Jonathan Reich 
Checks are slow, cost money to print and mail, get lost, and are one of the most common targets for payment fraud. None of that is news to the person signing a stack of them every Thursday afternoon. So what’s stopping paper holdouts from changing usually isn’t all the downsides; it’s the tangle underneath: a … Read more
Ask three accounting vendors what their AI does to the general ledger, and you will get three answers that sound identical but mean entirely different things. One means a categorization model that guesses the account based on a bank feed line. Another means a chat interface that drafts an invoice when you describe it in … Read more
Most accounting software was built for someone sitting at a desk with two monitors and an afternoon to spare. However, most founders don’t work that way. They get hard questions when they’re in an Uber, in a hallway between meetings, or at 10 p.m. when the laptop is already closed. The answer to those questions … Read more
Shopify makes it deceptively easy to sell but deceptively hard to account for what you sold. What’s not immediately clear to new sellers is that a single payout hitting your bank account is not revenue — it’s gross sales, minus discounts, minus refunds, plus shipping income, plus sales tax you collected on behalf of a … Read more
In recent years, the million-dollar question being asked of accounting software has been “does it have AI?” Most vendors these days have an easy “yes” answer waiting, so in my opinion, there are two narrower questions that are more important to ask. First: Can the AI tools your team already opens every morning reach your … Read more
Stop me if this sounds familiar: Somewhere on a shared drive, there’s a spreadsheet that controls a significant, material line on your balance sheet. It has a tab for each month, a formula column that’s archaic nonsense that no one currently employed understands, and a hard-coded cell from the quarter you closed a deal mid-month … Read more
A merchant services agreement is a business-to-business contract that doesn’t have the same consumer protections as your personal credit card or cell phone plan. Both parties are assumed to have read the document and understood it, and no regulator is going to unwind a clause you skimmed past. This should reframe how you treat the … Read more
Bill pay platforms sit between your client’s vendor invoices and the money that pays them. They capture the bill, route it for approval, move the funds by ACH/check/card, and push the entry back into the ledger so no one is keying it twice. For a business owner paying their own vendors, picking one is a … Read more
Most accounting software was built for a business that sends an invoice and waits to get paid. As we all know, e-commerce does not work that way. You sell through a storefront, a marketplace, a social channel, and maybe a wholesale portal, and each one settles on its own schedule, nets its own fees, and … Read more
This old question usually shows up the same way. It’s Sunday night, the board deck is due Tuesday, and you’re rebuilding the same three-statement model you rebuilt last quarter because half the assumptions have gone stale and the actuals never tied out cleanly in the first place. The controller closed the books on time. That … Read more
Xero is good at capturing a bill; it’s the payment itself that tends to fall out of the system. You code the bill, route it for approval, mark it awaiting payment… and then open a separate browser tab to your bank, cut a check, or hand a list to whoever has signing authority. The payment … Read more
The month-end close has always been a pressure cooker. For most firms, it means a wall of reconciliations, journal entries, and checklists that stack up regardless of what else needs to be done. The process hasn’t changed much in decades. The tools have gotten faster, but the workflow is still largely sequential, manual, and dependent … Read more
The month-end close has become the proving ground for AI in accounting, and several distinct takes have emerged on it. For example, Puzzle and Digits sit at opposite ends of the design spectrum. Both promise to compress a 10-day cycle into something closer to a rolling exercise, automating much of the close while still keeping … Read more
Most accounting software comparisons are really arguments about time. Old system versus new system, desktop versus cloud, spreadsheet versus platform. This one isn’t. Digits and Docyt are both AI-native platforms, both launched in the last several years by venture-backed teams, both promising books that stay current instead of getting reconstructed in a panic three weeks … Read more
Every business needs books that are current and correct — not because anyone enjoys them, but because tax deadlines, diligence requests, or a lender asking what last quarter looked like all arrive assuming the work was already done. While many SMBs start off with self-run QuickBooks and ad-hoc spreadsheets, there comes a point (often very … Read more
The fractional CFO market has matured rapidly in recent years. What began as a stopgap for early-stage startups has evolved into a sophisticated professional service, with experienced operators managing portfolios of multiple clients simultaneously. These aren’t bookkeepers running month-end close on a single set of books; they’re finance leaders who need to move at startup … Read more