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Straight answers, written by the people who’d file it.

1,423 plain-English guides on cross-border moves, US and Canadian returns, and small-business money. Each one ends in what to do next, and says when a written Position Check is the smarter first step.

CROSS-BORDER A Canadian Corporation With a U.S. Shareholder
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1,423 guides
Small Business Tax

Insurance Agency Entity Structure: The LLC, the S Election, the Carrier Appointments, and the Book That Transfers With the Entity

September 29, 2026

An insurance agency's entity decision runs on standard S election arithmetic — with a payroll that exists once the agency has staff, a producer's salary that the employed market documents, and a QBI deduction that survives because insurance agents are excluded from the specified-service list — plus two features the carriers impose: the agency itself must be licensed and appointed in every state where it writes, and the book of business is worth more inside an entity that can be sold whole. Here is the analysis for a solo producer, a small agency, and an agency planning a sale or perpetuation.

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Small Business Tax

Insurance Agent Tax Deductions: Commissions, Renewals, the Statutory Employee Rule, and the Book of Business You Can Sell

September 29, 2026

An insurance agent's tax picture depends on which kind of agent they are: a captive agent paid by one carrier, an independent agent paid by many, or a full-time life insurance salesperson the tax code calls a statutory employee — W-2 for payroll taxes, Schedule C for expenses. The deductions are the office, the licensing and continuing education in every state, the errors-and-omissions policy, the marketing, and the staff; the income is first-year commissions and renewals that arrive for years. Here is each category, the statutory employee rule, and the book of business as an asset.

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Small Business Tax

IT Services and MSP Tax Deductions: Recurring Revenue, Hardware Resale, the Consulting Line, and the Sales Tax on Software

September 29, 2026

A managed services provider or IT services firm sells three things — recurring managed services under monthly contracts, project and consulting work billed by the hour or the engagement, and hardware and software resold to clients — and each has its own tax treatment: the recurring revenue raises the advance-payment question, the resale line is inventory with sales tax in most states, and the consulting line is the one that can make the firm a specified service trade. Here is each deduction category, the revenue-recognition and sales-tax mechanics, and the classification of the technicians who work remotely.

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Small Business Tax

IT Services Firm Entity Structure: The LLC, the S Election, the Consulting Line That Needs Its Own Books, and the Technicians in Four States

September 29, 2026

An IT services firm's entity decision has the standard S election arithmetic on a technical director's salary, a liability profile that has changed with cyber risk, and two structural questions the profession raises more than others: whether the advisory practice should be a separate business so the managed-services firm keeps the QBI deduction, and how a remote workforce across several states shapes the entity's registrations. Here is the analysis for a solo consultant, a managed services firm with staff, and a firm whose advisory line has outgrown the de minimis rule.

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Small Business Tax

Law Firm Entity Structure: The PLLC, the Partnership, the S Election, and the Partners Who Can't Be Employees of Themselves

September 29, 2026

A law firm's entity decision runs on the same specified-service phase-out as the other professions — the QBI deduction disappears above the range — with a choice most firms make on compensation mechanics: a partnership-taxed PLLC pays partners guaranteed payments with self-employment tax on everything, while a professional corporation with the S election pays shareholder-lawyers salaries with distributions above them. Add the ethics rules on ownership, the malpractice structure, and the contingency firm's loss years, and the analysis is the firm's own. Here it is for a solo, a small partnership, and a contingency practice.

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Small Business Tax

Law Firm Estimated Taxes: Guaranteed Payments With Nothing Withheld, the Settlement That Lands in September, and the Pass-Through Entity Tax

September 29, 2026

A law partner's estimated taxes have no withholding behind them — guaranteed payments and distributive shares arrive gross, with self-employment tax and income tax owed on all of it — and a contingency firm's income arrives when cases resolve, which no calendar predicts. The setup that fits is a reserve on every draw, the annualized method for the firm whose fees are lumpy, and — in the states that offer it — the pass-through entity tax election that moves the state payment to the firm's level. Here is the routine for partners and for S corporation shareholder-lawyers.

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Small Business Tax

Law Firm Tax Deductions: The Trust Account That Isn't Income, Advanced Client Costs, and the Contingency Fee That Arrives in Year Three

September 29, 2026

A law firm's return has three items no other professional practice shares: the client trust account, which holds money that is never the firm's income until earned; the costs a firm advances on a client's behalf, which are loans rather than deductions when they are reimbursable; and the contingency fee, which is income only when the case resolves — years after the work was done. Add the malpractice tail, the bar and CLE costs, the referral fees, and the partner compensation, and the deductions have a shape built around the ethics rules. Here is each category.

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Small Business Tax

Personal Trainer Taxes: Deductions, Entity, and the Fitness Exclusion That Keeps You Out of the Specified-Service Rules

September 29, 2026

A personal trainer's tax picture depends on where the training happens — at a gym as an employee or a contractor, in clients' homes, in a home studio, online — and on a classification point in the trainer's favor: fitness services are excluded from the 'health' field, so personal training is not a specified service trade and the QBI deduction applies at every income level. Here is the deduction map, the gym-contractor arrangement, the entity analysis, and the estimated taxes for a trainer paid by the session.

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Small Business Tax

Photographer Tax Deductions: The Gear, the Studio, the Travel, and the Second Shooter Who Is or Isn't a Contractor

September 29, 2026

A photographer's deductions are equipment (bodies, lenses, lighting, computers — bought often and expensed under de minimis or section 179), a studio or a home office, travel to sessions and destination weddings, software subscriptions, and the second shooters and assistants whose classification depends on how the arrangement works. Prints and albums add a product line with sales tax; session fees may or may not carry it. Here is each category and the elections.

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Small Business Tax

Photography Business Entity Structure: The LLC, the S Election, and the Deposits That Arrive a Year Before the Wedding

September 29, 2026

A photographer's entity decision is the standard S election arithmetic on a working photographer's salary — which for most solo photographers doesn't pay until profit passes six figures — plus a liability profile (a light stand on a guest, a lost wedding's images, a drone) that makes the LLC worth forming early, and a cash pattern (wedding deposits a year ahead) that shapes the estimated taxes more than the entity. Here is the analysis for a solo photographer, a studio with associates, and a commercial photographer with licensing income.

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Small Business Tax

Real Estate Agent Entity Structure: The S Corporation, the Commissions Paid to an Entity, and the Brokerage Rule That Varies by State

September 29, 2026

A real estate agent's S election has a prerequisite the other trades don't: the commissions have to be payable to the entity, and whether a brokerage may pay an agent's LLC or professional corporation is a state licensing question. Where it's allowed, the election runs on the standard arithmetic against a producing agent's reasonable salary; where it isn't, the agent stays on Schedule C regardless of profit. Here is the state question, the worksheet, the QBI point for agents above the threshold, and the team structure.

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Small Business Tax

Real Estate Agent Estimated Taxes: Commissions That Close in Lumps, Nothing Withheld, and the Reserve That Fits

September 29, 2026

A real estate agent's income arrives as commission checks at closings — three in April, none in May, four in June — with nothing withheld, self-employment tax owed on all of it, and a spring-to-fall season in most markets. The estimated-tax setup that works is a reserve on every commission the day it lands, a safe harbor chosen for the year's trajectory, and the annualized method for the agent whose closings cluster. Here is the routine, the year-one problem, and the S corporation agent's withholding alternative.

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Small Business Tax

Real Estate Agent Tax Deductions: The Mileage, the Marketing, the Desk Fees, and the Statutory Non-Employee Rule

September 29, 2026

A real estate agent is self-employed by statute — commissions arrive on a 1099-NEC from the brokerage with nothing withheld — and the deductions are the costs of producing them: the car, the marketing, the brokerage's desk and transaction fees, the MLS and association dues, the licensing and continuing education, and the home office. Here is each category, the mileage discipline that dominates the return, the referral fees and client gifts with their own rules, and the bookkeeping that separates a good year's commissions from a good year's profit.

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