Jonathan Reich 
Payout speed is an important metric to judge payment processors by, but there’s more to it than just # of hours. As a CPA, I care more about what that speed does to working capital, payroll timing, vendor payments, margin, and how much cleanup your accounting team (ME!) may have to do after the fact. … Read more
When a finance partner gets acquired, clients start doing math. Not panic math, but practical math. They start to ask themselves questions like, will my main contact stay? Will pricing change? Will the new parent push a bigger-firm service model? Will my business still be the kind of client they built around, or am I … Read more
If you’re shopping for a Pilot alternative, you’re probably not looking for “bookkeeping but from someone else.” You’re looking for a finance partner that can help you close the books, forecast cash, clean up tax pain, support lenders or investors, and give you better answers than a dashboard ever could. After all, a good outsourced … Read more
If Stripe freezes your funds, the worst move is to panic, even though that’s probably instinctively your first response! The better move, however, is to get organized, find the exact reason, respond with the right documents, and protect your cash flow while the review is still open. Stripe can pause payouts for several reasons, including … Read more
Small business owners don’t need a tax preparer who shows up once a year, plugs numbers into a return, and disappears. They need a tax partner who can start with clean books, spot planning moves before year-end, keep estimates on track, and then file accurately. Good recordkeeping sits at the center of getting taxes right, … Read more
As a CPA, I’ve spent more hours than I care to admit staring at bank statements and general ledger exports, trying to figure out why a deposit doesn’t match anything in the system. Most of the time, it’s a simple timing difference or a merchant fee that wasn’t split out. But when you’re scaling a … Read more
As a CPA who spends most of my day digging into the guts of financial systems, I’ve seen firsthand how “growth” can quickly turn into a “grind” when your accounting software can’t keep up. Most founders start with a single entity, because it’s easy, logical, and makes sense. One set of books, one bank account, … Read more
Let’s be honest for a second. If you’re a business owner or a CEO, “Finance Transformation” sounds like one of those expensive, nebulous phrases dreamed up by a consultant in a suit to justify a very large invoice. It’s right up there with “synergy” and “digital paradigm shift,” industry terminology that you could expect to … Read more
The mantra for startup founders has shifted from “growth at all costs” to “sustainable growth at high velocity.” To achieve this, the modern finance stack has moved away from static spreadsheets and toward robust, dynamic platforms that interpret data with real-time visibility. These tools act as invisible team members, automating the mundane aspects of bookkeeping … Read more
In recent years, I’ve watched the monthly close evolve from a standard operating procedure into a liability. These days, a month is an eternity. Founders who wait until the 15th of the following month to see a report of their previous month’s performance are effectively flying a jet by looking at a map of where … Read more
I’ve always had a bit of a bone to pick with the way accounting is typically sold to small businesses. Most founders start out thinking they just need someone to do the taxes or keep the books clean, but I’ve seen time and again how that line of thinking leads to a major blind spot. … Read more
In the early days of a business, accounting is mostly about survival. You’re either hacking together a QuickBooks chart of accounts at night or relying on a part-time bookkeeper to keep transactions flowing and taxes filed. That’s good for lean teams, manageable volume, and “success” defined by positive cash at month’s end. But growth changes … Read more
If you’ve ever sat in a boardroom (or a Zoom room) trying to explain why the final numbers from three weeks ago just changed by 15%, you know the pain of a broken month-end close. As a CPA, I’ve had this awkward conversation more than I should. I’ve also seen the difference between a set … Read more
Whether you are an e-commerce merchant scaling past your first eight figures or a construction firm managing a complex web of subcontractors and progress billings, there comes a point where the numbers stop being a scoreboard and start becoming a bottleneck. As a CPA, I’ve seen this movie before. You start with a local bookkeeper. … Read more
In the rapidly maturing landscape of 2026 financial technology, the traditional, monolithic accounting software of the previous decade have been replaced by specialized, AI-driven operating systems. For modern founders, the choice is no longer between QuickBooks and Xero, but rather between high-velocity specialized platforms that promise to turn the back office into a strategic asset. … Read more
In recent years, the choice of a payment processor has transformed from a back-office decision into something much more strategic. For years, the industry was dominated by legacy, enterprise-grade systems designed for stability and high volume (often in a traditional retail setting). But as we shift more toward an integrated “everything-as-a-service” model, the friction between … Read more