Common reasons given for this lack of strategic tax planning and strategic exit planning is, "we need to make too many assumptions and guesses", "everything changes anyway", and often, "we are too busy and just never got to it".

Hence business owners who would never run their business with legacy software, put their crews in antique trucks, or run inefficient assembly lines often have old corporate elections and avoidable tax consequences because of strategic decisions made 20 years ago or more. (Just because you can't see it doesn't mean it isn't there.)

A recent example we saw was a meticulously run supplier of construction safety equipment. When the business was formed 25 years ago the owner elected C Corporation tax treatment. At the time there were many strategic tax benefits to that treatment and the election was the right thing to do. Yet somewhere between 12 and 15 years ago those benefits disappeared but no one ever looked forward to the long term strategic tax plan and strategic exit plan in order to foresee negative consequences.

The business had an estimated sales value of about $1,500,000 and because of the size and nature of the business buyers insist that the sale be structured as an asset sale. This scenario means the owner's Tax Partners are going to receive approximately an ADDITIONAL $300,000 from this transaction because of the old election. This is a huge price to pay for missing a change in tax status at the right time.

There are many other pitfalls and traps that can catch the small business owner. Because owners understand the day to day operations the traps tend to jump out and bite at times requiring major change and transition. Putting together the right team and asking the right questions periodically starting years in advance will help avoid these traps and produce superior results.

While long range transition, tax, and exit strategy planning and analysis seem expensive in the short run they are cheap in the long run. (Yes I mean cheap.) At the end of the day it is what you keep that counts. Keep more by planning.

Note: This is not tax advice but a sample case study based on similar situations. You are advised to seek professional assistance for your specific situation before taking any actions. No part of this is intended to be used to avoid tax penalties, or for promoting, marketing, or recommending to another any tax related action or activity.