Bookkeeping, tax, and fractional CFO services for businesses in Franklin and across Greater Nashville.

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My books are months behind — where do I even start?

First, take a breath. This is one of the most common situations business owners face. You got busy running your business and the books fell behind. It happens constantly and it’s fixable.

Start by figuring out the last month where your books were accurate and fully reconciled. That’s your starting point. Everything before that month is your baseline. Everything after it is what you need to catch up on. If you’re not sure where things went off track, look at your last bank reconciliation in QuickBooks or whatever software you use. That’s the last point you can trust.

Next, gather your bank statements and credit card statements for every month that’s behind. Download them from your bank’s website as PDFs and as CSV files if your software can import transactions. You’ll also want any loan statements, PayPal or Stripe records, and any other accounts where money moved. Don’t worry about organizing receipts yet. Statements are what matter for getting the books caught up.

Work forward one month at a time. Enter or import transactions, categorize them, and reconcile the bank account for that month before moving to the next one. Trying to do everything at once leads to errors that cascade through every following month. Sequential reconciliation is the only way to make sure each month ties out before you build on it.

As you work through each month, flag anything you’re unsure about rather than guessing. A “needs review” category or tag keeps things moving without burying mistakes in the wrong account. You can circle back to flagged items once the bulk of the work is done.

Prioritize based on deadlines. If you have a tax return due or quarterly payroll filings that are late, those months need attention first because penalties are accumulating. If nothing is immediately due, just work chronologically from the last clean month forward.

Be honest about whether this is something you can realistically do yourself. If you’re three or four months behind with relatively few transactions, you can probably knock it out over a few weekends. If you’re six months or more behind, have hundreds of monthly transactions, or run payroll, the time investment grows quickly. Catch-up bookkeeping is a specific service designed for exactly this situation, where someone works through the backlog systematically and hands you back a clean set of books.

The most important thing is to not let the catch-up work stop you from staying current going forward. If you start cleaning up January through June but keep falling behind on July and August, you’re running in place. Some business owners find it better to hire help for the backlog while they focus on keeping current months on track.

Once you’re caught up, build a routine that prevents this from happening again. Weekly transaction review takes 20 to 30 minutes for most small businesses. That’s dramatically less painful than the marathon cleanup session you’re facing now. Having CFO services for small businesses or even basic monthly bookkeeping support creates accountability so things don’t pile up a second time.

The worst thing you can do is nothing. Behind books don’t fix themselves, and the longer you wait the harder the catch-up becomes. Pick a starting point, gather your statements, and start moving forward one month at a time.

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More Questions

How does a fractional CFO help with business decision-making?

A fractional CFO translates your financial data into forward-looking analysis you can act on. They build models, forecast cash flow, and evaluate scenarios so that hiring, pricing, and growth decisions are grounded in real numbers instead of gut feeling.

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What financial reports should I be getting from my bookkeeper every month?

At minimum, you should receive a profit and loss statement, a balance sheet, and a cash flow summary every month. These three reports give you the full picture of how your business is performing and where your money is going.

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How much does outsourced bookkeeping cost for a small business?

Most small businesses pay between $300 and $1,500 per month for outsourced bookkeeping. The exact cost depends on transaction volume, number of accounts, and how complex your financial situation is.

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How do I choose the right bookkeeping service for my business?

Start by understanding what you actually need, then evaluate providers based on industry experience, software fit, communication style, and whether they can grow with your business.

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When does my business need a fractional CFO?

Your business likely needs a fractional CFO when you're making financial decisions based on gut feeling instead of data, experiencing cash flow surprises, or approaching growth that requires strategic planning beyond what basic bookkeeping provides.

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How do I transition from doing my own books to outsourced bookkeeping?

Start by gathering your login credentials, bank statements, and any records you've been keeping. A good bookkeeper will handle the rest, including cleaning up whatever state your books are in. The first month takes more effort, but after that your involvement drops significantly.

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Revallo is a Franklin, Tennessee firm providing bookkeeping, tax, and financial advisory services to businesses across Greater Nashville. Founded by James Manring, who brings Big 4 rigor and years of accounting experience to every engagement.

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