Jonathan Reich 
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
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