Here are a few thoughts:

#1

Content saturation is a slow moving train and higher quality content just has a slower race to "free" than other content. To combat free, you need to control the content. Netflix had to aggressively reinvest into its own exclusive high quality content to avoid someone outcompeting them on the same content at a lower price (which the owners of the licensed content could do). The more effective they are at growth, the better control they have over maintaining the licensing advantage which allows them to stay relevant as a cultural hub.

There is so much high quality culturally important content now that almost nobody can afford to pay for it all, which makes cost a concerning gatekeeper for culture. Additionally, television's linear nature and technological inferiority meant it was doing a poor job of providing the kind of access to content that people were becoming used to.

Now there are several services providing access to large collections of free movies and TV shows, but there are still plenty of classics missing in their libraries which feels like leaving history behind. You aren't the only one that noticed the TV of yesteryear has become harder to find and it's far from being only black content.

Unfortunately for premium content the situation may be even worse, as the competition is causing fragmentation and I think this fragmentation has an outsized negative impact on already under-represented niches that become even more thinned out as a result. In this case the fragmentation is more problematic, because black households have lower average incomes, yet the higher fragmentation increases monetary pressures involved in accessing the content across paid services. Look up people's favorite old shows, then see which streaming services have them and there are splits between Netflix, Hulu, HBO, Sling, etc.

There's already a lot of black content, but user friendly discovery and access are very real problems. The licensing of some existing content below a threshold might also be less valuable for the smaller audiences when you're facing stiff competition. The upside of this is that companies can compete by funding new projects (which they are doing), but of course those new projects are then exclusive which doesn't help unless they're exclusive to the service that everyone's already subscribed to.

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#2

So with those things said, where does BlackOak fit in this picture? It doesn't have control over its underlying technical infrastructure since it's based on a middleware service. The free originals I've seen on the site so far are relatively low budget and while some of it is interesting, there is clearly inexperience around the areas of production, acting, scriptwriting, editing and so on.

There's more effort put into them than typical YouTube videos, but the entertainment value is not that dense yet and I'd put the perception of it as very inconsistent even drooping to awkward improv sketch quality. Simply being original content doesn't feel like enough when YouTube has so much original content that has less than 1000 views and BlackOak still exists as part of the internet which keeps it in competition with other content on the internet.
There are definitely some actors in there that I'd be interested in watching more of if the whole thing was snapped together well, though.

I think if that quality trajectory is maintained, it would be difficult to keep viewers around through advertisement interruptions if you transition to free. The subscription cost is low, but my guess is if you hide the content behind a sizzle reel then people might pay for a month just to check it out and then not return.

If you can't invest more funding into those types of projects, perhaps you would be better off funding projects that already have lower budgets so you can increase the quality. When the content comes across as inauthentic in scenarios where the actors can't pull it off, then reality TV type approaches, interviews and other formats might have better success where people can play more loose. Unfortunately, unless you get really lucky, you're going to need some decent funding to hit a critical mass with whatever content you make or license and if you can't build that kind of confidence in investors then you may be better off pivoting to something you can create demand for.

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#3

Not a fan of the name, logo, domain, messaging, confrontational activist vibe or site design, but those aren't a big deal until you have content that draws in viewers unless potential future investors are also seeing it as their first impression of you.

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#4

Personally suspect blackness alone isn't enough for black audiences to dive into an upstart platform as the market isn't completely devoid of black content, I think it's just that there's a feeling of there not being enough of it in the public places that are deemed most visible which make some feel less culturally relevant. This same issue can apply to anyone, regardless of the characteristics they're measured by. YouTube's algorithmic sleight of hand can make people feel culturally relevant by drawing people to content that's relevant to their interests and letting you see a lot of other people engaged in it. Race is clearly not irrelevant and stronger racial culture can make it more relevant, but the relevance of it is probably greater in some contexts than others.

Netflix, Amazon, Hulu, Pluto, Sling, YouTube, Twitter, Facebook, advertising companies and so on are in a better position to address that I think. If you can maintain the funding to be relentless and create a critical mass of content then you might eventually be able to flip that prediction to become an observable public place. My guess is that African descent purchasing power will continue to increase over time around the globe and companies will find a way to capture those dollars as they always do. If you can navigate the insights to be one of those companies, then give it a go! There are a lot of classic shows with black actors that aren't on any streaming service anywhere, so opportunity does exist.