carpeaqua

I believe it was a recent episode of Build & Analyze where Marco was talking about his struggles with dealing with the less sexy side of running your own business: managing the books, paying taxes and the constant fear of being audited by the IRS.

As someone who has been dealing with those stresses for five years now, it resonated. Managing Second Gear’s financials has never really been difficult. Until recently I used Quickbooks for the Mac and would just input the week’s receipts into the register, generate the single invoice a month I have if necessary, and write any checks that needed to go out. It took an hour tops.

Despite how simple it was, I was never able to shake that “I’m doing something seriously wrong” vibe each time I tried to assign a transaction to a specific sub-account in QuickBooks. My first step to resolving this was hiring a CPA a few years ago. He is a fantastic resource and just lets me dump a load of paper on him in early February to turn into a coherent mass of paper to submit to the IRS. He also updates my estimated taxes a few weeks before they are due each quarter so I can send a more accurate assessment rather than having to write one large check in April to make up the difference.

Even with the help of a CPA, I was frustrated with managing QuickBooks myself because even after 4.5 years I was uncomfortable and unsure of what I was doing. I am a firm believer in hiring an expert to do things you aren’t comfortable doing, so I started looking around the area for a part-time bookkeeper. I found a local company who specializes in managing the books for small businesses like myself that was fairly affordable and worked over email and meeting at Starbucks.

This is the point in the story where things turn south.

The first suggestion from the bookkeeping service was to switch from QuickBooks for the Mac to QuickBooks Online. The reasoning was that it is easier for them to manage without me having to send them database files back and forth. My CPA had suggested it in the past, and I don’t really have true allegiance to the Mac product, so I decided to do the transition.

First problem: there is no good way to transfer Quickbooks for Mac to the online product. Intuit suggests installing Windows. Moreover, the import process requires the $25 a month plan rather than the $12.95 starter plan that is more than adequate for my small company. After a back and forth with Intuit, I decided to just let the bookkeeper manually re-add the transactions to QuickBooks Online and re-categorize them in a more sane way.¹ The process took about six hours of billable time, so I was willing to eat the cost and save the hassle of dancing Intuit’s dance.

Once the transactions were re-added to QuickBooks, the monthly process of working with the bookkeeper was supposed to be simple. I would email her an annotated copy of my monthly bank statement and BCC her on any invoices I sent out so she could input that data.

We went through this input process for two months when my bookkeeper abruptly quit the company she was contracting for, which left me high and dry. The owner of the bookkeeping company was apologetic and offered to connect me with another bookkeeper. As I had just invested the time and money going through the process of introducing someone to Second Gear’s business and getting them ramped up, I took it as a sign that I should probably manage the financials myself again.

That opinion was further validated when I sent my financial data to my CPA a few months ago and he complained that the bookkeeper had mis-categorized quite a bit of data into the wrong accounts. That was fun to fix. In the end, working with a bookkeeper for three months was an $800 lesson in not trying to get out of all responsibilities as a business owner.