I know Basecamp doesn't hire until someone at the company tries the job first. Have you and Jason handled nuts and bolts work like accounting, setting up health insurance, and legal paperwork? Did you learn those topics in business school?
You bet! We used to do all that stuff. It wasn't until, I think, 2009 that we hired an office manager. Jason and I have done all of it. From setting up insurance or typing in expenses for accounting. It might seem daunting, but be reassured that there are millions and millions of small business owners that figure it out every year. So why wouldn't you be able to? Also, you can use freelance accountants and insurance brokers to help you.