Tax explainers for business owners and the self-employed

Most business tax decisions are made too late

A business return is largely a record of decisions already taken. Whether the S election was made and when, what salary was run through payroll, whether equipment was bought in December or January, whether estimates were sized against the right safe harbour — all of it is settled by the time the return is prepared.

That is why this track spends most of its time between April and December. An episode on reasonable compensation is worth something in September and worth nothing in March. The calendar is arranged accordingly, with the planning material front-loaded into the autumn and the compliance material clustered before the March deadline.

What gets covered

Entity and structure: when the S election actually saves money and when it costs money, how the IRS decides what reasonable compensation is, and how to form an entity in New Jersey without collecting a penalty in year one.

Owner economics: the qualified business income deduction and who phases out of it, accountable plans for reimbursing yourself tax-free, Section 179 against bonus depreciation, and the retirement plans that let an owner put away far more than an employee can.

And the operational floor underneath all of it — quarterly estimates sized properly, 1099-NECs issued to the right people by the right date, payroll taxes from the first employee, and records that survive an audit.

Who these are for

LLC members, S corporation shareholders, partners and the self-employed — particularly anyone who took an election or a deduction because somebody said it was a good idea, and has never seen the arithmetic behind it. Every episode puts real dollars on the decision rather than describing it in principle.