Brockton track star becomes stock market millionaire: an unlikely Wall Street success story

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Instead, Gill channeled his energy into another passion: Picking stocks. And last month, he was unmasked as Roaring Kitty, the retail investor whose bullish $53,000 bet in GameStop made him fabulously wealthy and inspired legions of fellow traders who eventually shook Wall Street in one of the more implausible David and Goliath stories of late.

Gill might seem an unlikely mover of markets. But his cheeky online commentaries on investing, posted on YouTube and Reddit, where he goes by the profane handle Deep[expletive]Value, found an enthusiastic audience. Indeed, the 34-year-old married father of one has become something of a cult hero, proving that marquee market commentators aren’t the only ones whose opinions matter.

To some investors, Gill’s success is the product of supreme confidence. But the extreme trading in GameStop shares, which reportedly resulted in huge losses for some hedge funds, has also drawn scrutiny from state and federal regulators. Gill has been asked to testify before a congressional committee this week, and in Massachusetts, Secretary of State William Galvin has summoned Gill to learn if he violated securities rules by touting GameStop while employed by MassMutual, the financial services giant.

For his part, Gill has gone quiet. He left his job at MassMutual in January, and his chatty videos and daily updates on Reddit have stopped. Neither Gill nor his family or friends responded last week to repeated interview requests. Still, a portrait has emerged of a ferociously determined competitor with no compunction about betting on himself. Now, according to financial statements he posted on Reddit, that moxie has made him a millionaire many times over.

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“Keith’s incredibly tenacious,” said Rich Hart, a former assistant men’s track and field coach at Stonehill College. “A very, very competitive kid.”

….

Gill was giggling. It was Jan. 22 and he was live-streaming over YouTube from the basement of the house he and his wife, Caroline, rent in Wilmington. The stock market just delivered a staggering 50-percent increase in shares of GameStop, a video game retailer that has struggled to adjust to e-commerce. In a post on Reddit, Gill said the value of his initial investment had grown to $11.2 million that day.

He celebrated the moment by eating chicken tenders — tendies” is Reddit jargon for investment gains — and dipping the vittles in a glass of what appeared to be champagne. For the next seven hours, Gill was online, raving triumphantly about his astonishing windfall.

“For many of us who have been … bullish on GameStop for a while, what a day today was,” he said. “What an incredible day. Epic! Epic day today. Just huge.”

As he spoke, Gill’s followers reveled in what they viewed as an exuberant validation of his — and their — investment philosophy. The marathon live-stream has been viewed more than 867,000 times.

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“My parents told me about Warren Buffet,” one commenter wrote. “I’ll tell my kids about /u/deep[expletive]value.”

A year before, when Gill first endorsed GameStop, the reaction was decidedly less ebullient. “You honestly have a better chance playing roulette,” one Reddit user wrote in 2019.

But Gill was adamant. He said he believed in GameStop’s long-term prospects for success. And that’s his angle. Gill describes himself as a “value investor” and, in one of his Roaring Kitty videos, he sums up his approach to picking stocks thusly: “When no one wants to buy it and it looks like it’s going bankrupt or it’s dead, that’s when you really dig in deep.”

But it’s not that simple. What makes Gill appealing to fellow traders on Reddit — but unnerving to more demure investors — are his idiosyncratic methods. He uses the conventional tools of analysis — balance sheets and earnings reports — to identify sluggish, underperforming stocks. But Gill is also unafraid to take a flyer, or, as he puts it, to operate “by feel.”

He has a reputation for being a diligent, if irreverent, investor — the opposite of the button-down talking heads on the financial news channels. In his videos, he often wears a headband or a backwards ball cap, and a colorful T-shirt with the image of a kitten on it. In one video, Gill says he will occasionally consult UNO cards or a Magic 8-Ball to guide his thinking.

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“You just keep going until you get the answer you want,” Gill says in one video, shaking a Magic 8-Ball until, finally, it affirms his plan to buy 6,000 shares of Penn National Gaming — another stock that has been popular with online investors.

Steve Mazzini, a Denver-based investor and business adviser, stumbled upon Roaring Kitty’s videos almost by accident. Mazzini said he bought shares in GameStop last summer after concluding that the stock was undervalued, and he discovered Gill while researching the company.

At the time, Mazzini said, Gill’s live-streams had no more than a few dozen viewers. But he liked Gill. He seemed smart and funny, so Mazzini occasionally joined his online conversations or commented on his videos about GameStop.

Gill “really dug into, ‘Here’s my case, from a fundamental perspective,’” Mazzini said. “It was cool for me to see someone else who wasn’t just an analyst on Wall Street, somebody who does their own research, who enjoys the art of investing.”

Ken Fisher, the Canadian inventor of Wizard, recognizes the intensity Gill brings to investing. An arcane card game played mostly in Europe, Wizard “requires considerable skill and strategy in order to win,” Fisher said, and Gill had plenty of both.

Players use a set that resembles a normal 52-card deck, but with extra characters — four Wizard cards and four jesters — that create special abilities and challenges. The object is to predict correctly how many times in a round your card will best that of your opponent.

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Gill was introduced to Wizard by his aunt, and quickly became one of its biggest boosters. As a teenager, Fisher said, Gill and his brother, Kevin, traveled to Toronto with relatives to play in tournaments. Later, Gill represented the United States in international competitions in Germany, Greece, and elsewhere in Europe.

Fisher recalled that Gill was particularly proud to represent his country.

“He never missed an opportunity to push the USA as the greatest country on the planet,” Fisher said. “It’s clear from his athletic competitions that he enjoyed a challenge and always put his heart and soul into being number one.”

That tenacity was on full display at age 13, when he ran in the Brockton Kids Road Races for the first time and won his age group. He went on to win many more races at Brockton High School and at Stonehill, where he was Northeast-10 Freshman Runner of the Year for indoor track and All-New England for outdoors.

He was sidelined by illness and injury during much of his sophomore year, but after consulting several doctors, Gill was diagnosed with mononucleosis and anemia, and prescribed an iron supplement.

“He’s so darn tough he just kept trying to push through,” Karen Boen, the Stonehill cross-country and track coach, told the Globe in 2007. “But once we put him on iron pills, he took off.”

Inducted into the Stonehill College Athletics Hall of Fame in 2016, Gill holds school records for the 800-meter, 1000-meter, and the mile, which he ran indoors in 4:03:43. He’s still the only male athlete in the school’s history to earn All-America honors in cross-country and indoor and outdoor track and field.

Gill also had an uncommon work ethic. Rich Hart, who was an assistant track coach at Stonehill for 13 years, recalls Gill’s rigorous rehab in 2008, the year he was named Indoor Track & Field Athlete of the Year by the US Track & Field and Cross Country Coaches Association.

“A lot of Keith’s more difficult workouts were done over at the Easton YMCA pool because he was hurt and there’s a lot of pounding in track and field,” said Hart. “He was simulating the workouts the other kids were doing. He’d come out of the pool and just about be throwing up.”

By the time he began his social media appearances, Gill was deep into his GameStop investment, posting an image on Reddit shortly after creating his account in August 2019 that showed his initial investment had more than doubled — to about $114,000.

Mazzini, the Denver investor, said Gill always seemed careful to acknowledge the risk of his investment, actively soliciting questions and doubts from followers, conveying that “we don’t want to create our own self-confirmation bias, because we only hear about people who are obsessed with the GameStop stock.”

GameStop’s stock price began its improbable ascent in late 2020 after hovering in the $4 or $5 range for several months. Not coincidentally, Gill’s reputation in Reddit’s Wallstreetbets forum was rising, too.

Gill wasn’t posting much then, mostly just screenshots of his GameStop gains, tagged “YOLO,” for “you only live once,” a signal he’d taken a big risk on a moribund stock. As the stock price shot up, Gill’s Reddit posts became a cause for celebration in the forum.

“It provided content. That’s the fundamental rule of the Internet,” said Joe Cicalese, a regular in the Wallstreetbets forum. Gill’s “position provided people with content to make memes off of.”

Gill’s most recent Reddit post, on Feb. 3, revealed he had a cash balance of almost $14 million and still owned 50,000 GameStop shares, with options on more. He could be forgiven for cashing out completely, what with the stock making life-changing gains, hitting $483 per share on Jan. 28. But he didn’t — adding to his reputation as a fearless investor.

“IF HE’S STILL IN, I’M STILL IN,” was a common refrain among the thousands of replies to Gill’s post. Others said they planned to hold the stock, or buy more, to stick it to those hedge funds that had bet against GameStop. They were empowered and regarded themselves as a force to be reckoned with on Wall Street.

Days earlier, near the peak of GameStop’s spike, two enormous hedge funds had wriggled out of their positions against the stock, which reportedly cost them billions and further boosted GameStop’s price.

People who followed Gill on social media saw no indication he was egging on the populist charge against the hedge funds, and that his comments seemed to hew to his confidence in GameStop. In the one interview Gill gave since his stake in GameStop went stratospheric, he told The Wall Street Journal that he’s a hobbyist, not an insurgent trying to upend the stock market.

“I’m not out for anybody,” Gill insisted. “Roaring Kitty was an educational channel where I was showcasing my investment philosophy.”

Maybe so, but he bullishly promoted GameStop to his followers, imagining scenarios whereby the declining brick-and-mortar retailer would, somehow, rebound to become a major player in the gaming industry.

“Suppose, over the next year, management can craft a narrative that can carve out a 2-percent share of the rapidly growing $150 billion gaming industry. … What then?” Gill said in one video, spinning an optimistic tale to potential investors.

In recent days, GameStop stock has settled near $50 per share, which is still more than 10 times its price of much of the previous year.

And once Gill was revealed to be Roaring Kitty, the authorities wanted to talk to him. The Massachusetts securities division subpoenaed Gill to testify Feb. 26, and for its part, his employer MassMutual has said it didn’t know what Gill was up to on social media, according to Galvin’s office.

Gill, who holds licenses to sell most kinds of investments and offer financial advice, left the Springfield financial services company in late January, according to Galvin’s office. Ironically, Gill worked for a MassMutual unit that offered educational workplace programming on financial literacy, educating participants about prudent investing and retirement planning. Putting your savings into a languishing stock like GameStop is not the kind of advice most staid investment firms would recommend.

And in Washington, US Representative Maxine Waters of California, chair of the House Financial Services Committee, says Gill will be among the witnesses in a virtual hearing set for Feb. 18, titled “Game Stopped? Who Wins and Loses When Short Sellers, Social Media, and Retail Investors Collide.”

It’s not clear what Gill’s next act is. Though the worth of his GameStop bet appears to be down from its January peak of at least $48 million, the millions that remain are enough to buy a house even in the manic Massachusetts real estate market. Gill has also floated the idea of giving back to the running world, funding construction of a facility in his hometown.

“I always wanted to build an indoor track facility or a field house in Brockton,” he told The Wall Street Journal. “And now, it looks like I actually could do that.”

That sounds right to Hart, the former assistant track coach at Stonehill.

“That’s who Keith is. He’s very loyal to Brockton,” said Hart. “There’s nothing in the world Keith would want more than an indoor track facility in Brockton with his parents’ names on it.”


Mark Shanahan can be reached at mark.shanahan@globe.com. Follow him on Twitter @MarkAShanahan. Andy Rosen can be reached at andrew.rosen@globe.com. Follow him on Twitter @andyrosen.

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