Living The Red Life
Key Lessons From Building Household Brands With Chelsea Grayson
Thu, 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
Chapter 1: Who is Chelsea Grayson and what are her credentials?
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.
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Chapter 2: How did Chelsea transition from lawyer to CEO?
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.
And I've just joined the board of Sunrider International, which is a big MLM company privately held in the nutraceutical space. Previously, I was on the Morphe Cosmetics and Sugarfina board, also the Delta Dental board and a whole bunch of other boards. And Here I am, born and raised in Los Angeles, Los Angeles strong. I've got two kids who are up and out of the house, and that's me.
It's great. Obviously, a ton of experience, like I said, which we're going to dive into some of the biggest lessons from. So I'm excited. But I would love to dive into some of the experience you've got from these big brands, right? And maybe let's start at the top. You know, with these bigger companies you're a CEO of, you know, a lot of my audience are running 5, 10, 20, 30, 40 employees.
And I've ran up to about over 300 and it changes at every level, right? Which is what I teach. So what were some of the, you know, the highs and the lows from running some of these big companies and 10,000 staff?
Yeah, you know, I will say that I think first and foremost, the thing that I learned, the most important lesson I learned was that communication is key. Frequent, regular, transparent communication. with all of the stakeholders. So if it's a public company, that means the market and the investors. It means your lenders as well.
And with any company, it means your customers, your clients, your vendors, your suppliers. But most importantly, with any company, but particularly with big companies, especially if you're dealing with, yeah, 10,000 employees globally, it's your employees.
you know they are your absolute most important asset i don't have a different way of characterizing it i don't like the word asset so much in that sentence but they are the most important thing that you've got in your company they are the folks that can make or break you and no employees like to hear about their company and what's happening with their company and what's going to happen with their company from a press release or a leak in the media or on social media
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Chapter 3: Why is communication critical in large organizations?
I think it's great too, because, you know, even obviously I run more smaller companies, but even when we've had a hundred employees in my company or, you know, companies, bigger companies I've managed with 300 staff, I've always done a weekly call every Monday. And I, you know, appreciate it's farther when you're at 10,000 staff, but
they love so much, you know, being bought in and, and, you know, we just did for my own company, the start of the year, we did a, you know, big yearly planning session with the C-suite, but then I presented it to the whole company on a zoom and, you know, even the virtual assistants, right.
And the customer support people and the designers that you never speak to as a CEO, you want them to feel part of it. And I, I, Especially when you get big, like you said, they're the front line, right? So if they're upset and grumpy or nervous, someone's walking into one of your stores and gets bad customer service, right?
Yeah. I mean, listen, they are the most natural brand ambassadors you've got. Whether you're a big public-facing brand, you know, or whether you're just a B2B, you know, supplier and vendor or whatever.
I mean, the salespeople, right, the people in the stores, the people that are flying around, the people that are participating on social media, if you can weaponize them as brand ambassadors, weaponize them with as much information as possible, they will want to be cheerleaders. They will be much more engaged in their jobs. And when the water rises, all boats float. Yes, I love that.
And what would you say, you know, I mean, it's fascinating how, you know, at least for most of my audience is entrepreneurs that they have to reinvent themselves as leaders because most of them start as solo entrepreneurs, you know, more in this private sector, self-funded, they get a few staff and then 10, 20 staff and 50, then some get past that. And you have to totally transform.
You know, I used to do everything. Now I'm a hundred staff. I don't do anything apart from approvals, meetings, sign offs, big partnerships and deals. Can you talk to me about what an average day is like of a CEO of an even bigger company at that size?
Yeah. First, I want to key on something brilliant that you just said, and I don't want to let it go past because it's a hugely important part of your day-to-day life as a CEO, which is at some point you get big enough where you can't, as the CEO, have 18 direct reports, right?
You can't have your fingers in every single pie in the company, even though it's your baby, you created the baby, you raised the baby, right, to teenagehood or whatever, in young adolescence, you know, whatever it is. You've absolutely got to learn the art of delegation. And that means, generally speaking, you've got to hire a great number two. So you'll always have your CFO reporting to you.
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Chapter 4: What are the keys to effective delegation as a CEO?
The last thing you want is to surprise your board of directors with anything. Boards of directors are, and listen, I'm speaking in the first person here because this is what I do for a living now, were crotchety people. cranky, you know, we've been doing this for a long time. We're sort of grizzled. And when we get surprised by something, we get scared. And when we get scared, we get mad.
You know, we don't stay scared for too long. We're angry and we're irritable. So don't surprise us with stuff. You know, give us previews of coming attractions. Things that in three weeks you might need approvals on, you can't drop it on us in three weeks. You've got to start to lay the foundation for things.
And listen, the bigger you get, there are things that are going to require board approval. You can't ignore that. So I would say stay in touch with your chair, you know, regularly as a CEO.
That's good, because a lot of, you know, in the last few years, I built out a board for my business and was, you know, obviously running bigger companies, I had to report to people. And that was a learning experience for me.
And now, you know, a lot of the entrepreneurs that are growing, I kind of advise a little on even what that is, how to pick the right person as an advisor and all those things. And You know, it's good training wheels, right?
Because as you get bigger, you know, I don't think entrepreneurs listening probably understand this, but they kind of ruin your company from behind the scenes or can hold you back. And they're, you know, they make a lot of big decisions, which as an entrepreneur is always hard because you get into entrepreneurship freedom, right?
And then a board's there to kind of, which they have to when you get so big, but to keep you and the third parties and investors, you know, keep you in a lane, so to speak.
Yeah, and to your point, you haven't always handpicked your whole board, right? Some folks you may have handpicked, but others, sure, shareholders who put a lot of money into your company, they'll have rights to appoint one or two directors, and you really don't have a whole heck of a lot of say in it, you know? So, yeah, you've got to learn right about that. Yeah.
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Chapter 5: What role does a strategic CFO play in a company?
If they don't understand, like just a third grade level, big company, they take in a big investor or private equity investor or something, gets 10% of the company, they get to assign someone that checks that they're 10% and the company is being run appropriately. Is that a decent summary?
Yeah, absolutely. Boy, once you go public, if you're going to do that, you do that to avail yourself of all the dry powder in the capital markets, of course, and that's great, but it certainly doesn't come without its issues. Then you've not just got a board of directors, some of whom were designated as independent, so they're there just to represent all the shareholders.
But you've got big shareholder meetings. You've got folks weighing in constantly. You've got directors who know that they're being scrutinized by the public markets. And so they're really watching it. And then it becomes much, much more difficult to move things along or change things or switch up. And you're going to start to wonder why you went public in the first place. Yeah.
actually i've never gone public but i had friends that have and several entrepreneurs it's like always the big shiny object goal but several of them said it was the worst decision of their life because it's it comes with maybe an episode for another day but i know it's a different world uh when you do that. So I do want to ask you, you just touched about it, approvals and stuff.
So one good thing about entrepreneurial brands is they're fast and they move with speed. I describe them like a jet ski and I describe bigger companies like a cruise ship, right? They want to... It takes a long time, but they can go across the world and have restaurants and gyms and all this great stuff, whereas a jet ski can't.
So how do you, or maybe you don't have a good answer for this because I know it's hard, but 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?
Yeah, you know, right, 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 can to a certain extent, right? You know, you can hire folks that have that spirit. But yeah, 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.
Again, like I say, stay in touch with your board so they're very prepared to make decisions as you plop it on their laps, you know, so they're not surprised and they don't when you ask them to approve something, you know, come back with 20 questions and 20 diligence requests and 20 information requests and that slows you down for the next four weeks.
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Chapter 6: How can a company maintain a strong culture?
So again, it just comes back to Communications and long-term planning. It's a necessary evil that comes with getting bigger and we all want our companies to grow and get bigger, right? We don't want to stay on a jet ski forever.
Yeah, exactly. So last couple of rapid fire questions for you to wrap up. Different ones that I know people always ask me. So as a CEO of a big company, how often do you go into a store and audit it or look at its product? How removed are you from that?
Weekly. I was constantly visiting stores. I was always on these little pedal jumpers to different places in the middle of the country. And yeah, just, I would pop in sometimes with no warning. Sometimes I wouldn't even, they wouldn't even recognize me necessarily, you know, as I was walking around.
Or sometimes I would say, yes, I'm taking a big, you know, I'm going to look at 15 stores in the middle of the country and I'd let everyone know I was coming so that they knew that we were going to have meetings behind the scenes. But we, I was, I was hardly ever in my office. Yeah. When I was running retail.
I love that. Next question in line with that. How hard is it to maintain brand standards and SOPs as you get so big?
it's harder than it should be, you know. But I think the more disciplined you get, you know, with your, in particular, your marketing department, you know, the more you really reinforce the messages, then they'll start to do the work for you. They'll really start to care about it, you know. But it is very difficult. And that's why you need to have boots on the ground everywhere all the time.
You know, that's why you've got to have a really good visual merchandiser at the top of that department. Just to make sure that, you know, just even the windows are constantly going to be consistent and the floor planning is going to be consistent and where we're going to do sail racks is going to be. All those little details are really important.
When you walk into an American Apparel here, it should be the same as when you walk into an American Apparel in Dubai.
And I so admire that of big brands because like I'm so big on SOPs and like reputable systems. And I love how, you know, the good brands pull that off, right? Like you feel the same even halfway across the world.
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Chapter 7: What are the challenges of maintaining speed and innovation in large companies?
Exactly. It's like if you're a Soho House member, you know you're going to walk in to a Soho House anywhere. There might be some local flair, but the same general cocktails, the same general, you know, sort of food, the same vibe, right? And they've done that perfectly.
Yeah, I love that. Last question. If someone wants to learn more about you, learn more from you and follow you, where can they do that? Yeah.
Yeah, so I mean, you know, basic first, I'm on Instagram, Chelsea Grayson. I'm Chelsea Grayson everywhere. You can always find me there. But LinkedIn is probably the best place. You can message me there, follow me, and I'm generally really good at being responsive. And on LinkedIn, you'll see that there's a link to my intro. And so you can also book sessions with me over intro.
Thanks. Love it. Chelsea, been a pleasure. I love diving into some of those lessons and really looking at the differences, but also the parallels as you're growing. It's so great for entrepreneurs to see the future. So thanks for joining us and excited to share this episode. Guys, until next time, keep living the red life. I'll see you soon.