5. Donald Trump
The loss: President Donald Trump is a prime example of how keeping your personal and business finances as separate as possible is how you get to keep your yacht. Trump has filed Chapter 11 bankruptcy four times (all before he was President), but only with his first did he personally guarantee any of the debt — that’s how he lost the yacht.
The lesson: “You can file for business bankruptcy and still be loaded,” Bovee said. Even so, he stresses that it’s hard for the average business owner to keep personal and business finances totally separate. Most business loans will require you to personally guarantee the debt, he said, so if you default, the lender can go after your personal assets. It pays to protect your personal assets as much as you can when you start a business.