"It wasn't a perfectly straight path." Chelsea Grayson, the former general counsel and CEO of once-storied clothing giant American Apparel Inc. who recently finished an interim CEO term at urban denim brand True Religion Apparel Inc., didn't expect to become a supernova when she was tapped to save the struggling fashion empires.

A corporate lawyer who spent most of her career at Jones Day then Loeb & Loeb, Grayson played an integral role in the highly scrutinized American Apparel turnaround spanning 2015 to 2017 that elevated the company from near ruin amid two bankruptcy filings, ex-CEO and founder Dov Charney's pre-#MeToo sexual assault scandal, and declining sales. Under her guidance as general counsel then as CEO, she oversaw the revival of the brand and its sale to Gildan Activewear SRL for $88 million in early 2017.

Then she wanted a break. By the spring, she resigned.

Joining corporate boards was her goal. The Goldman Sachs hedge fund that worked with American Apparel invited Grayson to join the True Religion board. The company was emerging from bankruptcy and was in restructuring mode. Within a year, the group asked her to take over as interim CEO. How she would revive True Religion—the way she did with American Apparel—became another media mainstay until last June when she let the gig go. True Religion, still on the hunt for a permanent CEO, named retail consultant Farla Efros to be Grayson's successor.

"That was nice because that really solidified my transition away from the law into business," Grayson says about being named interim CEO at True Religion in November 2018.

"Sure, one CEO stripe that's great, that's impressive. You can still go back to law, right? Two CEO stripes and not just that, but for two companies that had been public, two companies that were headquartered in my hometown of LA… two companies that were backed by powerful funds like Goldman Sachs, now you're a full-fledged CEO."

At the time Grayson became American Apparel's CEO, only a few major companies such as United Airlines and Hyundai Motor America pushed their top lawyers to temporarily fill the CEO position. But in 2019, Wells Fargo led the trend with its general counsel becoming interim CEO, while Accenture and SodaStream named former general counsel who had moved up the C-suite to CEO. The chief lawyer to chief executive path wasn't on the career map for many lawyers, but more companies across industries are giving their lawyers the helm, many in times of crisis.

During her seven months heading True Religion, she wore the company's flashy activewear and denim pieces like she had worn the sophisticated collections at American Apparel. As CEO, she says it was essential to be a walking advertisement, especially when both companies needed a boost in consumer attention.

Wearing the clothes was not the only marketing tool Grayson used. She also hosted "The Sit Down," a digital talk show where she interviewed "supercharged, high-profile" entrepreneurs who were "filling a niche that maybe nobody saw that niche or they're filling it in a way that nobody has monetized it."

Chelsea Grayson with Chelsea Grayson Consulting in downtown Los Angeles. Tuesday, October 1, 2019.

As Grayson was leaving her role, potential interviewees were still reaching out to her about appearing on the show. True Religion allowed her to take the show, which she rebranded as "What's Your Water?" currently on YouTube. Fashion is still a theme: she recently interviewed "hot felon" turned supermodel Jeremy Meeks in snakeskin thigh-high boots with a black American Apparel dress.

Along with the show, Grayson is a director on three other corporate boards: Vireo Health International Inc., a Minneapolis-based medical cannabis products maker; Rex Mundi, a Los Angeles-based early-stage ­artificial intelligence startup; and Sugarfina Inc., the luxury alcohol-infused candy retailer also based in the LA area. In September, Sugarfina filed for Chapter 11 bankruptcy protection.

Lance Miller, the general counsel, corporate secretary and chief restructuring officer at Sugarfina, was one of the three in-house attorneys making up the American Apparel legal department in 2015 as the company was dealing with its own bankruptcy filing. Also a former Jones Day lawyer, he says he met Grayson at American Apparel when she came in five months after he started.

"There was always some [public relations] crisis, or some litigation that needed urgent attention," he says, in combination with hundreds of employees flowing from the sewing floors, on-site clinics, common areas, offices and a retail store that comprised the converted 1920s downtown LA warehouse American Apparel called headquarters. "I tried to plug in everything with my fingers and I ran out of fingers on day two, so it was that energy where you're running around everywhere putting out fires."

Miller says Grayson's infectious energy and high emotional intelligence created unity between teams that proved beneficial in making changes happen. When Miller became general counsel, he says CEO Grayson showed her support by giving him space to learn and grow, though their offices were next to each other. That was why he told her about the Sugarfina board opening. "It's rare to find somebody who knows what it's like from the operations side with what the company needs and the room where management needs to know about those problems, so she was an obvious choice for the selection committee," Miller says. "Another chapter in our relationship that we grew into."

Dawn Kennedy rounded up the legal team as senior labor and employment counsel. When Grayson became CEO, Kennedy became the head of labor and employment litigation at American Apparel.

"Chelsea is really like a unicorn who has the overlay of sophisticated ­corporate governance knowledge, is a strategic legal thinker, and has operations understanding," Kennedy says.

"From where I stand, she made the transition period very seamless. As a working mom, it was good to see Chelsea make that transition."

Through the two reorganizations, Kennedy says labor unrest brought on unique challenges like with the high-stakes litigation affecting operations and emergency crisis teams. But she says Grayson handled the unrest with grace.

"We had some really hard days at American Apparel with all the restructuring," Kennedy says. "There were some days we had to make difficult choices like reducing our workforce and making those communications with the workforce. I think that's where Chelsea really had shown. She was compassionate and thoughtful. Those decisions were made with a heavy heart. With all the blows American Apparel took, we were committed to our workforce. They were critical to our company's success, and Chelsea recognized that."

Kennedy is now associate general counsel of labor and employment at the University of Southern California, which is in recovery mode from the nationwide admissions cheating scandal and an ex-staff gynecologist's sexual assault allegations.

Grayson still sees Colleen Birdnow Brown, the former board chair of American Apparel who made company history as the first woman in that role. On the advisory board of Brown's corporate marketing company Marca Global, Grayson also connects with Brown at National Association of Corporate Directors events.

At American Apparel, Brown was tasked with leading the job search for a new C-suite. Splitting time between Seattle and Colorado, Brown says she flew to LA often, spending four days a week on-site. The temporary general counsel, Tobias Keller now of Keller & Benvenutti, was also flying from San Francisco on a regular basis.

Brown says she wasn't impressed with the general counsel job candidates until she met Grayson.

"When you meet somebody and they finish your sentences when you're in a turnaround and time is of the essence that's the person you want to hire," Brown says. "They give you that confidence they will take the initiative. That was critical for that role. Some had a lackadaisical attitude, so that was hard. The sun wasn't up when she got there and the sun was down by the time she left."

Grayson was named general counsel in November 2014. She says changing her employer from a law firm to a public company made her think of her future prospects.

"There's equity for sure when you go in-house, but I was an equity partner at Jones Day. That's just money that's hard to walk away from," she says. "But I do think that the practice of law has changed. I do think that it's much harder to make partner these days, especially at big law firms. I think it's harder to make equity partner… I think that lawyers do need to think about if they're not the rainmaker or if they're not going to inherit a big book, they need to start thinking about 'Am I going to have a more stable, satisfying life in-house? Is it going to be a more long-term solution for me?'"

Paula Schneider, now president of breast cancer advocacy organization Susan G. Komen, was soon named CEO. The revamped C-suite was shaping up. But by the end of 2014, American Apparel settled a lawsuit over a facility worker's death while bankruptcy-related lawsuits and Charney's sexual assault lawsuits weighed the company down.

Grayson saw American Apparel out of bankruptcy in 2015 as the company went private. While Grayson was cleaning up the legal affairs, Brown says another workplace accident occurred in a facility. Worker safety was under another department, but Brown says Grayson placed it as a high priority.

"She started visiting actual facilities and talking to people working on the knitting machines on the factory floor, overhauled the safety program even though it wasn't her job," Brown says. "She went down to the floor to see what was going on, and she completely changed our safety program… She forged a plan with the committee with common sense and the rank and file came up with a safety plan, which became embedded in our code of conduct."

Grayson soon assumed the chief administrative officer role.

Colleen Birdnow Brown, founder of Marca Global.

"That was me running human resources, that was me running environmental health and safety, that was me essentially running risk management. Those have nothing to do with generating revenue, and they seem really not sexy, but it was the first place I could get to that had zero to do with the law, so people saw me wear a different hat."

In fall 2016, Grayson was named CEO after Schneider, who claimed at a Fortune Media event she hired a bodyguard in response to death threats at American Apparel, went to fashion company DG Premium Brands. American Apparel had to file for bankruptcy protection again which led to the sale to Gildan.

"It was so difficult for me behind the scenes," she says.

A single mother of two, Grayson found herself sleeping in her office as her mother moved into her home to help with the kids.

"At American Apparel, I pretty much slept there almost every night," she says. "My mother was basically moved in for most of the time that I was working there. She is still married to my dad, but she moved into my house, and I never went home. On the weekends, I was constantly on board calls or on calls with my lawyers.

"If I would've known the time I was going to spend on that job was going to exceed even the time, the hours I devoted to making partner at Jones Day—which is the most amount of hours you're going to ever spend ­working in your life typically—I would've died before I took that job. And in the end, it was the best job I ever had. I love it to this day. I was so fulfilled when I had that gig. I look at those times fondly now, but the moment aged me like 10 years."

She had trained herself to avoid discussing her personal life, something she took seriously during her year up as equity partner at Jones Day, where she spent 13 years.

"Which anybody knows, and most big law firms are like this, they're conservative—they like married people. That's a stable person," she says. "So I didn't really talk to anyone about my divorce proceedings that whole year. That year I had to go 2,600 hours just like all the previous years yet I was going through a full-blown trial that year."

She also hid the emotional toll of her divorce at Jones Day as she says her kids' doctor appointments and extracurricular activities were masked as "client meetings," so she wouldn't fall into the "mommy bucket."

"Just being a lawyer at any level and having two young children and totally being there as the 100% support system and then being the hub for this whole community of people who depend on you for all the money that you're out making—that's a massive burden," she says.

Grayson remarried right before being offered the True Religion CEO job after she says she couldn't date until she knew her tenure at American Apparel was ending. She and her husband work out every morning at 5 a.m. and often play chess on dinner dates. Her 17-year-old daughter is preparing for community college with eyes on UCLA while her 15-year-old son goes to a private high school and is also eyeing top-tier universities.

With posting pictures on her Instagram while on vacation with her family or at glamorous Hollywood spots, she says some of her 8,600 followers ask her how they can reach similar success without a silver spoon, assuming she was raised in privilege.

"Every penny I have today I earned myself. Nothing was given to me," Grayson says.

Growing up in the Palms neighborhood in West LA, Grayson's humble beginnings started in a 900-square-foot home with one bathroom she shared with her parents and younger sister. Her mother was a primary school teacher. Her father had employment highs and lows in the aerospace defense industry as it traded Southern California roots for D.C. Her sister, who also had a stint in fashion through beachy brand Lilly Pulitzer, now works at food distributor Sysco Corp. Grayson says if she and her sister wanted to go to nearby Disneyland or buy new clothes, then they had to sell their toys at garage sales to get the funds.

"But my parents made the very most of all the resources available to us," she says. "I went to so many museums growing up. They involved us in so many community events. They really made us understand how important community was. I had a really cultured childhood because they took the time of what we could do without needing a lot of money to do it. It seemed like I grew up in privilege."

Grayson went on to attend UCLA and Loyola Law School. She soon nabbed an associate spot at Jones Day then spent almost three years at Loeb & Loeb before being plucked for American Apparel. There, she still found time to strengthen the company's philanthropy. She developed a program to donate the clothes that either did not pass quality control or were from past seasons to homeless shelters on LA's infamous Skid Row.

"We were at 7th [Street] and Alameda [Street], and Skid Row is on 7th; that's the main part of Skid Row. We were right there," she says. "It was very easy for us to get out there. We worked with a mission to distribute that stuff or for bigger events." She even takes her kids to a mission on Thanksgiving to serve the homeless.

California has the highest homeless population by far than any other state, according to the United States Interagency Council on Homelessness, with 130,000 individuals. Once at True Religion, chronic homelessness took a backseat.

"We started to work with organizations that focus on victims like families of victims impacted by gun violence because gang violence is still a big issue here in Los Angeles," she says. "So I really started to work with ­organizations that were focusing on that issue. That was really something a lot of my customers were messaging me about all the time. Can you pay attention to some of this? Can you focus on that kind of community work? Then Nipsey [Hussle] was killed. And that shed even more of a light on things that are still going on in the neighborhood."

The late rapper and community activist Nipsey Hussle, formally Ermias Asghedom, was shot and killed last March near LA's Crenshaw District, which rung the citywide alarm on the rising violence.

Grayson attended Asghedom's public funeral at Staples Center and says they both had graduated from the same high school years apart. The aftermath of the murder has kept the gang and gun violence in her passion purview, she says, along with the chronic homelessness. At 48, Grayson says she's noticed more law firm lawyers becoming ­general counsel then CEO. More ­lawyers, she says, are realizing they can't say no to every board suggestion. In her opinion, that stigma is starting to ebb. But going from general counsel to CEO and interim CEO is still a journey rarer than most.

"I don't know anyone specifically that's done what I did," she says. "It's crazy, even to me looking back at it now because it wasn't that long ago when I was just a partner at a big law firm." In her high school senior yearbook, Grayson says the students were asked to put a quote under their pictures of where they saw themselves in five to 10 years.

"I will be sitting in a corner office in a high-rise building in downtown Los Angeles running something," she says what made to print. "Maybe not the corner office, or the high-rise building is not secure anymore because that's not where apparel companies put their roots down, but it was clear I was thinking already about running something and operating a business, so it's cool that I got here."

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