This week, I had the joy of chatting with my friend and mentor, Chelsea Grayson. Chelsea is a lawyer turned seasoned CEO & board member. She’s been the CEO of several highly successful companies, including American Apparel, True Religion, and Spark Networks.
This episode originally aired as a casual chat on LinkedIn Live, but quickly turned into an insightful conversation on leadership, building teams, repairing cultures after toxic leadership leaves, and the importance of having a mentor.
For those who don’t yet know Chelsea Grayson, you’re in for a treat. Her career spans three dynamic chapters (with more likely on the horizon). Tune in for a very real, humor-filled conversation on being a CEO and entrepreneur today!
Meet Chelsea Grayson
Chelsea A. Grayson was the first ever female CEO of True Religion and also sat on the True Religion board of directors (where she chaired the Audit Committee). Previously, she was the CEO and a board member of American Apparel (formerly NYSE MKT: APP), a $650M vertically integrated apparel manufacturer (the largest in North America) (all Made in USA products) with a 50-country global footprint, served by 250 retail locations, a digital retail site and a wholesale business. She significantly improved the Company’s operations and supply chain. She then successfully sold the company to Gildan Activewear Inc.
The Legal Climb
Chelsea started her career at one of the world’s top law firms, Jones Day, where she worked her way up to partner. She led the California M&A practice and co-chaired the global cross-border team. “I loved being a zealous advocate,” she says. “I miss it all the time.” Her passion for helping companies grow and restructure was already clear, even in this first chapter of her career.
Stepping Into the Fire
Then came the call from American Apparel. The company was in crisis, facing investigations, leadership upheaval, and half a billion dollars in litigation. Chelsea’s assignment was to step in as General Counsel and help save the business. Her hometown roots in L.A. and the company’s massive workforce of primarily immigrant textile workers sealed the deal.
Chelsea eventually became CEO, leading the company through a massive turnaround and eventual sale. And when Goldman Sachs asked if she’d do it again for True Religion Jeans, she said yes.
The Boardroom and Beyond
Today, Chelsea serves on multiple high-profile boards, including Exponential Fitness (home to Club Pilates and Pure Barre), Beyond Meat, and Sunrider International. She also recently wrapped a stint as CEO of Spark Networks, parent company of JDate and other dating apps.
Her career is now focused on governance, growth strategy, and staying sharp. Some days it’s a full-time job, other days not. But she maintains that staying busy keeps her young!
Teamwork: It’s Not All About You
Chelsea opens up about how transitioning from being an individual contributor – like a junior lawyer focused on proving her own value – to working in corporate leadership meant unlearning the “I” mindset.
“If you’re not raised playing team sports, it actually is a little bit difficult when you get into corporate America to remember that it’s a ‘we’ not an ‘I,’” Chelsea shares.
She talks honestly about the challenges of adjusting her expectations in a team setting – realizing not everyone works the same way, and that doesn’t make them wrong. Her biggest early lesson was to let go of judgment. A strong work ethic can look very different from person to person.
“I always kind of felt like my ideas were right, and my style was right… but that’s just silly.”
Instead, Chelsea emphasized the value of listening – really listening – to others’ perspectives. Sitting in board meetings and taking time to hear opposing viewpoints has often led her to shift her stance, or at least meet in the middle. That kind of open-mindedness, she says, is critical to leadership.
I can’t agree more. Leaders often think they’re listening, but they’re really just waiting for their turn to talk. You have to listen not just with your ears but with your heart.
To do this, Chelsea suggested echoing back what someone just said in your own words. Not only does it show respect, it also helps you process their point of view more deeply. Even if you don’t ultimately change your mind, it shows you’re open.
You’re In the Business of People
Whether you’re running a tech company or a taco stand, Chelsea and I agree: you’re in the business of people.
That means asking better questions, showing genuine interest, and knowing where the line is. As a leader, you can be warm and supportive without crossing into therapist or best friend territory.
Chelsea raised a great question: “Where do you draw the line between connecting and overstepping?” For me, it’s about clear, kind boundaries. It’s about having direct conversations, being transparent, and reminding your team that caring about them and making decisions for the good of the business aren’t mutually exclusive. I want people to have an amazing experience on the other side of me, and I want them to know that I see them.
What Makes a Great Leader
Chelsea believes that listening, decisiveness, humility, and humanity all make a great leader. She asserts that most people want to be led. They want to feel confident that they’ve got the right person at the top.
Great leaders are both decisive and open, willing to listen to all perspectives and willing to stand behind a decision. They don’t flinch in the face of failure – in fact, they embrace it as part of the process. It’s through trying, pivoting, and trying again that the most successful ideas emerge.
She also made an often-overlooked point: hierarchy isn’t a bad thing. Flat structures can be useful, but people need something to aspire to. They want leaders who are transparent about their own accountability too. Even CEOs have bosses – their board, their shareholders, their customers. Leadership doesn’t mean perfection or invincibility; it means navigating responsibilities while staying grounded and connected.
“No one is untouchable,” Chelsea said. “We’ve all got flaws. And we’ve all got someone we answer to.”
Tune Into the Secret Podcast
Looking to improve employee engagement, build connections with your customers and get the freedom to finally take a vacation? Get access to my special, secret podcast Lead with Soul where I dive deep into what you can do to avoid the most common pitfalls in leadership while building a high performing team and a business that thrives no matter what the economy is doing. Head on over to https://theresacantley.com/lead-with-soul/ to join the movement!
Resources Mentioned
👋 Connect with Chelsea Grayson on her website
☕️ Schedule a Virtual Coffee with Theresa
🎙️ Get access to my secret podcast Lead with Soul
💻 Join me every Friday at 10 am on LinkedIn for my free workshop
📝 Uncover Your Biggest Blindspots with the Entrepreneur Quiz
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