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The Tech Whiz Behind Vine and HQ Trivia Made Millions in His 20s. He Was Dead by 34

The Wall Street Journal. logo The Wall Street Journal. 2/19/2019 Shalini Ramachandran, Zolan Kanno-Youngs, Yoree Koh
a statue of a man © Paul Ryding

Colin Kroll, a college dropout turned startup millionaire, drifted through his company’s holiday party at Gran Morsi, a cozy Italian restaurant in downtown Manhattan. Dressed in a gray sweater and jeans, he chatted up employees and their plus ones.

When one of his engineers offered to get Mr. Kroll a drink, he flashed a big smile. “I’ve stopped drinking. I’m trying to be healthier.” He’d started running regularly, too.

“Look at you, being such a great CEO,” she said. Co-workers at the party chuckled to themselves about his earnestness as he circulated among the crowd asking, “Are you having a good time?”

Mr. Kroll had co-founded two highflying startups—Vine, the six-second video-sharing platform bought by Twitter Inc. in 2012, and, most recently, Intermedia Labs, the company behind the popular game-show app HQ Trivia.

His performance at the HQ Trivia party was a foil for his often awkward personality. To friends, Mr. Kroll was a gentle, endearingly weird soul who identified with misfits and looked out for others. A Muslim classmate who was bullied in middle school remembers he was the only one who would hold her hand during games of Red Rover. Friends joked about how he bought Kraft Macaroni & Cheese in bulk, even after his success.

He also struggled with managerial duties. Colleagues said at times he made off-color remarks. If Mr. Kroll thought an idea was dumb, he said so. He sometimes reamed out subordinates. Old struggles with drugs and alcohol haunted him, friends said.

Twenty-four hours after the party, he was found dead in his apartment. He was 34 years old.

Silicon Valley has changed the traditional path of business success. Instead of toiling up the corporate ladder, young coding whizzes can take a fast track to wealth and fame. Like their wunderkind counterparts in sports and entertainment, they’re not always ready.

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This account of Mr. Kroll’s rise and untimely death is based on interviews with and documents from more than three dozen friends, family members, lovers, current and former colleagues, investors and police.

Rus Yusupov, a central figure in Mr. Kroll’s adult life who co-founded Intermedia Labs with him, discussed many aspects of their relationship in an interview, but declined to comment on some details. Colleagues said they fought bitterly at times. Mr. Yusupov said, “It’s sad and upsetting that anyone would continue to try to divide Colin and me and misrepresent our strong partnership, especially after his unfortunate passing.”

***

Family members saw Mr. Kroll’s intellect and doggedness at a young age. He grew up in the suburbs of Detroit; his parents divorced when he was 10.

In middle school he made a business bootlegging Japanese anime he had downloaded from Napster. He taught himself to code in multiple programming languages while jamming to Dave Matthews Band in his bedroom.

During his high-school years, Mr. Kroll became frustrated that his home’s slow internet connection was impeding his ability to download music, his father, Alan Kroll, said. So he wrote a program to boot his neighbors off the web, leaving him with more bandwidth. That prompted a visit from the cable company. The young Mr. Kroll feigned innocence.

“We didn’t know if Colin was going to grow up and be a famous app designer or if he was going after the Federal Reserve Bank’s computer,” the elder Mr. Kroll said. “We, at that point, understood he had skills probably to do either one.”

Mr. Kroll enrolled in community college, dropped out, then did coding jobs for local businesses. He frequently got high on marijuana and prescription drugs with his best friend from childhood, Jeff Dickinson. “He was struggling with addiction from an early age,” Mr. Dickinson said.

Similar troubles ran in Mr. Kroll’s family. His grandfather and father struggled for years with drinking, family members said. His uncle, Gene Kroll, once dove into a shallow lake while drunk, leaving him partially paralyzed. He eventually joined Alcoholics Anonymous and became a therapist, he confirmed.

Mr. Dickinson knew Mr. Kroll was never destined for a normal life. “He was determined to outdo himself,” he said.

It didn’t take long for the young men to realize they were squandering time. Mr. Dickinson took steps to get clean and, at 19, Mr. Kroll joined his Uncle Gene at Alcoholics Anonymous meetings.

Mr. Kroll began studying computer engineering at Oakland University in southeast Michigan, paying his way with freelance coding assignments for $50 an hour. An online advertising firm called Right Media soon offered him a job in New York. Mr. Kroll’s mentor at school told him, “You can teach me more than I can teach you,” his father recalled.

Mr. Kroll packed a rental van and drove to a 400-square-foot apartment in Manhattan. It was 2007.

That same year, the elder Mr. Kroll, who owns a furnishings business, resisted arrest after driving while drunk. He decided to sober up for good.

“I was never really a great role model,” his father said. “I drank too much. I smoked too much weed.… Sometimes you have blinders on when you’re doing it yourself and you don’t see your kids as clearly as when you’re straight.”

***

At 23, Mr. Kroll was determined to outshine the Ivy League talent he was meeting. He stayed sober and was active in AA. His fiancée had moved with him to New York—a Christian woman he met at AA—but their engagement broke apart after she committed to the ministry.

At Right Media, he worked 12-hour days, went home and worked some more, said Edward Kozek, who was VP of engineering and Mr. Kroll’s mentor.

He moved to a new company and was job-hunting again when he met Drew Patterson, the founder of Jetsetter, a travel e-commerce startup. Mr. Patterson was delighted by Mr. Kroll’s rough edges and direct style. In the job interview, Mr. Kroll fired off questions like: “How are you going to build a business that’s going to change the world?”

“It was immediately apparent he had a spark,” Mr. Patterson said. Mr. Kroll became chief technology officer, chain-smoked close to two packs a day of Marlboro Reds and worked incessantly.

He confided to his mentor Mr. Kozek that the Jetsetter staff didn’t like him. “Everyone thinks I’m an asshole, and I am an asshole, but I can’t help it because everyone around me is so stupid,” he said.

“He was right,” Mr. Kozek said. “Compared to him, they were stupid, but he just didn’t know how to manage people.”

At Jetsetter, Mr. Kroll met the two men, also in their 20s, who would lead him to his biggest windfall: Rus Yusupov, a graphic designer, and Dom Hofmann, an engineer.

Mr. Hofmann disliked Mr. Kroll’s abrasive ways so much he eventually quit. He began working on a video app called Vine with Mr. Yusupov—and despite their clashes decided to bring on Mr. Kroll as founding chief technology officer because of his technical skill. Messrs. Hofmann and Kroll made amends and became close friends.

Vine’s technology gave users a platform to make looping, six-second videos on their phones. It was so intriguing in beta testing that Twitter offered more than $30 million, mostly in stock, to acquire the company in October 2012, before the app officially launched.

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Mr. Kroll owned only a small portion of the company’s shares, but made more than $5 million thanks to cash bonuses and restricted stock, a person familiar with the deal terms said.

All three men were offered jobs at Twitter with the promise of annual bonuses of $1 million for the first few years. Mr. Kroll proposed to his then-girlfriend, Maggie Neuwald.

He also began to party a lot more, friends said. He was fond of Scotch, followed by shots, interspersed with beers, and would throw back three drinks for every one his friends would order, a close friend said. He smoked pot and occasionally did cocaine.

“He had been very careful for a very long time,” Ms. Neuwald said. “I think at some point he kind of wanted to let loose a little.”

Their engagement fell apart when she and Mr. Kroll realized they wanted different things, she said. For one, she wanted children. Mr. Kroll told her he didn’t know if he would ever be ready for kids.

He began to travel widely, and bought a white Porsche. He drifted apart from his mentor, Mr. Kozek, who is now a senior vice president at NBCUniversal.

“He was living the high life,” Mr. Kozek said. “All he could talk about was how much money he made and all the hot girls who were after him.”

Vine, launched in January 2013, was a hit, and the three founders started hanging out with the internet celebrities it created. Mr. Kroll dated a prominent Viner, Jessica Harmon.

He enjoyed sharing his new wealth with family. One Mother’s Day he had 100 roses delivered to his mom, a food sales representative. He gave his grandmother more than $15,000. He treated his father to a trip to London.

Mr. Hofmann left Twitter in late 2013 and Mr. Kroll was elevated to general manager of Vine. Competition from Facebook-owned Instagram was heating up, and Mr. Kroll complained to his father about what he considered laziness among his New York staff.

Twitter launched an internal investigation into Mr. Kroll’s behavior after a star female Vine engineer quit, according to a former senior Twitter executive. Twitter declined to comment.

One Monday morning at the office, Mr. Kroll told her explicit details about his weekend with another woman, said people familiar with the matter. Later, when she started reporting directly to him, he told her, “This means we can never date now.” She quit but never filed a formal complaint.

The Twitter inquiry turned up a handful of grievances from men and women about Mr. Kroll’s habit of lashing out at employees and his moodiness, the former executive said. Results of the investigation concluded he created a hostile work environment but hadn’t sexually harassed anyone.

The executive called Mr. Kroll blunt and insensitive. He added that Mr. Kroll overflowed with ideas.

In April 2014, Twitter fired Mr. Kroll. He negotiated an exit package to keep his bonuses. Twitter shut down Vine in 2016 after many top users, marketers and ad buyers defected to competitors like Facebook and Snapchat. It wouldn’t be the last time Mr. Kroll’s behavior at Twitter became an issue.

***

An early Snapchat investor, Jeremy Liew of Lightspeed Venture Partners, heard praise about Mr. Kroll’s engineering prowess and called on him. Mr. Liew was looking to recruit a partner at his firm, but Mr. Kroll said he had another startup idea in him. He eventually laid out a vision of creating a new kind of mobile live-video platform—one that would lead to an explosion in genres and formats.

“He could have wanted to open a bagel shop, and we would have funded him,” Mr. Liew said at Mr. Kroll’s memorial service in December.

With Lightspeed on board, Mr. Kroll used the seed funding to create Intermedia Labs with Mr. Yusupov, who had also left Twitter and was batting around the idea of a live game-show app hosted by astronauts.

Their first app, Hype, was in some respects an attempt to create a better Vine. After initial buzz, it plateaued.

Mr. Kroll brooded and experimented with some side projects. He played around with code on the “dark web,” a shadowy part of the internet known for criminal activity and drug trafficking, Mr. Kozek said. At one point, Mr. Kroll told Mr. Kozek he’d checked into a hospital for a week, saying he had worn himself thin.

By the spring of 2017, Messrs. Kroll and Yusupov settled on creating a game-show app to demonstrate the technical capabilities they had built. They invited a New York comedian, Scott Rogowsky, to audition as the host.

“A game show on an app? I didn’t know what the hell he was talking about,” said Mr. Rogowsky, who showed up to his audition wearing a moth-eaten striped sweater.

HQ Trivia came out in late summer 2017. The show took off thanks, in part, to its live nature and routine schedule, like network television of old. Users would open the app at a set time—first once a day, at 9 p.m., with a 3 p.m. show added later—and compete for prize money.

The 15-minute lightning rounds of multiple-choice questions covered topics from paleontology to SpongeBob SquarePants. Hundreds of thousands of fans logged in for shows, creating glitches that Mr. Kroll’s team worked feverishly to resolve.

Mr. Yusupov wanted Mr. Rogowsky, who started out hosting the show in vintage T-shirts, to buy a suit. Mr. Kroll thought suits, fancy cameras and a production studio were a waste.

By the end of 2017, the company needed more money. One hurdle that tripped up potential investors as they did their due diligence was Mr. Kroll’s Twitter history. The burgeoning #MeToo movement made investors wary of any hint of misconduct.

Silicon Valley venture firm Greylock Partners passed on the deal in part over concern about Mr. Kroll’s tenure at Twitter. Other firms passed as well.

When Mr. Liew, the Lightspeed investor who sat on the board, heard about the misgivings, he conducted his own investigation, tracking down the woman who left Mr. Kroll’s team at Twitter. She told him that while Mr. Kroll’s behavior was inappropriate, she didn’t think he deserved more punishment.

“It read to me like an awkward misreading of social interactions [by Mr. Kroll] that, frankly, I am used to with technical founders,” Mr. Liew said. He felt Mr. Kroll had matured.

On Dec. 18, the tech news site Recode wrote a piece about the company’s fundraising struggles. It described Mr. Kroll as difficult to work for and “creepy” with women at Twitter. Other outlets, including Fortune and New York magazine, followed.

Lisa Luo, who joined Mr. Kroll’s team the day the Recode article published, said Mr. Kroll apologized to colleagues for his past. He told Ms. Luo that “sometimes I guess I’m a bigger flirt than I realize.” In the ensuing weeks, he swung by to tell her he appreciated her work. When she worked without taking a break, he rolled over in an office chair to say, “Just making sure you still have a pulse.”

“He was the one person at the company that made me feel so comfortable,” she said.

After the articles came out, Mr. Kroll was deflated and Mr. Yusupov blindsided. Mr. Kroll stopped coming to venture-capital pitches, leaving Mr. Yusupov as the face of the company. Mr. Kroll offered to resign, but Mr. Liew wouldn’t hear of it.

Intermedia Labs was rescued by Cyan Banister, a venture partner at Founders Fund, created by tech billionaire Peter Thiel. The fund prioritizes keeping founders in charge of the companies they started.

Ms. Banister investigated his behavior, talking to people at Twitter and others who knew him. Her conclusion: Mr. Kroll’s offenses were in the past. She led the company’s Series A-1 round of $15 million at a $100 million valuation in February 2018.

“I’m not saying that nothing happened. There is a spectrum of things and he was very, very, low, low, low on that spectrum,” she said. “The more I got to know him the more delightful he became.”

Still, the reputational damage had taken a toll. Facebook showed informal interest in acquiring the company, but talks cooled after the Recode article, according to people close to the company. Facebook didn’t respond to requests for comment. Until that point, the two founders had essentially served as co-CEOs. Now Mr. Yusupov took the title of CEO.

Mr. Kroll told friends and family he suspected Mr. Yusupov of leaking damaging information to edge him out. Mr. Yusupov declined to comment on the allegation. Mr. Liew brought in an executive coach to help the men rebuild trust. Mr. Kroll apologized to Mr. Yusupov for causing issues and said he wanted to move past them.

Vindicated by the funding and hoping the Twitter story would fade away, Mr. Kroll texted a friend that he was “soooo charged now. Let someone make the case I shouldn’t invent things. The only person in my way is me.”

***

Mr. Kroll was intent on resetting his life. He wanted to make his company the size of Facebook, with a campus in Detroit that would hire people with nontraditional backgrounds like his own. He quit smoking and started cooking and baking oatmeal cookies.

HQ Trivia users were losing interest. The app’s audience peaked at 2.4 million concurrent streamers during a $250,000 jackpot game last March and then began falling.

Mr. Yusupov raised the jackpots to attract more players. Messrs. Kroll and Rogowsky, fearful of bleeding money, proposed giving smaller prizes, including noncash rewards, to more people to spread the sense of winning. The number of viewers kept falling.

By May, the founders’ relationship had deteriorated dramatically, colleagues said.

Mr. Kroll left New York for a few days “for my own sanity,” he told a colleague on Slack. “I’m not in a great place.” He texted a friend that he wanted to quit.

That month, HQ’s star host complained to Mr. Liew and Ms. Banister—the other two board members besides Mr. Kroll and Mr. Yusupov—that Mr. Yusupov’s decisions were leading the company to ruin.

Mr. Yusupov began calling Mr. Kroll a criminal and a drug addict in conversations, current and former colleagues said. Mr. Yusupov denied the allegation in an interview. Mr. Kroll would tell people close to him that his partner lacked business acumen. Mr. Kroll asked the executive coach for a reference to a psychiatrist, said people familiar with the matter.

Their squabbles put the company in a creative paralysis, colleagues said. Mr. Kroll pushed the need to roll out new interactive shows for the app, they said, while Mr. Yusupov prioritized building up HQ Trivia and courting publicity.

“The biggest problem that I saw under Rus’s tenure was his inability to let the leads of the company do their job,” Mr. Rogowsky said. “We were just stuck in this inertia.”

“I’ve always welcomed and appreciated candid feedback. I’m evolving as a leader and will continue to do so,” Mr. Yusupov said.

Employee complaints about Mr. Yusupov’s micromanagement filtered up to the board. Many employees were considering leaving, and some senior managers questioned Mr. Yusupov’s truthfulness, according to people familiar with a report the executive coach shared with board members after canvassing the office. Some employees criticized Mr. Kroll as recalcitrant.

Mr. Liew wanted to push out Mr. Yusupov and find a new CEO, and Mr. Kroll was a top candidate. Colleagues said Mr. Kroll expressed loyalty to Mr. Yusupov in conversations. Ms. Banister resigned from the board rather than choose between the co-founders.

At one point, Mr. Yusupov asked Mr. Rogowsky if he’d like to be CEO—complete with cameras, turning the job into a reality show for the app. Mr. Rogowsky told him that was ridiculous.

Mr. Yusupov told Mr. Rogowsky that if Mr. Kroll became CEO, he would “piss off a lot of people and they will leave.”

***

In August, a female employee who worked for Mr. Yusupov lodged a complaint with human resources regarding Mr. Kroll’s behavior. Given his prior management history, the complaint set off alarms.

The woman said in an interview with The Wall Street Journal that Mr. Yusupov had called her into his office and asked, “What do you dislike about working here?” She told him Mr. Kroll was obstructionist, could take things too personally and had, at times, acted erratically. Mr. Yusupov strongly encouraged her to write a complaint, she said.

She said she was uncomfortable doing so, but she emailed human resources to outline her concerns. She also called Mr. Liew and Ms. Banister. Her complaints included Mr. Kroll ranting on Slack about work in a way she insinuated could be drug- or alcohol-fueled, though she told Mr. Liew that she hadn’t seen him partying.

She said Mr. Kroll seemed irrationally upset when he found out some HQ users were cheating, sparring with one alleged cheater so much the man came into the office demanding money. After the incident, the company hired armed security. She also said Mr. Kroll talked about rival entrepreneurs and their apps in threatening terms, saying he wanted to “kill” the competition.

Mr. Yusupov said in an interview that “when an employee made multiple complaints and expressed that they were scared, they were encouraged to follow company HR policies to report their experience.”

Mr. Kroll told people close to him he believed Mr. Yusupov compelled the woman to file the complaint to hurt Mr. Kroll’s chances of taking over the company. Messrs. Yusupov and Liew—by that time the only board members besides Mr. Kroll—retained an outside investigator to look into the allegations. The investigation found nothing that warranted denying Mr. Kroll the CEO job.

Mr. Liew and Ms. Banister said they were aware that Mr. Kroll had used cocaine recreationally—he had openly told them at different times. But he had promised Mr. Liew early in 2018 that he wouldn’t use it again, Mr. Liew said. The two venture partners had discussed Mr. Kroll’s cocaine use at one point and decided that it wasn’t affecting his work. At the time of the CEO transition, Mr. Liew said he was only aware of Mr. Kroll’s marijuana use.

The three men hashed out a deal where Mr. Yusupov would stay on as chief creative officer and Mr. Kroll would become CEO—although Mr. Kroll confessed to some investors and friends he wasn’t sure he was cut out for the job.

Recode soon called again. Someone had leaked the woman’s complaint, and Recode published a story on Nov. 4. Mr. Kroll accused Mr. Yusupov of sabotage and considered firing him. Mr. Yusupov denied to Mr. Kroll that he leaked anything.

After finding out about the behind-the-scenes CEO battle and the leak, the woman quit, feeling she may have been used as a pawn by Mr. Yusupov. By that point, she said, she and Mr. Kroll “were on good terms, and he even offered to connect me to people in his network.” She added that she hadn’t been scared when she expressed her concerns, but she was worried about the business.

The rest of the fall, Messrs. Yusupov and Kroll remained distant, employees said, but seemed to be making the new power dynamic work. Mr. Yusupov brought in new brand partners. Mr. Kroll made a product road map that allowed engineers to work more quickly on improving the app’s user experience.

Meanwhile, Mr. Kroll was house-hunting in Miami and Manhattan’s West Village. He told several former girlfriends he wished things had ended differently, telling one ex that he wanted to have children while he was young enough to take them scuba-diving. He brainstormed baby names: Strategy, Cadence and Pepper.

He texted his ex-girlfriend Ms. Harmon that he was prepared to buy three houses but was waiting to meet the right woman. Though his financial advisers had scolded him for a recent $75,000 credit card bill, he wrote, “I’m never worried about making more money TBH. I’m worried about everything else.”

***

At the holiday party on Dec. 14, Mr. Kroll made an early exit.

As he headed back to his apartment, he texted Julie Antonio, a woman few friends or family members knew about, to tell her he had heroin at his place, Ms. Antonio said. While several in Mr. Kroll’s close circle knew about his occasional cocaine use, none had ever heard him talk about heroin.

It was also not well known how close Mr. Kroll had become to Ms. Antonio, 27, now an Uber driver. The two met five years earlier through Vine connections and developed a sporadic romantic relationship.

Ms. Antonio said Mr. Kroll joked he was “a smarter Michael Scott”—the awkward boss from the television show “The Office”—and discussed work pressures. “He was a human being trying to do superhuman things,” she said.

His mention of heroin that night worried her. “I was like, ‘I’m coming over because this is weird. This is not you,’ ” she said. Ms. Antonio, who was arrested and charged with possession of heroin in 2015, said she stopped using the drug after that incident.

After she arrived at his apartment, the two snorted coke. Mr. Kroll, wearing an HQ Trivia T-shirt, also snorted heroin as they talked on his couch, she said.

Before they went to sleep, “he seemed completely lucid.” Lying together, Mr. Kroll spoke longingly of moving home and starting a family.

The two drifted off. Early Saturday afternoon, Mr. Kroll was asleep on his side, “snoring in my ear,” Ms. Antonio said. She kissed him goodbye and left, but almost immediately started sending a series of text messages.

At 1:47 p.m.: “sorry to sneak out. I didn’t wanna wake you, text me when you wake up.”

At 5:42 p.m.: “Are you still sleeping? Can you please let me know you’re okay, I’m getting worried.”

At 9 p.m.: “I don’t want to invade your space but I’m pretty close to coming to check on you. If you don’t wanna talk to me, it’s fine. Please just let me know you’re good.”

At 10:30 p.m.: “So I’m coming to check on you.”

Ms. Antonio’s knocks on the door only elicited barking from Mr. Kroll’s Shar-Pei-Pug mix Tater Tot. She called 911. Firefighters entered through an elevator that went directly into his apartment. Ms. Antonio said she jumped on the bed where Mr. Kroll was still lying on his side. He was cold and lifeless, with a trickle of blood coming out of his nose. Heroin and cocaine were nearby.

In early February, the New York City medical examiner’s office found Mr. Kroll’s cause of death was an accidental overdose by fentanyl-laced heroin, a phenomenon that has driven a recent increase in fatal overdoses citywide.

The weekend of Mr. Kroll’s death, the board held an emergency meeting and made Mr. Yusupov interim CEO.

Mr. Kroll didn’t have a will, so his assets, including a nearly 28% stake of outstanding shares in the company, are going to his immediate family.

Two days before Christmas, Mr. Yusupov launched HQ Words, a “Wheel of Fortune”-style puzzle game Mr. Kroll had pushed to develop. In-app purchases have increased revenue, which has totaled about $15 million since the company’s inception. Together, in recent weeks, the games have been gaining viewers.

Write to Shalini Ramachandran at shalini.ramachandran@wsj.com, Zolan Kanno-Youngs at Zolan.Kanno-Youngs@wsj.com and Yoree Koh at yoree.koh@wsj.com

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