It did invest that money, according to the countersuit, acquiring Holler in December 2023, and investing $14.5 million in the messaging platform.

A tangled web

As you might have picked up on, much of the melodrama here stems from the entangled nature of the various businesses involved. 

Dennis was chairman of the board of Group Black during the time it allegedly withheld funds from Essence and Afropunk.

And until his resignation in 2024, Montaque was the CEO of both Group Black and Holler during the time that Dennis’ group alleges Group Black withheld funds in order to invest in Holler.

But in a twist, Dennis was also a significant investor in Holler. That means that—and try and keep up here—Dennis is suing Group Black, a company he cofounded and led as chairman, for alleged nonpayment to Essence and Afropunk, companies he now owns, because Group Black had allegedly used the owed funds to invest in Holler, a company in which he had invested.

Holler’s assets are still owned by Group Black, though the messaging platform is no longer active. Its former URL now directs to a Vietnamese streaming website.

An uncertain future

In retrospect, the commingling of these various business interests now seems like a fraught proposition. On some level, the companies simply appeared to be handing around the same dollar in a circle.  

This kind of financial maneuvering is not uncommon among startups, where cash is in short supply and the focus is on building something rather than turning an immediate profit. Plus, Essence, Afropunk, and Holler are the exact kind of companies that Group Black was trying to support—even if their owners happened to benefit from that support.

Unfortunately, in this case the tripartite management of the company, combined with each founder trying to serve both the interests of their portfolio companies and the interests of Group Black, seems to have backfired. 

Group Black, to its credit, is still alive and kicking. Bough is running the company now, and last month he announced the launch of Portrait, a venture with a mission similar to Group Black but with a focus on minority audiences more broadly. Group Black will now become Group Black Holdings, Bough said in a LinkedIn post. 

Personally, I hope that Group Black can persist. It was and is an organization with an important mission, however muddled that might have become amid this power struggle. Over the years I have spoken with dozens of Group Black employees, and down to the one they all believed in the work they were doing—a refreshing anomaly in an often disillusioned industry.

I know that for many in the Black media community, Group Black has been at times a polarizing organization. Some operators believed it sucked up all the oxygen in the room and then failed to execute on its core promise. But most Black media executives I’ve spoken to are conflicted on the issue: critical of its operations, but worried its failure would affect funding for other Black media companies. 

For the moment, the fallout from the situation is at least contained to its internal stakeholders. But if Group Black itself collapses, the blast radius of its implosion could be much wider.