“I’m a hustler, I know how to make money—but once it comes in, I don’t know where it goes or how I should be spending it.”

“I don’t have a handle on what it costs monthly to run this business.”

“I was busy running the business, then I looked up and didn’t have money for payroll. I never want to feel like that again. I can’t operate without understanding how my numbers work.”

“I feel like I make a lot of money, but I also feel like I don’t have a lot of money. Do you understand what I mean?”

If these statements resonate with you, you’re not alone. Many business owners at the $5M+ revenue mark struggle with cash flow and financial clarity.

The Root of the Problem: Poor Bookkeeping

After hearing these concerns repeatedly, we found that most of these businesses suffer from poor bookkeeping—meaning their books are either inaccurate, incomplete, or outdated.

Think of your books like a garden. If they haven’t been properly maintained for months (or if they’ve been handled by someone who isn’t a professional), they become an overgrown mess.

Using the same metaphor of the overgrown garden, business owners then scramble to find a landscaper (accounting/financial person) to work magic on a shoestring budget, hoping a quick fix will restore order.

But the truth is, it takes more than a weedwacker and a few hundred dollars to get financial clarity.

Prioritize Bookkeeping: It’s Critical to Your Financial Health

Bookkeeping is not something you do once or twice a year just for tax reporting. That’s like waiting for a wedding or vacation to lose weight—it doesn’t work. Consistency is key. Your books should be updated monthly, but no later than quarterly.

Bookkeeping Mistakes to Avoid

  • Don’t hire someone unqualified. Handing your books to someone who doesn’t understand accounting or choosing the lowest-cost provider will likely cost you more in the long run.
  • Don’t DIY your books unless you’re an expert. Being “good at math” isn’t enough. You started your business to focus on your passion, not to spend hours staring at spreadsheets.

The Benefits of Good Bookkeeping

When your bookkeeping is accurate and up to date, you:

  • Know where your money is coming from, where it’s going, and what’s left.
  • Understand your true operating costs—so you can cut waste and invest where it matters.
  • Manage seasonality and avoid cash flow crises.
  • Boost investor and lender confidence. Clean books = reliable financial statements = faster access to funding.
  • Reduce tax season stress. Sloppy books lead to missed deductions and IRS headaches. Clean books help you maximize tax savings and keep more money in your pocket.

Get the Right Help: Don’t Freestyle Your Finances

If you want to grow, make money, and move like a boss, invest in a qualified bookkeeper. Successful entrepreneurs, artists, and athletes don’t operate solo—they have a team that helps them excel.

How to Find the Right Bookkeeper

  • Have a finance or accounting expert interview candidates.
  • Use bookkeeping tests (available online) to gauge their expertise.
  • Ask for client referrals to verify their track record.
  • Ensure they have experience with businesses of your size and industry.
  • Engage them for at least six months and evaluate their ability to work seamlessly with your CPA and fractional CFO.

The Bottom Line: You Can’t Afford NOT to Have Good Bookkeeping

Good bookkeeping is the foundation of financial excellence. It enables you to make smarter, faster, and more profitable decisions. Make the investment now—or suffer costly consequences later.

At FinCore, we help our fractional CFO clients maintain accurate, up-to-date, and reliable books. If they already have a bookkeeper, we oversee the process so they don’t have to.

Need a financial partner with an experienced bookkeeping team? Let’s talk. 😉 Book a Complimentary 30 Minute Financial Strategy Session.

Tricia Taitt is the CEO and Chief Financial Choreographer of FinCore. She holds an M.B.A from The Fuqua School of Business of Duke University, and a BS in Economics with a Finance concentration from The Wharton School at the University of Pennsylvania. For over 20 years, she’s been a finance professional. Half of the time was spent working on Wall Street while the other half was spent in the trenches side by side with small business owners. As a result of working with FinCore, clients have been able to take control of their numbers and feel more confident in their ability to make decisions, while increasing profits by 10% and building a cash stash to invest in growth. Follow Tricia on LinkedIn and Instagram.

If you’re ready to see what our team of CFOs can do for your small business, Schedule a Financial Strategy Session.