Cross + Co - Insights
Your Bank Deposit Is Not Your Revenue
One of the most common bookkeeping mistakes I see is business owners recording the lump sum that lands in their account from Square, Stripe, Toast, or Clover as a single line of “sales.” The problem is that deposit has already been stripped of processing fees, refunds, chargebacks, tips, and sales tax—so booking it as revenue…
Your Books Aren’t Broken—They’re Just Behind
Six months in with financials you don’t trust? That’s not a crisis—it’s a catch-up, and it’s more routine than most owners realize. The mistake is believing you have to white-knuckle it until year-end before anything gets cleaned up. A focused reset—reconciling accounts, recategorizing transactions, and rebuilding a chart of accounts that actually reflects your business—can…
Your Business Account Isn’t Your Personal Wallet
“Just use the bank statements” is one of the most common shortcuts I see business owners take with their books—and one of the most costly. A bank statement only tells you what moved in and out of your account, not what you actually earned, what you owe, or what’s owed to you—and that gap gets…
Cheap to Ignore, Expensive to Fix: The Bookkeeping Trap
I’ve watched too many promising small businesses stumble not because their product failed, but because their books were an afterthought. When bookkeeping gets pushed to “I’ll deal with it later,” owners lose the one thing they need most: a clear picture of where their money actually is. Suddenly it’s tax season, cash flow is a…
Accurate Financials Are a Gift and a Mirror
After 20+ years in the books, here’s something most people don’t say out loud: accurate financials are a gift and a mirror. The advantages are obvious — clean books mean smarter decisions, faster financing, smoother audits, and a business you can actually steer instead of guess at. But here’s the disadvantage no one warns you…
Robots Can Reconcile. They Can’t Strategize
As a CPA and CFO, I get asked weekly: “Is AI coming for accounting jobs?” My answer: it’s coming for the boring parts — data entry, coding, reconciliations — and honestly? Good riddance. That grunt work disappearing means we get to do what we’re actually trained for: analysis, strategy, and the judgment calls that move…
Your Retirement Plan Is a Tax Loophole. Use It Like One.
If you’re a profitable business owner still parking money in a basic IRA, the IRS thanks you for the overpayment. As a CPA and CFO, I watch successful owners hand the government tens of thousands more than they owe—simply because they never upgraded past the retirement plan they opened on day one. A SEP-IRA, SIMPLE…
The State Is Already Counting Your Sales Tax. Are You?
You’d think “is this taxable?” would have a simple yes-or-no answer—but a plain bagel can be tax-free until you slice it, clothing is exempt in some states and taxable in others, and digital products follow no consistent logic at all. Layer in nexus, where a single threshold of sales, a remote employee can suddenly obligate…
The Letter No Business Owner Wants — DOL Audit
Department of Labor audit rarely arrives with a warning, and the businesses that weather them best are the ones that got their house in order long before the letter showed up. Most DOL audits zero in on the same fundamentals: worker classification, overtime and wage calculations, and whether your recordkeeping can actually back up your…
Your Business Is Unique. Your AI Has No Idea.
AI can count your transactions. It can’t count on knowing your business. As a CPA and CFO, I’ll be direct: AI accounting tools are impressive — until they meet the real world. A restaurant managing cash tips and food cost variances looks nothing like a construction company navigating job costing and retention billing. Neither looks…