Christian Osgood says he'd raise more capital upfront and keep deal structures simple. Complex contracts look clever but banks hate them for refinancing. Lenders told him his early deals were held together with bubble gum and duct tape.
Chapters
If I was going back and starting over again, I would raise more money on the front end of my deals. I would not change the deal structures that Cody and I use, not significantly. We kept simple structures, simple contracts that we were able to actually structure correctly and then bring to a bank to refinance, which is something that I didn't realize. If you get too creative in your contracts, you do tons of crazy deals. I remember the first and second time we went for a bank loan, the lenders are like, dude, your portfolio is amazing what you guys put together. But it is held together with like bubble gum and duct tape. Like this, this works. This is legal. They're like, this is going to be really difficult to explain to a lender because every single loan you have, no bank has ever bet on you ever. You structured everything creatively. So one of the things that Cody and I learned through this adventure is this: the simpler the contract is and the simpler the structure, the easier it is to take it to the bank.