Business basics: taxes, insurance, contracts

Start simple, then add pieces

You do not need an LLC, an accountant and a lawyer before your first night. You do need three habits from the start: write down every payment, keep every receipt, and put some money aside for tax. Most of the trouble new hosts get into comes from skipping those, not from choosing the wrong business structure.

The rest can come in order as the work grows: a separate bank account in the first month or two, insurance once a venue or client asks for it (or before, if you bring your own gear), and an LLC if and when the reasons below apply to you.

Sole proprietor or LLC

If you host on your own and have not registered anything, you are already a sole proprietor. That is a legitimate way to run a hosting business, and plenty of hosts never change it.

Two things people often get wrong. First, an LLC does not lower your tax on its own: by default a single-member LLC is taxed exactly like a sole proprietor. Second, it does not protect you from your own mistakes. If you personally trip someone with a speaker cable, an LLC does little; insurance is what pays that claim.

An LLC starts to make sense when you sign contracts with companies, hire other hosts, carry a lot of equipment, or simply want the business kept apart from your personal life. Many hosts doing one or two weekly nights stay sole proprietors and buy insurance instead.

If you form an LLC

1. File articles of organization with your state, usually through the Secretary of State's website. Check that your business name is available first.
2. Get an EIN (employer identification number) from the IRS website. It is free and takes a few minutes. Sole proprietors can get one too, which means you can give venues an EIN instead of your Social Security number.
3. Open a business bank account in the LLC's name.
4. Put your state's annual filing date in your calendar.
5. Check whether your city or county also wants a business license.

Insurance

Hosts on r/triviahosts report that many weekly venues never ask about insurance. Some do, and corporate clients, event spaces and hotels usually do. Insurance is also what protects you if a guest trips over your speaker stand or your gear damages the venue's sound system, which is more likely than it sounds when you set up in the dark.

General liability

This covers claims that you caused injury or property damage while working. Hosts report paying around $25 to $50 a month for a policy. Venues and clients that require it will often ask you to name them as an "additional insured" and send a certificate of insurance before the event. Most insurers can produce one quickly, so ask how it works when you buy the policy.

If you only do the odd private event, one-day event policies exist and can be bought per booking. Get quotes from a local agent or an online small-business insurer, and tell them exactly what you do: hosting trivia and games, whether you bring sound equipment, and whether alcohol is served.

Your equipment

A homeowner's or renter's policy may not cover business equipment, and often does not cover it once it leaves the house. If you own a laptop, speakers, microphones and a screen that you carry to venues, ask about equipment cover (sometimes called inland marine) or a business owner's policy that includes it.

Keeping the money separate

Open a separate bank account for hosting, even as a sole proprietor. Pay venue fees, tips and event payments into it, and pay your hosting costs out of it. Tax time becomes a matter of reading one account rather than searching a year of personal spending. If you have an LLC, keeping the money separate is also part of what keeps its protection intact.

Then track every payment and expense somewhere. Wave, QuickBooks or a spreadsheet all work. Brainflood's Host Books (Starter plan and up) is a ledger built for this: it records payments by cash, Venmo, Cash App, PayPal, Zelle, check or invoice, sorts expenses into categories with receipt links, shows totals by month, quarter and year along with profit by venue and by category, and exports a CSV in its own, a QuickBooks-style or a Wave layout.

Move a share of every payment into savings the day it arrives. 25% to 30% is a common rule of thumb for self-employed income; your accountant can tell you whether yours should be higher or lower.

Taxes

All of it is income

Every dollar you earn from hosting is reportable income: the venue fee, event fees, and tips, whether paid in cash, by check or through an app. There is no amount small enough to leave out. Self-employed income usually goes on Schedule C with your normal tax return.

On top of income tax, you owe self-employment tax once your net self-employment earnings for the year reach $400. It is 15.3%, covering Social Security (12.4%) and Medicare (2.9%). An employee pays half of that and the employer pays the other half; when you are self-employed, you pay both halves.

W-9s and 1099s

A venue that pays you will often ask for a W-9. It gives them your name, address and taxpayer number (your SSN, or an EIN if you have one) so they can report what they pay you.

A business that pays you more than the IRS reporting threshold in a year may send you a Form 1099-NEC. The threshold was $600 for years and rises to $2,000 for payments made from 2026; check irs.gov for the current figure. Payments through Venmo, PayPal and similar apps may be reported on a 1099-K instead. None of this changes what you owe: income is reportable whether or not anyone sends you a form.

Paying during the year

Nobody withholds tax from a host's fee. If you expect to owe $1,000 or more for the year, the IRS expects estimated payments four times a year, usually around April 15, June 15, September 15 and January 15, using Form 1040-ES. Missing them can mean a penalty even if you pay everything in April.

If you also have a regular job, there is a simpler route: raise the tax withheld from your paycheck to cover your hosting income. Many part-time hosts do this rather than making quarterly payments.

What you can usually deduct

Business expenses reduce the profit you pay tax on. For hosts, that commonly includes:

• Software, including your hosting platform and music or image subscriptions you use for rounds.
• Equipment: speakers, microphones, cables, a laptop or screen used for hosting.
• Printing, paper and ink for answer sheets and picture handouts.
• Prizes you pay for yourself.
• Driving for the business, at the IRS standard mileage rate (70 cents a mile for 2025; check irs.gov for the current year), with a log of dates, places and miles.
• The business share of your phone, and insurance premiums.
• Half the cost of business meals, such as lunch with a venue manager to discuss a new night.

Some rules have edges. Whether the drive from home to a venue counts as business driving depends on things like whether your home is your main place of business. A home office has to be used regularly and only for the business. Ask an accountant before you count either.

Later, if your hosting profit gets large, an accountant may suggest an S corporation election for an LLC. It can lower self-employment tax but adds payroll and paperwork costs, so it only pays at higher profits. Do not do it on your own.

Written agreements

Most weekly nights start with a handshake, and many run that way for years. A short written record still saves arguments later, when the manager who hired you has moved on. An email is enough.

For a weekly night, put in writing: the night and times, your fee, how and when you are paid, who supplies prizes, what equipment each side provides, who promotes the night, and how much notice either side gives to cancel a week or end the arrangement.

For corporate and private events, use a fuller agreement, because the fee is larger and the date cannot move. Include what you will provide and for how long, setup time, the total fee and what it covers, the deposit (half up front is common), when the balance is due, what happens if they cancel and when the deposit is kept, what happens if you cannot attend, and who is responsible for your equipment at their site. The corporate and private events guide covers proposals and booking.

If you host for a trivia company, read their agreement before signing. Some include a non-compete that stops you hosting anywhere else within a set distance, sometimes for a period after you leave. That matters if you hope to go independent.

Invoicing and getting paid

Send an invoice even when a venue pays cash. It gives you and them a record and makes tax time easier. An invoice needs your name or business name and contact details, an invoice number (count up from 001), the date and description of the service, the amount, and how to pay. Wave, QuickBooks, PayPal or a document template will all produce one.

If a venue falls behind, raise it the first week, politely and in writing. Two missed payments is a pattern, and it is easier to sort out at $150 owed than at $600.

Prizes and the law

In many US states, charging players to enter and paying out a prize can turn a trivia night or league into a lottery or illegal gambling. Some states also restrict alcohol or bar tabs as prizes. Free-to-play nights with prizes the venue provides avoid most of this, which is one reason most weekly nights work that way.

If you want to charge entry for a league, a tournament or a fundraiser, check your state's rules first. Charities often need a gaming or raffle permit to run a paid-entry event with prizes. When a night is the venue's promotion, the venue's licenses are on the line too, so make sure the manager has checked with whoever handles their liquor license.

Music licensing and picture copyright

Music

Playing recorded music in public, including between rounds, needs a public performance license from the organizations that collect for songwriters: ASCAP, BMI, SESAC and GMR. Many bars and restaurants hold these licenses, and when they do, they generally cover recorded music played in the venue. Not every venue holds them, so ask the manager before your first night rather than assuming. Offices and rented rooms often have none.

If the venue has no license, use music you have the rights to play in public (royalty-free libraries sell this), or skip the between-round playlist. The same question applies to karaoke and to music rounds, so raise it once and cover everything.

Pictures

Picture rounds built from photos you found online carry real risk. Hosts report that trivia businesses have received settlement demands of $2,000 to $5,000 from rights holders over images used without permission. Use your own photos, public domain images, or images licensed for this use. Brainflood's image search draws from Openverse, Pixabay and Wikimedia, which carry open licenses, but check each image's terms and credit the creator where the license asks you to.

Looking professional without spending much

• An email address with your business name looks better on a proposal than a nickname at a free provider.
• A one-page sheet for venues: what your night looks like, what you need from them, your rate and a couple of photos of a full room. Ask people before you use photos of them.
• Somewhere people can look you up. Your Brainflood Host Site (app.brainflood.com/h/your-name) lists your upcoming nights and venues and lets players follow you; a simple website or social page does the same job.
• Business cards, still. Bar staff and players will pass them on when someone asks who runs the quiz.

A first-year checklist

1. From the first night: log every payment and expense, keep receipts, keep a mileage log, and set aside 25% to 30%.
2. First month or two: open a separate bank account and get a free EIN so you can stop handing out your SSN.
3. Before you need it: price a general liability policy, and buy it when a venue asks or when you start bringing your own equipment.
4. Each new venue: send a confirmation email, fill in their W-9, ask about music licenses, and agree who supplies prizes.
5. Each quarter: make an estimated tax payment, or raise the withholding at your day job.
6. When the work grows: talk to an accountant about an LLC, deductions and whether anything else applies in your state.
7. Before any paid-entry event: check your state's rules on prizes and gambling.