FAQ

Answers to the Questions Owners Ask Most

Whether you're comparing bookkeepers or just trying to get your books in order, here's what business owners, contractors, and property investors ask me most.



General Bookkeeping
What's the difference between a bookkeeper and an accountant?+

I handle the day-to-day: recording every transaction, reconciling your accounts, and making sure your books are accurate every month. Your CPA or accountant uses those books to file your taxes and give you tax strategy. Think of me as the person who keeps your numbers clean, so when tax season comes, your accountant isn't starting from scratch.

Do I really need a bookkeeper, or can I do this myself?+

You can, plenty of owners do for a while. But most come to me once bookkeeping starts eating into time they'd rather spend running their business, or once a mistake costs them more than a bookkeeper would have. If your books are simple and you enjoy managing them, that's great. If you'd rather have accurate numbers and your time back, that's where I come in.

How much does a monthly bookkeeping service cost?+

Pricing depends on your transaction volume and how complex your books are, which is exactly why I don't publish a flat number online for every business. What's fixed is the process: you get a free discovery call, I review your books, and you get a custom proposal with flat, transparent pricing before you commit to anything. No hourly billing, no surprise invoices.

What's actually included in your monthly bookkeeping service?+

Every month I record and categorize your transactions, reconcile your bank and credit card accounts, and send you a clean set of financial statements you can actually read. Depending on your business, that also includes 1099 tracking, job costing, or property-level reporting. Everything gets scoped in your custom proposal so you know exactly what you're paying for, no guessing.

What should I look for in a bookkeeper?+

The two things worth checking are software fluency and consistency of who you're actually talking to. I'm a QuickBooks Online ProAdvisor Level 2 and Payroll Certified, and you deal directly with me, not a rotating junior staff or an offshore team that changes month to month.

Is it better to outsource bookkeeping or hire someone in-house?+

For most small businesses, outsourcing costs meaningfully less than hiring in-house. Industry research puts the typical savings around 40% lower than an in-house hire, while also freeing up the 20+ hours a month owners tend to spend trying to do it themselves.

How often should my books actually be updated?+

Ideally every month, not just at tax time. Waiting until year-end to reconcile means small mistakes pile up and you lose the ability to make decisions off real numbers during the year. That's the whole idea behind monthly bookkeeping instead of an annual cleanup: your books stay current enough to actually use.

How do I switch bookkeepers without disrupting my business?+

It's more common than people think, and it doesn't have to be messy. I start by reviewing your current books and QuickBooks file to see where things stand, get you set up as the primary account owner if you aren't already, and pick a clean cutoff date, usually the start of a month, so reconciliation stays simple. Most switches take one to two weeks and you keep running your business the whole time.

What do I need to give my bookkeeper to get started?+

Nothing complicated up front. It starts with a discovery call, then I review your current books and flag anything that needs attention before you commit to anything. From there you get a custom proposal built for your business, sign an engagement letter, and work begins.

Bookkeeping for Contractors & Trades
Why does job costing matter for my business?+

Job costing means every project has its own profit and loss instead of getting blended into one general number for the whole business. Without it, you might think your business is profitable overall while individual jobs are actually losing money, or the other way around. It's how you find out which types of jobs, clients, or crews are actually worth taking on.

How do you handle 1099s for my subcontractors?+

Every subcontractor gets tracked as a vendor and their payments get tied to the specific job they worked, not just lumped into one expense line. As of 2026, the federal threshold for issuing a 1099-NEC is $2,000 paid to a subcontractor in a calendar year, up from the old $600 threshold. I track it throughout the year so nothing gets missed or rushed at year-end.

What is retainage and how should it be tracked?+

Retainage is the percentage, usually 5 to 10%, that a client or general contractor holds back until a project is finished and approved. It shouldn't just sit inside your regular income numbers, it needs its own account so you can see what's actually been collected versus what's still owed to you per project.

What's the difference between a 1099 subcontractor and a W-2 employee, for my books?+

1099 subcontractors are tracked as vendors, you don't withhold payroll taxes, and they get a 1099-NEC at year-end if they cross the filing threshold. W-2 employees go through payroll, with taxes withheld and reported differently. Misclassifying one as the other is one of the more expensive mistakes a contractor can make, so it's worth getting this set up correctly from the start.

Can you handle bookkeeping if I have multiple crews or subcontractors working different jobs at once?+

Yes, that's exactly what job costing is built for. Each job gets its own cost codes for materials, labor, subcontractors, and equipment, so you can run several projects at once and still see the real profitability of each one individually.

Should my construction business use cash or accrual accounting?+

Most small contractors start on cash basis because it's simpler, but once you're running multi-month jobs with retainage and progress billing, accrual gives a much more accurate picture of what you've actually earned versus what's just sitting in your bank account. I'll help you figure out which fits your business, and your CPA will weigh in on how it affects your taxes.

Bookkeeping for Real Estate & Short-Term Rentals
Can you handle bookkeeping for multiple properties, including different platforms?+

Yes. I set up QuickBooks so each property is tracked separately, whether it's a long-term rental or a short-term listing on Airbnb, VRBO, or another platform. You get to see how each property performs individually, not just one combined number for your whole portfolio.

Should my books show the gross booking amount or just what actually lands in my bank account?+

Gross. Airbnb and similar platforms already subtract their service fees, cleaning fee adjustments, and occupancy taxes before the payout hits your account. If your books only record the net deposit, you're understating your revenue and missing deductible expenses. I record the full reservation amount as income and the platform's fees as a separate expense line, so nothing gets lost.

What's the difference between Schedule E and Schedule C for my rental income?+

Generally, long-term rentals are reported on Schedule E, while some short-term rentals can fall under Schedule C instead, which changes how the income is taxed. Which one applies depends on your specific situation, so that's a conversation for your CPA, but your books need to be organized to support either one when the time comes.

How do you handle it when one payout from Airbnb covers several of my listings at once?+

Platforms like Airbnb often bundle multiple reservations from different listings into a single payout. I break that payout down and allocate it back to the correct property, so each listing's income and profit margin stays accurate instead of getting blended together.

What reports do I actually get to see how each property is performing?+

You get property-level numbers, not just one combined total, so you can see income, expenses, and profitability for each property on its own. That's the whole point of setting the books up by property from the start, so tax season and everyday decisions are both based on real numbers.

Do I still need a bookkeeper if I only have one rental property?+

You can manage one property in a spreadsheet for a while, plenty of owners do. Where it gets tricky is mixing personal and rental expenses in the same account, or missing deductible expenses because nothing was categorized along the way. If you're planning to add more properties or just want clean numbers for tax season without the hassle, that's exactly where I come in.

FAQ