We optimized tax structures in a way that was very technical and awesome — until one of our founders lost the plot, accused everyone of fraud, went to our investors, and blew up the company.
After the fallout cleared it turned out we, the other founders, had done nothing wrong. Not even non-standard, just advanced. But now the lawyers had all the money and the company failed.
Perhaps it would have been more efficient to not optimize taxes and instead optimize founder alignment.
Keep the parts of the business that are not directly on the critical path to success completely normal and standard.
After the fallout cleared it turned out we, the other founders, had done nothing wrong. Not even non-standard, just advanced. But now the lawyers had all the money and the company failed.
Perhaps it would have been more efficient to not optimize taxes and instead optimize founder alignment.
Keep the parts of the business that are not directly on the critical path to success completely normal and standard.