An Inexpensive Way to Learn From the Very Expensive Mistakes of Others
I enjoy reading tax court cases because they are great way to identify what the courts are scrutinizing and what they find important. It’s also a very inexpensive way to learn from the very expensive mistakes of others. It’s a great form of leverage.
A recent tax case caught my attention. It involved a doctor who operated his practice as a sole proprietorship for several years, and then changed the structure. The new structure involved several changes that provided significant tax savings.
Two of the key changes were:
1. Putting the practice in an LLC. The LLC was owned by the doctor and a newly formed corporation (owned by the doctor).
2. Forming another new corporation (owned by the doctor) to provide management services to the LLC.
On the surface, the structure isn’t unusual. It’s not uncommon for a doctor’s practice to outsource its management function, nor is it uncommon for a practice to undergo ownership and entity changes.
The court, however, disregarded the two corporations as separate entities for tax purposes. This had a significant impact on the tax savings because all the income earned by the corporations was attributed to the doctor. At the end of the day, because the corporations were disregarded by the court, the tax result was no different than when the doctor was a sole proprietorship.
What went wrong? While this was a U.S. Tax Court case, the lessons to be learned are universal. There is a lot to be learned here about what went wrong.
The main issue the court had with the structure was that the doctor continued business as usual and changes were not made to the business operations to reflect the new structure.
Here are few of the specific findings that the court relied on in its decision:
- Neither corporation ever had employees
- Neither corporation ever paid salaries
- There was no evidence that the management service corporation ever performed the management services for which it was paid
- There was no service agreement between either corporation and the LLC – Only one of the corporations had a bank account
- Neither corporation had assets (other than a bank account)
- Neither corporation had day-to-day activity
- Assets were not retitled to / from the LLC






