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Healthy vs. Unhealthy Debt for Small Businesses
Some business owners avoid debt at all costs. They bootstrap everything, pay cash for equipment, and feel a sense of pride in owing nothing to anyone. Other business owners use debt aggressively. They finance growth, leverage other people's money, and view debt as a tool to accelerate what would otherwise take years to build. Neither approach is inherently right or wrong. What matters is whether the debt you're taking on is healthy or unhealthy, and too many business owners d
Jason Medlin
6 days ago5 min read


Why AI Won't Replace Your Financial Partner: The Human Element in Business Finance
There's no shortage of AI tools promising to handle your bookkeeping, prepare your taxes, and manage your finances. Upload your bank statements, connect your accounts, and let the algorithm do the rest. These tools are genuinely useful. They can categorize transactions, flag anomalies, generate reports, and automate repetitive tasks. I use AI tools in my own practice. They make certain work faster and more efficient. But there's a gap between what AI can do and what a financi
Jason Medlin
Mar 94 min read


Tennessee Business Tax Explained: What Every Business Owner Needs to Know
Tennessee doesn't have a state income tax. That's the headline most people know. But what many Tennessee business owners don't realize is that the state does have a business tax, and if you're operating a business here, you're probably required to deal with it. The Tennessee Business Tax catches a lot of business owners off guard. It's not complicated once you understand it, but the requirements for registration, licensing, and filing depend on your revenue level, and getting
Jason Medlin
Mar 25 min read


Estimated Tax Payments for Small Business Owners: What You Need to Know
When you work as an employee, taxes are withheld from every paycheck. By the time April rolls around, you've already paid most of what you owe. Filing is just a matter of squaring up. When you run a business, nobody withholds anything. The IRS still expects to be paid throughout the year, but now it's your job to make that happen. That's where estimated tax payments come in. And for many business owners, this is where tax planning goes sideways. Who Needs to Make Estimated Ta
Jason Medlin
Feb 235 min read


Receipt Management for Small Business Owners: What the IRS Actually Requires
Most small business owners believe they need to keep a paper receipt for every single business expense. The shoebox full of crumpled receipts. The overstuffed folder in the filing cabinet. The anxiety every time a receipt fades or gets lost. Here's the truth: the IRS requirements for receipt management are much more relaxed than most people think. That doesn't mean you can ignore documentation entirely. But it does mean you can stop hoarding every coffee shop receipt and star
Jason Medlin
Feb 165 min read


Employee vs. 1099: How to Classify Workers Correctly
One of the most common and most dangerous mistakes small business owners make is misclassifying workers. Calling someone a 1099 contractor when they should be an employee might seem like a simple payroll decision, but it carries real legal and financial consequences. The distinction between employee vs. 1099 isn't about what's convenient or what the worker prefers. It's determined by the nature of the working relationship, and the IRS, Department of Labor, and state agencies
Jason Medlin
Feb 95 min read


Understanding Your True Labor Costs: What Every Business Owner Needs to Know
When most business owners think about what an employee costs, they think about the hourly rate or annual salary. If you're paying someone $25 an hour, that's what they cost, right? Not even close. The true cost of an employee is significantly higher than their base wage. Depending on your industry and benefits structure, you could be paying 25% to 40% more than that hourly rate once you factor in payroll taxes, insurance, benefits, and the hidden costs that rarely make it int
Jason Medlin
Feb 25 min read


Vehicle and Home Office Deductions: What Small Business Owners Need to Know
Two of the most commonly claimed deductions for small business owners are also two of the most commonly misunderstood: the vehicle deduction and the home office deduction. These aren't exotic tax loopholes. They're legitimate deductions available to nearly every business owner who uses their personal vehicle for business or dedicates space in their home to their work. The challenge isn't whether you qualify. The challenge is understanding the rules well enough to claim what y
Jason Medlin
Jan 266 min read


Pricing for Profit: How to Stop Undercharging for Your Services
Most small business owners are undercharging. Here's how to calculate what you need to charge, implement value-based pricing, and build a business that actually supports your life.
Jason Medlin
Jan 196 min read


Should You Elect S Corp Status in Tennessee? What Business Owners Need to Know
S Corp election is often pitched as a tax no-brainer. But when you factor in the QBI deduction, Tennessee's F&E tax, overhead costs, and compliance requirements, the break-even is higher than you think.
Jason Medlin
Jan 126 min read


How to Set Financial Goals for Small Business: A New Year Guide
Every January, business owners set financial goals they abandon by March. Here's how to set specific, measurable goals you'll actually achieve—and build systems to track progress.
Jason Medlin
Jan 58 min read


How to Read a Profit & Loss Statement Like a CEO
Most business owners glance at their P&L and check if the bottom line is positive. CEOs read it differently—looking for signals, trends, and strategic insights. Here's how to interpret your profit and loss statement for smarter decisions.
Jason Medlin
Dec 26, 20258 min read


Bookkeeping for Real Estate Investors: What You Need to Know
Real estate investing builds wealth—but only if you track the numbers accurately. Here's what you need to know about rent rolls, CapEx, debt service, and investor reporting.
Jason Medlin
Dec 12, 20259 min read


Top 5 Year-End Tax Strategies for Small Business Owners
The best tax planning happens before December 31st. Here are five strategic moves small business owners should make now to reduce taxes and avoid April surprises.
Jason Medlin
Dec 5, 20258 min read


Understanding Owner's Draw vs Salary: How to Pay Yourself the Right Way
How you pay yourself isn't just about getting money in your pocket—it's a strategic decision that affects your taxes, cash flow, and long-term wealth building. Here's what works for each business entity.
Jason Medlin
Nov 28, 20255 min read


Year-End Financial Prep for Small Business: Checklist & When to Hire Help
Year-end financial prep isn't just about tax compliance—it's about setting your business up for a stronger start to the new year. Here's what needs to happen, why it matters, and when professional support makes sense.
Jason Medlin
Nov 21, 20256 min read


When to Bring on a Fractional CFO for Small Business (And What Changes When You Do)
There's a gap between recording transactions and making financial decisions—and most small businesses live in that gap longer than they should. Here's how to know when you've outgrown basic bookkeeping.
Jason Medlin
Nov 14, 20255 min read


The Financial Playbook for Home Service Businesses
Every thriving home service company runs on more than hard work — it runs on a financial playbook. Learn how to build a smarter system for cash flow, pricing, and growth in your business.
Jason Medlin
Nov 7, 20252 min read


Financial Playbook for Marketing Agencies
Marketing agencies scale quickly, but without structure, cash flow and margins can get messy. This playbook outlines four essential financial pillars—pricing, cash flow, reporting, and tax strategy—to help agencies grow with confidence and clarity.
Jason Medlin
Nov 3, 20252 min read


How to Read Financial Statements for Small Business
Understanding your financial statements isn’t about accounting jargon—it’s about knowing your numbers well enough to make confident business moves. Here’s how to read the P&L, Balance Sheet, and Cash Flow Statement like a pro.
Jason Medlin
Oct 24, 20252 min read
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