The short answer: before you need to show your books to anyone. If you’re six months from a fundraise and your books are a mess, you’re already behind.

Most founders wait too long. They’re busy building product, talking to customers, doing everything except accounting. The books get neglected until something forces the issue. An investor asks for financials. A bank wants documentation for a line of credit. Suddenly there’s a deadline and twelve months of transactions to sort through.

Hire a bookkeeper when you hit any of these points: you’ve raised money and need to track how you’re spending it, you’re about to raise and need investor-ready financials, you have more than a few months of transactions piling up, you can’t answer basic questions about your burn rate or runway, or you’re spending more than a couple hours a month doing it yourself.

For startups, the fundraising angle matters most. Investors will look at your books during due diligence. Messy financials slow things down and raise questions about how you run the business. Clean books, closed monthly, signal that you know what you’re doing.

The cost of waiting is higher than the cost of starting. A few months of catch-up work costs more than staying current from the beginning. And the stress of scrambling before a deadline costs more than either.