Jonathan Reich 
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
In recent years, startups have increasingly shifted away from the centralized office and toward a globally distributed workforce. These days, founders are hiring the best engineers, marketers, and sales professionals in the world — regardless of location. The hard part is paying and managing those people across borders, which is where Deel earns its keep … Read more
One of the most significant advantages of building your e-commerce store on WooCommerce rather than Shopify is the absolute freedom you have over your payment infrastructure. While Shopify heavily incentivizes its users to stick with Shopify Payments by penalizing them with extra transaction fees if they use third-party gateways, WooCommerce remains open-source and agnostic. You … Read more
As a startup, the payment processor you choose on day one is rarely the financial engine that will carry you to an exit. What works flawlessly during your seed round when you’re testing product-market fit can become a massive liability once you secure Series A funding and start pushing volume. For example, Stripe is the … Read more
Evaluating the “best value” in startup accounting software requires a reassessment of how founders and finance operators calculate cost. In the early stages of building a company, it is incredibly tempting to navigate to a software provider’s pricing page, sort from lowest to highest, and select the platform with the cheapest monthly subscription fee (a … Read more
The transition from a signed term sheet to a functioning, private equity-backed finance department is the most critical operational hurdle in the investment lifecycle. In the middle market, acquirers frequently purchase companies that possess phenomenal products or services but operate with severely underdeveloped financial infrastructure. The target company’s financial reality on Day 1 typically consists … Read more
Kimblewick Group sits in the operator-led finance advisory lane. It’s positioned around foundational finance, strategic finance, and transaction advisory, with services that include accounting oversight, budgeting, reporting, financial modeling, KPI tracking, fundraising support, sell-side M&A, buy-side M&A, and investor relations. Basically, they can help you run your business if you don’t know how to best … Read more
Selling your business is one of the hardest decisions you’ll ever make. But to private equity firms who are buying your cash flow, it’s not much more than a transaction. So even if you’ve poured your heart and soul into your life’s work, if your financials are messy, undocumented, or rely on informal startup-era accounting, … Read more
Switching accounting software sounds simple at first — until you remember what lives inside the old system: your chart of accounts, customer list, vendor list, transaction history, bank reconciliations, open invoices, unpaid bills… the list goes on and on. That’s why I see most business owners stay in the wrong accounting system too long. It’s … Read more
I didn’t switch from QuickBooks Online because it was bad software. That’s oversimplifying it, and it’s not true anyway. QBO works, works well, and is overall a great software. It’s ubiquitous for a reason, after all. Besides, QBO did a lot for us. It held the books together, handled the basics, and gave us the … Read more
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