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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


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


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


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
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