Chelsea Grayson

Into The Entrepreneurial Mindset
Chelsea Grayson | © THE CIRCLE
July 21, 2022
We had the pleasure of interviewing Chelsea Grayson, former CEO of American Apparel and True Religion, corporate board member and advisor to public and private companies, including Xponential Fitness (NYSE: XPOF), Spark Networks (NASDAQ: LOV) and Goodness Growth Holdings (FKA Vireo Health) (CSE: GNDSF). She is also a Board Leadership Fellow and a Corporate Governance Fellow with the National Association of Corporate Directors (NACD) and a member of the Board of Advisors for the Department of English at UCLA. Prior to joining American Apparel, Ms. Grayson was a partner in the Mergers & Acquisitions/corporate governance practice groups of Jones Day and Loeb & Loeb.

You have been a partner in Mergers and Acquisitions/corporate governance practice groups, CEO, corporate board member and advisor to public and private companies. What do you consider the highlight of your career so far and what are you most proud of?

I have had a wonderfully successful career with many accomplishments that I am proud of, but I will mention a couple of highlights here: First, when I made partner at Jones Day. Lawyers at big law firms really just have one possible, meaningful promotion, and that’s a promotion from associate to partner. I was fortunate not just to achieve that promotion, but to achieve it at a best-in-first-class, global, 125-year old firm – rarified air, to be sure. The second achievement I will highlight here is when I was tapped to be the CEO of American Apparel. I had served as American Apparel’s General Counsel for about a year and a half when a group of our largest shareholders, including Goldman Sachs, offered me the CEO position. This was the rare opportunity for a lawyer to cross over to the business side of the corporate world. Accepting that offer completely changed my career path; ultimately, I successfully sold American Apparel and was offered the CEO role at True Religion, which was partly owned by none other than Goldman Sachs (bringing everything full circle).

What did you learn from your experiences as CEO of True Religion and American Apparel?

In serving as the CEO of both American Apparel and True Religion, I developed a truly deep understanding of the power of social media and marketing technologies (aka performance or digital marketing), and the importance of developing and preserving your brand’s voice and culture while harnessing that power. This very much came into practical use for me later when social movements like #metoo and #blacklivesmatter required that brands have a voice – i.e., an authentic voice – on the issues, and I was advising companies on how to navigate the terrain. Then, during the pandemic, when brands were forced to dramatically accelerate their digital transformations, I was frequently called upon to advise, based on my track record as a CEO who had successfully shifted two legacy brands into modern e-commerce.

Is there a person you are grateful towards who helped you grow into a corporate governance expert?

I am particularly grateful for my mentor, Colleen Brown, who, herself, is a corporate powerhouse. We first met when she recruited me to join American Apparel as the General Counsel (ultimately, she served as the first ever woman to chair that board). Colleen is the consummate board member – governance and process are always at the forefront of her mind; actions taken by her boards are meticulously deliberated and generally beyond reproach. From her, I learned the art of backchanneling with board members ahead of each meeting, so that there are no surprises in the boardroom and board meetings are highly productive, and the nimbleness that handling things in committee can afford you, when the board is a bit too cumbersome to tackle certain issues. Colleen and I have continued to work together – we currently sit on a public company board together, and I continue to learn things from her, including how to be an effective board chair and how to manage public company shareholders. In fact, I have modeled the current chapter of my career – i.e., sitting on boards of directors for a living – on the example Colleen has set.
“I am definitely the type of person who was born to run into the burning building to put out the fire.”

What is the biggest challenge that you faced in your professional life?

Without a doubt, the biggest challenge I have faced in my professional career was my first year as the General Counsel of American Apparel, which at that time was a public company. I stepped into the company at the height of its culture and liquidity crisis. That year, we battled over half a billion dollars’ worth of litigation (all of which we won or successfully settled), an SEC investigation into former management, a proxy contest designed to replace the entire board and a unionization attempt that we defeated. Also, that year, we successfully ran and closed a rare at-the-market capital raise and we took the company private by negotiating a debt-for-equity swap with our largest bondholders. By the way, that was also the most fun I have ever had. I am definitely the type of person who was born to run into the burning building to put out the fire.

Can you share the most interesting story that occurred to you in the course of your career?

My career has spanned 25 years at this point, so, as you might imagine, interesting stories abound. The one that came to mind when I read this question was from my time as CEO of one of my companies. I was at a music festival that we were sponsoring – one that the company had not participated in previous to my tenure but was important to me in terms of connecting with a new segment of customers. I attended the festival, so that I could show people that I was authentically interested in connecting with them, listening to their opinions about the brand and then delivering product that was aligned with those opinions. I was walking through the festival, nowhere near our booth, when someone popped out of the audience and came running over to me, calling my name. I turned around and asked if we knew each other, and he said that, no, we didn’t, but that he recognized me from the company’s social media. He said that he really appreciated what I was doing with the brand, and how I was changing the product, and the marketing, to better serve his segment of the customer population. This meant everything to me, because it anecdotally proved that my thinking was right on point, and also that customers truly do appreciate the genuineness with which a brand develops and markets products. This was a wonderfully touching moment for me as a CEO and as the steward of a brand with a haloed heritage.
“There is no harm in listening.”

Which character traits do you think were most instrumental to your success?

First, I never have my ego on the table – I take positions because they are in the best interests of the stakeholders, and I am always very open to compromise if it gets everyone across the finish line. Second, I listen to everyone at the table; there is no harm in listening – just because someone says something doesn’t mean that position will win the day, and people tend to be much more flexible if they feel they are being heard. Third, I am a natural leader (you’re born with this or not), so when I step up, people tend to follow and we get a lot accomplished. Fourth, I am incredibly transparent, so people ultimately trust me and don’t think I have a hidden agenda; this helps us get to a group solution fairly quickly. Fifth, I have a keen sense for what issues must be tackled urgently, and what issues have yet to ripen; in fact, sometimes when you solve urgent issues, the others fix themselves and you don’t need to waste time and energy on them. If you are sensing a theme here, you’re right: my goal always is to get to a final decision and move to the next thing; it’s the best contribution I can make in the positions I hold.

What is your typical workday like?

I usually start with an early morning board meeting for one of my international companies (for China, for example, our early morning in Los Angeles is already their late night) and then move on to meetings for my domestic companies. For the big quarterly meetings, we will meet in person, which could involve me heading abroad to Europe or Asia, or to NYC. Throughout the day, I am fielding calls and emails from board members and legal and financial advisors, because I chair most of the boards I sit on (or at the very least, I chair board committees), so I am a central repository for a lot of information and I have to make high-level decisions all day. On any given day, I might also have a speaking engagement, or host a regular women-in-leadership wine tasting event that we’ve been doing for a couple of years now. Similarly, at least a few times a week I have a lunch or dinner with a current, former or future colleague (these are far better than networking events, which are too surface level to establish meaningful connections). No matter what, I will always get a workout in – I block out my calendar for those, just as I do for any meeting – fitness is a top priority for me – always has been and always will be.

Is there a motto you live by?

Work hard, play hard. You must earn, but then also make the most of your downtime.
“Never forget that people are not mind readers.”

What rules do you follow to become more successful?

Regularly communicate with those who can either facilitate your process or those who, if they are not kept in the loop, can stand in the way of your progress. Never forget that people are not mind readers, so before you are off to the races with some idea, take a beat to consider stakeholders and advisors that should be filled in. At the very least, you will get their sign-off, and you might even get some great guidance or have a door opened for you. Also, don’t get personal when its business – your reputation is in every room that you enter, before you get there; you will see the same people over and over again throughout your career, so even if you are on opposite sides of a situation with someone, be sure to make the disagreement amicable and to approach it with honor and dignity.

You are now a Board Member of several companies. What does the future hold for you?

I love what I do, so I hope the future looks a lot like the present (minus the pandemic, of course!).

What legacy do you want to leave behind?

First and foremost, I would like to have set a shining example for my children (and their offspring, and their offspring and…) of visionary leadership, courage, consistency and focused work ethic. I would also want them to remember that I took time to enjoy life and take care of myself – including by traveling everywhere in the world that I wanted to go (usually taking them along with me!).
Share this interview
All Rights Reserved

Material on this website may not be reproduced, distributed, transmitted, cached or otherwise used, except with prior written permission of THE CIRCLE.

Share this article