Which is amazing but irrelevant - if the lesson is "build something obsessively for years until you have an audience to then, also over the course of 4 years, monetize on another project - assuming you get both of these things exactly right even though they're both unbelievably hard" there's no lesson.
I know this from experience. I helped build a site used by millions of people in a particular demographic, and some of my collaborators on that project have been building products to help that demographic in deeper ways. The problem? It's still hard to get that right! 2 years into that effort they're still just starting to find product market fit for the second products.
We hit the absolute lottery to somehow get 5 million users for the original product, and they'll be hitting the lottery again if they get profitable on the second product to that audience. It's hard. Having money helps.
Why do you presume these were two separate projects? He built fandalism, then realized from running it that his users wanted something like distrokid. It is one big company called Pud Inc.
I know this from experience. I helped build a site used by millions of people in a particular demographic, and some of my collaborators on that project have been building products to help that demographic in deeper ways. The problem? It's still hard to get that right! 2 years into that effort they're still just starting to find product market fit for the second products.
We hit the absolute lottery to somehow get 5 million users for the original product, and they'll be hitting the lottery again if they get profitable on the second product to that audience. It's hard. Having money helps.