Heyward CPA PLLC

11/04/2026

Crypto in a business is not just a technology conversation. It is a bookkeeping and substantiation conversation.

For your Wednesday 12:00 PM ET mid-week listen, this HeywardCPA Live replay explores why business owners who accept, hold, or pay in digital assets should treat them as real balance-sheet items, with records that can stand up to review.

Start organizing the paper trail before the rules catch up:
• Wallet and exchange records
• Cost basis and lot-by-lot tracking
• Fair market value at the moment of receipt
• Documented business purpose
• Consistent revenue and asset recognition in the books and workpapers

The IRS/Treasury Priority Guidance Plan for the year beginning October 1, 2026, lists digital assets, alongside tax-exempt organizations, among its focus areas. This remains a watch-this-space issue, so business owners should confirm current guidance.

Listen to the replay at the HeywardCPA Live hub: https://heywardcpa.com/live

Also available on YouTube: https://youtu.be/VDyzFKHu6gA
Apple Podcasts search: https://podcasts.apple.com/us/search?term=HeywardCPA%20Live

For nonprofit and crypto-holding clients: is this something to act on now or watch, and what is the one thing you would tell them to document in the meantime?

Digital-asset and crypto tax treatment, valuation, and reporting depend on individual facts and applicable law, and guidance may change. No guarantee of outcomes, and nothing here is a promise of any particular tax result.

11/04/2026

If your business skipped or underpaid estimated taxes in the unfiled years, there is a piece of the puzzle most owners have never heard of: the underpayment-of-estimated-tax penalty itself.

When each late business return is filed, the IRS checks whether the year's payments and credits fell short of the required installments. If they did, an additional penalty attaches, computed year by year (on Form 2210 for individuals and most S Corp owners, and Form 2220 for corporations).

Here is the hopeful part:

- The penalty follows when income actually arrived. If most of a year's income came in late in the year, the annualized income installment method can lower the required installments and shrink the penalty.
- Safe harbors exist. Hitting a threshold tied to the prior year's tax (with adjustments for higher earners) or to the current year's tax can eliminate the penalty entirely.
- Credits and overpayments from other years count toward each year, once they are matched to the right year.

And one detail worth knowing: this penalty is calculated on the return when it is filed. Paying later does not undo it, but rebuilding the record accurately can reduce it.

So on your backlog map, alongside every year to file, list: estimated payments made, extension payments, credits carried forward, and when income actually landed during each year. That timing detail is not trivia. It can change the bottom line.

You are not behind because you failed. You are behind because running a business is demanding, and cash arrives on its own schedule, not the IRS's. 🧭📊

👉 Grab the free checklist: 5 Steps to Filing Late Business Returns Without Panicking → https://www.heywardcpa.info/unfiled-taxes

And follow Heyward CPA PLLC on YouTube for more tax education that meets you where you are.



Disclaimer: Educational content only, not tax advice. Estimated tax penalty rules (Forms 2210 and 2220), safe harbors, and the annualized income installment method depend on tax year, entity type, income timing, and individual facts, and change over time. Filing does not automatically erase balances, penalties, or interest. No outcome is guaranteed.

A defined, step-by-step path from missing returns to a clean IRS record — handled by a CPA who's done this before.

11/02/2026

Q4 2026 is not just the end of the year. It is the opening move for your 2027 tax plan.

In Monday’s 10:00 AM ET HeywardCPA Live replay, we break down the projected 2027 inflation-adjusted federal tax changes, including higher tax brackets, a projected standard deduction of approximately $33,200 for joint filers, and higher projected Code Sec. 179 limits.

The practical takeaway: use November and December to evaluate the decisions that shape 2027:
• Income timing and deferral
• Deduction bunching or acceleration
• Retirement contribution amounts
• Entity-structure math

This is a Q4 2026 bridge-to-2027 checklist, not a promise of savings. Because official IRS figures are released later and may differ, especially with the missing-CPI-data issue, planning conversations should begin before the final numbers arrive.

Listen to the replay hub: https://heywardcpa.com/live

Also available on YouTube: https://youtu.be/VDyzFKHu6gA
Apple Podcasts search: https://podcasts.apple.com/us/search?term=HeywardCPA%20Live

When the new bracket and standard deduction numbers come out, what is the first Q4 move you make: income deferral, accelerating deductions, or something else? Is it a real planning conversation or just a footnote?

Disclaimer: Projected figures are estimates from published inflation adjustments. Official IRS amounts are released later and may differ. Tax outcomes depend on individual facts and applicable law. No guarantee of tax savings or results.

11/02/2026

A multi-year tax backlog is a chain, and every link matters 🧭

If the last business return you filed was a few years ago, it's tempting to start with the newest year and skip the middle. Here's the catch: business returns (Forms 1120, 1120-S, and 1065) carry balance sheets, and each year's opening balances have to connect to the prior year's closing balances. Equity rolls forward year by year: beginning equity, plus net income, plus owner contributions, minus owner distributions, equals ending equity. Skip a year in the middle, and the chain breaks 🗓️

That's why the backlog usually has to be rebuilt in order, and that's actually the hopeful part. Your last filed return is an anchor. It holds the beginning balances for the very next unfiled year. Rebuild one year at a time, forward, and each return ties cleanly into the next. No guesswork, no contradictory numbers from one year to the next.

You are not behind because you failed. You are behind because running a business is demanding, and the chain is rebuildable ✅

Where to start: pull the last filed return's balance sheet, list every unfiled year in order, and confirm what beginning balances each one will inherit.

More catch-up walkthroughs are on our YouTube channel (Heyward CPA PLLC).

Get the free checklist: 5 Steps to Filing Late Business Returns Without Panicking → https://www.heywardcpa.info/unfiled-taxes



Educational only, not tax advice. Balance sheet and equity reporting requirements vary by form, entity type, and tax year and change over time. Filing does not automatically erase balances, penalties, or interest. No outcome is guaranteed.

A defined, step-by-step path from missing returns to a clean IRS record — handled by a CPA who's done this before.

10/31/2026

Your tax position is not a one-year snapshot. It is a multi-year story shaped by decisions made before the books close.

In this week’s HeywardCPA Live replay, we connect three essential planning themes:

• Cash versus accrual accounting, and how the Form 3115 and Section 481(a) window can affect the transition
• Net operating losses as a carried-forward asset that may continue supporting future tax planning
• Estate and gift planning for business owners who want to transfer wealth intentionally

The integrated lesson: your reporting method, the losses you preserve, and the wealth you transfer are connected to a longer-term strategy. These decisions are best evaluated proactively, not discovered at filing time.

Watch the full episode and turn year-end reporting into forward-looking planning: https://youtu.be/VDyzFKHu6gA

10/31/2026

For the first time in roughly 40 years, personal car loan interest may be deductible again, but qualification is not automatic.

Through 2028, up to $10,000 of personal car loan interest may qualify when the vehicle and loan meet specific requirements:

1. The vehicle is new, not used.
2. It is used for personal purposes.
3. It weighs less than 14,000 pounds.
4. Final assembly occurred in the United States.
5. The loan is secured by that vehicle.
6. The vehicle is not leased.

Your action step: Pull the sales agreement and loan documents showing final assembly and origin. Confirm the vehicle is not leased or used, then bring the documents to your CPA before year-end.

If you also use the same vehicle for business mileage, coordinate this personal-interest rule with your mileage or actual-expense treatment. Keep detailed mileage records, and do not assume the same costs can be deducted twice.

How should an owner walk through whether their vehicle qualifies: by reviewing the purchase documents first, the loan terms, or the business-use records?

Listen to the HeywardCPA Live replay during your Saturday 11 AM ET catch-up:
YouTube: https://youtu.be/VDyzFKHu6gA
Replay hub: https://heywardcpa.com/live
Apple Podcasts: https://podcasts.apple.com/us/search?term=HeywardCPA%20Live

Vehicle deduction, mileage, and personal car loan interest treatment depend on individual facts, substantiation, vehicle and loan specifics, entity type, and applicable law. No deduction, tax savings, or outcome is guaranteed.

10/31/2026

Your business is more than an asset. It is part of the legacy your family will carry forward.

With roughly two months left in 2026, estate and gift planning cannot wait for the calendar to run out. On HeywardCPA Live, we’ll examine decisions business owners can still act on before December 31:

• The 2026 lifetime gift and estate exclusion: $15 million per individual
• The annual gift exclusion: $19,000 per recipient
• Gifting business interests, and why defensible valuations and clean entity records matter
• The potential step-up in basis at death, and why the sequence and timing of transfers can change the outcome
• The cost of waiting: rushed valuations, incomplete records, limited planning options, and added stress for your family and successors

Legacy planning is business protection. It helps preserve the value you built, clarify who is prepared to lead, and give your family a more deliberate path forward.

Watch HeywardCPA Live Saturday, October 31 at 10:30 AM ET:
https://youtu.be/VDyzFKHu6gA

Start the conversation now. Your year-end deadline is closer than it looks.

10/30/2026

Filing a return from four years ago is not the same project as filing last year's return. Not because the math is harder, but because of HOW older returns actually get filed. 🗂️

Here is the piece most catch-up plans skip: electronic filing for business returns (Forms 1120, 1120-S, and 1065) and for personal returns is generally available only for the current year and the two years before it. Beyond that window, an older year typically has to go on paper: printed, signed and dated, mailed to the correct IRS service center (the address depends on the form and on whether a payment is enclosed), with every schedule and every K-1 attached. State systems have their own e-file windows and their own paper procedures. ✉️

That is why a backlog can feel stuck even after the numbers are rebuilt. The returns are ready, but a missing signature, a skipped attachment, a wrong address, or a mailing nobody can trace quietly resets the whole wait. These are all fixable, and none of them say anything about you as an owner. They are logistics, not verdicts.

The path that works: map each unfiled year as e-file eligible or paper, confirm every signature and date, use trackable mailing with copies of everything kept, and then follow up on account transcripts to confirm each year actually posted. An old return is not "filed" when it leaves your hands. It is filed when it shows up on the record.

The full checklist walks through this step by step, including how to organize a paper-filing backlog without panicking: https://www.heywardcpa.info/unfiled-taxes ✅

More catch-up walkthroughs live on the Heyward CPA PLLC YouTube channel.

Educational only, not tax or legal advice. E-file availability, paper-filing procedures, and processing timelines vary by tax year, form, entity type, and jurisdiction, and change over time. Filing does not automatically erase balances, penalties, or interest, and no outcome is guaranteed.

A defined, step-by-step path from missing returns to a clean IRS record — handled by a CPA who's done this before.

10/30/2026

FRIDAY REMINDER: A difficult year is not necessarily a dead end. It may create a valuable multi-year tax asset.

Eligible federal net operating losses generated in tax years beginning after December 31, 2017, generally carry forward indefinitely. However, their use is typically limited to 80% of taxable income in a future year. Ordering rules, the type and timing of the loss, and future profitability all affect when and how much relief you can use.

Documentation matters. So does demonstrating a genuine profit motive. Entity structure matters, too: basis, at-risk, passive-activity, and pass-through rules may limit how business losses reach owners or offset future income.

The right question is not simply, “Did we lose money?” It is: “How can we plan to use this loss responsibly when profitability returns?” Before year-end, review your entity structure, projected income, documentation, and tax strategy. Do not wait until filing season to discover a loss you cannot fully use.

Join HeywardCPA Live for a practical discussion on turning a hard year into forward-looking tax strategy.

Watch here: https://youtu.be/VDyzFKHu6gA

10/30/2026

Can your business make payroll six weeks from now, or will the gap surprise you first?

A P&L tells you whether the business is profitable. It does not always tell you when cash will arrive or when obligations will come due.

Growth-minded owners use a rolling 13-week cash-flow forecast alongside clean pipeline data: expected close dates, average deal size, recurring revenue, payment timing, and upcoming expenses. That visibility can reveal a timing gap before it arrives.

The result? Less reactive borrowing. More confident decisions about hiring, investments, and growth.

As you watch this HeywardCPA Live replay over the weekend, consider: What surprises owners most when a 13-week forecast is built, the timing gap, expense concentration, or late-payment trend?

Listen to the HeywardCPA Live replay Friday at 10 AM ET:
YouTube: https://youtu.be/VDyzFKHu6gA
Replay hub: https://heywardcpa.com/live
Apple Podcasts: https://podcasts.apple.com/us/search?term=HeywardCPA%20Live

Budgeting, forecasting, and cash-flow outcomes depend on each business’s facts, data quality, and circumstances. No cash-flow improvement, profit, or growth results are guaranteed.