Tag Archives: small businesses

How to Issue 1099s and W-2s from Gusto Payroll (for 2023)

As a CPA whose company works with loads of small businesses that need to process payroll, I’ve used quite a few payroll systems through the years… and Gusto has become our favorite. It’s not without its quirks and issues, but overall it does a great job for a great price, and — key for the work we do — it syncs nicely with QuickBooks Online, as well as their own Benefits company and with Guideline retirement.

(By the way, our referral link will get you a $100 prepaid Visa card if you sign up and run your first paid payroll before Jan 31st, 2024! Bonus! Happy New Year!)

It seems that for 2023, Gusto has slightly changed the details for how they handle distribution of 1099 and W-2 forms — and so that no one ends up without a copy of their important documents, I am sharing the step-by-step process that we went through for our own firm, in hopes that it helps you manage it in your own small business.

Spoiler alert: the process of DIY-ing (aka creating the packet of 1099 or W-2 PDFs, going to the Tax documents section and finding/ downloading these PDFs, printing them, and mailing them) was enough of a pain that for sure next year I will just click the option to pay $3 per form to have them mailed for me for anyone who hasn’t selected “electronic-only delivery”. But before then, I will contact all my employees and contractors and ask them to please change their preferences to be electronic-only delivery next year, since the thing I would be mailing them is literally a printout of the same PDF that they can download themselves from their Gusto account.

And now — here’s the process I went through, in real time, as I walked through the steps myself.

First off, as the company/ employer, I received an email from Gusto (though it incorrectly stated that these are client tasks, rather than firm tasks) stating that I need to distribute important payroll forms to recipients before the IRS deadline of January 31, 2024.

When I click on the “Let’s do it” button for 1099s, it takes me (after logging in) to the screen below, which notes “If you have us mail forms for you, you can choose to exclude anyone who’s consented to have them delivered electronically.” This is pretty important, as I encourage everyone to accept this delivery method, even if they also request a paper copy. I am curious to see if they make this option clear even if I select “I’d like to download and distribute them on my own,” and will give that approach a try.

After selecting the second option — “I’d like to download and distribute them on my own” (DIY), I get this screen:

And then this screen:

And good news! Even in the DIY version, you can select “Only contractors who haven’t requested electronic-only copies,” which is a real win for everyone. It would be nice if they made that clearer on the first page, and simply said, “you can choose to exclude anyone who’s consented to have them delivered electronically.”

I take that back! NOTE: After going through the whole process (you’ll see this below), I never did get a packet that was just for the electronic-only folks. I was only able to download a packet for ALL employees. I will have to pick out which ones selected paper delivery and only print and mail those. Or I can go into each employee and download the form individually. What a pain! I don’t want to reward Gusto for handling this poorly, but if I could go back again, I’d have chosen to have them mail the ones who set their preferences for paper forms, for $3 each.

I clicked on “Create packet”, and nothing happened. However, this box shows on the right-side, so I’m guessing that’s why:

(I think this could have been handled a bit better by the Gusto programmers.)

Now, if you had any contractors who did not select electronic delivery, you would in theory eventually get a copy of that packet, and use the PDFs of the 1099s that were made available to you by Gusto — you would print and mail them yourself. But in my experience with the W-2s (below), I was only ever able to download a copy of ALL the forms, not just the ones that set their preference to receive a paper copy. Or I could go to each employee and download them individually. Therefore, as I keep saying… if I had this to do over, I’d pay Gusto the $3 per form for just the ones that requested paper forms. And in future onboarding, I’d ask them to set it to “electronic-only”.


Next, we’re going to give the W-2 form distribution a try. I clicked “Home” to get to the main page of my Gusto account but got an error message, probably because as an accountant user, it got confused about whether to take me to my own firm homepage or my client dashboard. So I went back to the original email and started from there. As expected, it brought me here:

And after selecting DIY, it took me here:

After clicking “Continue” it took me to a page that nicely spelled everything out for me:

It turns out that four of my employees have requested paper copies. They may have also requested electronic copies, but since that doesn’t matter one way or the other here, it’s not indicated. (Note to self: ask your team members to select electronic-delivery-only!)

So this time when I clicked the “Create packet” button, I got a pop-up.

I clicked on the “Go to Tax documents” button and it took me to a very familiar screen (since I have to download this information on behalf of clients from time-to-time), with a tab for each type of tax document.

I clicked on W-2s and followed the prompt to download my 2023 W-2 packet — but this turned out to be the entire employer-copy of the W-2 packet. So, I clicked below that on the option to “Distribute 2023 W-2s” — but that just took me back to “Choose how to distribute W-2s” starting page.

To be fair, it did say in the pop-up that they’re creating my packet and would email me when it’s ready… I’ll go check email next.

But first I want to point out that this page also makes it clear in the employee list at the bottom what the delivery preference for each employee is, making it easy for me to make good on my “note to self” above and reach out to those who requested “paper and electronic”. (By the way, my own name is on that list. Sigh.)

It’s many minutes later and I still don’t have an email saying my packet is ready.

At this point, I’m wishing I’d just paid Gusto $3 each for them to mail these for me.

I’m going to sign off on this blog post for now and return to it once I get an email from Gusto. And if I don’t, I will shake my fist at them and ask my team members if I really have to spend $3 each to send them a paper W-2 when they already have a PDF.

Update: I never did get an email from Gusto saying my packet of just the ones that need paper copies was ready. And when I went back in to just pay Gusto the dang $3 each, I got this screen:

So apparently that’s not even an option anymore. Heads-up! (This is the part where I scroll back to the top of my post and give everyone a spoiler alert before starting this process.)

The key takeaway I’d like to share with clients and readers is that you should absolutely, unquestionably go into “Tax Documents” and look at the list of people under the W-2s and 1099s tab to see if anyone chose paper-only (I am presuming that’s an option but do not truly know… because it’s 2024 and who would choose that, anyway). If anyone did *not* consent to electronic delivery, then go spend that $3 per employee. For everyone else, reach out and ask if this is really necessary, and suggest they (myself included, whoops) change their settings — not because the $3 per form is a prohibitive cost, but because the amount of time and energy spent in making that happen (any at all) is simply not worth it in this day and age of electronic communication.

I will leave you with a hilarious poem that a dear colleague of mine shared with me recently.


If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.

Rules for When To Issue a 1099 Form to a Vendor – Updated for 2023

As is the case every year, we’re hearing from lots of folks confused about when to send a 1099 form or other “information returns” to someone.  It is true that over time, these forms have continued to change, and the rules have become more specific… but the basics remain the same. The most important point is that only businesses need to issue 1099s — if you paid someone for personal purposes, you are not (yet) required to send them or the IRS a Form 1099.

WHAT’S NEW (or isn’t) FOR 2023:
– Beginning in 2022, the 1099-NEC was made so that it’s no longer year-specific; there are no changes to the form for 2023.
– The IRS launched IRIS, a new free online portal, for businesses to file 1099 returns. (Beginning January 2024, you will no longer be able to file using a legacy transmitter code using the old FIRE system.)
– You must file now file 1099 Forms electronically if you have 10 or more information returns (down from 250).

– There are even more complexities regarding whether or not to issue a 1099 based on the payment type, and I expect this area to become even more challenging in future years, as new payment platforms continuously come into being.

Here’s a crash course for each type of form, followed by an FAQ.

1099-NEC
This form was new for 2020 and replaces the old Box 7 of Form 1099-MISC. “NEC” stands for “non-employee compensation”. It is due to recipients and the IRS by January 31st (or the first business day after that, if 1/31 falls on a weekend).

If you paid:
1) a NON-corporation (*see below);
2) for services (not products);
3) via check, cash, ACH, Zelle, or wire transfer — but not merchant services or electronic payments (such as credit & debit cards, PayPal Business, Venmo Business (**see below);
4) $600 or more in a calendar year;
then you need to send them a 1099-NEC.

(*) A lot of folks get confused and think the rule is if you paid an “individual,” but really the rule is a “non-corporation,” which means that partnerships and LLCs are included. Just because they have a business name doesn’t mean they’re incorporated. You cannot depend on the company’s name to determine corporate status, nor can you rely on the state LLC/Corp database, as it only indicates the entity type at the state level — almost any type of entity may elect corporate status with the IRS.

So, keep in mind that a company can be an LLC but be taxed as a corporation. In this case, you would not need to send them a 1099, because in the eyes of the IRS, they are incorporated. Here’s an example of a W-9 showing an LLC that is taxed as an S-Corp:

This is one of many reasons you should collect Form W-9 from all service vendors before giving them their first check, just to be safe. The person filling out the W-9 will indicate their entity type and whether or not they are taxed as a corporation.

There’s also an exception to the incorporation rule for attorneys and law firms. You must issue a 1099 to a lawyer or law firm regardless of whether they are incorporated. (Law firms and attorneys have so many specialized 1099 issues, they get their own blog post.)

(**) There’s a lot of confusion over Venmo and PayPal, because there are personal-use “Friends & Family” versions as well as business versions of both platforms. Legally, no business should be using the non-business versions of these payment types… but in real life, many do. It’s very hard to distinguish which payments were made using which method — in theory, a 1099-NEC would need to be issued to a vendor who was paid via a personal Venmo or PayPal method, but I’m not sure how this would be tracked. My recommendation (for many reasons) is to only use the business versions, and then the 1099-NEC is a non-issue (because Venmo and PayPal will issue a 1099-K instead).

I know, that’s all very confusing. Here’s a nice, simplified decision-tree provided by our friends over at Bookkeepers.com, courtesy of Bookkeeping Buds.

However, it’s easy to end up with issues like “what if I paid with my credit card, but used PayPal Friends & Family,” or “I use a practice management system that is funded with a bank account, so why do they issue a 1099-K,” or any number of confusing situations based on payment type. There’s simply no easy answer to these questions.

It’s so confusing, in fact, that my colleague Jennifer Dymond saw the need, and created an absolutely incredible resource at 1099problems.io which goes into detail about which payment methods are included on a 1099-K versus which ones you must issue 1099-NEC or 1099-MISC for yourself; it’s maintained regularly and updated as the proliferation of non-traditional payment methods continues. The first 1,099 people to subscribe using code DANCING1099 will receive 10% off their first order (offer expires March 31, 2024).

1099-MISC

Items such as rent payments, royalties, attorney settlements (as mentioned above, not payments for legal services), and medical healthcare payments will still be reported on Form 1099-MISC, though the form has been redesigned and the boxes renumbered.

Report prizes and awards of $600 or more that are not for services performed in Box 3. Include the fair market value of merchandise won. And be careful here, as it is easy to accidentally include these on Form 1099-NEC if the recipient also provided unrelated services.

  • Rent paid ($600 or more) (Box 1)
  • Royalties paid of at least $10 or more (Box 2)
  • Prizes and awards and certain other payments ($600 or more, see instructions for Form 1099-MISC, Box 3 for more information)
  • Backup withholding or federal income tax withheld (any amount) (Box 4)
  • Amounts paid specifically to physicians, physicians’ corporations, or other suppliers of health and medical services ($600 or more) (Box 6)
  • Direct sales of at least $5,000 of consumer products to a buyer for resale anywhere other than a permanent retail establishment (Box 7)
  • Gross proceeds paid to an attorney ($600 or more whether or not incorporated) (Box 10) – “made to an attorney in the course of your trade or business in connection with legal services, but not for the attorney’s services”; for example, a settlement agreement.

The deadline for providing this form to recipients is the same as above, January 31st. However, the deadline for filing 1099-MISC with the IRS is February 28 if filing on paper, and March 31 if filing electronically.

1099-K

It’s unlikely that anyone reading this will be in the position of issuing Form 1099-K to vendors — but you should know about this form, for a few reasons:
1) You are likely to receive one.
2) It’s the reason you don’t have to issue 1099-NEC to anyone you pay via credit card/debit card, a business PayPal account, a business Venmo account, or any “merchant service” system.
3) You may need to reconcile this form against the amount of sales income you report on your tax return.

Form 1099-K is for payments made in settlement of “reportable payment transactions”, which is any credit card, payment card or third-party network transaction. So if you receive payments in this way (unless you only accept checks, e-checks, ACH, or zelle/QuickPay, you probably do), then you’ll get a 1099-K for this total.

But because these amounts are reported to the IRS for you, you don’t need to issue 1099-NEC or 1099-MISC forms to vendors whom you paid using one of these methods. In that case, the recipient could end up having the same income reported to the IRS twice.

The rule used to be that this form was issued to anyone who had more than 200 transactions or $20,000 worth of transactions — but starting in 2024, that threshold will drop to only $600. (This implementation has been delayed twice already and AICPA is lobbying for a more reasonable threshold.) The IRS is now planning a phase-in of $5,000 for tax year 2024.

As a bookkeeper, accountant or tax preparer, it’s important to protect your small business clients by making sure all taxable income is being reported on their books/returns. If the 1099-K is for an amount that is lower than what’s on the income section of the Profit & Loss, it’s not likely to be an issue. But if it’s higher, you’ll need to do a reconciliation to show that the difference was due to non-taxable receipts such as sales taxes collected, tips collected, refunded sales, and the like.

1099-INT

This form is issued to anyone who lent your business money, and your business paid them at least $10 of interest in the past calendar year. It includes owners, partners, and shareholders.

Note: do not issue this form for accrued interest; it is only for actual payouts of interest in cash or trade.

The form is due to recipients by January 31 (February 1 in 2021), but isn’t due to the IRS until March 1 if filing on paper and March 31 if e-filing.

If not e-filing, you can use the IRS’s fill-in pdf Copy B for the recipient copy, but for the version that goes to the IRS, you have to order an official form with special scannable ink — they’re free, but they take a while to be mailed, so fill out your request early. Make sure to mark the year you are filing for, not the current year — an easy mistake to make.

Another note: I have had clients reach out confused by the language “You are not required to file Form 1099-INT for interest on an obligation issued by an individual”. This means if the loan were TO an individual rather than FROM one, and the individual paid interest to the company. (This is not usually the case.) In that situation, the individual would not have to issue the company a 1099-INT (although the company would still have to declare the interest income).

1099-DIV

This form is issued to a shareholder of a C-Corporation for dividends or other distributions paid in the past calendar year.

Most folks don’t think this applies to them — but if you own a business that is taxed as a C-Corp, and you took money out that wasn’t W-2 or loan repayments, then you may have issued yourself dividends. (And if it was for a loan repayment, did you pay the required amount of interest? If so, see the “1099-INT” section above.)

The form is due to recipients by January 31 (February 1 in 2021), but isn’t due to the IRS until March 1 if filing on paper and March 31 if e-filing.

If not e-filing, you can use the IRS’s fill-in pdf Copy B for the recipient copy, but for the version that goes to the IRS, you have to order an official form with special scannable ink — they’re free, but they take a while to be mailed, so fill out your request early. Make sure to mark the year you are filing for, not the current year — an easy mistake to make.

1098

This form is to report mortgage interest and real estate taxes. You may not think it applies to you, but if you do the bookkeeping for or are a member of a housing cooperative, you may find that it does. This needs to be issued to housing co-op members for their allocated portion of mortgage interest and real estate taxes paid by the cooperative, so they can deduct them on their personal tax return, Form 1040, Schedule A. If not e-filing, you can use the IRS’s fill-in pdf Copy B for the recipient copy, but for the version that goes to the IRS, you have to order an official form with special scannable ink — they’re free, but they take a while to be mailed, so fill out your request early. Make sure to mark the year you are filing for, not the current year — an easy mistake to make.

Frequently Asked Questions

What do I do if the vendor will not give me their Tax ID Number, which I need to file the 1099?

First off, it’s the business’ responsibility to obtain this number. That’s why I recommend getting the W-9 from the vendor before giving them their first payment. But in the case where it’s 1099-time and you still don’t have that TIN for some reason, respectfully let the vendor know that not having their info will not prevent you from filing the 1099. It just means the IRS will receive it with “REFUSED” written in the field where the number should be (or if you use an e-filing program, you will check the box that the number is unavailable). This will almost always trigger an audit for both the business and the recipient, which no one wants. Presented with this information, I find that most non-compliant vendors are suddenly able to fill out that W-9 form after all.

Do I really have to send one to my landlord? They get angry when I bring it up.

If your landlord is not incorporated, yes, you do. If it makes them mad, then consider why… are they trying to avoid declaring it as taxable income? Is that the type of person you want to rent from?

What if you forgot to issue a 1099 to someone?

It’s never too late! Since the statute of limitations never starts if you don’t file a return, penalties and interest can continue to accrue forever. If you noticed that you forgot to file a 1099, even for a prior year, reach out to the recipient in question and make sure they declared and paid taxes on the income you inadvertently forgot to remind them about — and hopefully they have. In this case, no amended return will be required on their end, and the form’s arrival will not come as an unwelcome surprise. If not, then that’s a bigger concern. It is the responsibility of each recipient of income to declare it on their return, regardless of having received the 1099. Not getting the form does not exempt a taxpayer from declaring the income they earned. So, the business owner needs to evaluate the risk involved to their company in knowingly refusing to comply with tax law, versus the recipient’s desire to evade taxes.

What do you do if you receive a 1099 that is incorrect or unnecessary?

If you receive a 1099 that has incorrect information on it, simply reach out to the issuer to ask for a corrected 1099. Do this as soon as possible, as it will help them to fix it before it is submitted to the IRS.

If they will not correct the total, then declare the full amount on your tax return, but “back out” the incorrect amount as a negative, with an explanation to the IRS for why this amount was inaccurate. If you receive an audit notice, provide the IRS with the documentation showing why your calculation is correct, and the support showing you reached out to the issuer when you realized the form was not right.

If you should not have received a 1099 at all, follow the same advice as above. A good example of this would be if you received a 1099-K for credit card payments, but also received a 1099-NEC from the company that paid you (this is quite common… it is extremely challenging in most bookkeeping software to distinguish how a bill was paid in most reports). In this case, if the customer will not void the 1099 form for some reason, simply declare the full amount on your business’ tax return and “back out” the amount that was double-issued, with the explanation that it was already declared in income via 1099-K or some similar wording.

However, if the reason you should not have received the 1099 was that you are taxed as a corporation, and you’ve already declared this income on your tax return, then you can ignore the form — it will have no effect on anything and was just a waste of time on the part of the issuer.

How do I run the 1099 report in QuickBooks? Won’t it tell me who needs a form from my company?

Most bookkeeping professionals don’t use the 1099 report that QuickBooks generates — it’s too prone to user error when setting up the vendors, accounts, and dollar-thresholds. Instead we use a program like Keeper to help us identify potential 1099 vendors and transactions, or in QuickBooks, we run the detail of the cash accounts and filter by transaction type – Check, Expense, Bill Payment… then sort by Name. The problem may be that there is not a name in there, or it is not a Vendor Name: another great reason to make sure you’re setting up bank rules and being careful about data entry to include vendor information on all transactions.

How does PayPal work?

Oh my goodness, is this ever complicated.

If you pay a business using your personal bank or Paypal account, or pay through “Friends & Family” PayPal you do need to send a 1099 (if over $600), because PayPal thinks this was a personal transaction — because, as I mentioned at the top of this post, personal transactions do not require 1099 forms. If you had used “Business” PayPal, then PayPal would send the 1099-K and there would be no reason to issue a 1099-NEC.

A colleague of mine recently called PayPal support about this and here was their response:
If the transaction detail says “money sent”, those qualify as Friends & Family transactions. However, if the transaction says “invoice paid” or “payment”, then it is a business payment — even if it’s within a personal Paypal account.

What about Venmo?

According to Venmo’s term of service, using it for business is a violation, and they can seize whatever money you have sitting in your Venmo account if they catch you using it for business.

However, we know sometimes this is the best way to collect money from folks, or that customers will send you Venmo funds without thinking about it, or that you’ll do the same with your vendors.

Venmo is considered a “peer-to-peer transfer service”, and not a third-party network. Therefore, treat these like cash payments from a business and send a 1099 form to your vendor.

(Side note: Venmo is starting to accept applications from a number of businesses for a new “Business Venmo”, but it’s brand new and very limited. Be careful with this. The problem with Venmo, PayPal, Bento, and other similar companies like that is that they don’t act like they’re banks — and their staff doesn’t realize that banking is actually the primary function of the company they work for — they don’t get the same kind of intensive training that bankers do. I recommend avoiding Venmo for business payments as much as possible.)

What about the states?

Okay, this gets pretty overwhelming pretty fast, so I am linking to a site that has all the states’ rules in one place — https://www.taxbandits.com/state-filing-requirements/

The short version here is that not all states have the same rules. Some allow the IRS filing of certain information returns to substitute for state filing requirements, and some don’t. Some require e-filing and some allow physical mailings. Many states participate in the Combined Federal/State Filing Program. The IRS will automatically forward 1099 information to participating states, eliminating the need to file separately with these states.

So please, do your homework when it comes to state filings.

Where can I find more info on due dates, penalties, and real-life scenarios?

Check out my colleague Mark Kohler’s excellent blog post. His charts for deadlines and penalties are very handy.

Another colleague, Questian Telka, and I worked together on a video series on what a W-9 is, and how to prepare a W-9 for each type of entity; and she followed it up with another video on whether or not you need to issue a 1099.

And as I mentioned earlier, yet another trusted colleague, Jennifer Dymond saw the need for a resource that details which payment methods are included on a 1099-K versus which ones you must issue 1099-NEC or 1099-MISC for yourself, and created 1099problems.io to help navigate these complexities. It’s updated regularly, as the proliferation of non-traditional payment methods continues. The first 1,099 people to subscribe using code DANCING1099 will receive 10% off their first order (offer expires March 31, 2024).

And there you have it! Simple, see?

**many thanks to The Bookkeeping Buds for editing assistance**


If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.

IRS Sent 8955-SSA Penalty Notices In Error

We received a few frantic calls and emails in the past month from clients who opened their mail to find a penalty notice from the IRS for their 2022 Form 8955-SSA — some for tens of thousands of dollars.

As background, Form 8955-SSA, also known as the “Annual Registration Statement Identifying Separated Participants With Deferred Vested Benefits,” is an report that retirement plan sponsors (the entity that established the plan for a company and its employees — usually the employer itself, or a union) must file with the IRS to report information about certain participants (typically former employees) who have vested benefits that have been deferred according to the plan. It’s a required annual filing with the IRS for those who file Form 5500 and has the same filing deadline (July 31, 2023 for 2022 plans — October 15, 2023 on extension).

But most businesses contract this work out to a plan administrator, a service provider that has expertise in managing 401k plans. So you can only imagine how terrifying it must have been for a bunch of business owners to get these notices — meaning that presumably, their trusted outsourcing agency was not doing their job. (Or… let’s be honest — more likely, very few of the small businesses had any clue what the notice was for, apart from the fact that a-it was from the IRS, b-said they’d done something wrong, and c-they owed money. Scary stuff.)

Thankfully, it turns out that these notices were the result of an IRS glitch in the program that receives and processes these forms. The IRS acknowledged the error, fixed the issue, and updated its records to “reflect the accurate filing status of the affected plan sponsors”.

The IRS believes the problem originated with organizations using the Department of Labor’s EFAST2 system to file their Form 8500 Annual Return/Report of Employee Benefit Plan before the July 31 deadline, rather than electronically through the IRS’s Filing Information Returns Electronically (FIRE) system.

If you received a CP 283-C penalty notice dated before September 1, 2023, and you are sure that you filed your 2022 Form 8955-SSA on time and completely, you do not need to take any action. You can ignore the notice and rest assured that your filing is in good order. The IRS will not impose any penalties or interest on your account.

However, if you want to verify your filing status, you have a couple options.
1) First off, contact your plan administrator or service provider for confirmation of your filing.
2) You can also request a transcript of your filing from the IRS to double-check the assurance of your provider.

The IRS released a bulletin addressing the mistake and asked readers to contact them at 877-829-5500 with any questions.

At retirement age, the Social Security Administration informs affected individuals that they may be eligible for benefits under previous employers’ retirement plans based on information reported to the IRS on Form 8955-A, explained Allison Wielobob, Chief Legal Officer of the American Retirement Association, so it’s essential that this information is filed accurately and timely.

Take a deep breath. We all make mistakes. Even the IRS.


If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.

Urge Congress To Delay FinCEN “BOI” Reporting Burden for Small Businesses

The past few months, we’ve been keeping an eye on a new reporting requirement that will create a massive burden on small business owners. Starting in 2024, millions of small businesses will be required — as part of an anti-money-laundering initiative — to file a “beneficial ownership information” (BOI) report with the Financial Crimes Enforcement Network (FinCEN, a branch of the U.S. Department of Treasury). Failure to comply can cause the company and those responsible steep fines — $500 per day up to $10,000 — and even possible jail time. 

And yet, the vast majority of small business owners know nothing about this new rule, and just a few months before year-end, guidance is still forthcoming. Too many questions remain regarding how it will affect the targeted small business owners — those who run a business that had to file a document with the Secretary of State to create the company (C-Corps, S-Corps, and LLCs, most commonly).

The super-surprising part here is that exemptions are only designed for larger companies — not small businesses. Corporations or LLCs with more than 20 full-time employees, more than $5 million in gross receipts, and an operating presence at a physical office in the USA — as well as those already regulated by the federal or state government — qualify for a “large operating company” exemption.

The National Federation of Independent Businesses has prepared a handy fact sheet available to the public that includes a great summary of the information that owners will need to provide:

The NFIB Government Relations Director Jeff Brabant comments, “anyone who has a 25% or greater stake in the company or senior officer will have to register a copy of their driver’s license and business information. This is a daunting task and probably the biggest regulation that no one is talking about right now.”

“NFIB is pushing for a full repeal of this legislation,” said Brabant. “We feel it’s unnecessary; however, administratively there is a chance that FinCEN delays it, and there’s also a chance that Congress delays it for one year. The statute allowed for up to two years for reporting for companies once this is passed on January 1; however, FinCEN chose one year. So FinCEN can choose to delay it another year and that’s something we hope they do.”

In today’s AICPA Town Hall, they issued a call to action, asking small business owners — CPA firms especially — to contact their representatives by September 15th and request a delay of the implementation. They’ve provided a Word Doc template with background and speaking points for your email or phone call, and have encouraged members to share it widely.

From the AICPA:

Two bills have been introduced in U.S. Congress to delay this rule – H.R. 4035 and S. 2623, both titled the Protecting Small Business Information Act of 2023. These identical bills introduced in the U.S. House by Representative Patrick McHenry and introduced in the U.S. Senate by Senator Mike Rounds would delay the start date of the rule providing additional time for small businesses to learn about and better understand their new reporting requirements. We want to obtain as many cosponsors in both the U.S. House and U.S. Senate as possible, to keep these bills moving. We are asking you to reach out to your House of Representatives Member to ask them to cosponsor H.R. 4035, and to also reach out to your two United States Senators to ask them to cosponsor S. 2623.

· You can find your House of Representatives Member at https://www.house.gov/
· You can find your two U.S. Senators at: https://www.senate.gov/senators/senators-contact.htm

In addition to the Word Doc and Town Hall presentation, the AICPA has created a Beneficial Ownership Information resource page, and an FAQ for CPA firm practitioners — many of whom are struggling with how to help their small business clients implement yet one more set of compliance requirements.

Wolters Kluwer has also created a free set of resources for those who may be affected by the new legislation, which you can access here, including an on-demand webinar where you can learn more.


If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.

What Illinois Secure Choice Retirement Means for Your Small Business or Non-Profit

Click the image to watch an excellent 20-minute overview video of the IL Secure Choice Program.

There have been rumblings in the news for quite some time now about small businesses being required to provide retirement plans for their employees — but most owners seem to be turning a deaf ear, presuming that their small size exempts them from the requirement.

Not so! There is a phased-in approach to the State of Illinois’ new plan, and this November (2023) is going to catch a bunch of folks unprepared, as the requirements will extend to any business with five or more employees.

That probably means you — and if this sends you into a panic, no fear… we’re going to outline what the requirements are and will offer a couple of suggestions for getting into compliance.

What Is Illinois Secure Choice?

It’s a combination of legislation that requires most employers to offer a retirement plan to their employees — and a system that fills the gap for employers who do not currently offer retirement savings via payroll deductions.

In the words of the Illinois Department of Revenue, “Secure Choice is a program administered by the Illinois Secure Choice Savings Board for the purpose of providing a retirement savings option to private-sector employees in Illinois who lack access to an employer-sponsored plan.” Check out this excellent 20-minute video for an overview.

Enacted in 2015, the Illinois Secure Choice Savings Program Act has been phased in over many years, starting with companies with many employees, and working its way to those with very few staff by comparison.

Wave One began in 2018, and included employers with 500 or more employees. Wave Two, in 2019, included employers with 100‑499 employees, and another wave later that same year included employers with 25-99 employees. The deadline for wave Four — employers with 16 or more employees — was Nov. 1, 2022. The deadline for wave Five, employers with five or more employees, is Nov. 1, 2023.

Why Is Illinois Making Small Business Owners Do This?

Research has shown that Americans are 15 times more likely to save for retirement when it’s done through a payroll deduction at work. With more than 50% of us unprepared to retire when the time comes — even taking Social Security into account — the state decided that one way to address this problem would be to offer a program that helped the 40% of employers who do not offer a retirement plan a way to auto-enroll its team members into making payroll deductions into a Roth IRA.

Since it is estimated that most of us, when we retire, will need around 70-80% of pre-retirement income, the need to save is essential. The stress that it places on the social safety net when folks do not have sufficient funds to care for themselves after they stop working is enormous, so it’s not surprising that the state decided to facilitate individual savings through their workplaces.

It’s worth mentioning that the gap in retirement savings disproportionately affects workers at small businesses, lower-wage workers, people of color, and women. According to AARP, among businesses with 10-24 employees, nearly 59% of workers are not covered by a workplace retirement plan, and for businesses with fewer than 10 employees, that figure is nearly 73%.

Are Employees Being Forced To Save For Retirement?

No. Although the program starts with auto-enrollment, employees may opt-out (or back in) at any time, just like the majority of 401k plans out there. And as a reminder, the employer is able to offer their own 401k plan instead of IL Secure Choice; there is no obligation to participate in this particular program, as long as another qualified plan exists.

The default option for program participants is to enroll in a target-date Roth IRA with a 5 percent contribution rate. Participants can choose to change their contribution level or fund option at any time. Accounts are owned by individual participants and are portable from job-to-job.

Is The State of Illinois Going To Manage My Retirement Plan?

No. Investments are held in a separate trust outside the Illinois Treasury and are managed by private-sector investment managers. Acensus, a private-sector financial services firm, administers the program, which is overseen by a public board chaired by the Illinois State Treasurer. Each employee gets their own IRA account, which like any other IRA, belongs to them and is not associated with which employer or job they have.

As of January of this year, the program has hit the $100 Million mark in savings.

Does My Small Business Have to Participate?

If your company (or non-profit) has been in business for two or more years, has five or more employees, and does not already offer a qualified retirement plan, then you have two choices:

  • start offering a qualified retirement plan (more on that later); or,
  • participate in the Illinois Secure Choice program.

Supposedly, Illinois Secure Choice was not intended to replace or compete with traditional employer-sponsored qualified retirement plans, like 401(k), 403(b), SEP and SIMPLE programs. So if you’ve been thinking about starting one of those for your company — especially if you are interested in being able to sock away more retirement money for yourself than an IRA allows — this is the time to adopt a plan for your business, rather than signing up for IL Secure Choice.

That said, the fees and employer contributions involved in these types of plans can be prohibitive to many small businesses, which is one of the reasons the IL Secure Choice program was developed. The three “hurdles” that employers deal with that prevent them from having a retirement plan are 1) the administrative burden, 2) fees, and 3) fiduciary liability. The program was designed to reduce and, as much as possible, eliminate these concerns.

What Do Employers Need To Do To Comply?

Employers need to do the following:

  1. Choose whether to establish a qualified retirement plan or facilitate IL Secure Choice.
  2. Register your organization at employer.ilsecurechoice.com by the state-required deadline (or note that you are exempt because you already have a qualifying plan). All employers should receive a “welcome notification” email or letter with an Access Code; use this to register or inform them of your exemption.
  3. If facilitating IL Secure Choice:
    • set up account portal
    • submit and maintain employee roster
    • submit employee contributions every pay period
    • keep employee lists up-to-date
    • reconcile the employee contributions liability account each month and annually (to make sure the correct amounts have been both withheld and submitted)

Why Would We Choose To Sponsor A Qualified Retirement Plan (401k/403b) Instead of Illinois Secure Choice?

Our company, like many others, has chosen to offer a 401(k) plan instead of IL Secure Choice. Why?

  1. We are fans of increasing our own retirement contribution limits well beyond what can be saved with an IRA-based plan like IL Secure Choice (generally $6,500);
  2. The competitive advantage of offering a plan that includes employer contributions (not allowed with IL Secure Choice) is significant in our field of work;
  3. Guideline’s use of Vanguard “Admiral Shares” means we get the lowest expense ratio in the industry;
  4. The SECURE 2.0 Act offers tax credits of up to $15,000 over three years, to offset costs of setting up and contributing to the plan (!!!); and,
  5. We love the ease of not having to maintain employee lists or submit contributions (more on this below).

With Gusto, our preferred payroll provider (my referral link gets you $100 or more when you run your first payroll), and Guideline, our preferred retirement plan, the two systems sync with each other, so there’s no need to maintain employee lists or submit contributions — it all happens automatically. This is a huge administrative burden lifted for us. (Plus, our clients receive the first five months of Guideline fees free of charge, so that’s an added bonus.) This alone certainly isn’t worth it for your company when deciding which path to choose, but if you’re also eager to increase your own retirement contributions as a business owner, and to distinguish yourselves as a desirable employer in a competitive labor market, then in my opinion, it’s a no-brainer.

https://storage.googleapis.com/www.guideline.com/public-assets/outreach/State%20Mandate%20-%20IL%20-%202023.pdf

What Happens If I Missed The Deadline?

This came up in the Q&A in my state rep’s presentation (see the bottom of this post for the link), and the response was that although by statute, penalties can certainly be assessed, the goal is not to punish employers who are trying to do the right thing. Right now they are focused on outreach, education, and trying to ensure they are reaching employers who are required to comply. As long as you register as soon as you discover that you missed the deadline, you should be fine. Otherwise, employers that do not comply could face penalties of $250 per employee for the first year and $500 per employee for each subsequent year.

What Options Do My Employees Have For Investing?

Lots. And they’re good — the board who developed this program really was thoughtful in their design. To learn more, please watch the video I referenced at the beginning of the post, as this is meant to be a guide for employers who are trying to suss out their requirements. If you’ve already decided to go for it and facilitate the IL Secure Choice Plan, then you should definitely watch the video to learn more. It’s only 20 minutes long, you can do it!

How Do I Onboard And Submit Contributions?

Again, this blog post is meant to help employers sort out their requirements and get their bearings. To learn how it all works, please watch the 20-minute video referenced at the beginning of the post. (Honestly, if you can’t even watch a short video, then you’re really not going to like the administrative overhead of facilitating the program, and might want to consider going with the Gusto/Guideline combo I mentioned earlier.)

Where Can I Learn More?

The FAQ on the Illinois Secure Choice website is astounding in its comprehensiveness. Check it out. If you have a question, someone has likely already answered it there.

Additionally, there are these handy downloadable Program Resources:
Employer Overview
Eligibility and Rollout
Communication To Your Employees

As well as an excellent DIY Step-By-Step Guide for Employers.

They also offer these resources:

And if that all wasn’t enough for you, check out the most excellent version of this same presentation that was offered by my state rep’s office in December of 2022. It’s the same presenters of the slideshow portion as above, but there are also other participants that offer more context, and a very long and informative Q&A. They’ve granted me permission to share it here, and you can use passcode Vd*Uqgn2 to view or download the zoom recording.

Click the image above to access a zoom recording of the IL Secure Choice webinar — Passcode: Vd*Uqgn2

They truly did a great job with both the presentation and the Q&A and I encourage you to watch the whole thing while you’re reviewing the program details on the IL Secure Choice website.

Good luck navigating the system (if you are one of our clients — please reach out and we’ll help you), and congratulations on helping your employees save for retirement!


If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.

Nancy McClelland Featured on Accounting Insiders Podcast

Check out the podcast on Insightful Accountant’s YouTube channel.

I met the charming and intelligent Christine Gervais earlier this year, having shared an article of hers from Tax Practice News to my LinkedIn feed with my own perspectives. We immediately connected and met via zoom to get to know each other better, compare notes on our practices, and discuss ways in which we might collaborate. (Side note: TPN picked up an important article of mine shortly afterwards due to Christine’s recommendation.)

What an honor that some months later, I was named one of Insightful Accountant’s Top 100 ProAdvisors of the Year and accepted the award at the annual Scaling New Heights conference. I had recommended the jam-packed educational event to Christine, and to my delight, she attended and we met in-person. What neither of us expected was that she ended up being the interviewer in my Top 100 spot with Insightful Accountant, as Tax Practice News is a sister publication.

The question posed was, “if you could start your own practice over again, what would you do differently?” As anyone who has been in the industry — or run their own business — for a while knows, we are constantly making mistakes and learning from them. The goal is not to make the same one twice. So it’s natural to have regrets. But sharing those stories can be immensely helpful to others in the space — whether it’s younger entrepreneurs wondering which next steps to take, or colleagues who feel isolated because they think they’re the only ones who don’t have it all figured out yet.

We had a lovely chat — she’s very easygoing and conversational — and covered the following topics, among others:

  • Hiring your first employee
  • Traits in an ideal team member – intelligence, written skills, ability to learn, detail-oriented, team-player, caring attitude, enthusiasm
  • Interviewing with an eye toward building team culture
  • How teams can collaborate
  • Networking with colleagues
  • Trusting your team and clients to support each other
  • Importance of joining a professional organization and attending conferences
  • Standardizing systems and establishing workflows
  • Teaching accountants and bookkeepers what they need to know to specialize and establish a niche
  • How to find your professional community
  • Identifying and improving processes

I also give a shout-out to a few favorite resources, such as Keeper, AICPA Town Hall series, NATP’s tax education, NSAC and Co-op Professionals Guild, and of course, Bookkeeping Buds.

So check it out! And as always, please give us a like and a comment if you enjoyed it — really does mean so much to us and is very helpful in continuing to reach our audience.


If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.

Happy 22nd “Birthday” To The Dancing Accountant!

It’s been almost a year since our shindig with the Logan Square Chamber of Commerce, clients, and friends — celebrating 21 years of working with small businesses in our community. Today we celebrate our 22nd trip around the sun in this amazing neighborhood, and it’s high time we share all those great memories of the blow-out party that was.

Here are a few highlights — but there are so many more! Check out our photo album to view the rest of the festivities.

Many thanks to Gracie Hammond Photography for capturing so much joy in her photos that day. We treasure these memories. Again, catch the whole reel here (and if you’re a client, you have permission to download and use them for your socials).

Gratitude also goes out to cherished long-time client Vinejoy for the prosecco, Revolution Brewing for the beer, SipJeng for the CBD mocktails, Dill Pickle Food Co-op for the soft drinks, and the amazing Nick Connell for the balloon twisting and general merriment. We couldn’t have done any of this without the dedicated help of Sage Ferguson and her family, as well as the enthusiastic Candy Minx.

Most importantly, we have to thank our entertainers for the event: the best honky-tonk band in Chicago, if not the world — Wild Earp & The Free-For-Alls, with special guest Michelle Billingsley. We are indebted to them for their spirit, talent, charm, camaraderie, generosity — and patience, as the Chamber dealt with power and light challenges at the newly-activated Solidarity Triangle.

Speaking of the Logan Square Chamber of Commerce — this whole crazy event was dreamed up by their energetic Executive Director, who also invited our wonderful drink and food pop-ups, and we were touched that the two previous directors of the Chamber also attended (wish I’d thought to get a photo of all three of them together)! What an honor. Our neighborhood owes so much to LSCC, as well as their incredible Farmers Market.

A recap of the awards ceremony:

Many thanks to all our clients for contributing to the goodie bags, and especially to Jo Snow Syrups, Dill Pickle Food Co-op, and Soap Distillery for providing special prizes to the award-winners!

I could go on and on about what an incredible celebration it was — pretty sure I floated on Cloud Nine for weeks afterwards. Suffice it to say that having hundreds of clients, community members, friends and neighbors come together to commemorate the difference we’ve made together… feels really great. Thank you for letting us be a part of your neighborhood.


Interview: Meet the Brilliant & Insightful Nancy McClelland, CPA

Nancy modeling at the Beehive In Bloom Fashion Show | photo by Zak Jacobson

It’s not often I am described as either brilliant or insightful — so it’s a banner day when referred to as both.

And what better day than today, the 22nd anniversary of starting my own accounting firm?

To celebrate, I am delighted to share a recent interview with CanvasRebel, an online magazine and podcast that highlights voices of small business owners — in their words, “stories about our business or career that we might share at dinner or over coffee, but that wouldn’t necessarily make it into our memoir at the end of our lives; stories that illustrate the nitty-gritty details of what it takes to be successful day to day, how to build and grow a client base, recruit, train and manage a team or generate a living.”

I agree wholeheartedly with the folks who interviewed me. “There is so much we can learn from each other, and we hope these stories inspire you to pursue your passion and support those who are doing so themselves.”

Their questions were thought-provoking and caused me to truly reflect and think about some of the universal truths that I’ve learned in working with small business owners as their CPA. Questions such as:

  • What’s the best advice you’ve ever given to a client?
  • How did you get to where you are today?
  • What do you think helped you build your reputation within your market?
  • Do you have any insights you can share related to maintaining high team morale?

For the answers to these questions — and some top-notch in-costume photos, at various performances — please take a look at the interview. And if you just can’t get enough of the photos, check out some from our 21st anniversary party, last summer.


If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.

Final Restaurant Revitalization Fund (RRF) SBA Report Due April 30, 2023 — Here’s How to File

In this YouTube video, I demonstrate how to use the AICPA RRF tracker tool for SBA reporting.

Only 60% of restaurants that applied actually received funding for the popular Restaurant Revitalization Fund program (RRF), due to a failure of Congress to replenish the kitty with leftover PPP money, as was envisioned. (A substitute Restaurant Revitalization Tax Credit bill is currently languishing.) After the SBA disbursed the last of the funds in November of 2022, you might think that all was said and done on the topic; but in fact, recipients of those funds still need to report to the SBA that the money was indeed used according to the program’s rules.

There were three SBA reporting dates: December 31, 2021; December 31, 2022; and a final report date of April 30, 2023 — which is fast approaching. The RRF eligible expense period, however, allows costs from the very beginning of the pandemic, February 15, 2020, clear through to March 11, 2023. The two year-end reporting dates were intended as just a progress report of what the recipients had spent so far in eligible costs.

The great news for most businesses was that if all the RRF funds were allocated to eligible costs before the first reporting date, no additional reporting was required. If not, then the business needed to come back the following year and report a second time. At this point, most restaurants have (hopefully) already submitted their final report.

However, for those who missed the first two reporting dates; or somehow didn’t expend all the funds before the end of 2022; or simply did not understand how to report properly; or didn’t realize what a wide date range of eligible expenses they could use… there is one shot left at a final report to the SBA, or they risk having to pay back the funds.

This blog post (with a 20-min video walking you through the process) is our suggestion of how to translate the info you already have in your bookkeeping software into a format that will easily conform to the Restaurant Revitalization Award Portal requirements.

Sample email from SBA regarding the initial RRF year-end reporting

Spoiler alert: the process takes more than 5 minutes. It can easily take an hour or more. The actual entering of data into the SBA RRF portal is the part that only takes 5 or so minutes.

Our recommendation is to download the free Restaurant Revitalization Fund Tracker from the American Institute of CPAs (AICPA) website (as with their PPP Forgiveness Calculator, you do have to register for an account, but there’s no charge). However, instead of entering each individual transaction on the form (as it’s designed for you to do), our suggested shortcut is to take the information you already have in your bookkeeping file and enter each category as one line — then subtract all the non-RRF grants and assistance received, so that you’re not double-dipping.

As mentioned earlier, the RRF period runs from February 15, 2020 — the very beginning of the pandemic — to March 11, 2023. So we suggest you run a Profit & Loss for your company for the period of February 15, 2020 all the way through March 11, 2023 (or February 28, 2023 if you’re doing this before March 2023 is reconciled), and use those numbers to report what has been spent so far. Then enter the non-RRF grant funds as negative numbers on the same Expense Tracker tab, so that they net against each other. The result will be the data you submit to the SBA at restaurants.sba.gov once you log in to your portal.

I recorded a video illustrating the whole process back in December 2021 — the one big difference is simply the ending date of the report you’ll run.

Here are the steps:

Step 1 – download the AICPA RRF Tracking Tool
Step 2 – enter the name of your company in the Summary tab, cell A9
Step 3 – enter the RRF amount in the Expense Tracker tab, cell C6
Step 4 – run your Profit & Loss from 2/15/2020-2/28/2023 (or 3/11/23 if you’re doing this in April 2023)
Step 5 – export to Excel and save to your RRF file folder
Step 6 – on the Expense Tracker tab, enter summary amounts from the Profit & Loss for Payroll, Rent, Utilities, Food & Beverage, Maintenance, Supplies, Covered Supplier Costs, and Business Operations Expenses

Tip: skip Mortgage Payments, Debt Service, Outdoor Seating Construction, and Depreciation, or ask your accountant for help with these, as they are usually on the Balance Sheet or in the Non-Operating Expense section of the Profit & Loss, and are therefore harder to DIY.

Tip: Business Operations Expenses are all operating expenses that are not already accounted for in one of the other categories.

Step 7 – IMPORTANT: enter all the non-RRF grants and financial assistance as negative amounts on the Expense Tracker tab — this is to prevent any double-dipping
Step 8 – go to restaurants.sba.gov and log in
Step 9 – enter your name, address, EIN, phone, and email (if this information is not already there)
Step 10 – enter the amounts from the Summary tab — Note: you cannot enter more than the total RRF grant, so you may need to reduce one or more of the categories so that you don’t exceed the total.
Step 11 – if you have allocated all the RRF funds, certify as such — you will not be required to repeat this progress report next year; if you have not allocated all the RRF funds, you will be able to “Save” but not “Submit”.

You have until March 11, 2023 to allocate all the funds (aka spend them on eligible expenses), and until April 30, 2023 for final reporting. If it turns out you didn’t have enough eligible expenses from 2/15/20-3/11/23 using Profit & Loss Operating Expenses, then take some time to work with your accountant to determine if you have debt service, mortgage payments, capital expenses for outdoor seating, or depreciation that counts toward allowable costs.

In all cases: make sure to subtract all other grant income from expenses so you are not double-dipping!

23-minute video walking you through the whole process in Dec 2021

If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.

How to Find a Qualified Tax Preparer In Your Geographic Area

As you might imagine, we get quite a few inquiries for tax preparation services, but a) we only do taxes for our small business accounting & bookkeeping clients, and b) we only work with clients in Illinois, Indiana and Wisconsin. I’m currently in the process of interviewing qualified CPAs and bookkeepers to develop a vetted list of firms to whom I can refer potential clients, but in the meantime, I do have a solution for finding a good local tax preparer — the National Association of Tax Professionals’ Find a Tax Preparer (natptax.com) searchable directory.

NATP is one of my favorite professional organizations, and their “Find A Tax Pro” tool works great! When you use the link above, it will automatically filter for folks who are NATP members — which means these people are voluntarily taking the extra step to obtain excellent education in the field on a monthly basis (via e-newsletters, webinars, conferences, their research service, quizzes, and the regular TaxPro magazine), as tax guidance changes so frequently.

(No, I don’t earn commissions for this — I just have great respect for them, have been a member most of my career, have taken countless courses with their instructors, and have been generally impressed with their research service. I also really appreciate what a solid ratio they have of female officers, managers and instructors, which is not always the case in my field. They still need to work on DEI, but let’s be real: so does everyone in accounting and tax, to be honest. It’s an arena rife with underrepresentation issues.)

My suggestion is to use the search box on the right (after you click the button on the bottom of the landing page) and enter the following:

1) What do you need? Tax Preparer

2) Specializing in? All

3) Located in? Type in your city and see if it comes up — if not, pick a slightly larger city nearby, or even your entire state if you prefer.

The thing is, taxes don’t have to be done by a local preparer (so many of us are remote at this point) — however, you do want to work with someone who understands the specific requirements of your geographic area.

Let’s say you were in Chicago, for example — as a local accountant who specializes in small businesses, I might ask things like: whether or not you are collecting/paying sales tax, use tax, bag tax, soda tax, restaurant tax; or if you’re licensed properly with the city; or if your staff is up-to-date on requirements for sexual harassment training; or whether or not your company is in compliance with minimum wage, sick pay, and retirement requirements for employees… but someone outside of this area might not even know those requirements exist.

So even though it might be a remote relationship, it’s still best to go with someone from your area if you can. They might know something about your industry’s requirements in that area that a non-local would not.

Then lastly, scan or do an on-screen search of whatever list comes up based on your filters, and look for people who have the letters “CPA” or “EA” after their names. These are practitioners who went the extra mile (or twenty) to get a professional designation — it doesn’t mean they know everything, but they’re clearly committed to learning everything they can about tax law, so you want one of them!

And if you find a fabulous CPA in the Chicago area who is still taking on new clients, please let me know in the comments! (Bonus points for women-owned firms; extra bonus points for CPAs that offer tax, accounting, bookkeeping and advisory services.)


If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.