We've been trying to sell our car in Brooklyn for the past month or so, but have been stymied by issues with our title. The lender apparently never got around to putting themselves on it. So, in order to sell the thing in good faith I'm paying off the loan (very) early. Unfortunately, that means an unexpected short-term expense of about $25,000.

Covering that would require me to sell some ADBE stock that has appreciated quite a bit in the past couple of years. This is obviously a great situation to be in, but unfortunately it means I'll owe a fair bit in capital gains taxes. Luckily, there's a classic trick of high-end personal finance that works perfectly for me here. What many executives with an equity-heavy compensation or net-worth will do in this situation is use their assets as collateral on a loan. The loan isn't taxable, and the lender knows that the debt is backed fully by your portfolio.

Usually this isn't accessible to people like me, but I happen to run a side project that facilitates interpersonal credit transactions, so I happen to be able to do this, weirdly. For the car transaction, all I have to do is explain the details, offer a hefty interest rate (10% seems reasonable) and borrow their money for a couple months while I pay off the car, sell it, and return their money to them with interest. This way I turn what would have been thousands of dollars in taxes into a few hundred in interest payments to a friend.

It's win-win, if you ask me. (Tax-man aside.)