Jonathan Reich 
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
If your books are a mess, fix the foundation first. If your books are clean but you’re flying blind on what comes next, bring in the strategist. And if you’re at the point where comes a critical inflection point in the life of every company where the founding team realizes their current financial infrastructure is … Read more
Few scenarios are more agonizing for a business owner than logging into a dashboard to discover that tens of thousands of dollars in hard-earned revenue have been frozen for seemingly no reason. You can’t make payroll, you can’t pay your suppliers, and your customer service inbox is flooding while you sit trapped in an automated … Read more
There are few things more anxiety-inducing than looking at a cash flow forecast that promises a comfortable runway — only to log into the company bank account a week later and realize you’re staring at a completely different, much darker reality. When this happens repeatedly, the spreadsheet ceases to be a tool for strategic decision-making … Read more
Managing the books is one of the most time-consuming parts of running a small business, and also one of the most consequential. A missed invoice, a misclassified expense, or a tax deadline slipped past can cost more than just money. The good news is that modern accounting software has come a long way from desktop … Read more
Digits built its reputation on real-time financial intelligence, giving founders and operators a clean, AI-assisted window into their company’s money. It’s elegant, fast, and purpose-built for startups that want clarity without complexity. But depending on your business size, budget, or how hands-on you want your bookkeeping workflow to be, it may not be the right … Read more
In my years as a CPA, I’ve seen firsthand that B2B payments are a completely different beast than B2C. You’re typically dealing with five-figure invoices, net-30 terms, and multi-layered corporate approval chains. Ditching paper checks and wire transfers means finding a platform that understands complex financial workflows, like handling ACH seamlessly, automating Level 2 and … Read more