Jonathan Reich 
Payment processing for digital products can get messy faster than you might think. A shoe store can prove delivery with just a tracking number, whereas a digital template seller has to prove that a download link worked, an email was sent, or a customer accessed the file. This means that a course creator might have … Read more
Most merchants don’t really think about their chargeback ratio until someone else brings it up, and unfortunately, that someone else is usually the payment processor. Maybe you get an email saying your account is being reviewed. Maybe your processor warns you that your dispute activity is trending too high (usually around the 1% mark). Or … Read more
Start Tax Planning Before the Buyer Shows Up Most founders start thinking about taxes after the letter of intent shows up, and I think that is totally backwards. By the time a buyer is serious, the tax levers may already be locked in. Your entity structure is what it is. Your books either support the … Read more
Most merchants learn about chargebacks the hard way. A customer disputes a charge, and suddenly the money is pulled from their merchant account. A fee shows up, and your processor sends a notice with a strict deadline. You look at the reason code, the transaction record, the shipping details, and the emails, trying to figure … Read more
Rippling is great when it comes to handling the people side of the business: payroll, benefits, onboarding, device management, employee data, contractor payments, and a growing list of finance workflows. But Rippling has its shortcomings as a general ledger or accounting system. Why is this important? It matters because payroll does not stop at paying … Read more
SaaS accounting looks simple from the outside. You sell software, customers pay monthly or annually, and revenue comes in through Stripe, ACH, credit card, or invoice. You’ll have payroll, contractors, hosting costs, software subscriptions, sales commissions, and maybe a few vendors, but on paper, it seems cleaner than a restaurant or even a retail business … Read more
I’m a CPA, so I tend to look at merchant fees the same way I look at any other line item on a P&L: not as a fixed cost, but as a cost that can be measured, challenged, and improved! Too many business owners treat credit card processing like rent and they assume it is … Read more
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