I feel like one of the problems moot will always face, simply because of his legacy, is that his core userbase with any venture will end up being those who frequent 4chan...possibly be the hardest to monetize group in the world.
While the app was successful in the sense of popularity, it was not successful in the sense of profitability. That line is far too blurred for far too many startup founders nowadays.
I commented in another thread about the "4chan users don't buy anything/aren't monetizable" problem[1], but while I used neither service, I don't think that 4chan users were a signficiant userbase of either Canvas or DrawQuest. Those services didn't really appeal to the average 4chan user at all. I think this was a deliberate decision to keep 4chan users from scaring the rest of the internet away, but I'm not sure it was the right one to make, because it's essentially throwing away the power of moot's name amongst a large and influential audience.
The real challenge would be coming up with a startup that could benefit from an early infusion of curious 4chan users without being "poisoned" by it. Probably one with less of a community focus, which is unfortunate for moot, since that seems to be what he likes working on the most.
The ability to easily seed any community-driven site is a godsend. Whether they can monetize them or not, it helps jumpstart the activity so they can then focus on bringing new, outside users that can then (hopefully) be monetized.
That's a trivial problem to solve. Simply don't even mention you're the founder. Or demote yourself to a tech lead, or someone. It's only a problem if you glamorize yourself and jump and shout to everyone that you're the founder of so and so.
Yeah but simply mentioning his association with a project will lead to 10s if not 100s of thousands of users basically instantly. They're just not the kind of users who you can monetize easily.
There's also a question of ego, greed and fear-of-failure here. I mean, I can imagine it being pretty damn hard to ignore the fact that you have a "Gain 100.000 Users Instantly" button(that being a tweet, blog post or whatever), right at your finger tips.
While the app was successful in the sense of popularity, it was not successful in the sense of profitability. That line is far too blurred for far too many startup founders nowadays.