Jonathan Reich 
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
For merchants, predictable cash flow is the absolute lifeblood of sustainable growth. Whether you’re stocking inventory for the upcoming holiday rush, managing a growing payroll, or investing in marketing campaigns, waiting two to three business days for your hard-earned revenue to clear can severely bottleneck your operations. And in an era where commerce moves at … Read more
For too many finance leads, controllers, and business owners, the month-end close is a grueling headache of chasing receipts, untangling spreadsheets, and reconciling mismatched data. It drains your team’s energy, delays decision-making, and turns highly skilled financial professionals into glorified data-entry clerks, leaving them with little to no time for actual financial analysis. However, a … Read more
For most business owners, the decision of how to manage the books is a point of anxiety. In the early days, you can get away with a low-cost software provider and handle the reconciliation yourself on a Sunday afternoon. But as the business grows, the time spent coding expenses and chasing invoices begins to eat … Read more
In the early days of a business, the financials are usually an ad hoc assembly of spreadsheets, receipts, and a business checking account. But as revenue grows, so does the administrative burden, and eventually, every business owner faces a classic dilemma: Do you keep using a spreadsheet, or is it time to pay for a … Read more
If you’re a founder preparing for a liquidity event or a private equity sponsor sizing up a platform acquisition, your standard CPA is not equipped to handle your deal. Trust me, I am that standard CPA, and I just don’t have the chops to give deals of that size what they deserve. The reason for … Read more