Simple.com Tax Preparation Lovefest

I am crushing on my +Simple account now that I am gathering my expenses for tax purposes. While Simple is not so useful this year, due to limited use in 2015, it is going to be awesome next year. Simple currently only offers personal accounts, although their Help section mentions that they are considering business accounts in future, which would be even better.

The one feature that will make my tax preparation less demanding next year is the ability to tag my expenses. By adding a #business tag to the appropriate income and expenses, I instantly create a filter for my searches. Next year, for example, I would simply search "2016 #business" to get a report listing all my business expenses and income. Then, it is as simple as exporting the list. Done.

Another excellent tax feature is the ability to upload invoices to the individual transactions. This is great in that I would have access to the actual invoice should I ever need to verify that the expense is business-related.

Finally, the ability to add memos to my transactions is extremely useful, not only for tax purposes. Sticking to taxes for now, a memo would allow me to document why an otherwise personal transaction is business-related. For example, I frequent Walmart to purchase groceries and other items. On occasion, I need to purchase a wireless router or a tool to finish a tech job. In a sea of Walmart transactions, it would be difficult to distinguish a business expense from an everyday expense. That is, it would be difficult unless I tag, attach the receipt to, and annotate the transaction.

The reason all of this is easier with Simple is because this can be done as you go. As soon as you purchase and have the receipt in your hand, you can tag, photograph the receipt, and add a memo. The entry is automatically made for you when you swipe your card. You no longer have to go home, sync your accounting software, hunt for receipts, and then match them to transactions. Part of what makes keeping records is the drudgery of batch work. However, if bookkeeping is as simple as posting a tweet or other social update, it simplifies tax season.

If Simple ever does come around to creating business accounts, you bet I'll sign up in a heartbeat. Imagine that your accounting software was also your bank. One login. No syncing. No manual entries. Instant updates with every transaction.

I'm actually excited about doing taxes next year because of Simple.