Business guides
Short guides for people running a business: what to do, why it matters and what usually goes wrong. Written by GHL Financial Services, which owns GoProOffice. For the numbers behind starting and pricing, see the planning guides.
101 guides
Business & S-Corp
- A Cash Flow ForecastA thirteen-week forecast of money in and money out, why its timing differs from profit, and how to read a low week while there is still time to do something about it.5 min read
- A Written ProcessHow to pick one recurring task, write the steps with who does them, when and what done looks like, then have somebody try it as written and revise it.4 min read
- Accountable PlanHow an S-Corp owner recovers business costs paid personally — home office, phone, mileage — without the reimbursement landing on the W-2, and what the plan has to say.6 min read
- Actual Vehicle CostsThe actual-expense method against the standard mileage rate: when tracking real costs is worth the effort, what the log has to show, and the choices that cannot be undone.6 min read
Start Here
- Accuracy PenaltiesBeing wrong about a position is one thing; being penalized for it is another, and three separate defenses stand between them. What each requires, and what disclosure actually buys.7 min read
- Amending a ReturnNot every error needs an amendment, and the best fix is often a different one. What the deadline actually is, why a superseding return is cleaner, and when leaving it alone is right.6 min read
- Annualized InstallmentsThe default assumes income arrives evenly through the year. When it does not, there are two ways to avoid a penalty on money you had not earned yet — and one of them takes no records at all.6 min read
- Estimated PaymentsTax is due as income is earned, not when the return is filed. The safe harbor is the amount that stops a penalty regardless of what you eventually owe — and for most people it is a figure from last year's return.5 min read
Retirement & Withdrawals
- 403(b)The 403(b) works much like a 401(k), with one thing most people are never told about: long service at the same qualifying employer can open an extra catch-up nobody mentions at enrollment.5 min read
- 457(b)A plan under section 457 sits on its own limit. For somebody who already has a 401(k) or a 403(b), that is a second full bucket in the same year — and a special catch-up in the run-up to retirement.5 min read
- Defined Benefit PlanA defined benefit plan works backwards from a target retirement benefit: an actuary calculates what has to go in each year. For an older owner with high, steady profit, that figure can be several times what any other plan allows — and it is a commitment, not an option.6 min read
- Mega Backdoor RothSome 401(k) plans allow contributions beyond the ordinary deferral limit, and allow those dollars to be moved to the Roth side. Most plans do not. The plan document decides, and it is the first thing to check.5 min read
Selling a Business
- Closing a BusinessStopping trading is not closing. What has to be filed, why the last payroll deposit is personal, and what distributing the assets does before anybody gets anything.8 min read
- Closing With the IRSThe six steps IRS.gov lists for closing a business, and why the IRS account stays open until every return is filed and paid. Contractor reporting uses the current $2,000 figure.4 min read
- Exit PlanningThe structure of a sale usually matters more to the after-tax result than the price negotiated, and most of the structural choices have to be made a year or two before anybody is at the table.7 min read
- F-ReorganizationA restructuring done a year or two before a sale puts the operating business under a holding company. The buyer can then buy the operating business in the form they want, and the seller can keep the property or the brand behind it.5 min read
Property & Rentals
- 1031 ExchangeRolling the gain on investment property into a replacement instead of reporting it now — the two clocks that start on the day you sell, and the ways people fall out of the rules.6 min read
- Cost SegregationA cost segregation study moves part of a property's cost into faster recovery periods — what the study is, when it pays for itself, and the passive-loss question that decides whether the deduction is usable.6 min read
- Grouping ElectionWhere activities genuinely form a single economic unit, they can be grouped and tested for participation together. Somebody who cannot meet the hours on any one of them may be able to meet them across the group.5 min read
- Repair or ImprovementFixing something is deductible now; improving it is written off over decades. What separates them, the safe harbors that settle most of it, and the accounting policy that has to exist before the year starts.8 min read
Health & Insurance
- Group Term LifeA business can provide a limited amount of group term life coverage to employees without it being taxed to them. Above that amount, a figure from a published table is added to their pay — which is where this usually goes wrong.4 min read
- Long-Term Care PremiumsPremiums on a qualifying long-term care policy are deductible, but how much counts depends on age, and which route you take depends on how you are paid. The C-corporation route is the only one with no cap.7 min read
- Owner Benefits by EntityWhat a business can provide an owner without it becoming pay depends almost entirely on how the business is taxed. The S-corporation answer is the one that surprises people.7 min read
- Reimbursing Health CoverAn arrangement that lets an employer of any size pay toward employees' own health insurance instead of running a group plan — how classes work, and the notice period that has to be met.5 min read
Family & Estate
- Family PartnershipA partnership holding family assets, with interests given to the next generation over time. The valuation discounts are the attraction, they are heavily litigated, and the structure has to be real in substance as well as on paper.6 min read
- Household EmployeesWho counts, what has to be withheld and filed, and why paying cash forfeits the dependent care credit you were entitled to anyway.7 min read
- Related PartiesSelling at a loss to family disallows it entirely. Selling depreciable property to a company you control turns the gain ordinary. And a loan without interest has interest anyway. Who counts as related, and what changes when they are.7 min read
Personal Deductions
- Overtime and TipsTwo temporary deductions for hourly and tipped work — what part of overtime pay actually counts, which tips qualify, and the income level where both fade out.6 min read
- The Two SurtaxesTwo separate charges sit on top of ordinary tax once income passes a threshold. Neither is a bracket, both use their own definition of income, and crossing one is not the same as crossing the other.5 min read
- Trader StatusThree different treatments for the same activity. What separates an investor from a trader, what the mark-to-market election buys and costs, and the deadline that has already passed by the time most people hear about it.8 min read
State Tax
- CaliforniaCalifornia's rate is the headline. The part that costs more is what it refuses to follow the federal rules on — the pass-through deduction, bonus depreciation, expensing and health savings accounts.6 min read
- OhioOhio's state rate is among the lower ones and its first slice of income is untaxed. The bill most people actually pay includes a municipal tax the state figure says nothing about.5 min read
General education, not financial, tax or legal advice. See our disclaimer.