I have a theory that failure sells better to his fanbase. I kind of get a pre 2016 Chicago Cubs "Wait'll next year!" vibe.
His subscribers are middle of the pack runners that are really amazed by his training, shoe reviews, family life, and sporadic successes in niche races and FKT runs. They are attracted to a "lovable loser" type that tries hard but doesn't quite succeed with everything going on around him because they see a bit of themselves in his exploits. He posts post race videos with excuses like, "just training through it" and "weather wasn't optimal" or " bad days happen" and his fans eat it up because they have all used the same excuses to brush off a bad Turkey Trot performance or DNF'd a marathon. So long as he keeps coming up just a wee bit short of his goals, he is still a working class hero to his subscriber base.
If he hits a big goal, then that brings additional pressures. What happens if he gets his OTQ? Will there be an expectation amongst his fans that don't know much about the sport that he will make the Olympic team? If he finishes 20th at the Trials, does that take the luster off? What happens when COVID relents and better European athletes start showing up for Pike's Peak? Will they stay tuned in and, more importantly, pay premium subscription money to watch him go for masters division awards in a few years time?