Surviving a Certified Professional Assassin

If there were such a thing as a business horror movie it’d probably start calm and cheery as 2014 did for me and my small business. There was money, great clients and everyone was getting along. Conversations tended to focus on our personal lives and the wonderful projects we were tackling to change the world. If anything life was actually a little too good.

The reality was that even though our clients were well served our business was neglected. We were focused on delivering great software and had passed the core of the business into the arms of a Certified Public Accountant that we hadn’t vetted and failed to properly check-in with. They paid our bills, recorded our spending, filed taxes; everything. Of course, we’d occasionally talk but the conversations were mostly about family, the weather in Greenville, tech… someone might toss out a number with “gross” or “net” but it didn’t register much and they didn’t insist that it register. We had no idea that CPA could easily stand for something much more dangerous.

The plot turn was precipitated by our growing profits which, as an LLC, stacked significant tax liability onto the partners’ personal tax returns. This acute personal pain is what made us finally venture into the dark unknown of our business’s finances; There had to be a way out of such high taxes. So we called our CPA and asked them to fix the issue. They suggested that moving to an S corp would be easy and should result in a dramatic reduction of personal tax liability: We’d save money. Sounded good to us; our CPA was great! We grabbed our failure-prone flashlights and gamely followed along.

At this point, our naivety had already placed us in serious danger and just like a movie we were clueless. If I could look back and watch it all on my TV I imagine this would be that squirmy moment where the outcome is so clear, the blind trust so impossible, and the tension so high that you yell “go back!” to the poor on-screen sap that’s about to get whacked.

But we didn’t turn back or even ponder the situation. We didn’t seek the advice of others or ask questions or even bother to glance at our own books…