Brandon Chu — As an previous owner of a small eCommerce company, I had this problem many times over. You are right about the procrastination. It’s the one thing that I hated — accounting and gov’t paperwork even though I understood the need. I am no accounting expert but why couldn’t you have taken the dates from the scanned receipts and use that as a transaction date? It wouldn’t have solved all the problems for manually entered transactions but one way to ask the question when entering is “when did this event occur?” (put up a warning to the user of the tax implications). I am guessing here since I didn’t use Freshbooks, I used Quickbooks and thought about using FB but it didn’t support our needs at the time. Thanks for your posts. I have been around the block and made some bad mistakes — you’re dead on about these things. You can’t learn in school or from a class. It’s take time and experience to figure out how to be a good PM and still is a work in progress.