What is challenging for me is the fact that most people cannot relate to my life. They can't understand why you'd work 60+ hours a week on a fledgling business. They can't understand the obsession and inability to "turn it off." They don't understand what it takes to get a customer to actually pay you, let alone build something people enjoy using and solves problems. I do find that many folks assume you just "lucked" your way in to success.
And I think bootstrapped business owners have it the worst of all. It's comparably easy to spend VC cash once you get funding, rather than money from "your own pocket." It's not hard to justify hiring 5 people when the VCs explicitly tell you that's what the money is for. Bootstrapping a successful business is indeed a rare feat, and only the people who've been there can understand exactly how all consuming and difficult it is. (At least, that's been my experience so far)