Christian Osgood argues that simple deal structures beat complex ones. He describes a seller-finance deal with an overly creative tax benefit that was hard to execute and couldn't be repeated. Simple deals scale; complicated ones close once and stop.
Chapters
The first thing and most important thing about creative finance is that no matter what type of creative finance you apply, when you are doing creative finance, the way to play the game is that it is not about getting as creative as possible. I got so creative that I did a special assignment of the tax benefits in a seller finance transaction with one of the equity partners. Now, while this seems like a genius way to borrow inexpensive money, they were harder to assign than I thought. More importantly, I did a deal I otherwise wouldn't have done in a structure I wouldn't have used. Which made it non-repeatable. When you're doing creative finance, the answer you're looking for is what is the simplest way to close the deal? That is it. And that is today's lesson is keeping it unbelievably simple. Just because you can get creative, you can get way out of the box. The farther out of the box you go, the more dangerous your deal is. I've seen a bunch of people online talking about these like crazy deal structures. It's like, while that might have closed a deal for you, if it's simple, it's repeatable. If it's repeatable, it's scalable. If it's scalable, you can buy infinite rentals.