Bookkeeping FAQs
THINGS TO KNOW AS A CLIENT AND BUSINESS OWNER
Education and communication are so important in ensuring we work together in your best interest to avoid costly mistakes and keep you out of trouble with the IRS.
Below is helpful information and things you should be up to speed on.
Please read and reference back to the list below.
IF YOU HAVE ANY QUESTIONS...

Bookkeeping FAQs
THINGS TO KNOW AS A CLIENT AND BUSINESS OWNER
Education and communication are so important in ensuring we work together in your best interest to avoid costly mistakes and keep you out of trouble with the IRS.
Below is helpful information and things you should be up to speed on.
Please read and reference back to the list below.
IF YOU HAVE ANY QUESTIONS...
Communication
What we need from you and when
It's our goal to have your reports to you by the 15th of each month or the business day prior.
Ideally, we will have accountant read-only access to all of your bank accounts so we can pull statements on your behalf.
We aim to have questions for you as early as possible.
Your timely response allows us to turn your books around by our promised date of the 15th of each month.
Delayed responses lead to delayed reports.
Please do your best to answer promptly so we can ensure timely reports so you can make better business decisions.
If you prefer one form of communication over another, just let us know, and we'll do our best to honor that.
DELAYS:
If reports are delayed beyond our internal deadline of the 15th, we will send a status update. If the reason is due to incomplete information from the client, we will let you know what is missing.
Once this status email is sent, we won't send any additional follow-ups, and we will be waiting for the information necessary to complete your books.
The first half of each month is when we are laser-focused on our clients and getting their reports turned around. The last half of each month is when we focus on aspects of the business outside of existing client work. We can be busy with other projects or even off during this time.
Because of this, if information is received during the last half of the month, it may take up to 5 business days for us to turn the information around.
Things you need to tell us about
Alert us if you:
- Open a new credit card or bank account
- Change banks
- Begin selling physical products
- Hire any new staff
- Apply for or receive new loans
- Accidentally pay a personal expense from the business
- Accidentally pay a business expense personally
Rate increases and what can trigger them
Our rates are based on the time it takes to complete your books, and not your income.
Rates are subject to increase with written notice and upon your acceptance. In the event of an increase, you will be notified of the amount and the date it goes effective in advance and with your consent.
We dislike busy work, so most of the time, we will be happy to brainstorm ways to work faster and keep your bill down. To make that work, we need your flexibility and willingness to implement efficient systems.
However, we do understand when the priority is in maintaining your system and dealing with the inefficiencies on the books. And we're open to doing that work, but absent an efficient system, the bill is subject to increase and we will discuss the increase then.
Things that can trigger rate increases, aside from general inflation, are:
- manual processes (example: keying in each transaction versus a bank feed, coding items of income one at a time in a separate platform)
- increases in volume of transactions that adds time (sometimes an increase in volume doesn't add time)
- granular detail of reporting (example: showing you detail by project or division)
- an increase in how many accounts you have
- management of inventory, payroll, or sales tax
Elevated services we offer
In addition to regular bookkeeping, I offer a CFO service on a limited basis.
This service includes:
- a monthly 45 minute 1:1 Zoom call,
- unlimited Voxer access,
- templates plus the creation of custom templates as needed to help you meet your goals
- monthly visual reporting with goal and income tracking as well as comparisons to prior periods
We also offer visual reporting as a stand-alone upgrade to bookkeeping.
If you're interested in either of these, send me a Voxer or email.
How do I update my card on file?
Follow the steps below to update your card on file with Simply Booked:
- CLICK HERE to login to your account. (This link will open in a new window so you can still refer to these instructions).
- Your login is the email address where you received your email notification.
- If you forgot your password, you can reset it by clicking Forgot Password at the bottom of the page.
- Once you're in, click Update next to the currently listed credit card.
- Complete the prompt to enter the updated card information.
- Then, click Update Card to apply and keep the changes.
Please email [email protected] if you have any questions!
Good Habits
Separating business & personal funds
It's important to keep business and personal separate for several reasons.
The one that affects our relationship most is that it makes it exponentially easier to track. That means fewer questions, less guesswork, reduced room for error, and time saved which means a lower fee and more accuracy.
But it's also a good practice and would really help you in the event of an audit.
That means you should pay personal expenses from your personal accounts and business expenses from your business account. If cash is tight on either side, transfer between accounts.
If you use PayPal, you should have a separate profile for business and personal. Your business profile should only be linked to business accounts. You can edit this in PayPal under Pay & Get Paid > Banks & Cards > and then delete any accounts that are not business.
If you accidentally pay a personal expense from a business account:
We will typically code it as owner's draw and it will not count as a business deduction. If this is an autopay item, please correct the billing account.
If you accidentally pay a business expense from a personal account:
We have no way of knowing unless you tell us. That means you miss the ability to deduct what you spent... which is no bueno. So just shoot us an email letting us know the date, amount, and vendor and we will enter it in your books. You can also reimburse yourself by writing a check or transferring from your business to your checking with a memo and telling us it is a reimbursement. If you don't tell us this was done, it may accidentally get coded to owner's draw which means you miss the deduction.
We kindly request you keep this to a minimum as it creates more work and an inefficient process with more room for error.
Fun Fact: estimated tax payments and payments on your personal tax return are actually personal expenses and are not deductible. If you pay them from your business we will treat them as owner's draw.
How to manage receipts
Long story short: receipts are a client responsibility and used to back yourself up should you ever get audited. We don't manage your receipts and we won't ask you for them. Here is more info on receipts, including how to manage them and why.
When your business needs more cash
If you're feeling cash poor, my first recommended step is to look at your profit and try to find ways to increase sales or cut back expenses.
If that is not possible in this exact time frame and you have a clear amount you need to borrow and a plan to pay it back, you may need a loan.
Discuss it with me before applying and also discuss with your CPA, especially if you are an S Corp.
When possible, a 0% credit card is a great way to go. I prefer Chase Ink Cards.
Searching grants are also a great idea. Advise with your CPA about the taxability and your options.
Payroll & Hiring
Contractor or employee?
Determining if a new hire is an employee or contractor is not a choice. It's a matter of which one the IRS would determine them to be and ultimately it comes down to control.
The IRS has a 20 point test to determine if someone is a contractor or employee.
The 20 factors are listed below (reference this article):
- Level of instruction. If the company directs when, where, and how work is done, this control indicates an employer-employee relationship.
- Amount of training. Requesting or requiring workers to undergo company-provided training suggests an employment relationship since the company is directing the methods by which a worker performs their duties.
- Degree of business integration. Workers whose services are central to the business operations or significantly affect business outcomes are likely to be considered employees.
- Extent of personal services. Companies that insist or demand that a particular person performs the work have asserted a high degree of control, which indicates an employment relationship. In contrast, independent contractors are typically free to assign work to anyone.
- Control of assistants. If a company hires, supervises, and pays a worker’s assistants, this control suggests an employment relationship. If the worker gets to control the hiring, supervising, and paying of assistants, they could be defined as an independent contractor.
- Continuity of relationship. A continuous relationship between a company and a worker indicates an employment relationship. However, an independent contractor arrangement can also be an ongoing relationship that spans multiple, sequential projects.
- Flexibility of schedule. If a company gets to dictate a worker’s days and hours of work, this degree of control suggests an employer-employee relationship.
- Demands for full-time work. Workers who work full-time hours suggests a company has control over most of their time, which indicates an employment relationship.
- Need for on-site services. Requiring someone to work on company premises — particularly if the work could be performed elsewhere — suggest an employer-employee relationship.
- Sequence of work. If a company requires work to be performed in specific order or sequence, this type of control suggests an employment relationship.
- Requirements for reports. If a worker has to regularly provide written or oral reports on project status, they could be viewed as an employee.
- Method of payment. If a worker is paid hourly, weekly, or monthly, this could suggest an employment relationship, unless the payments simply are a convenient way of distributing a lump-sum fee. It is more characteristic to pay freelancers upon project completion or commission.
- Repayment of business or travel expenses. Independent contractors are typically responsible for paying for travel or business expenses, and most contractors set their fees high enough to cover these costs. In contrast, reimbursement of travel and other business expenses by a company suggests an employment relationship.
- Provision of tools and materials. Workers who use company-provided equipment, tools, and materials to perform their work are more likely to be considered employees. Work largely done using independently obtained supplies or tools supports an independent contractor classification.
- Investment in facilities. While independent contractors and freelancers usually pay for their own work facilities, most employees rely on their employer to provide work facilities.
- Realization of profit or loss. If a worker’s earnings are predetermined and have little chance to realize significant profit or loss through their work, they are generally considered to be an employee.
- Work for multiple companies. Workers who provide services for multiple companies concurrently are likely to qualify as independent contractors.
- Availability to the public. If a worker regularly makes services available to the general public, they could qualify as an independent contractor.
- Control over discharge. If a company has the unilateral right to discharge a worker, this suggests an employment relationship. In contrast, a company’s ability to end an independent contractor relationship generally depends on the terms specified in the contract.
- Right of termination. Most employees can terminate their work for a company unilaterally without liability. Independent contractors cannot quit their work engagements without liability, except as permitted under their contracts.
What happens when you hire an employee?
If you hire an employee you will need to register with your state and begin running payroll, if not already. I recommend using Gusto. Let's chat to determine what is best before you make any moves.
Gusto integrates with Xero, and offers HR packages should you need help with employment contracts, benefits, and job descriptions.
How to pay contractors & 1099s
If your hire is a contractor, it's best practice to obtain a W9 from them upfront. You can do this by sending this form and retaining for your records.
You should pay them in a way that either prepares the 1099 for you (a payroll system) or allows you to not need to file one.
Email me to help you decide, but here are my general recommendations.
Payroll systems will handle the 1099 for you and allow you to send payment to your contractor. They have monthly fees. If you're paying yourself a salary as an S Corp owner anyway and this person will be ongoing, this is a good way to pay.
To avoid having to issue a 1099 at all, pay via a third party processor. This may happen if you contractor invoices you through a payment processor like Stripe, PayPal, Dubsado, Honeybook, Wave, QBO, or Xero. In this event you do not need to file a 1099-NEC because the payment processor will issue a 1099-K if requirements and thresholds are met. This is my preferred method though your worker may get confused. See the next question.
How to handle W9 requests from your clients
If you have a client who paid you via cash, check, bank transfer, or a personal app (Zelle, Venmo, PayPal friends & family), then your client is right to ask you for a W9. If you need help filling that out, just ask.
However, most of my clients should not receive 1099s from their clients because they accept payment via a third party processor (Stripe, PayPal goods and services, Wave, Honeybook, Dubsado, etc etc etc).
Below is the swipe copy you can share with your client who is making this request.
_____________________
Per our accountant, a 1099-NEC is not required because we were paid via a third party payment network that will issue a 1099-K instead.
Please reference the 1099 instructions, page 3 bottom right that reads “Form 1099-K. Payments made with a credit card or payment card and certain other types of payments, including third-party network transactions, must be reported on Form 1099-K by the payment settlement entity under section 6050W and are not subject to reporting on Form 1099-MISC. See the separate Instructions for Form 1099-K.”
https://www.irs.gov/pub/irs-pdf/i1099mec.pdf
_____________________
Sometimes you will still receive pushback saying they want to file "just in case". I just keep pushing back because you don't file returns you aren't required to file "just in case". Since your income received from a third party processor is reported on a 1099K, if your client also reports it then it is double reported. If you are having trouble, just reach out.
Reporting & Taxes
How to make sense of my financial reports?
You hired us to make sense of your financials. These resources will take it to the next level!
HOW TO READ AND INTERPRET REPORTS - pdf document explaining each report in detail.
CASH SUMMARY CHEAT SHEET - turn your cash summary report into plain English!
Things you can't deduct (and the risk you take if you do anyway)
For the most part, you are able to deduct expenses you pay from your business for the purpose of generating income that are necessary and ordinary in your line of work.
It gets tricky when the expense can double as a personal expense.
If you have a question about deductions, email me and ask. I will likely defer to your tax preparer for the final decision but am happy to chat it through specifically.
If you tell us something is a business expense, we will take your word at faith.
Our engagement does not have us auditing your books - we are simply recording the information and answers you provide to us.
That means if you tell us something is a business expense but it is not, the onus lies with you.
If you take the standard mileage deduction (see Business Mileage below) you cannot also write off fuel and automobile maintenance.
Clothing for photoshoots is not a business expense if it can be worn personally.
Your Amazon purchases can be written off if you are purchasing office supplies or other business expenses, but your personal Amazon charges should be paid with your personal card.
Apps used for business can be purchased on your business card, but your personal apps should be paid personally.
Meals can be deducted if there was a business purpose, but a family and friends dinner or your morning coffee or afternoon Uber Eats cannot.
We have no way of knowing if your Amazon, Apple, Target, Meals, or Travel purchases are truly for business.
Most of the time we have this conversation upfront and ensure you know that if you are paying for any of the above on your business cards, we are going to treat it as a business expense unless otherwise notified.
If these expenses are not for business, and you get audited, it is your responsibility to have receipts to back up your deductions.
If you have taken non-business expenses as business expenses and therefore underreported your taxes, you may be subject to having to pay the tax you should have paid, plus penalties, interest, and the cost of representation under audit. You should consult with your CPA regarding deductions and also understand your responsibility and risk.
Business Mileage
My clients typically use the standard mileage rate, and for my clients who like to see this reflected in their books, I have them send me their previous month's business mileage so I can make a journal entry.
You can read my blog post about the different ways to deduct business milage here.
Estimated Taxes
You should save 25% or more of your profit for taxes. You should work with your CPA to determine what your estimated taxes should be and when you should file.
Here are some general tips:
Who needs to file: Sole proprietors who have a profit in their business. Sole proprietors file their business income on Schedule C of their 1040. Sole proprietors are either doing business by themselves with no business registered, as a registered sole proprietorship, with a DBA, or as a single-member LLC.
What estimated tax payments are: An estimate of taxes that allows you to avoid penalties and avoid paying in taxes all at the end of the year when they money may have been spent already.
How to calculate your payment: 25% or more of your profit
How to file your estimated payment: Either online or by mailing a check and a paper voucher. Your CPA can help with this and should be involved.
Partnerships & Referrals
Ways we can partner outside of your books
Podcasts: I love to share tips and stories on podcasts. I'd love to be on yours or have you on mine! Email me!
Expert Trainings: I'd be happy to speak inside of your program, whether live or prerecorded, to answer financial questions your members have.
Happy? Refer my services & earn!
The greatest way to say "I love you" is by referring your friends who could use a good bookkeeper!
Just send them to my quote form at www.simplybooked.llc/quote and tell them to put your name in the field for "Client Referral."
If they sign on for monthly bookkeeping services I'll send you a $100 referral fee via PayPal when their first payment is made.