That answer is different for everyone. For some owners, that may not want to be involved in the bookkeeping side of things, the best time may be when you are starting your business. For other businesses, it could be when the business owner has become frustrated with working late hours trying to stay on top of the books. For other, larger businesses they will hire an outsourced professional bookkeeper to act as a second set of eyes and make certain the in house staff is taking care of things correctly and accurately. An Outsourced Professional Bookkeeper will help you to maximize your profitability and let you get back to running your business.