I don't think he would honestly. Dame has too much ego. The Roc was always going to break up imo. They started off like the hood version of Warner Brothers (which was obviously started by a family of brothers who all had equal say) but as Jay gained power and notoriety, he didn't want to split decision making with Dame and Biggs anymore nor put up with Dame's personality. And he shouldn't have to. But Dame shouldve been shrewd enough to know that Jay was gonna pull that move once got famous enough. It was hella obvious in hindsight. And a better business man wouldve peeped game and set himself up with other investments once Jay started acting funny. Like there's zero reason why Dame shouldn't have had the same investment track record that Nas had except Dame was sleeping. Going on....I'm not mad Dame wouldn't sell the Reasonable Doubt masters. Jay was acting like he did it all alone when Biggs and Dame saw it more like a startup business they founded together. With all that said, Dame is not gonna go be a kiss ass to Jay and act like he's Maverick Carter to Jay's LeBron. Not when they all built a 9 figure business together. Is it smart? IDK. But if Dame was smarter, he would've never ended up in that situation in the first place.
I think that Dame also had a ceiling. Of course you can tell Roc was his life, and his baby, so he was hard pressed to let that go and it took a lot of him when he lost it, but he was already an exec (middleman) in an industry that was looking to x out the middleman. If he didn't want to truly venture over into other venues...real venues and not those flash-in-the-pan hustles...there was nowhere else for him to go outside of the head of another entertainment conglomerate. Of course, his lack of industry friends closed that door for him, so he always had a ceiling. The rest of those execs just kept trading seats.
Jay was an artist. And while he was an exec on paper, he really wasn't at Roc - as noted by everyone that was around. There's always the opportunity for an artist of his caliber to become an exec, especially as long as he cultivated relationships with those already at the table.
I do think Dame is more than just a marketer. He had vision and a know-how and the drive to get things done...and they're all learning on the job anyway. I think when everything else fails, he goes back to what he knows, which is hustling. So he doesn't want to invest a good amount of his own money into something substantial, with no steady stream of income available...so he goes with the cheapest ideas/brands/strategies that come his way, hoping they take off. He also won't hire a team to help him...not one which he has to pay. He basically at a point of trying to hit the lottery, or jackpot of penny machines. They did the same at Roc, they just had more leverage for higher return ventures.
We can surmise that there's no place in the music industry for him, but he should've went full fledged into movies...starting a production company, finding investors, funding flicks/scripts/directors...and getting them on major streaming services. Of course, he would still be playing roulette with how much return he would get, but if he could get the indie ones into festivals, I'm sure he could've found a way to take off that way.