That summer, Montaque, the wunderkind chief executive and founder of messaging technology service Holler, quietly left Group Black.
Dennis, who made his fortune by selling his personal care company, Sundial Brands, to Unilever in 2017 for $1.6 billion, left the collective shortly after. He had increasingly begun to focus on building out a separate media portfolio, called Sundial Media and Technology Group, which includes publishers like Essence, Refinery29, and Afropunk, among others.
The departures left Bough as the sole remaining cofounder. Then the lawsuits began.
The first, in October 2024, was filed by Essence Communications, a subsidiary of Dennis’ Sundial Media and Technology Group. It alleged that Group Black owed two of its publishers, Essence and Afropunk, $20 million in unpaid bills and had improperly used those funds to enrich Group Black and Holler, as Business Insider first reported.
That lawsuit has since been dismissed. But new litigation has emerged in recent months, which I was able to get my hands on and which has not been previously reported.
Two new lawsuits—a lawsuit filed by Essence Communications and countersuit by Group Black—were filed in May and June of this year and are still active. Bough, Dennis, and Montaque each declined to comment, citing the ongoing litigation.
The documents that surfaced as a result of the litigation have shed new light on the internal drama roiling the company. They also reveal, for the first time, the complexity of the Group Black portfolio and the competing interests that are now threatening to tear it apart.
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What both parties can agree on is that, between 2021 and 2023, Group Black arranged for Essence and Afropunk to execute millions of dollars’ worth of advertising campaigns, which they did.
In the suit filed against Group Black this May, Dennis’ group makes many of the same allegations as before and claims $7 million in missed payments. It also claims that Group Black had the money to pay Essence and Afropunk, but instead used it to invest in Group Black and Holler, the messaging platform founded by Montaque.
In its countersuit, Group Black alleges that while it did indeed owe Essence and Afropunk $7 million, Dennis had agreed in January 2024 to convert that $7 million debt into equity in Group Black. Then, after a fallout that occurred in the summer of 2024 when Dennis left the company, he changed his mind and decided to sue for the money, the countersuit alleges.
Group Black cited emails that mention Carta, a software used to structure capital tables, in corroborating these claims. Indeed, turning a $7 million debt into equity would enable Group Black to invest that money back in its business, a common tactic for startups.
