I think it’s a hard thing to do, haha! This was part of our motivation in raising debt to buy out our investors. We wanted to be able to make those decisions and not have to explain them to folks outside of Wistia.
More practically speaking, it was once we were profitable that we started being able to take those creative risks. Because the core business was strong, investors were happy and didn’t scrutinize investments in content marketing and more creative projects.
If those types of creative risks are what motivates you, I also think it’s possible to find investors who understand that and value it to who will cheer you on when you do it. There are probably a small set of institutional investors in that camp, but I’d bet there are many more angels.
Additionally, there are so many new types of funding available now. I’d take a look at what Bryce is doing at Indie.vc (https://www.indie.vc/) if you haven’t already. That model of funding is designed for folks who really want to grow and run independent businesses.