Tax Season Survival: What Every Entrepreneur Needs to Know

Don't want to face a tax disaster this year?

Tax season is every entrepreneur's worst nightmare. With estimated payments, payroll taxes, and constantly shifting deadlines…

It's incredibly easy to get behind.

The Problem:

Tax problems won't go away. They compound. Penalties pile up. Interest accrues daily.

What once may have been a minor tax problem turns into a big freaking headache.

The good news is…

If you know what to look for and take action early, tax season can actually be survivable. Tax resolution services are available to help fix your business tax troubles before the IRS sues you or attempts to shut you down.

What you'll learn:

• How Tax Problems Spiral Out of Control
• 5 Entrepreneur Tax Mistakes You Should Avoid
• How Tax Resolution Services Work To Help You
• What you can do to protect your business right now

Why Tax Problems Spiral Out of Control

Let's talk about money for a minute…

The IRS issued civil penalties totaling $84.1 billion in 2024. $84.1 billion!

Taxpayers are hit with these penalties because they made mistakes or simply fell behind on their tax obligations.

And unfortunately…

The IRS didn't pull these penalties out of thin air. They were triggered by missed deadlines, underpayments, math errors, and filing improper tax returns.

The IRS is not your friend.

If you fail to file on time, you may be charged a penalty of 5% of your unpaid taxes per month. If you fail to pay, you'll be penalized an additional 0.5% per month. Not to mention interest on your tax debt, which compounds daily.

That $10k tax debt you're ignoring? Will grow to $15k+ in a year.

By the time most entrepreneurs need IRS defense help, they realize they waited too long and their ability to resolve their tax problems with the IRS has been significantly reduced.

Tax problems can and will destroy your business if you ignore them.

The IRS can garnish wages, seize bank accounts, seize business assets, and shutter your business up. Without a court hearing.

Entrepreneur Tax Mistakes You Should Avoid

Running a business is difficult. Between managing employees, keeping track of expenses, and serving customers… you're busy.

Then you throw taxes into the mix and it becomes overwhelming.

Entrepreneurs make these tax mistakes more than any other:

• Missing quarterly estimated tax payments. Quarterly taxes are a nightmare for small business owners but you don't get a waiver just because you're self-employed. If you miss the deadline you'll be charged a failure to pay penalty.
• Misclassifying your employees. Payroll hackers think they can save money by classifying employees as "Independent Contractors." The IRS is cracking down on this improper classification and will hold businesses liable.
• Poor record keeping. Say you can't back up that $10,000 deduction with a receipt. The IRS will deny it. Period.
• Mixing personal and business expenses. This will create an audit nightmare for you and your business. The IRS may also deny legitimate business deductions.
• Filing your taxes late. If you can't pay your taxes filing on time is more important than ever. The failure to file penalty is 5x greater than the failure to pay penalty.

Here's the kicker…

The IRS collected $77.6 billion in revenue through tax collection/enforcement in fiscal year 2024. That's 13.6% more than last year!

It's obvious the IRS is coming after small businesses.

How Tax Resolution Services WORK

Tax resolution services? What the heck are those?

Tax resolution services are:

Tax resolution services work with business owners to resolve their tax problems. They prevent the IRS from shutting you down and can often negotiate your tax debt down significantly.

Each tax professional has their own way of doing things but they all understand the tax code and IRS processes. They know what programs are available and how to qualify your business for them.

Here are a few common tax resolutions:

• Installment Agreements – Pay your taxes off in monthly installments that fit your budget. The IRS offers installment agreements up to 72 months.
• Offer in Compromise – Pay the IRS less than the full amount you owe. In 2024, the IRS accepted over 7,100 offers totaling $163 million.
• Penalty Abatement – Request the IRS remove penalties if you can prove you have reasonable cause. Last year the IRS abated $75.7 billion in penalties.
• Currently Not Collectible – Temporarily stop collections if you can prove paying your tax debt will cause you financial hardship.

Imagine how much stress you could save yourself…

By paying a professional to help you instead of going it alone. Tax resolution specialists speak IRS agent speak. They know how to push the right buttons.

The earlier you act, the better your chances of qualifying for these programs.

Steps To Protect Your Business From The IRS Right Now

You can prevent tax season mayhem with just a few simple tips.

Know your deadlines.

This should be step 1 and 2 combined. Know every tax deadline that applies to your business. Calendar them. For 2025, the deadlines are March 17 for S-corps/partnerships and April 15 for sole proprietors/C-corps. Trust me. I triple checked the calendar. If you miss these deadlines you'll be charged a penalty.

Pay quarterly.

Estimated taxes are due quarterly as well. Set aside money as you earn it so you're not overwhelmed when payment is due. Many small businesses receive penalties for underpayment because they simply forgot.

Keep accurate records.

Keep impeccable records of every transaction. Every receipt. Every business mile you drive. If the IRS asks you about a deduction, you had better be able to prove it.

Separate Business Expenses.

Open a business bank account and use it ONLY for business expenses. Seriously. This will save you from countless personal vs business expense headaches during an audit.

Don't ignore the IRS.

Got an IRS letter in the mail? Open it. These typically give you a deadline to respond. If you ignore it, you'll likely receive another letter. The last thing you want is for the IRS to assume you're ignoring them because you don't plan on paying.

Get Professional Help

Tax help isn't just for people behind on their taxes. If you owe taxes and are struggling to pay them, contact a tax resolution service. The sooner you get help, the more options you'll have.

Trust me. If you wait too long you'll limit your options and likely be forced to file for bankruptcy.

Working with tax pros can mean the difference between life and death for your business. Tax resolution services have years of experience negotiating with the IRS and know what levers to pull.

Wrap Up

Tax season isn't the end of your business.

Successful entrepreneurs have something in common. They are organized, meet their deadlines, and ask for help when they need it.

Most importantly? They don't ignore their tax problems.

Remember:

• Interest and penalties will bury you if you ignore them
• The IRS is cracking down on small businesses every year
• Tax resolution services exist to negotiate on your behalf
• The earlier you file for help, the more options you'll have

Tax law is complicated and most entrepreneurs are sucked into their business. There is enough to learn and do without becoming a tax expert.

Let tax season come and go without destroying your business. Whether you need current tax filing help or have 10 years of unfiled returns. There are solutions.

You just need to take action.