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The School of Greatness

Why I Cried Myself to Sleep Running a Billion-Dollar Brand

30 Jan 2026

Transcription

Chapter 1: What is the main topic discussed in this episode?

4.267 - 31.607 Lewis Howes

Welcome to the School of Greatness. My name is Lewis Howes, former pro athlete turned lifestyle entrepreneur. And each week we bring you an inspiring person or message to help you discover how to unlock your inner greatness. Thanks for spending some time with me today. Now let the class begin. But how did you overcome all these obstacles in the last few years?

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31.627 - 34.49 Lewis Howes

And how long did that stress or pain last for?

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34.891 - 55.598 Kendra Scott

Well, you know, you look at 2020 and obviously the whole world was suffering, you know, and you turn on the TV, you couldn't escape it. And you're stuck in your house just dealing with all this. But in the midst of all that, my father, who is my rock in my book, you'll just see he and I have this unbelievable bond. had suffered two major heart attacks.

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56.079 - 77.602 Kendra Scott

I had to go pick him up in Wisconsin on New Year's Eve of 2019, going into 2020. So New Year's Eve, welcoming in this new year, I was on a plane flying from Colorado to Kenosha, Wisconsin. because he wasn't getting the medical care he needed and brought him to Austin where I lived. Wow.

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77.622 - 102.949 Kendra Scott

Ambulances at the, you know, on the airport waiting to take him to the hospital and where he spent until March, almost March 12th from, you know, December 31st. Wow. Ringing in that year was already starting out stressful. Going through a divorce, I had some of my own personal health issues happen. I ended up being in the same hospital that my dad was in during that time period.

103.51 - 122.907 Kendra Scott

It was one of those years where, but on the outside, everyone thought Kendra Scott was fine. The Instagrams are great, she's smiling, things are good. And I just felt so, like this isn't real and I'm suffering. And why am I so afraid to say I'm suffering?

123.308 - 147.539 Kendra Scott

So I started writing a journal and just keeping track of what was going on personally, emotionally, and wanting to share that the struggle is what makes us stronger. And now coming out on the other side of that, really scary year for my business, for my family, myself personally, is actually I had to go through that to get to this next most beautiful place I'm at in my life.

148.059 - 160.6 Kendra Scott

But when we're in the middle of it, sometimes it can feel hopeless and that you're alone and that you're the only one that is feeling like this. And so sharing it, and I think there's so much power in being vulnerable.

160.715 - 183.731 Kendra Scott

And I realized that my journal notes I needed to make into a book simply because I wanted anyone out there who might be struggling in their own place in life to know this is part of their journey and to own it and to know this is their unique, amazing life. And they're going through this for a reason and something great is going to wait for them. It's waiting around the corner. Take a breath.

Chapter 2: What personal challenges did Kendra Scott face during the pandemic?

183.751 - 187.176 Kendra Scott

This is only a moment in time and two shall pass.

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187.196 - 195.111 Lewis Howes

Yeah, of course. You know, and I think people see you and they see everything you've accomplished in the last 20 years of your brand. 20 years with your brand?

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195.211 - 200.542 Kendra Scott

Not an overnight success. I always love to be like, oh, this is an overnight success. I'm like, well, 20 years. Yeah, of course.

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200.562 - 209.8 Lewis Howes

But when they see the success in 20 years, they see you on Shark Tank. They see you at the book. They see you as this inspiring leader in the business world as well.

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210.281 - 210.381

Yeah.

211.238 - 223.405 Lewis Howes

What is the thing that most people don't see? What is the biggest insecurity, shame, or fear that you never share that people, if they knew you were working on overcoming, would see you differently?

223.505 - 244.485 Kendra Scott

You know, I think one of the things that's so important is that no one is superwoman. And yet we try so hard in our life to make people think that we're Superman or Superwoman, that we are these just, we've got it all together. And I think as a mom, I'm always struggling. People will be like, oh, how do you balance it all, Kendra? That is a myth.

244.465 - 256.739 Kendra Scott

No, if anyone tells you they've got it figured out, they are lying, okay? That is a total myth. I work every day to be like, okay, how do I make sure that I'm there for my kids when they need me? Or if I forgot, is it a bake sale?

256.759 - 277.83 Kendra Scott

Oh my gosh, I'm racing to the store, picking up cookies and trying to package them in a Tupperware so I don't feel like my kid doesn't think I actually baked the cookie. We do things right because we are doing the best that we can every day. And I think for us to say to one another and have these open conversations of, I've got this, thank you for helping me, or reaching out and asking for help.

Chapter 3: How did Kendra's early failures shape her business philosophy?

352.995 - 371.062 Kendra Scott

I was afraid for people to learn where my education from because it came from my first failed business. So that's not always a conversation starter you want to start with. And so I was trying to build up my own, like, I want them to think I'm this person because if they know who I really am, then I'm really out of luck.

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371.082 - 371.723 Lewis Howes

Who were you really?

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372.123 - 388.674 Kendra Scott

I was scared. I was scared that they would see that I wasn't all the things I thought I should be to be in that room. and get their attention or get the check for my business. And that insecurity of trying to be someone I wasn't was the worst thing I could have done.

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388.734 - 389.035 Unknown

Really?

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389.375 - 408.667 Kendra Scott

Being my authentic self, being vulnerable and saying, I'm a single mom. I didn't finish college, but I'm a hard worker. And I'm the first one there in the morning. And I am not going, I mean, if you give me money for my company, I'm going to make sure you get a return. I will not let you down. But I was too scared to say that.

409.048 - 417.724 Lewis Howes

How long did it take you until you said you're to start stepping into being 100% authentic as opposed to controlling an identity or an image that you wanted others to see?

417.822 - 432.348 Kendra Scott

You know, I think it took a while. I'd love to say that it didn't, but I think it took, it didn't around the people around me, right? I had a very small team of amazing women that I like to call the super seven. And we were very vulnerable with each other.

Chapter 4: What lessons did Kendra learn from her first failed business?

432.809 - 452.506 Kendra Scott

We were, a lot of us were new moms. We had young children. We'd bring them to the office. We had pack and plays at our office. We'd be passing around babies in between calls with buyers. And we were this village of support where we could just be ourselves. We could come in and talk about our day being difficult or, you know, and it was amazing.

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452.907 - 471.805 Kendra Scott

But I think, you know, on the outside, I felt like I had to be, because I remember going to market in New York City, for example. and setting up my little trade show booth and these buyers coming in and be like, oh, where are you from? And I'm like, Austin, Texas. This is now, you have to remember, probably 18 years ago when we were doing our first markets.

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471.825 - 473.888 Lewis Howes

This isn't the hub of design and fashion.

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473.908 - 482.016 Kendra Scott

No, it's not what now people know of Austin. And they're like, oh, well, you can't make it as a designer if you're not on the coasts. You need to be in New York or LA.

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482.256 - 482.937 Lewis Howes

Or San Francisco.

482.957 - 499.821 Kendra Scott

In San Francisco. But in my heart of hearts, I knew that Austin was the special place. It was part of the DNA of our brand. So even though I had insecurities about some things, I had total dedication to others. Like we are an Austin, Texas brand. We have our own voice. And when you walked through markets,

500.122 - 521.547 Kendra Scott

all these buyers would be attracted to our booth because we didn't look like everybody else. We weren't trying to do what everybody else was doing. We had our own unique personality. And that own unique personality was part of me. And so as I started to see people loving us for who we were, I started to have more confidence to just say, yeah, just be myself.

521.707 - 526.976 Lewis Howes

Interesting. When would you say that was though? 10 years in, five years in, 20 years in?

526.997 - 542.706 Kendra Scott

You know, I think it was an evolution. You know, I don't think one day you wake up and you're like, today I'm just gonna be me, you know? It was, you'd get a win. You get a little win and you go, okay. That gave me confidence or someone else believed in me.

Chapter 5: How did Kendra Scott redefine success and vulnerability?

589.306 - 603.321 Kendra Scott

And I wanted to show him that I was good on my word because my word is everything. When I tell somebody I'm going to do something, I do it, right? And I think over time, those interactions, buyers, Nordstrom ordering from you, right?

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603.381 - 605.724 Lewis Howes

It was like- More and more confidence.

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605.764 - 631.163 Kendra Scott

Confidence. And I started to not be afraid. And I remember the first time I had to say, I actually went to an entrepreneurial master's course through Entrepreneurs EO, which is a fantastic organization. Any young entrepreneur out there, I say, join an organization like EO because you start to meet other people who have their same insecurities and worries that you have.

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631.583 - 643.714 Kendra Scott

And you're in this safe environment where you can talk about those things and you realize, I'm not alone in this anymore. And once you're opening up to someone else, they open up to you. And that's why I say there is such

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644.167 - 657.722 Kendra Scott

power in vulnerability where you think it's the opposite, but when you can actually say to somebody, this is something that I've always bothered me, then they feel like they can share that about themselves. And all of a sudden you're having a real conversation.

658.002 - 674.224 Kendra Scott

You're not having a conversation anymore of, I did this and I'm this and I'm all, my business is having, you know, and then they're just puffing back up and it's this whole, and there's nothing real happening where you go, God, the first time I walked in this room with you all, I was so intimidated. I felt like I didn't belong here.

674.785 - 694.063 Kendra Scott

You know, I've got Harvard grads in the room and I'm a college dropout. And then all of a sudden they're this welcoming force, right? Of, are you kidding me, Kendra? When you walked in the room and you had, you know, and it was this, it changes perspective. And I think if we could all embrace that, So it's a dynamic, amazing thing to be part of.

694.163 - 707.333 Lewis Howes

If you could go back 20 years ago when you started and been the 100% authentic you, public facing, where do you think you'd be today? Or do you think it worked out perfectly, the lessons you needed to learn from that journey?

707.532 - 729.81 Kendra Scott

think everyone, our story is our story for a reason. And I had to go through those aches and pains and knots in my stomach and feeling uncomfortable to become comfortable within myself. It wasn't like I could just wake up one day and have that. It's the failures that build the next success in your life. And I always say,

Chapter 6: What strategies helped Kendra pivot her business during economic downturns?

819.835 - 841.725 Kendra Scott

and created a hat business at age 19, dropped out of college. And I think seeing this person that I love struggling, wanting to save his life, really. And at 19, you're kind of an idealist. This was my way. I could do something, right? I felt so helpless in that moment. And after five years of trying to run this little hat company,

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842.195 - 868.74 Kendra Scott

And it not working, wanting hats to be the next big thing again, like it was 1940. I had these big grand plans for this business and it just failing day in and day out. And after five years knowing I had to close it. And now I'd already just lost my stepfather to cancer. So the person I had done this for, I had lost. The business I had started is failing. The thing he was so proud of me to do.

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868.76 - 891.511 Kendra Scott

I'm now a dropout. So all of my friends have graduated from college now or are getting jobs. So I have no degree. You're 24 or something, yeah. No degree. I have a failed business. I lost my stepfather. And I remember just thinking, wow, like I'm a complete loser. I'm a loser. I really did. And now what am I going to do? Well, I've got to go get a job.

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891.712 - 908.089 Kendra Scott

I'm going to get an entry-level job somewhere because I don't have a college degree. And I was able to get a job at a travel company that did a travel magazine in their marketing department. And I still had customers calling me from the hat store and they weren't calling for hats.

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908.35 - 914.178 Kendra Scott

I was making jewelry in that little store and I'd put it on the counter and the day that it would go out, it would sell.

914.238 - 914.599 Lewis Howes

No way.

914.699 - 917.263 Kendra Scott

But I was so focused on the hats working.

917.283 - 917.883 Lewis Howes

The mission of the hat, yeah.

917.903 - 920.447 Kendra Scott

Yeah, that I couldn't see what was working.

Chapter 7: What role does community play in Kendra's business model?

1163.797 - 1174.716 Kendra Scott

And I put Kate in a baby Bjorn. And we started to go to local boutiques in Austin, Texas, and I showed my collection. And didn't want to really tell anyone I was starting a business.

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1174.776 - 1176.88 Lewis Howes

I thought if I can- Right, because you don't want to fail.

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1176.9 - 1179.824 Kendra Scott

No, and they already know. They already know that I'm a failure, okay?

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1179.844 - 1182.328 Lewis Howes

Yeah, I'm not announcing this to the world so that I fail again.

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1182.368 - 1191.244 Kendra Scott

No. So yeah, I took Cade and thought if I can create a business that allows me to be a present mom, for this little unbelievable human.

1191.264 - 1192.607 Lewis Howes

And make some money on the weekends.

1192.707 - 1196.857 Kendra Scott

Yeah. And bring money and help our family. And, you know, that would be success.

1197.217 - 1197.438 Lewis Howes

Sure.

1197.578 - 1218.009 Kendra Scott

I didn't write the plan like I did for the hat box of opening stores all over the country and this being a huge thing. I started with it. Let's just small, small. Yeah. And it I'd sell into a store and I'd make my little orders and they would sell out. So I would write orders down and I'd show my collection.

Chapter 8: How has Kendra Scott's approach to customer experience evolved?

1416.118 - 1416.96 Lewis Howes

I was going to say four.

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1417.04 - 1434.256 Kendra Scott

No, 400. I was like, geez. But 200 stores is a lot, right? So I'm going through this and I'm thinking, I mean, I remember shipping one huge order to a company that had been in business 100 years, Lewis, filed for bankruptcy. No way. Two days after I shipped an order. Yes.

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1434.696 - 1435.438 Lewis Howes

So what happens?

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1435.418 - 1438.142 Kendra Scott

Never got, never saw that money again. No, no.

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1438.202 - 1439.103 Lewis Howes

You didn't get the product back?

1439.504 - 1453.984 Kendra Scott

No, no. Oh my gosh. No, that's what I'm saying. So it was a scary time. And here I have a line of credit. I have no investment capital. Nobody would invest in me. I've gone and pitched my idea. Really? Doors closed a million times.

1454.064 - 1456.327 Lewis Howes

Had you already raised money or were you just giving credit?

1456.667 - 1461.654 Kendra Scott

No, I just had a line of credit. I had signed everything I owned up for collateral. I used credit card debt.

1462.055 - 1462.135

Wow.

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