The short answer is that Digi never wanted to grow up. Digi has spent his entire life avoiding work, and asking people to lift him out his problems. The only reason he made it as far as he did, was because he had a shining passion for anime and wasn't afraid to shine a light on sleezy Otaku culture and relate it to social and mental issues.
However, after that time he moved to Boston to form the content house, he became more and more disillusioned with his job. His breaking point was when him and May went on their week long drug bender, and it ended with May going to a mental hospital. At the time, it was the "Worst moment of Digi's life" and slowly he began wearing a skirt and eventually just fully trooned out. Since then, Digi has been desperate for someone to "man-up" and take care of him instead.
Although, Bird and his gaggle of wiggers haven't done anything of note since they adopted Digi. Which is why Digi is now forcing himself into whatever Fandom he can fit into. Digi's still in denial about burning his career for almost nothing, and it's likely that he'll eventually kill himself once he squanders his parent's inheritance after they die.