In the late 2010s, Greg Glassman’s private plane was less than an hour from Denver when he decided he couldn’t wait that long for Chick-fil-A. The CrossFit founder instructed his pilot to land in Grand Junction and arranged for two chauffeured Chevy Suburbans to meet him and his entourage at the airport.
According to Jeffrey Cain, then the company’s CEO, they drove to the fast-food restaurant, picked up their order and returned to the plane to finish the flight. Cain put the cost of the detour at more than $5,000.
“That anecdote is entirely typical of Glassman and his spending habits,” said Calum Marsh, whose new book, “The Glass Box: The Shocking True Story of How CrossFit Broke the Rules, Made Millions, and Changed Fitness Forever” (HarperOne, out Oct. 27), recounts the excursion. “If he got a sudden hankering for fast food mid-trip, they’d land the plane and get some.”
Marsh tracks Glassman’s journey from a broke California trainer to the owner of a fitness company that generated an estimated $100 million in annual revenue by 2015. But the edgy charisma that helped Glassman, now 70, build a well-muscled empire was ultimately his downfall.
When Glassman arrived in Santa Cruz in 1995, he was a college gymnast-turned-college dropout who didn’t own a car or a house. He shared a room with his young son in a friend’s house and started training local police officers.
His workouts could seem alarming to anyone accustomed to doing just a few curls and heading for the showers. Glassman mixed demanding weightlifting with gymnastics, sending clients outside to do lunges across the parking lot and sometimes leaving them vomiting into a trash can. He also timed them, turning exercise into a competition. Clients could watch their scores improve, or discover that someone they thought they could easily beat was considerably fitter.
“It is our observation that men will die for points,” Glassman later wrote. Keeping score, he explained, could “motivate unprecedented output.”
Lauren Jenai, a young hairdresser who wanted to lose weight, became a client that summer. She was so impressed by the results that she quit her job and community college to help him train people, although she wasn’t entirely sure what to make of her new boss.
“This guy is either the biggest f–king con man in history,” she told a friend, “or he’s onto something pretty f–king spectacular.”
The two began dating and married in 1998, wearing Hawaiian shirts and leis at a backyard ceremony.
Their growing following and loud, aggressive workouts didn’t make them popular with gym owners, so in, 2001, they opened their own gym dedicated to what they called CrossFit.
Jenai handled much of the financial administration while Glassman developed the workouts and talked about the possibilities. Money remained tight enough that clients helped finance equipment purchases. Glassman recalled sleeping on a futon with Jenai while his son had the bedroom and a friend slept in the kitchen.
“I was fundamentally broke at forty-five,” he told Marsh. “I was always worrying about money.”
Posting daily workouts online changed the size of their audience. People who had never met Glassman began following his program, comparing scores in the comments and asking how they could teach it themselves.
Soon, weekends certifying trainers in the CrossFit method were packed. Newly trained muscleheads wanted gyms of their own, and Glassman let them license the CrossFit name for a modest annual fee while retaining control of their businesses.
By 2005, according to Marsh, there were more than 50 CrossFit gyms across 21 states and several countries. Two years later, the first CrossFit Games was held on a California ranch.
But, as CrossFit expanded, the couple’s marriage began to unravel. Jenai was spending years pregnant or caring for their children while Glassman traveled to seminars and affiliates.
At one point, she told Marsh, he announced, “This next year I’m going to have a lot more sex, either with you or without you.” She said they had never discussed an open relationship.
In 2009, while Jenai was pregnant with twins, Glassman began a relationship with the wife of a CrossFit gym owner, Marsh reports. He hired the woman as his personal assistant and reportedly persuaded the couple to move a few houses away from his Arizona home.
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Affairs were so common within the organization that Jenai had T-shirts made with a warning. “If you sleep with one of my trainers,” they read, “I’m going to tell your wife.”
Several former employees told Marsh they were uncomfortable with Glassman’s affairs and how openly he conducted them.
“It was baked into the culture from the beginning,” the author told The Post. “It made some women uncomfortable.”
Meanwhile, corporate sponsors were discovering CrossFit’s appeal. In 2010, Reebok signed a ten-year licensing and sponsorship agreement that would put its name on the Games and produce CrossFit-branded footwear and clothing.
During negotiations, Reebok executives tried to demonstrate their commitment to Glassman’s dietary advice by avoiding bread and alcohol at dinner. They arrived to find him eating dinner rolls and drinking tequila, Marsh writes.
The entertaining could leave even his companions struggling to keep up. Former executive Brian Mulvaney recalled a Fourth of July stop at the Four Seasons in Scottsdale in the early 2010s, when an all-night party left him furious before a business meeting the following day.
Glassman proposed a remedy. They would buy cocaine, then get Bloody Marys at the airport lounge before continuing their trip, Mulvaney recounts.
“It ended up being a great day,” he told Marsh.
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, Jenai later said.
With control secured, “his whims really took over,” Marsh told The Post. The man who once worried about paying rent was traveling with an entourage — including “overpaid yes men,” some without precise job titles or clearly defined responsibilities, according to the author. They expected first-class flights and rooms at the Four Seasons.
When Cain became CEO in 2016, he began examining what that generosity cost. One item that caught his attention was a Verizon bill approaching $200,000 a month.
CrossFit was paying for several hundred phones and service plans, including those belonging to employees’ relatives and people who didn’t work for the company, Cain told Marsh. He recalled Glassman buying iPhones for attractive women he met and adding them to the company plan.
“I was fortunate enough to receive a lot of financial records, internal documents, emails, and other documentation from that period that outlined some of the extreme spending and the lack of oversight for the finances at CrossFit,” Marsh told The Post. “The Verizon bill was just one line item amid a wide array of unreasonable expenditures.”
Cain canceled the phone contracts, Marsh said. He also repeatedly warned Glassman that the company couldn’t keep spending this way.
Some expenses would be reined in temporarily, according to Marsh. But “it would always balloon again soon.”
CrossFit was also paying for nearly a thousand gym memberships, according to Cain’s account. He said Glassman would meet women and arrange a full year of membership at their local affiliate.
Glassman defended the practice as helping the recipients and supporting local gyms. “When you look at the money we were making, it didn’t seem like a waste,” he told Marsh.
The business was still enormous, with more than 15,000 affiliates worldwide at its 2018 peak. Glassman rejected the suggestion that his spending should be treated as a corporate scandal. Reporters questioning his parties, he told Marsh, acted as though he had taken money from a publicly traded company.
“But the till was mine,” he said. “I owned 100 percent of the company.”
That ownership did not protect him from the revolt that followed his comments in June 2020. As protests spread after the police killing of George Floyd, Glassman responded to a health institute’s statement about racism with the tweet “It’s FLOYD-19.”
Reebok announced it would end its partnership, and gym owners pledged to abandon the CrossFit name. Glassman apologized and stepped down as CEO on June 9.
Later that month, workers publicly accused him of sexual harassment and demeaning treatment of women. Marsh recounts allegations that Glassman made vulgar comments about female employees and tried to photograph their breasts.
Glassman called the accounts of his crude comments “complete made-up bulls**t” in interviews with Marsh. He also denied pressuring women to sleep with him, saying, “I’m just not that guy.”
Marsh says Glassman participated extensively in the book, speaking with him for more than 15 hours and answering subsequent questions by text and email. Glassman did not respond to The Post’s request for comment.
His resignation initially left him as CrossFit’s owner, but later in 2020 he sold the company to entrepreneur Eric Roza and investment firm Berkshire Partners. Marsh puts the deal at $200 million.
“I was sixty-four years old and I had little kids,” Glassman told Marsh. “I saw a $200 million buyout.”
In 2024, Glassman and former journalist Emily Kaplan launched MetFix, a nutrition and fitness venture.
CrossFit, meanwhile, has continued without him, though its network is smaller. The company now advertises more than 9,000 affiliated gyms across over 150 countries, down from its peak of more than 15,000. Former chief operating officer Bruce Edwards was brought back on as CEO in May.
Its influence extends well beyond the gyms still paying to use its name. Marsh argues that CrossFit helped make mixed workouts and competing against a clock familiar enough to support a new generation of fitness businesses.
Among them is the extreme Hyrox, whose races combine eight one-kilometer runs with eight exercise stations. Participants push weighted sleds and perform lunges, competing on a standardized course that allows them to compare results across events.
“[It’s] basically a single CrossFit workout scaled as a mass participation event,” Marsh writes. In one form or another, he notes, “CrossFit the methodology will almost inevitably continue.”