Living The Red Life
Former CEO of American Apparel on Leading Through Chaos and Corporate Turnarounds
23 Jan 2025
Chelsea Grayson, a distinguished business leader with vast experience in both law and high-profile executive roles, joins the podcast to discuss her impressive career trajectory. Having held CEO positions at major brands like True Religion, American Apparel, and Spark Networks, Chelsea now serves on several high-profile boards, including Beyond Meat. Throughout the conversation, she offers valuable insights into leadership and scaling companies, drawing from her experience running large organizations with thousands of employees.In addition to her corporate expertise, Chelsea emphasizes the importance of transparent communication, particularly in large companies. She also explores the nuances of leadership, such as the critical role of strategic delegation, the necessity of a strong CFO, and how to maintain a healthy company culture. Reflecting on her journey, she shares how navigating change and balancing innovation with stability have shaped her approach to leading big brands and guiding entrepreneurs through their own growth challenges.CHAPTER TITLES02:00 - Introduction to Chelsea Grayson04:11 - Career Evolution from Lawyer to CEO06:13 - The Importance of Regular Communication08:12 - Delegation and the Art of Scaling10:08 - The Role of a Strategic CFO12:05 - Addressing Company Culture14:06 - Understanding the Role of a Board of Directors16:01 - Speed vs. Stability in Big Companies18:09 - Maintaining Entrepreneurial Innovation20:00 - Managing Change in Large OrganizationsConnect with Chelsea Grayson:SOCIALS - Chelsea GraysonConnect with Rudy Mawer:LinkedInInstagramFacebookTwitter
Full Episode
How do you maintain that speed and innovation as a big company that you have as an entrepreneurial smaller company, which I think helps you become successful in the early days?
You're never going to be able to be as entrepreneurial. And the best of CEOs say, oh, I want to maintain that entrepreneurial spirit within the four walls of this company. And, you know, it's like trying to turn the Titanic away from the iceberg. You know, sometimes it works and sometimes it doesn't. It takes a minute to, you know, get things turned. But that's the key.
spotting that iceberg from really far away and starting to turn and starting to switch the engine. So I think the key to being able to be entrepreneurial and to getting things done the way you want to get them done is to have long, long term strategizing and planning.
My name's Rudy Moore, host of Living the Red Life podcast, and I'm here to change the way you see your life in your earpiece every single week. If you're ready to start living the red life, ditch the blue pill, take the red pill, join me in Wonderland, and change your life.
What's up, guys? Welcome back to another episode of Living the Red Life. Joining me today is Chelsea, who is a powerhouse. She's managed some of the biggest companies in America. In fact, first ever female CEO of True Religion, a brand I'm sure you know, American Apparel. and many more. So Chelsea, excited to dive into some of the big lessons from some of these big, infamous brands.
Welcome to the show.
Thank you, Rudy. I'm really privileged to be here with you. Yeah, so I'm Chelsea Grayson. I guess I can divide my career up into three chapters really quickly for you. First, I was a lawyer. I was a partner at a big firm. Now I'm a recovering lawyer. So I'm still weaponized, but no longer super dangerous. And I transitioned from that to become the CEO of three big brands.
So first, American Apparel, and then True Religion, and then Spark Networks, which owned a bunch of huge dating apps like JDate and Elite Single and Silver Single and Christian Mingle. And now in the third chapter of my career, I'm sitting on boards of directors, mostly public company boards, but some private.
So I currently sit on the board of Exponential Fitness, which owns Club Pilates and Pure Bar and Rumble Boxing and Lindora and Stretch Lab and a whole bunch of other fitness and wellness companies. boutique fitness brands. I also sit on the board of Beyond Meat, which fits in with that whole health and wellness theme.
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