdog Tax reviews the transfer, valuation, forfeiture risk, and filing record.
Is My Settlement Taxable? Start With What Each Payment Replaces
Is my settlement taxable? Review physical injury, emotional distress, wages, interest, and legal fees before treating the net check as spendable.
Does Your Startup Stock Qualify for the Section 1202 Exclusion?
Review section 1202 stock exclusion rules, 2025 changes, holding periods, issuer evidence, and tax limits before a startup share sale.
Selling Employee Shares in a Tender Offer or Secondary Transaction
An employee tender offer tax review separates compensation, stock-sale gain, basis, issuer redemption rules, and the cash available after tax.
Your Stock Sale and W-2 Both Show Income: Check the Cost Basis
A stock sale and W-2 can report different parts of one equity award. Sheepdog Tax reconciles compensation, cost basis, and Form 8949 reporting.
Restricted Stock Units at a Private Company: When Does the Tax Bill Arrive?
Private company RSU taxes depend on settlement terms and deferral rules. Sheepdog Tax reviews the award, payment timing, withholding, and cash reserve.
Exercising Stock Options Before a Sale: How to Model the Tax and Cash Risk
Exercising stock options before sale can create taxes without cash. Sheepdog Tax models exercise costs, minimum tax, sale timing, and reserves.
Your Employer May Go Public: Tax Questions to Resolve Before the IPO
Pre-IPO tax planning connects stock awards, exercise costs, tax timing, withholding, and access to cash before an employee makes a decision.
A Windfall Arrived: Is Withholding Enough to Cover the Tax?
Windfall tax withholding may not cover the final bill. Sheepdog Tax reviews projected liability, payment timing, and the cash still needed.
A Large Financial Event Is Coming: What Should Your Tax Plan Cover?
Sudden wealth tax planning starts before the transaction. Review the income, timing, tax payments, and cash you can retain with Sheepdog Tax.
Selling All or Part of Future Lottery Payments: What Changes on Your Tax Return?
Selling future lottery payments can concentrate ordinary income in one year. Sheepdog Tax reviews the offer, projected taxes, and cash you keep.