Tax planning done with the audit exposure in view.

Entity choice and elections, timing of income and deductions, estimated payments, retirement and equity decisions, and the crypto strategies that still work. Every recommendation is made by people who also prepare the return and defend it, so the plan is one the return can carry.

Attorney Andrew Gordon wearing a confident and relaxed smile during a legal meeting.

What planning covers

A tax plan is a set of decisions made before the year ends and before the deadlines that cannot be moved: the S corporation election, the 83(b) election within 30 days of a grant, the Section 1202 holding period, estimated payment safe harbors, and the year in which a gain or loss is realized. We identify which of these apply to you, model the alternatives, and put the ones that make sense in place, with Gordon Tax handling the filings.

Partner, Corporate Law and Tax Compliance

Where the savings usually are

Planning services

Entity structure and S corporation compensation, retirement plan design, timing of income and deductions, estimated payments, and multi-state exposure for owners who work or live in more than one state.

Loss harvesting without a wash sale rule, specific identification of lots, holding periods, charitable gifts of appreciated coins, and the wallet-level records that make each of these defensible. Crypto tax

The 83(b) election, qualified small business stock under Section 1202, equity compensation timing, and the structure of a sale before terms are set. Mergers and acquisitions

Residency and sourcing for people who move or work across state lines, and the foreign earned income exclusion, foreign tax credit, and treaty positions for those abroad. International tax

The people who do the planning

Planning is done by a corporate attorney who began in tax, with a tax attorney and CPA, and executed by Gordon Tax.

Andrew Gordon

MANAGING PARTNER

Michael Brandwein

PARTNER | CORPORATE LAW & TAX COMPLIANCE

Tax planning | Skokie, Illinois and nationwide

Why plan before year end

Most tax is decided by December 31, not April 15. Once the year closes, the return records what happened; it cannot change it. Planning during the year is where the choices exist: which lots to sell, whether to make an election, how to pay yourself from the business, and when to recognize income. A fall planning meeting with the current numbers is the single most valuable hour in the tax year for most business owners and investors.

Start with these guides

Tax planning | Individuals, business owners, crypto investors

What a planning engagement looks like

We start with last year’s return and this year’s numbers, identify the decisions available before year end, model the ones that matter, and give you a short written plan with the actions, the deadlines, and the estimated effect. Gordon Tax implements the elections and prepares the return the plan was built for. We give a rough fee estimate after the consultation.