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“Don’t Sell Your Company!” What HQ Trivia Learned—or Didn’t Learn—From Vine

Episode 3 of our documentary podcast series ‘Boom/Bust: The Rise and Fall of HQ Trivia’ examines the Silicon Valley founders myth and the lessons of Rus Yusupov and Colin Kroll’s first company, Vine

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The live trivia app HQ Trivia was once the obsession of the internet, garnering millions of players and an international spotlight. But then it all went wrong. Boom/Bust: The Rise and Fall of HQ Trivia tells the story of the once-viral trivia app and examines vagaries of the attention economy.

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There’s a lot of mythologizing around Silicon Valley giants and the partnerships that start them. When I was growing up, my mom worked at HP. It was 2000 and the company wasn’t exactly thriving under the direction of CEO Carly Fiorina. And I remember my mom being baffled by its decision to spend $1.7 million on the modest Palo Alto home—and more specifically, the extremely modest Palo Alto garage—where Bill Hewlett and David Packard built their first device. It was already a designated California Historic Landmark, but HP completely refurbished it and turned it into a museum. If you visit it today, a plaque on the outside of the home calls it “the birthplace of Silicon Valley.”

There’s no question that Bill and David’s accomplishments were historic. But the legacies of early Silicon Valley giants have motivated today’s CEOs—who are known for their large egos—to internalize the importance of their work, and do their best to tout it, early and often.

The brief history of Silicon Valley also tells us that the effort to secure a legacy can sometimes play out in ugly ways, especially when a company is founded as a partnership. A working relationship between two people with complementary skills can suffer when it’s time to divvy up the spoils that come from running a multimillion-dollar company. Microsoft cofounders Bill Gates and Paul Allen, for instance, began as young equals, spending all their free time tinkering on their high school’s single teletype computer. But Allen later revealed in his memoir that as the company grew, Gates became a competitive bully. Gates was so wrapped up in controlling Microsoft that he tried to force Allen out and cut his shares while Allen was recovering from lymphoma.

Apple’s cofounders, Steve Jobs and Steve Wozniak, have a similar story. They were introduced when Woz was in college and Jobs was a senior at Homestead High School, my alma mater, and began collaborating on a handful of projects. Early on in their partnership, Woz discovered that Jobs was secretly taking a cut of their earnings from work that relied on Woz’s engineering.

Though all these technologists have said that they nevertheless valued their working relationships, they were clearly not without strife. Things get crowded. And once a company gets big enough, so do its founders’ egos.

So how did this founder dynamic play out in Rus Yusupov and Colin Kroll’s relationship? To understand what was at stake, you need to know what brought them to a fancy Soho office with millions of dollars in VC funding. Way before HQ Trivia, their working relationship began more than a decade ago, at a luxury travel startup called Jetsetter.

Rus, Colin, and an engineer named Dominik Hofmann all helped build it from the ground up. Rus’s firm was contracted to do creative direction. Dom was doing user experience, or UX, and Colin was covering the technical end. Drew Patterson, the company’s CEO, remembers being especially impressed with Colin from his very first interview.

“He had an energy and an inquisitiveness and a curiosity and an ambition that it was, like, absolutely, this is the person,” says Patterson. “He was pushing me on the like, ‘OK, what’s the vision for how we’re going to take over the world? Where is this thing going? I’m not interviewing for a job. I’m interviewing you to explain your vision to me and get me excited.’”

Colin was so adept at what he was doing that he eventually replaced his supervisor and began running the engineering team himself. They all spent a lot of late nights working in this loft space in the Flatiron District. “We’d end up getting takeout and work until midnight, one, two in the morning, and Colin would be smoking cigarettes out the window,” Patterson recalls. “It was not without friction, right? Kind of like in the spirit of ‘How do you get to the right answer,’ we had our arguments or creative process. But yeah, I mean I think we worked incredibly well together.”

That was a matter of opinion, depending on who you were asking at the company. Colin always threw himself into whatever project he was working on, but was often abrasive and dismissive of other people’s ideas. And he seemed to be aware of this, at least according to a Wall Street Journal story from last year. Colin reportedly told his mentor at the time, “Everyone thinks I’m an asshole, and I am an asshole, but I can’t help it because everyone around me is so stupid.” That tension came to a head in 2012, when both Drew and Colin were booted from the company during an exodus of executives and a staff mutiny.

Dom, the UX engineer, was part of that exodus. He had other ideas anyway. He had been toying with a concept for a video-editing tool. A product he was calling Vine.

From the very beginning, Vine was a pretty simple idea. Dom imagined a modern way to edit online clips recorded from your phone, stripped of all the unnecessary buttons and dials borrowed from analog technology. All you had to do was touch to shoot and lift to pause. The software blended your footage together seamlessly, and in the end, you’d get a looping six-second clip that fell somewhere between a GIF and a YouTube video.

After leaving Jetsetter, Dom had enlisted Rus to help him design the product. But it wasn’t long until he realized he needed Colin’s technical expertise to make Vine shine from the inside. They were able to sort out their working relationship under the common goal of making this cool new thing happen.

And then, while they were still in beta, they had a meeting with Twitter to discuss a potential collaboration. At the time, Twitter was looking for a way to get a leg up on Facebook, which had just purchased Instagram.

“I don’t think he was at Vine more than a month or two when they had an opportunity to show Vine to Jack Dorsey, who founded Twitter,” recalls Alan Kroll, Colin’s dad. “He was so impressed with this, they made an immediate offer. The guys didn’t really want to sell it at that point. They came back with a ridiculous—double what they asked, and Twitter took it without even negotiating.”

Twitter’s acquisition of Vine made Dom, Colin, and Rus all very rich in both literal capital and professional capital. Especially because, when the app was released in January 2013, it immediately hit a cultural nerve. Vine’s user base was producing these amazing memes at a dizzying rate. The fact that these clips were videos, not images or text, made them easily remixable. I remember there was this one Vine where this kid spells out the word “iridocyclitis” at a spelling bee. People just went wild with it.

As all of this was happening, songs from unknown artists on the platform were blowing up, and teens from all parts of the country were starring in their own videos and becoming famous in the process. New faces like Logan Paul and Lele Pons—now famous YouTubers—were landing real brand deals for their content.

Vine was laying the foundation for a newfound influencer economy. The only problem was that Vine itself didn’t have any kind of strategy to capitalize on that. And Twitter, which was struggling to figure out its identity in the market, wasn’t really in a place to help.

“They could have put front-roll ads in front of Vines,” says Verge editor Casey Newton, who was covering the company when things started going wrong. “They didn’t do that. They could have introduced some kind of paid partnership program with the Viners where they would split revenue for, like, paid placements. They never did that. They did acquire a talent agency, and I think the thought was that they would start to work with brands and take some brand money to work with big influencers to do some kind of promotional things. But that basically never really got off the blocks.”

Meanwhile, Instagram launched its own video feature. And YouTube was luring away Vine’s talent with an ads program that actually guaranteed creators some kind of stable income.

“I think because Twitter had so many other problems, with Vine it was always like, ‘We’ll worry about the monetization later,’” says Newton. “And then by the time it came time to really worry about it, they decided to shut it down.”

The day the shutdown was announced, Rus tweeted: “Don’t sell your company!” There was a sense that all the founders really lost something they loved. And not only that, but whatever long-term legacy they were trying to build was cut short.