More digital media mergers: Josh Topolsky is going to work for Bryan Goldberg.

In the past year, Bustle Digital Group bought Gawker, the pioneering blog that ended up in bankruptcy court, and Mic, a publisher aimed at millennials that ran out of money. Now it has a new asset: the Outline, a tech/culture site launched by veteran journalist Josh Topolsky more than two years ago.

Part of this story will sound familiar to people who’ve followed digital media: Facebook’s and Google’s dominance has frustrated publishers trying to build a business around free, ad-supported sites like Topolsky’s.

And Bustle founder Bryan Goldberg has shown an appetite for buying high-profile, foundering companies he thinks he can boost.

Another part of it will raise eyebrows for people who follow digital media, because the deal joins Goldberg and Topolsky: two men who pride themselves on expressing their opinions forcefully.

Adding to the spiciness of the mix: Goldberg has found success by unapologetically building businesses based around Google search results, while Topolsky has spent the past few years running down attempts by digital publishers to build scale on the backs of Google or Facebook.

And yes, Topolsky says, he didn’t expect to end up working with Goldberg, either.

When the two men first met last fall, Topolsky said, “I went into the conversation with high skepticism — ‘Okay, let’s hear this bullshit.’ … I did not go into the room expecting for us to hit it off.”

But here they are. Goldberg says his plan is to use the custom publishing platform Topolsky’s team built across his portfolio of sites, and he thinks it will be particularly attractive to advertisers looking for unique takes on web display ads.

And Topolsky says he will continue to run the Outline and still intends to launch the Input, a tech site he announced plans to start earlier this year.

The two men wouldn’t disclose terms for the deal. Topolsky had previously raised more than $10 million. A year ago, when he announced a $5 million funding round, he said investors valued his company at more than $21 million.

Topolsky has said he wanted to build a series of modestly scaled sites in the vein of the Outline, which specialized in long-form stories featuring eye-popping designs, and hoped to generate revenue by appealing to advertisers who wanted to reach an elite audience. But that business failed to materialize: A person familiar with the company’s business said it generated less than $1 million in revenue last year.

“The hard thing for Josh is that the scale hasn’t been there,” Goldberg said. “It got to the point where he doesn’t have the scale behind it, and we do.”

Last year, Topolsky laid off his staff’s in-house writers and moved to a freelance model. His masthead currently lists 11 employees, including chief technology officer Ivar Vong; Topolsky says all of them will go to work for Goldberg.

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Peter Kafka

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