Night Owl Tax & Resolution

Night Owl Tax & Resolution No high-pressure sales sharks. No annoying tax professional lingo. Just straight, authoritative and friendly advice.

Visit us: www.nightowltaxresolution.com
Or give us a call: (605) 799-5388 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. Through 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

Here's something that might sting a little:Most small business owners overpay on their taxes every single year — not bec...
06/17/2026

Here's something that might sting a little:
Most small business owners overpay on their taxes every single year — not because they did anything wrong, but because they simply didn't know what they could deduct.
Every missed deduction is money you already earned. And you deserve to keep it.
Here are some of the most commonly missed deductions for small business owners:
✅ Home office — if you have a dedicated workspace at home, a portion of your rent, mortgage, and utilities may be deductible

✅ Mileage & vehicle expenses — every mile driven for business has real dollar value; are you tracking it?

✅ Software & subscriptions — tools you use to run your business are often fully deductible

✅ Professional development & education — courses, books, coaching, and conferences related to your business qualify

✅ Health insurance premiums — self-employed owners may be able to deduct 100% of their premiums

This is just the beginning. There are dozens of deductions available to small business owners that never get claimed simply because nobody pointed them out.
This week's tax tip: Pull up last year's tax return and ask yourself — did I claim all of these? If not, let's talk about what you may have missed.
Ready to stop leaving money on the table?
Visit https://nightowltaxpro.com/small-business-help — let's make sure you're keeping everything you're entitled to.

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

Monday Money MovesLet's talk about something every small business owner has either experienced — or is afraid of experie...
06/15/2026

Monday Money Moves
Let's talk about something every small business owner has either experienced — or is afraid of experiencing.
A bad hire.
It's one of those things nobody wants to admit happened. But the reality is that a wrong hiring decision is one of the most expensive mistakes a small business can make — and the cost goes far deeper than most people realize.
Here's what a bad hire actually costs you:
✅ Lost revenue — productivity drops while the wrong person is in the seat ✅ Rehiring & retraining costs — the time and money to start the process all over again
✅ Team morale — one wrong hire can quietly damage your entire team's culture
✅ Your mental load — the stress, the difficult conversations, the sleepless nights
Studies suggest a bad hire can cost anywhere from 30% to 150% of that person's annual salary when you factor everything in. For a small business that's not just a financial hit — it's a survival issue.
This week's Money Move: Before your next hire, slow down. Write out exactly what the role requires, what success looks like in 90 days, and what kind of person thrives in your culture. Hiring slow saves you from firing fast.

Need help building a financially healthy business that can support smart growth? Visit https://nightowltaxpro.com/irs-help — let's talk.

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

Real Talk FridayRaise your hand if getting a letter from the IRS makes your stomach drop. 🙋You're not alone — and honest...
06/12/2026

Real Talk Friday
Raise your hand if getting a letter from the IRS makes your stomach drop. 🙋
You're not alone — and honestly, that reaction makes complete sense. But here's what I want you to know:
Most IRS notices are not as scary as they look.
The IRS sends millions of notices every year for all kinds of reasons — many of them are purely informational, or requesting clarification on something simple. Getting a letter does NOT automatically mean you're in serious trouble.
Here's what actually matters when you get an IRS notice:

✅ Every notice has a specific number in the top right corner — that number tells you exactly what it means

✅ Many notices are simply asking you to verify information or confirm a payment

✅ Some require action by a deadline — which is why reading it matters

✅ Ignoring it IS the real problem — that's when a small issue becomes a big one
The notice itself isn't the threat. Not opening it is.
So next time that envelope shows up — take a breath, open it, find the notice number, and find out what it actually means before you panic.

Got a notice you're not sure about?

Visit https://nightowltaxpro.com/irs-help — let's look at it together.

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

Monday Money MovesCan I ask you something personal?When was the last time you actually paid yourself a consistent salary...
06/09/2026

Monday Money Moves
Can I ask you something personal?

When was the last time you actually paid yourself a consistent salary from your business?
If you hesitated — you're not alone. This is one of the most common struggles small business owners face.
You pour everything into your business — your time, your energy, your money — and somehow you end up last on the list. But here's the truth: if your business can't pay you, it's not working for you.
Here's what paying yourself consistently actually does:
✅ Forces your business to operate on a real budget
✅ Separates your personal and business finances cleanly
✅ Helps you plan for taxes properly
✅ Reminds you — and your business — that your time has real value.

This week's Money Move: Look at your business finances and ask yourself honestly — am I paying myself what I deserve?

If the answer is no, let's change that.

Need help building a financial structure that actually pays you?

Visit https://nightowltaxpro.com/small-business-help — let's build a plan together.

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

Real Talk FridayLet's talk about something that's hard to hear — but important.Every single day you wait to deal with IR...
06/05/2026

Real Talk Friday
Let's talk about something that's hard to hear — but important.
Every single day you wait to deal with IRS debt, it gets more expensive.
This isn't meant to scare you. It's meant to help you understand why acting sooner — even when it feels overwhelming — is always better than waiting.
Here's what's happening behind the scenes while you wait:
✅ Interest is compounding daily on your unpaid balance
✅ Penalties are stacking on top of penalties
✅ IRS collection actions escalate the longer the debt sits
✅ Your resolution options narrow as time goes on
The hardest part for most small business owners isn't the debt itself — it's taking that first step. The shame, the fear, the "I'll deal with it later" that turns into months and then years.
But here's what I know: the earlier you act, the more options you have. And there are always more options than people realize.
You don't have to have it all figured out before you reach out. You just have to start.
📌 Ready to take that first step?
Visit https://nightowltaxpro.com/irs-help — no judgment, just real solutions.

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

Night Owl Tax Tip — Offer in CompromiseDid you know you may be able to settle your IRS debt for less than you actually o...
06/03/2026

Night Owl Tax Tip — Offer in Compromise
Did you know you may be able to settle your IRS debt for less than you actually owe?
It's called an Offer in Compromise — and it's a completely legal IRS program that allows qualifying taxpayers to resolve their tax debt for a reduced amount.
Here's what you need to know:
✅ It's a real IRS program — not a loophole or a gimmick
✅ The IRS considers your income, expenses, and assets to determine what you can realistically pay
✅ It can settle debt for significantly less than the full balance
✅ Not everyone qualifies — but more people do than you'd think
✅ Having professional guidance dramatically improves your chances
Here's the truth: the IRS would rather settle than spend years chasing. That's why this program exists.
If you've been carrying IRS debt and assuming you just have to pay every penny — it's worth finding out if you qualify.
📌 Let's look at your situation together.
Visithttps://nightowltaxpro.com/irs-help — confidential, no pressure, just answers.
Night Owl Tax & Resolution
Protect your income. Build your legacy.

Monday Money MovesRaise your hand if you've ever been hit with a surprise tax bill in April. For small business owners, ...
06/01/2026

Monday Money Moves
Raise your hand if you've ever been hit with a surprise tax bill in April.
For small business owners, that moment is stressful, expensive — and honestly, very preventable.
Here's what most business owners don't realize: the IRS expects you to pay taxes as you earn, not just once a year. That's what estimated quarterly taxes are for.
Missing them doesn't just hurt in April — it also triggers underpayment penalties that add up fast.
Here's what you need to know right now:
✅ Q2 estimated taxes are due June 15th
✅ Paying quarterly keeps your cash flow predictable
✅ A simple plan now saves you a major headache later
✅ You don't have to figure out the numbers alone
This week's Money Move: Pull up your books and look at what you've earned so far this year. If you haven't set aside taxes yet — now is the time.

Need help calculating what you owe?

Visit https://nightowltaxpro.com/small-business-help — let's build a plan together.
Night Owl Tax & Resolution
Protect your income. Build your legacy.

Real Talk Friday — Let's talk about something nobody wants to admit.Tax debt is one of the most common and most silent s...
05/29/2026

Real Talk Friday — Let's talk about something nobody wants to admit.
Tax debt is one of the most common and most silent struggles small business owners carry.
You're not behind because you're irresponsible.
You're not in trouble because you're a bad business owner.
You got here because running a business is hard — and sometimes life and taxes collide in ways we don't see coming.
Here's what I want you to know today:
🦉 You are not alone
🦉 You are not out of options
🦉 Waiting only makes it harder — acting makes it better
The IRS has more resolution options than most people realize. But they work best when you reach out before the situation gets worse — not after.
You built your business through hard things.
This is just another one — and you don't have to figure it out alone.

Ready to talk? No judgment. Just real solutions.
Visit https://nightowltaxpro.com/small-business-help and let's start the conversation.
Protect your income. Build your legacy.

Night Owl Tax Tip — Did you know the IRS can actually REMOVE your penalties?It's called Penalty Abatement — and it's one...
05/28/2026

Night Owl Tax Tip — Did you know the IRS can actually REMOVE your penalties?
It's called Penalty Abatement — and it's one of the most underused relief options available to small business owners.
Here's what most people don't know:
✅ First-time penalty abatement doesn't require financial hardship
✅ Reasonable cause can also qualify you
✅ It can save you hundreds — even thousands of dollars
✅ The IRS will NOT offer it automatically — you have to ask.
If you've received IRS penalties, please don't just pay them without asking questions first. You may be leaving serious money on the table.

Have you ever received an IRS penalty notice? Drop a 🦉 in the comments — you're not alone.
📌 Not sure if you qualify? Let's find out together.
Visit https://nightowltaxpro.com/irs-help — confidential, no pressure, just answers.
🦉 Night Owl Tax & Resolution
Protect your income. Build your legacy.

Monday Money MovesYou can have a packed client roster, a great month of sales, and still struggle to cover your expenses...
05/25/2026

Monday Money Moves
You can have a packed client roster, a great month of sales, and still struggle to cover your expenses.
Why? Because profit and cash flow are not the same thing.
Here's what your profit doesn't account for:
Expenses that haven't been paid yet
Taxes that are still owed
Money that's invoiced but not collected
This week's Money Move: Start tracking what's actually in your account versus what's owed to you. They tell two very different stories — and knowing the difference can protect your business.
💬 Drop a 🦉 in the comments if this hits home!
Need help getting your business finances working FOR you? Visit https://nightowltaxpro.com/small-business-help, no judgement just real solution.
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

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