Frequently Asked Questions

Rest assured, we've got your back! If you need a trusted tax professional or accountant, we have a network of qualified professionals ready to assist you. Simply reach out to us and share your requirements. We're here to help you every step of the way.

Yes! Although we are located in North Carolina and Pennsylvania, we work with clients in any state. It's also likely we have other clients in your state.

Portside is a fully virtual tax and accounting practice — I don't hold in-person appointments or keep a physical office; I work from my home office, which keeps costs (and your fees) lower. You can expect the same level of service, if not better, than any in-person tax professional. I'll communicate with you throughout the entire process using an easy-to-navigate secure portal that even has a mobile app.

Most firms hand you off to whoever's available and bill you after the work is done. At Portside, you work directly with an IRS-licensed Enrolled Agent — never a junior preparer — and you can verify the credential yourself at IRS.gov. Pricing comes first too: you get an instant, itemized estimate before you commit to anything. And Portside is fully virtual, serving clients in all 50 states, with no office overhead passed on to you. On top of that, Portside doesn't just file your past returns — the focus is on planning ahead so you keep more of what you earn going forward.

Foreign income and expatriate tax returns are not supported by Portside.

Yes. Portside is 100% virtual and serves individuals nationwide, so you can work with us from any state.

For 2025 individual returns, the extended filing deadline is October 15, 2026. An extension requested by the April filing deadline gives you until October 15 to file, but it only extends the time to file. Any tax you owe was still due in April.

If you are on extension with us, please upload any remaining documents as soon as possible so we can finish before the deadline. You can read the IRS's guidance on getting an extension or our guide to filing Form 4868.

Not at all, but rest assured a human is on the other side working on your return. 

Our process is designed to be fully asynchronous. All communication happens through your secure portal, and you’ll receive a personalized video reviewing your return. You can also ask questions directly in the portal's chat and we respond live during business hours. 

For most clients, we aim to file on time - not extend. That’s because extensions require additional time to ensure you’ve paid enough in taxes, and they delay important advisor conversations and planning.

To keep things on track, we ask for all documents by an internal deadline that's generally 2 to 3 weeks ahead of the IRS filing deadline (depending on workload and capacities). If documents come in after that date, we'll to have a conversation about potentially extending. We also reserve the right to apply rush surcharges due to increased strain and bottleneck of last-minute filings if documents are submitted after the internal deadline.

That said, we understand life happens - whether it’s a missing form or an unexpected delay. If that’s your situation, reach out early. We’re happy to be flexible when there’s open communication.

No, we are a virtual-only firm. To optimize efficiency, security, and to promote environmental responsibility, we are a paperless tax and accounting firm. Our client portal contains a document scanning feature to turn your paper documents into PDF. Go green with us!

We do not price match - as what we offer isn’t just filing: it’s confidence, continuity, and care.

Every return is reviewed by a credentialed Enrolled Agent (EA), not seasonal untrained staff or software logic. Our expert team doesn’t turn over. We’re here year after year, building long-term trust with both clients and their advisors.

We charge more because we offer more:

• Expert review from professionals who stay with you over time.
• A personalized video walkthrough of your return.
• Optional collaboration with your financial advisor.

We’ve corrected hundreds of errors made by DIY platforms and volume-driven tax shops. If you’re looking for the cheapest option, we may not be the right fit. If you’re looking to get it done right, with people who remember you next year - we are.

Real example: John came to us after years of DIY filing and working with a well known volume-driven tax shop. During our intake process, we reviewed his prior returns and discovered he had been paying taxes to two states unnecessarily - for the past three years. We helped him file amendments and recovered nearly $15,000 in refunds.

One state and one local tax return are included in all our tax return packages - whether you are an individual taxpayer, a business, or a nonprofit organization. We also help many clients that have multi-state filing obligations, such as when you work in one state and live in a different state. If you need to file in more than one state or locality, that's no problem.

Absolutely! You'll get a personalized quote that takes into account multiple years of filings if that situation applies to you.

An inherent limitation in the tax preparation process is that any tax professional is only aware of the information you provide.

Unfortunately, even tax professionals do not have a method of obtaining lost information on your behalf. If you've lost a W-2 form, I recommend getting in contact with the employer that issued the W-2 to request a reprint.

Another option is to use the IRS' online Get Transcript tool to obtain wage & income transcripts that list Federal tax information from all income documents the IRS received copies of. However, please be aware these wage & income tax transcripts from the IRS do not include state or local tax information, so there will still be missing information that remains even after obtaining IRS transcripts.

Our secure portal is designed to take you through a step-by-step process that gathers each piece of information and documentation we need to prepare accurate tax returns on your behalf. The portal will take it one step at a time! At a bare minimum, all tax returns will always require your full name, mailing address, taxpayer identification number, telephone number, email address, date of birth, copy of a valid photo ID, and any income documents you've received.

If we notice that something obvious is missing, we’ll reach out through your secure portal to request it. That said, it is your responsibility to upload the right documents. As much as we wish we had a crystal tax ball, we’ll need your help to make sure nothing gets missed! 😉

Once all your tax documents are uploaded, we will get to work preparing your tax returns. We strive to have your tax returns ready for your review within 15 business days after we receive ALL documents. We may ask clarifying questions before we are able to finalize your tax returns, so the speed of preparation directly depends on the speed of your responses back to us as well.

We use a secure client portal to share information. We will communicate with you in this online portal, and you will also be able to upload your tax documents here. The secure portal also includes a messaging system that allows you to communicate with us in real-time. You can even use our secure portal on your mobile device (download the app on Apple or Android devices).

Portside serves service-based businesses only. We do not serve businesses whose chief business is to sell or manufacture products.

Yes. Business Tax Filings pair with Bookkeeping + Accounting and Payroll Services (we are a Gusto payroll partner) for full back-office support from Portside.

Yes. Portside is 100% virtual and serves clients nationwide, and we prepare Form 1120-S for S corporations.

For calendar-year businesses, partnership (Form 1065) and S corporation (Form 1120-S) returns are due on March 15, and C corporation (Form 1120) returns are due on April 15. When a due date falls on a weekend or legal holiday, it moves to the next business day. For the 2026 tax year, that means March 15, 2027 for partnerships and S corporations, and April 15, 2027 for C corporations.

Form 7004 requests an automatic six-month extension to file. Businesses with a fiscal year follow the same pattern, counted from the end of their tax year: the 15th day of the 3rd month for Forms 1065 and 1120-S, and the 15th day of the 4th month for Form 1120. See the IRS's Publication 509 for the full tax calendar.

Not at all, but rest assured a human is on the other side working on your return. 

Our process is designed to be fully asynchronous. All communication happens through your secure portal, and you’ll receive a personalized video reviewing your return. You can also ask questions directly in the portal's chat and we respond live during business hours. 

For most clients, we aim to file on time - not extend. That’s because extensions require additional time to ensure you’ve paid enough in taxes, and they delay important advisor conversations and planning.

To keep things on track, we ask for all documents by an internal deadline that's generally 2 to 3 weeks ahead of the IRS filing deadline (depending on workload and capacities). If documents come in after that date, we'll to have a conversation about potentially extending. We also reserve the right to apply rush surcharges due to increased strain and bottleneck of last-minute filings if documents are submitted after the internal deadline.

That said, we understand life happens - whether it’s a missing form or an unexpected delay. If that’s your situation, reach out early. We’re happy to be flexible when there’s open communication.

No, we are a virtual-only firm. To optimize efficiency, security, and to promote environmental responsibility, we are a paperless tax and accounting firm. Our client portal contains a document scanning feature to turn your paper documents into PDF. Go green with us!

We do not price match - as what we offer isn’t just filing: it’s confidence, continuity, and care.

Every return is reviewed by a credentialed Enrolled Agent (EA), not seasonal untrained staff or software logic. Our expert team doesn’t turn over. We’re here year after year, building long-term trust with both clients and their advisors.

We charge more because we offer more:

• Expert review from professionals who stay with you over time.
• A personalized video walkthrough of your return.
• Optional collaboration with your financial advisor.

We’ve corrected hundreds of errors made by DIY platforms and volume-driven tax shops. If you’re looking for the cheapest option, we may not be the right fit. If you’re looking to get it done right, with people who remember you next year - we are.

Real example: John came to us after years of DIY filing and working with a well known volume-driven tax shop. During our intake process, we reviewed his prior returns and discovered he had been paying taxes to two states unnecessarily - for the past three years. We helped him file amendments and recovered nearly $15,000 in refunds.

One state and one local tax return are included in all our tax return packages - whether you are an individual taxpayer, a business, or a nonprofit organization. We also help many clients that have multi-state filing obligations, such as when you work in one state and live in a different state. If you need to file in more than one state or locality, that's no problem.

Absolutely! You'll get a personalized quote that takes into account multiple years of filings if that situation applies to you.

Once all your tax documents are uploaded, we will get to work preparing your tax returns. We strive to have your tax returns ready for your review within 15 business days after we receive ALL documents. We may ask clarifying questions before we are able to finalize your tax returns, so the speed of preparation directly depends on the speed of your responses back to us as well.

We use a secure client portal to share information. We will communicate with you in this online portal, and you will also be able to upload your tax documents here. The secure portal also includes a messaging system that allows you to communicate with us in real-time. You can even use our secure portal on your mobile device (download the app on Apple or Android devices).

Yes. Everything is handled online through our secure client portal, so your team can share documents whenever it suits them, and you work directly with an IRS-licensed Enrolled Agent.

The right form depends on your organization's type and size. Portside prepares the full 990 series: Form 990, 990-EZ, 990-T, 990-PF and 990-N, so we can help you determine the right one.

Form 990, 990-EZ, and 990-PF returns are due on the 15th day of the 5th month after the end of your tax year, which is May 15 for calendar-year organizations. Form 8868 gives an automatic six-month extension. The Form 990-N (e-Postcard) due date cannot be extended.

If a required return is filed late, the IRS can charge a penalty for each day it is late, and the daily rate and maximum are higher for larger organizations. The penalty may be abated if there was reasonable cause. The more serious risk is that an organization that does not file a required return or e-Postcard for three consecutive years automatically loses its federal tax-exempt status.

If you have missed a filing, contact us as soon as possible so we can help you catch up. The IRS explains the rules on its failure-to-file penalties page.

Not at all, but rest assured a human is on the other side working on your return. 

Our process is designed to be fully asynchronous. All communication happens through your secure portal, and you’ll receive a personalized video reviewing your return. You can also ask questions directly in the portal's chat and we respond live during business hours. 

No, we are a virtual-only firm. To optimize efficiency, security, and to promote environmental responsibility, we are a paperless tax and accounting firm. Our client portal contains a document scanning feature to turn your paper documents into PDF. Go green with us!

We do not price match - as what we offer isn’t just filing: it’s confidence, continuity, and care.

Every return is reviewed by a credentialed Enrolled Agent (EA), not seasonal untrained staff or software logic. Our expert team doesn’t turn over. We’re here year after year, building long-term trust with both clients and their advisors.

We charge more because we offer more:

• Expert review from professionals who stay with you over time.
• A personalized video walkthrough of your return.
• Optional collaboration with your financial advisor.

We’ve corrected hundreds of errors made by DIY platforms and volume-driven tax shops. If you’re looking for the cheapest option, we may not be the right fit. If you’re looking to get it done right, with people who remember you next year - we are.

Real example: John came to us after years of DIY filing and working with a well known volume-driven tax shop. During our intake process, we reviewed his prior returns and discovered he had been paying taxes to two states unnecessarily - for the past three years. We helped him file amendments and recovered nearly $15,000 in refunds.

One state and one local tax return are included in all our tax return packages - whether you are an individual taxpayer, a business, or a nonprofit organization. We also help many clients that have multi-state filing obligations, such as when you work in one state and live in a different state. If you need to file in more than one state or locality, that's no problem.

Absolutely! You'll get a personalized quote that takes into account multiple years of filings if that situation applies to you.

Once all your tax documents are uploaded, we will get to work preparing your tax returns. We strive to have your tax returns ready for your review within 15 business days after we receive ALL documents. We may ask clarifying questions before we are able to finalize your tax returns, so the speed of preparation directly depends on the speed of your responses back to us as well.

We use a secure client portal to share information. We will communicate with you in this online portal, and you will also be able to upload your tax documents here. The secure portal also includes a messaging system that allows you to communicate with us in real-time. You can even use our secure portal on your mobile device (download the app on Apple or Android devices).

It is designed for businesses and nonprofits with less than $10M in annual revenue.

You can start with bookkeeping on its own through our bookkeeping intake form. Many clients also pair it with Business Tax Filings and Payroll Services for full back-office support.

It depends on the package you select. Lower-priced packages have a lighter cadence, and higher-priced packages have a more frequent one.

Portside works exclusively with service-based businesses, entrepreneurs, and nonprofit organizations. This may include (but is not limited to) medical providers, restaurants, online creators, influencers, entrepreneurs in the service industry, janitorial providers, and other professional service providers.

For bookkeeping/accounting services only, we do not work with businesses whose main purpose is to sell products.

Yes! We can handle filing sales and use tax returns for your business, no matter how many states you do business in!

Sure do!

If you have payroll services with us, that includes preparation, filing, and mailing of W-2 forms, as well as 1099 forms for contractors paid through your payroll software package.

If you have bookkeeping services with us, that includes preparation, filing, and mailing of 1099 forms to all necessary vendors and independent contractors.

We can also provide 1099 services even if your books aren't done by Portside - we would just need some extra information from you to ensure everything is up to snuff.

Yes, we have done this for a number of clients!

If you're already working with a system and love it, we wouldn't dream of making you switch - as long as we are familiar with it! We prefer to set up new clients on Quickbooks Online, but also work with Xero, Freshbooks, and Wave.

Yes, we use industry-standard bookkeeping and payroll software that you will gain a subscription to as part of our services.

For bookkeeping, we prefer Quickbooks Online as we are Quickbooks ProAdvisors (meaning we are experts in everything to do with Quickbooks).

For payroll, we usually use Gusto.‍

If you are already using a bookkeeping or payroll system you love, that's okay with us - provided that we know how to use it so we can work together! We help clients with Quickbooks Online, Xero, Freshbooks, Wave, Gusto, ADP, OnPay, and more.

Absolutely! Support and questions are included in your plan, and actively encouraged. Bookkeeping and payroll are services that are very much a two-way street when it comes to communication, so I expect to develop communication with you on a regular basis.

We have three requirements that allow us to deliver the most accurate bookkeeping and accounting services:‍

1. Electronic transaction access from your bank (most banks have this)‍
2. Expense reporting software (we get you set up on Quickbooks Online)
3. No commingling of personal expenses in your business - this is a big one!

Payroll compliance support is full-service. Payroll tax filings, W-2 and 1099 issuance, and state registrations are all included.

Yes. Multi-state payroll is supported at a higher cost.

Gusto provides the payroll platform. Portside is a Gusto payroll partner that offers payroll as a full-service solution, including payroll tax filings, W-2 and 1099 issuance, and state registrations, and we can pair it with bookkeeping and tax services.

Sure do!

If you have payroll services with us, that includes preparation, filing, and mailing of W-2 forms, as well as 1099 forms for contractors paid through your payroll software package.

If you have bookkeeping services with us, that includes preparation, filing, and mailing of 1099 forms to all necessary vendors and independent contractors.

We can also provide 1099 services even if your books aren't done by Portside - we would just need some extra information from you to ensure everything is up to snuff.

Yes, we have done this for a number of clients!

If you're already working with a system and love it, we wouldn't dream of making you switch - as long as we are familiar with it! We prefer to set up new clients on Quickbooks Online, but also work with Xero, Freshbooks, and Wave.

Yes, we use industry-standard bookkeeping and payroll software that you will gain a subscription to as part of our services.

For bookkeeping, we prefer Quickbooks Online as we are Quickbooks ProAdvisors (meaning we are experts in everything to do with Quickbooks).

For payroll, we usually use Gusto.‍

If you are already using a bookkeeping or payroll system you love, that's okay with us - provided that we know how to use it so we can work together! We help clients with Quickbooks Online, Xero, Freshbooks, Wave, Gusto, ADP, OnPay, and more.

Yes. Portside is 100% virtual and serves clients nationwide.

Through our referral to Community Tax, help is available for situations such as unfiled back tax returns, wage garnishment, payment plans (installment agreements), offers in compromise, penalty abatement and payroll tax issues. Start with a no-cost consult.

Fees vary for this type of service since it is personalized to your tax issues. A way to put any service fees in perspective is if we get a $5,000 tax bill forgiven, most would pay $1,500 to save $3,500.

If you've fallen behind on filing your tax returns, you're not alone. Life changes or overwhelming circumstances can lead to this situation, but inaction only exacerbates it. The IRS estimates that over a million taxpayers face this issue each year. No matter your filing status or situation, I am here to assist you. My services include reconstructing lost records, preparing and submitting overdue returns, negotiating with the IRS, and exploring options like Offers in Compromise and Installment Agreements. It's never too late to address this, and you may even be entitled to a refund or have the opportunity to reduce your owed amount. Filing late is always better than not filing at all, so contact me today and I'll start to get everything straightened out for you.

One option is the IRS Offer in Compromise program, a powerful opportunity to settle your tax debt for less than the full amount you owe. With expert guidance, it's possible to eliminate your taxes, along with penalties and interest, at a significant discount. There's no fixed minimum amount, especially when the offer is meticulously prepared. In fact, your debt may be resolved for just 5-15% of the current owed amount.

If the IRS Offer in Compromise program isn't an option for you, consider a Payment Plan as an alternative solution. This arrangement grants you extra time to settle your tax debts. While penalties and interest will persist on the remaining balance, it provides a structured approach to gradually pay off what you owe.‍

The best option for you will depend on your unique financial and tax situation, so feel free to get in touch.

Each year, millions of taxpayers receive letters or notices from the IRS. While often harmless, there are cases that require attention, like owing back taxes or neglecting to file. It's possible they could just be notifying you of delays in processing, or they could be requesting more information. But, if the IRS is seeking payment, it may resort to measures like wage garnishment, liens, or bank levies. Follow the instructions on the notice, and you have any questions, get in touch with us.

Yes! Nonprofits are eligible, including those accepting cards or ACH for donations. Approval is subject to Helcim's underwriting.

No. Bundling does not lower your bookkeeping fees. The benefit is that your payment processing is easier to reconcile when Portside handles your bookkeeping.

Portside refers merchant processing to Helcim. Helcim provides all payment processing directly to approved merchants under its own terms and underwriting.

Go to our exclusive link through our merchant services partner, Helcim. The application is completed online and you can sign up directly from your phone or computer without filling out lengthy contract paperwork.

Not at all. This service is available to any qualifying small business. That said, existing clients benefit from seamless integration with their bookkeeping and financial reporting.

Those processors use flat-rate pricing, which is simple but often more expensive — especially as your volume grows. Helcim uses interchange-plus pricing, which passes you the actual wholesale cost of each transaction plus a transparent markup. Most businesses save 20–40% compared to flat-rate processors.

No. There are no monthly fees, setup fees, or cancellation fees through our merchant services partner, Helcim. You only pay a small percentage per transaction processed.

Yes. Nonprofit organizations are one of the entity types we form. Portside also assists with IRS Form 1023 for 501(c)(3) status and prepares 990-series returns afterward.

Yes. Formation is available in every state, and we register your entity in the state of your choosing.

Yes. Our formation service includes an entity type analysis, and we handle formation with tax strategy in mind because Portside also prepares your entity's tax returns. An S-corp election is available as an optional part of formation.

By default, all Corporations (regardless of which state they were formed in) are known as “C-Corporations“. So, if you have not specifically filed a form to elect to become an S-Corporation, then your company is still a C-Corporation. By submitting a Form 2553 the IRS and adopting the appropriate corporate resolution, you can become an S-Corporation. If you utilize my S-Corporation Election service, we can prepare the resolution and the form for you and send it to the IRS (they only take submissions via mail or fax at this time). The IRS then confirms via mail within a few months.

‍Note that some states like California and New Jersey also require their own state version of the S-Corporation Election.

Yes, there are many reasons a company would form an LLC or corporation in a state outside where they conduct business. Some of those reasons are related to taxation and ownership transparency. Your LLC or corporation would have to be Foreign Qualified in the state of formation, and we can do that for you.

We process most orders in just a few business days once we receive your initial formation questionnaire back completed. However, how long the state will take to process the paperwork once they receive it varies widely depending on the state (and the season). Some states take 3 days, others take 3-4 weeks or longer. Upon ordering our new business formation services, we will provide an estimated time to process an order in your selected state.

We also offer expedited services that can speed up the process. The expedite fees vary from state to state.

An LLC is organized with members who own the business and managers who handle daily operations. Any LLC can be managed by either its members or by Managers. An LLC may even be owned by another LLC.

The most common type of LLC is a Member-Managed LLC. The company is managed like a partnership or sole proprietorship in a corporation. Each Member is involved in daily operations. Members may be assigned titles, such as “President” or “Treasurer”, but it’s not necessary. Most LLC owners just refer to themselves as “Managing Member” or simply “Member”.

In a Manager-Managed LLC, the company designates a Manager or Managers who may or may not be Members. They run the daily operations of the company. The other Members may or may not be involved in the daily activities. They simply provide money or assets for the managers to operate the company. This is fairly rare for small businesses.

A Limited Liability Company, or LLC, can be best described as a hybrid between a corporation and a partnership. It provides easy “pass-through” taxation like a Sole Proprietorship/Partnership, with the liability protection of a corporation.

Sales tax is imposed by states (and often local governments), not the IRS. Whether you must collect it depends on what you sell and whether you have nexus, meaning a sufficient connection to a state, through a physical presence or economic activity such as sales volume. We review where you sell and tell you where you need to register.

States generally charge penalties and interest on late or unfiled returns, and sales tax collected from customers is treated as money held in trust for the state. If you have fallen behind, we can help you file past-due returns and explore penalty relief or voluntary disclosure options where available.

Each state assigns a filing frequency, usually monthly, quarterly or annually, based on your expected or actual taxable sales. The state tells you your frequency when you register, and it can change as your sales grow. We track your due dates and file on schedule.

Possibly. Since the U.S. Supreme Court's 2018 Wayfair decision, states can require out-of-state sellers to collect sales tax once they pass an economic nexus threshold, which varies by state. Marketplace facilitators may collect for you on some sales. We map your sales by state and handle registration and filing.

Often, but it is a state-level decision. Many states require a separate application or exemption certificate even after the IRS recognizes an organization as tax-exempt. We can help you apply for the state exemption and keep the paperwork current.

It is a form a buyer gives a seller to document why a purchase is not subject to sales tax, such as a resale, manufacturing or nonprofit exemption. Requirements and form names vary by state. Sellers who accept a valid, complete certificate are generally protected if the state later audits the sale.

Retention periods are set by each state, and many tie them to the audit statute of limitations, often three to four years or longer. Keeping certificates organized and easy to retrieve is the best protection in an audit, and we can help you set up a system for it.

Common exemptions cover purchases for resale, certain manufacturing and agricultural inputs, and purchases by qualifying nonprofits and government entities. Rules differ by state, and federal 501(c)(3) status does not automatically create a state sales tax exemption. We check the rules for each state where you operate.

Form 1023 is the application an organization files with the IRS to be recognized as exempt from federal income tax under section 501(c)(3). It describes your purpose, activities, governance and finances. Applications are submitted electronically through Pay.gov.

To be treated as exempt from your formation date, an organization generally must file within 27 months of the end of the month in which it was legally formed. Applying later can mean exemption starts only from the filing date, so it is best to apply early.

Most organizations seeking 501(c)(3) status must apply. Churches and certain public charities with annual gross receipts normally not more than $5,000 are not required to file, although many still choose to in order to have an IRS determination letter. We help you decide which route fits.

Processing time varies with IRS workload and with whether the IRS needs more information from you. A complete, well-organized application with a clear narrative of your activities is the best way to avoid delays. We prepare the application and respond to IRS follow-up requests.