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From broke fitness trainer to $200 million buyout: The rise and fall of CrossFit founder Greg Glassman
Glassman’s lifestyle included expensive travel, lavish hotel stays, affairs and corporate expenses that ran into hundreds of thousands of dollars a month.
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Greg Glassman, the controversial founder of CrossFit, once diverted his private plane to another city because he could not wait until reaching his destination to eat Chick-fil-A. The detour, which involved two chauffeured Chevrolet Suburbans meeting him and his entourage at an airport, reportedly cost more than $5,000.
The incident offers a glimpse into the lavish spending habits of Glassman, who transformed a struggling fitness venture into a global business generating an estimated $100 million in annual revenue before his controversial remarks about racism led to his resignation in 2020.
Citing Calum Marsh’s new book, ‘The Glass Box: The Shocking True Story of How CrossFit Broke the Rules, Made Millions, and Changed Fitness Forever’, the New York Post reported that Glassman’s extravagant lifestyle included expensive travel, lavish hotel stays, affairs and corporate expenses that ran into hundreds of thousands of dollars a month. The book, released on October 27, traces Glassman’s journey from a financially struggling personal trainer to the owner of a fitness empire and the controversies that ultimately cost him control of the company.
From struggling trainer to fitness empire
Glassman arrived in Santa Cruz, California, in 1995, with little money and no car or house. A college gymnast who had dropped out, he shared a room with his young son in a friend’s house and began training local police officers.
His approach to fitness was unconventional and intense, combining weightlifting, gymnastics and timed workouts. Clients were pushed through demanding exercises, sometimes to the point of vomiting, while their performances were recorded and compared. He believed competition could motivate people to push themselves harder.
Glassman’s system attracted Lauren Jenai, a young hairdresser who initially wanted to lose weight. Impressed by the results, she quit her job and college to help him train clients. The two began dating and married in 1998. In 2001, they opened a gym dedicated to their growing fitness programme, CrossFit.
The business expanded after Glassman began publishing daily workouts online. Followers started comparing scores and seeking certification to teach the method themselves. Glassman allowed trainers to open affiliated gyms using the CrossFit name in exchange for annual fees.
By 2005, CrossFit had more than 50 gyms across 21 US states and several countries. The first CrossFit Games followed in 2007, helping establish the programme as a competitive fitness movement.
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Affairs, lavish parties and a $200,000 phone bill
As CrossFit grew, Glassman’s personal life and management style became sources of controversy.
According to Marsh, Glassman’s marriage to Jenai deteriorated as he travelled extensively for seminars and business events. He allegedly began a relationship with the wife of a CrossFit gym owner in 2009, while Jenai was pregnant with twins.
Jenai also reportedly made T-shirts warning other women against having affairs with her trainers. Former employees told Marsh that Glassman’s relationships and the way he conducted them had become part of the organisation’s culture.
Meanwhile, CrossFit’s commercial success brought corporate partnerships, including a 10-year licensing and sponsorship agreement with Reebok in 2010. But the business also became associated with extravagant entertaining. Former executive Brian Mulvaney recalled an all-night party at a Four Seasons hotel in Scottsdale, Arizona, that left him exhausted before a business meeting. According to Marsh’s account, Glassman suggested buying cocaine and drinking Bloody Marys at the airport lounge before continuing their trip.
By 2012, the breakdown of Glassman and Jenai’s marriage had become a battle over CrossFit’s ownership. Jenai wanted to sell her half to investment firm Anthos Capital, while Glassman was determined to keep an outside investor from becoming his equal partner. He ultimately secured financing to buy her out that year, leaving him the company’s sole owner. Their divorce was finalized in 2013.
The company’s spending practices attracted scrutiny when Jeffrey Cain became CEO in 2016. Cain recalled discovering a Verizon bill approaching $200,000 a month, covering hundreds of phones and service plans. He said that the company was paying for phones used by employees’ relatives and people who did not work for CrossFit. Glassman also reportedly bought iPhones for women he met and added them to the corporate plan.
Cain cancelled the contracts and repeatedly warned Glassman about the expenditure, Marsh said. However, spending would reportedly rise again after temporary cutbacks.
CrossFit was also paying for nearly 1,000 gym memberships, Cain said, including memberships Glassman arranged for women he met. Glassman defended the practice, arguing that it helped recipients and supported local gyms.
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Controversial remarks cost him CrossFit
By 2018, CrossFit had more than 15,000 affiliated gyms worldwide. Glassman, meanwhile, maintained that his spending was justified because he owned the company outright. However, his position became increasingly untenable in June 2020, when he responded to a health institute’s statement about racism following the killing of George Floyd by police with the tweet, “It’s FLOYD-19.”
The remark triggered a backlash across the fitness community. Reebok announced it would end its partnership, while gym owners pledged to abandon the CrossFit name. Glassman apologised and stepped down as CEO on June 9.
Later that month, employees publicly accused him of sexual harassment and demeaning treatment of women. Marsh’s book recounts allegations of vulgar comments about female employees and attempts to photograph their breasts. However, Glassman denied the allegations of crude comments as fabricated and rejected claims that he pressured women to sleep with him.
Glassman initially remained CrossFit’s owner after resigning. Later in 2020, he sold the company to entrepreneur Eric Roza and investment firm Berkshire Partners in a deal Marsh values at $200 million. “I saw a $200 million buyout,” Glassman told Marsh, reflecting on his decision to sell.
In 2024, Glassman and former journalist Emily Kaplan launched MetFix, a nutrition and fitness venture.
CrossFit continues to operate, although its affiliated network has shrunk to more than 9,000 gyms across over 150 countries. Its influence, however, remains visible in the growing popularity of high-intensity fitness competitions, including Hyrox, which combines running with exercise stations.
