In April, Jaymee Messler's efforts to build a sports betting platform focused on women's sports brought her to the cover of Inc. Magazine alongside Eva Longoria and other women as the faces of its 200 female founders list.
Despite the buzz, by June, her startup Gaming Society had run out of money and most of its staff departed, several people close to the company told Business Insider.
Today, the company is working with an investor to relaunch next year, the cofounder told BI. Five people close to the startup said some employees and freelancers have still not been paid for all of their work.
"It happened the way it happened, I can't go back," Messler said, "but we do have so much conviction around what we set out to do."
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It's been a tough year for startups, especially in sports betting. Venture capital funding for sports betting and online gambling startups slowed in 2023 compared to the previous two years.
Gaming Society, which Messler cofounded with NBA legend Kevin Garnett, sprung up in 2020 as a platform to encourage betting on women's sports. The company produced written, audio, video, and social media content about how to bet, women's sports, and football, though it hasn't published anything on its website or social channels since June. The company also published newsletters and a WNBA pick 'em-style game.
Messler cofounded in 2014 The Players' Tribune, an athlete storytelling media company, with MLB Hall-of-Famer Derek Jeter. She left in 2019 and later that year cofounded (Co)Laboratory, a sports entertainment startup that quickly shut down due to the pandemic, Messler said. Before Players' Tribune, she worked for over a decade at Excel Sports Management, including as the company's CMO.
Financial challenges impacting employees
Several of the people BI spoke with said Messler's optimism and continued reassurances that more funding for the company would arrive shortly had given them confidence in Gaming Society's future. Gaming Society's last reported funding round was announced in April 2022, when it raised $3.5 million in seed funding led by Acies Investments and TLI Bedrock, according to Sports Business Journal. The startup confirmed in October 2022 this figure to BI.
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In early May, Gaming Society secured two additional large commitments from investors, including one seven-figure amount, according to Marissa Coleman, a former WNBA player who's now the company's vice president of business development. But a few weeks later, both investors pulled out for personal reasons, Coleman said.
The funding drop was not officially communicated to employees, said two people familiar with the situation. But, in May, the staff of about a dozen employees was underpaid twice, BI verified with documentation, making thousands of dollars less than they should have.
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Staffers were told about the changes after they'd already worked several days of the pay period, then got half of what had been communicated for that cycle, per those two people.
After the second underpayment, most of the staff departed at some point in June, those two people and a third source said. Messler said she offered unemployment benefits to anyone who wanted to leave, and that eventually only she and Coleman remained.
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A handful of freelancers also worked for the site. Two additional people said some freelancers are still owed thousands of dollars for some of their work from this spring.
"She owes so many people so much money, I don't anticipate seeing any of that money," one of the five sources said.
Coleman, who is also invested in the company, said she wasn't paid during this time either. But once things are figured out with the main investor, she said, paying everyone back is the top priority.
"No. 1 on the whiteboard is to make everybody whole," Coleman told BI.
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Optimism for the company's future
Gaming Society has been dormant since most of its staff departed in June, but Messler and Coleman said the company would make a return next year. The duo are still figuring out exactly what "Gaming Society 2.0" would look like, in Messler's words, but Coleman said it would look similar to the old product.
Coleman said the past several months have been filled with conversations with potential and current investors, as well as about possible mergers or acquisitions.
Messler said the startup isn't holding a fundraising round or seeking outside investors at the moment, but that its lead investor, Andrew Siegel from TLI Bedrock, would "capitalize the company" as it prepares to relaunch.
"I think there's a tremendous opportunity in women's sports and the concept that Gaming Society has pursued of betting on women," Siegel told BI. "We're very supportive of Jaymee and her vision, and we're very hopeful for the future of Gaming Society."
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Messler and Coleman also said they remain optimistic about the startup's future, citing the recent surge of women's sports and betting topics into mainstream sports conversations. The goal is to reopen during the first quarter of 2024, Messler said.
"I still have so much conviction on what the company set out to do," Messler said.
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