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Author name: Chris Barrett

Through the use of technology and strategic thinking, Chris brings executive-level financial support into your business.

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The Risk Most SBA Buyers Don’t Put in the Model

SBA 7(a) financing has made business ownership accessible to thousands of acquisition entrepreneurs. It can provide meaningful leverage, long amortization, and a capital structure that would be difficult to replicate with conventional financing.

That can create extraordinary upside for the right operator buying the right business.

But the same structure comes with an important tradeoff: the personal guarantee.

Buyers often spend weeks diligencing normalized earnings, customer concentration, working
capital, margins, capex, and debt service coverage. They should put the same rigor into
understanding what a failed deal could mean for their personal balance sheet.

A good acquisition model should show both sides of the distribution: what success could create
and what failure could cost.

The Risk Most SBA Buyers Don’t Put in the Model Read More »

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Using an SBA Loan to Buy a Business? You Need Due Diligence!

In a recent episode of the EntreLeadership podcast with Dave Ramsey, a caller shared a cautionary story that every aspiring business buyer needs to hear. The caller had taken out an SBA loan to expand their daycare business and open a second location. But what seemed like a smart move quickly turned disastrous.

Using an SBA Loan to Buy a Business? You Need Due Diligence! Read More »

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First Year Business Owner Tax Tip: Convert Your 401(k)

Here’s something most young entrepreneurs don’t realize:
The year you buy a business is often one of your lowest taxable income years, which creates a rare tax planning opportunity.
Instead of just surviving year one, you can use it strategically, potentially reducing your lifetime tax liability by making one smart move: a Roth conversion.
Let’s break it down.

First Year Business Owner Tax Tip: Convert Your 401(k) Read More »

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Avoid Tax Trouble: Common Home Office Deduction Mistakes

Operating a small business from home offers flexibility, convenience, and meaningful tax advantages. One of the most valuable benefits available to U.S. small business owners is the home office deduction. However, while the deduction can lower taxable income, it must be handled carefully. Misunderstanding the rules, miscalculating expenses, or failing to document properly can create unnecessary IRS scrutiny and financial consequences.
Many business owners either overclaim the deduction or avoid it entirely out of fear. The reality is that the IRS allows this deduction when it is calculated correctly and supported with proper records. Understanding the most common home office tax deduction mistakes

Avoid Tax Trouble: Common Home Office Deduction Mistakes Read More »

Income tax folders, forms, a pen and a calculator on a desk

Business Tax Filing Extensions: What They Do and Don’t Do

As a small business owner, tax season can be stressful, especially if you need extra time to organize your paperwork. Many entrepreneurs assume that filing a business tax extension payment deadline for small business automatically gives them more time to pay what they owe. Unfortunately, that’s not true. Understanding the difference between filing and payment deadlines is critical to avoid costly IRS penalties and interest. So, what is a business tax extension? A tax extension is a request to delay your filing deadline, not your payment deadline. For most businesses, this involves submitting IRS Form 7004 (or Form 4868 for sole proprietors) by your original due date so you get up to six extra months to submit your tax return. It’s a lifeline for busy entrepreneurs, but don’t confuse it with more time to pay what you owe.

Business Tax Filing Extensions: What They Do and Don’t Do Read More »

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