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Monday 8am - 6pm Tuesday 8am - 6pm Wednesday 8am - 6pm Thursday 8am - 6pm Friday 8am - 6pm Saturday 9am - 4pm

Night Owl Tax & Resolution

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United States
Parker, SD
Night Owl Tax & Resolution

Night Owl Tax helps business owners and entrepreneurs navigate taxes with confidence. We help you protect what you've built and help build your legacy.

From business advisory services, tax strategies and proactive planning to IRS resolution. Empowering individuals and businesses to overcome tax challenges and regain financial stability. With more than 14 years in the accounting and tax industry, our mission at Night Owl Tax Resolution is to provide expert guidance and compassionate support throughout every step of the tax resolution process. Thro

ugh personalized strategies, transparent communication, and relentless advocacy, we strive to alleviate the burden of tax debt, negotiate favorable resolutions with taxing authorities, and pave the way for a brighter financial future for our clients. With integrity, professionalism, and a commitment to excellence, we are dedicated to being a trusted partner on the journey to resolution, offering clarity, relief, and peace of mind to those facing tax-related obstacles." As an enrolled agent, Jackie Benson is an Enrolled Agent and tax resolution expert. She has helped countless clients overcome the burden of back tax liability. Night Owl Tax Resolution is dedicated to providing peace of mind from the first contact because it’s always about our clients. Hours of Availability:

Monday - Friday 8:00 am - 6:00 pm CT

Saturday 9:00 am - 4:00 pm CT

Sunday - by appointment only

07/20/2026

Monday Money Moves
Do you know how much revenue your business must generate each month just to cover its expenses?
That number is your break-even point—and it should be one of the first numbers you review when setting sales goals, pricing services, or making spending decisions.
If your monthly expenses are $10,000, bringing in $10,000 doesn’t necessarily mean you have broken even. You must also account for the costs that increase with each sale, such as materials, inventory, delivery, merchant fees, or direct labor.
Once you know your true break-even point, you can:
✓ Set more meaningful sales goals
✓ Price your products or services more confidently
✓ Identify when expenses are growing too quickly
✓ Determine how much revenue is actually producing profit
Revenue tells you how much came in. Your break-even point tells you when the business started making money.
Do you know how much your business must generate each month before it begins producing a profit?
Download my free Small Business Break-Even Starter Worksheet and calculate the number every business owner should know.
Get your free worksheet here:
https://www.nightowltaxpro.com/break-even-worksheet

07/19/2026

Welcome to Night Owl Tax & Resolution

If you're a small business owner, you're in the right place.

Running a business is challenging enough without wondering if you're making the right financial decisions or missing opportunities to save on taxes.

Here's my promise to you:

Every week, I'll share practical tax tips, business insights, financial strategies, and IRS guidance you can actually use—whether you're my client or not.

My goal is simple: to help you make smarter financial decisions, avoid costly mistakes, and build a stronger, more profitable business.

Whether you're just getting started or you've been in business for years, I hope this page becomes a trusted resource you can count on.

Welcome to the Night Owl community.

Protect your income. Build your legacy.

07/17/2026

Did you know your business may be able to rent your home for legitimate business meetings—and the rental income may be tax-free to you?
It's called the Augusta Rule (Section 280A), and it's one of the most overlooked tax strategies available to qualifying business owners.
When used correctly:
✔ Your business may deduct the rental expense.
✔ You may receive the rental income tax-free.
✔ It's a legitimate strategy written into the tax code—not a loophole.
Like any tax strategy, there are important rules. The meetings must have a legitimate business purpose, the rental rate must be reasonable, and good documentation is essential.
Could the Augusta Rule work for your business?
Take the free Business Financial Health Assessment to discover opportunities to strengthen your business and reduce taxes: https://www.nightowltaxpro.com/business-health-quiz

07/15/2026

Many small business owners are surprised when they look at their year-end profits and wonder, "Where did the money go?"
Often, the problem isn't how much they're charging—it's how they set their prices.
Most business owners price their products or services based on what competitors charge or what feels fair. But very few calculate what they actually need to keep after taxes and expenses.
Here's the part many people overlook: if you're self-employed, the first 15.3% of your earnings goes toward self-employment tax. Then come federal (and possibly state) income taxes, along with your business expenses. That means a $100 sale may leave you with far less than you expected.
Before setting your prices, ask yourself:
✔ What do I need to take home?
✔ What are my business expenses?
✔ How much will I owe in taxes?
The answer is your minimum profitable rate.
Pricing isn't just a sales decision—it's a financial strategy. When you understand your numbers, you can build a business that supports your goals today and your future tomorrow.
Curious how financially healthy your business really is?
🦉 Take the free Business Financial Health Assessment at https://www.nightowltaxpro.com/business-health-quiz

07/14/2026

Most business owners think retirement planning and tax planning are two separate conversations. They're not.
The right retirement account can reduce your taxable income while helping you build long-term wealth.
Two of the most common options are:
✔ SEP-IRA
✔ Solo 401(k)
Each has different rules, contribution limits, and advantages depending on your business.
The key is choosing the strategy that fits your goals—not just opening an account because someone told you to.
Curious which option makes the most sense? Let's talk.
https://www.nightowltaxpro.com/free-consultation

07/10/2026

Real talk — how many months behind are your books right now?
If that question made you wince, you're not alone. Bookkeeping is the task that almost every small business owner knows they should be doing consistently and almost none of them actually do. It gets pushed to the back burner week after week until tax season arrives and suddenly there's a mountain to climb.
Here's what that habit is actually costing you.
• It costs you in missed deductions
• It costs you in accounting fees
• It costs you in bad decisions
• It costs you in stress
If you hate doing it, or need to spend your time in your business, hire someone. The cost is almost always less than what you're losing by not doing it.
Ready to get your books in order before the year gets away from you?

Let's talk — reach out to schedule your free business assessment: https://www.nightowltaxpro.com/free-consultation

Night Owl Tax & Resolution
Protect your income. Build your legacy.

07/08/2026

Wednesday Tax Strategy
Did you know you can overpay your quarterly taxes — and it's costing your business money?
Most self-employed people and business owners guess high on their quarterly payments because they're afraid of penalties. But the IRS "safe harbor rule" means you're protected from penalties as long as you pay 90% of what you owe this year (or 100–110% of last year) — nothing more.
That extra cash you're sending the IRS "just in case"? It could be working in your business instead.
Not sure if your quarterly payments are optimized? Let's run the numbers — reach out to schedule your free business tax assessment with Night Owl Tax: https://www.nightowltaxpro.com/free-consultation
Night Owl Tax & Resolution
Protect your income. Build your legacy.

07/06/2026

Here's a mistake that costs small business owners thousands of dollars every year — and it doesn't cost a single dollar to make.
It's the decision to run your business without a written financial plan.
Most small business owners don't think of this as a decision at all. They think of it as just how things are — you're busy, you're focused on serving clients and generating revenue, and financial planning feels like something bigger businesses do. Something that requires a CFO or a finance degree or a conference room full of spreadsheets.
So instead, you wing it. You check your bank balance before you spend money. You estimate what you might owe in taxes. You set prices based on a gut feeling. You hope that revenue stays ahead of expenses.
And for a while, it works. Until it doesn't.
Here's what operating without a financial plan costs you:
It costs you in tax preparation. Without a plan, there's no intentional strategy around deductions, entity structure, retirement contributions, or income timing.
It costs you in cash flow. Without a plan, you don't see cash crunches coming.
It costs you in decision making. Should you hire someone? Buy new equipment? Take on a large client that requires upfront costs? Without a financial plan, every one of these decisions is a guess.
It costs you in growth. Businesses that grow intentionally do so because they know their numbers.
A written financial plan doesn't have to be complicated. It starts with knowing your revenue goal, understanding your expenses, building a simple cash flow projection, and setting a tax savings target. That's it. Four things. One document.
The $0 mistake is entirely fixable. And the return on fixing it is immediate.
Ready to build a financial plan that works for your business? Let's start the conversation — https://www.nightowltaxpro.com/free-consultation

Night Owl Tax & Resolution
Protect your income. Build your legacy.

Address

45730 SD Highway 44
Parker, SD
57053

Opening Hours

Monday	8am - 6pm
Tuesday	8am - 6pm
Wednesday	8am - 6pm
Thursday	8am - 6pm
Friday	8am - 6pm
Saturday	9am - 4pm

Telephone

(605)7995388

Website

http://nightowltaxpro.com/

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