Amy Smilovic: Founder of TIBI & Author of Almost Reckless

Episode 808

On today’s episode, we welcome Amy Smilovic, Founder & Creative Director of Tibi and author of the new book Almost Reckless. What started in 1997 with $15,000 and no formal fashion training has grown into one of the most respected independently owned luxury brands — built not on focus groups or algorithms, but on rigorously defined principles and instinct.
In this conversation, Amy shares how she rebuilt her $70M business by rejecting sameness, redefining traditional success metrics, and embracing what she calls the “Creative Pragmatist” mindset — balancing bold creativity with discipline and utility. We talk about navigating “the good ick” before growth, knowing when a risk aligns with your values, building community without chasing trends, and leading with conviction in an era dominated by data. A thoughtful episode for founders, creatives, and anyone committed to building something original with structure, clarity, and courage.

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Transcript

Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be. I want to be you. Just want to make sure you will get knocked down. But just make sure you don’t get knocked out, knocked out. So your only choice should be go focus on what you can control. Control. Control. Hi everyone, and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs and really, some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hi everyone, and welcome back to the Kara Goldin show. So, so excited to have my next guest on our podcast. Today, we are joined by Amy Smilovic, who is the founder and creative director of an incredible brand called TIBI. She is also the author of the brand new book just launched yesterday called Almost Reckless, which I got a preview of. And it is so good, so inspiring, so honest. Thank you. So wonderful. And I know how hard it is to find the time find the courage right to own it and do what she’s done. So I just love, love, loved, loved everything about Almost Reckless, but I’ll give you a hint. So have you ever been told to follow the data, run the focus groups, listen to the consultants, scale the way everyone else does? Amy did not do that, and she launched TIBI in 1997 with $15,000 and no formal fashion training. What she did have was taste instinct and a set of principles she was willing to define rigorously and defend. Today, she leads one of the most respected, coolest, independently owned luxury brands grounded in her philosophy of creative pragmatism, balancing bold creativity with discipline and utility. So I am so excited to have Amy with us here today and to speak about her brand new book, Almost Reckless. So, so good, and thank you so much for coming on. Amy, so nice to meet you.

Amy Smilovic 2:29
Thank you. Nice to meet you too. So for listeners

Kara Goldin 2:33
just discovering the TIBI brand, how do you describe the brand that you created and what, I guess, what it has always stood for, and what it stands for today,

Amy Smilovic 2:45
I would describe the brand as based on some core principles of really following your through line of your personal style. And it’s based on my personal style, which happens to be a lot of others as well, which is something very clean, very modern and grounded in the classics. And what I found, though, is through designing, through those principles of things that are clean and modern and classic, that I was kind of describing the way that I lived my life. And this, this went well beyond clothing. When I talked about wearing things that were effortless, things had a point of view and were forward thinking, things that were grounded in heritage and history and the past that I was describing the way that I kind of act and behave every day. And so that’s this conversation evolved from just style and style principles to the principles of how we lead our life in general.

Kara Goldin 3:46
I love it. So you launched TIBI, I understand in 1997 with $15,000 and no formal fashion training. How did you do this? And what gave you the confidence to just go and do it,

Amy Smilovic 4:02
you know, it was, it was that work ethic ambition, but, but combined with the ignorance of just someone who just thought that they could do something that they loved based on what inspired them creatively, and then just, you know, what they thought They could execute on and Hong Kong was a great place to start a clothing brand because I didn’t have the naysayers around me. I didn’t have the industry experts explaining to me how things should be done. And when someone’s not telling you how should how it should be done, why it should be done this way, you tend to proceed in a way that makes sense for you. Like, what do I want to do creatively and how can I get it done? And, you know, I really describe my brand as taking off with that kind of just very narrow vision of what could I do and how can I get it done. Yeah, and then things faltered once I found out the way it should be done. And you start questioning, how did I get to be so successful without knowing anything?

Kara Goldin 5:10
It’s, it’s so, so true. So you started the brand in Hong Kong. Can you talk a little bit about those early days? And you know, what did you start with? How? How did you get going?

Amy Smilovic 5:24
You know, Hong Kong is such an entrepreneurial place, right? Like you just say, I want to do something, and all of a sudden you are knee deep in it. But we had a lot of debates. My husband and I up front about, you know, how do you get started with a business from scratch? And he really wanted to see this five year, 10 year business plan. And I remember we were at the American club in Hong Kong, and it was getting pretty contentious, and he was like, you have to have a plan. You have to have a plan. And I was like, but this is what I want to make, and I know that I can do it. And a guy at the table next to us leaned over and he said, I can’t help but interject here, because I hear you having this discussion, and I want to let you know, here’s a great business plan. You make a product, if you sell it, you have a business. If you don’t sell it, you don’t have a business. And he was absolutely right, and I went the next day, and I had four designs, and that’s what I started with. And it turns out that’s all you needed to find out if you have the beginnings of a business, and I did, and it was just step by step, day by day.

Kara Goldin 6:30
So in Almost Reckless you argue for trusting rigorously defined principles over blind risk. How do you know when a risk aligns with your principles versus when it’s just reaction.

Amy Smilovic 6:45
I guess it’s impossible to really know it if you have not really articulated the principles. And so, you know, this is where we found ourselves. In 2020 we were sitting atop a $70 million brand. I should have been on top of the world. And I felt terrible. I was completely discontent. I thought it was maybe because I was overworked. Maybe I’m just not cut out for this industry. And when we really sat down and wrote down what were the core principles that we wanted to live by the things that when we knew that when we went against them, they made us unhappy, we were able to get drilled down to really first principles. There were three principles we needed to have agency, which meant we had control of our lives. Our problems were ours to solve, our opportunities were ours to to win. And we realized that if we had people around us who didn’t share a similar mindset, meaning that they weren’t solutions focused, they weren’t hard workers, they weren’t open minded when we when we weren’t around people who shared our mindset, we were deeply unhappy and when we were creating things that we didn’t find valuable, whether it was even A spreadsheet that told a great story or a dress that had meaning to us, we were deeply unhappy. So when we nailed those three principles, agency, shared mindset and finding value in everything we do, everything else became really easy. A risk was not so risky if it aligned with our principles, and a risk was terribly risky if it didn’t align with our principles, because the risk was that we were going to be deeply unhappy as a result. And this is our life. You know, we want to enjoy the life we have now, not later.

Kara Goldin 8:37
So interesting. So would you say that that was one of the hardest times that you had. Obviously, the world was adjusting for everyone at that point. But so many people, and you know, during that time in 2020 were just, I mean it, I can only imagine also just trying to rework what you stand for inside of a company, too, in addition to dealing with maybe problems with manufacturing and everything else that was going on in the world and your health and your family’s health,

Amy Smilovic 9:11
Yep, exactly. Yeah, it was. It was one of the most problematic times that ended up giving us an opportunity that I don’t know we would have had otherwise, because it allowed me to just be stripped of every choice that I thought I had, and I had only one choice in front of me, which was get in front of the camera, get on Instagram and start talking about who I am and what we had to offer. And before that, I had always been hidden behind the camera. I was not there was nothing sexy about me. You know, I was, at the time, a 50 something year old mom with two boys and no industry experience, even though I was. Completely devaluing what was around 23 years of industry experience at that time, but I just did not see myself as anything that anyone would be interested in in the fashion world, I was behind my label, but not in front of it, and so 2020, forced me to get in front of it, and when I did, and I started having conversations with other people out there, I started realizing what a connection I was having with people and what those common denominators were of that connection, I was attracting people who were deeply curious and had an ease about them and a modern outlook and that they were enjoying discourse and wanted to know about history and why things were the way that they were, and so all of those things just kept reinforcing, then the ideals of the clothing and what we were creating. And it was all very circular, and it it super focused me. And you know what? Once those principles were in place, once I had that focus, we were able to really, really scale back the business so that we could really push it forward for the future, and I have not looked back since.

Kara Goldin 11:15
So TIBI really thrives on Less is More I Love. Love, love the style. And I really think that it’s, it’s timeless. I mean that what you’re producing today is just, it’s, you know, practical restraint in an industry that is built on newness, and, you know changes, not only for for different color, but also just because you feel like that designer, that maybe your consumer is also enjoying is producing. How? How do you practice restraint in an industry that is built on constant newness?

Amy Smilovic 12:07
I think people underestimate the value of limited resources. I mean, having a small pocketbook was my greatest asset when we started. You really can’t get out above your skis. You know, when I started with four styles, that’s what I could afford to start with, and you start and then you sell, and then you grow, and you sell more, and then you grow a little bit more. But staying independently owned has always kept us incredibly focused in that way. So you know, when we if we were to really look at growing the brand the line exponentially, we would have to bring out outside investors, we would have to really change the structure of the company, and I would lose agency. I would likely be working with people who I do not share a similar mindset with. I would probably be asked to create a lot of things that I don’t love. So, you know, I’m constantly aligning everything to the principles, because I found out the 70 million didn’t do it for me, for the happiness. What does it for me is when those principles are in place? You know, I can only drive one car at a time. I can only be in one house at a time, I really understand what makes me happy in life and what doesn’t. And this just feels great right now, doing what we want to do with the people that we want to do it with, making the things that we want to make it can’t help but just can lead to good things.

Kara Goldin 13:41
No, it’s, it’s so, so true. I feel like too what i The more I dug in, not only after reading Almost Reckless, but also dug into your brand a little bit more. I mean, you started this brand in 1997 right? And you’ve continued to grow it and pivot when you need it to pivot. But you’ve done an incredible job and have a very, very loyal consumer base, but you also continue to bring in a younger base of consumers that love what what you’re doing. I think it’s it’s fascinating, because there’s a, I think there’s a thinking that once you’ve started with one consumer base, and you’re continuing to really bring them along as they get older, as you get older, you can’t bring in this younger base of consumers, but you are, so you’re you’re against, you know, conventional wisdom, I guess, with what most brand builders would say, like, what would you say to that?

Amy Smilovic 14:51
I would say that we, we do not sell to a consumer base. We sell to a mindset. And so that kind of provocative mindset. That really loves, like engaging in a good discussion, and loving risk and loving friction. You know, they’re not looking for just this frictionless life. They want to be stimulated constantly. And you know that is going to hit an 18 year old, a 38 year old, a 48 year old, it’s going to hit a 78 year old and an 88 year old, it’s going to hit someone in China, someone in India, someone in Dubai and someone in New York. So when you are selling to a mindset, I just don’t have any limitations. If they are human, you know they if they’ve got to have two legs like they just need to be human with a mind and the same mindset, and then they are in our sphere, and a lot of people don’t share our mindset, and that’s okay too, but it’s not a slice by age or demographic, geographic or psychographic

Kara Goldin 15:56
I love in Your recent collection, where you’ve added just these pops of color here and there, but otherwise, very classic, very beautiful in everything that you’ve done. You’re a global brand. Now, there’s many people who, even if they can’t come to your physical location. They’re going online and they’re purchasing it. Have you noticed a lot of differences throughout the world as it relates to color that you think is pretty interesting?

Amy Smilovic 16:32
You know? It’s interesting because when I first started to be in I was born in the Midwest. I was raised in the south. I moved to New York. I marry an Eastern European, a different religion. We moved to Hong Kong. I’ve now, like had this global scope in front of me. And I remember when I first started, a woman editor asked me, she said, how do you how do you do color? Because that’s so bold, it takes someone who’s such a risk taker to wear color. And at the time, I thought, Well, I mean, I’m from Georgia. You know, that was, like, the most basic thing in the world to wear color. It didn’t require a certain level of boldness and but so what I see, though, with color now around the world is people do associate it with different personality traits or different emotions that they feel when they wear it. But again, with that really curious customer that we have, they’re kind of game for exploring them and trying a lot of things. I’ll, you know, I’ll have a customer who’ll write to me every now and then, and they’ll say, you know, no one would ever wear red to this event, and I’m like, I just know also that’s not our customer. So that might be ingrained in the way the tropes that they’ve been brought up with, but it’s not our customer to be so finite about the way something must or must not be.

Kara Goldin 17:57
I loved your comment in the book, never miss a moment to embrace the ick happening. Can you talk about those good ick moments and just ick moments overall?

Amy Smilovic 18:11
You know, ick is where the good happens. I mean, I can’t tell you the number of times that you get something back from the sewers or from the printer, that is absolutely not at all what you were supposed to get. And if you just sit with it for a second, you realize it’s not what you were supposed to get, but maybe it’s exactly what’s going to be great. And I think a lot of people get so focused on what they had in their head, how it was supposed to be, and the frustration they feel when it isn’t and they miss the opportunity when just you miss the opportunity for something great. This is where unique things happen. It’s where people come up with the things that end up defining their whole brand is by doing what you had to do in the moment, or accepting what you thought was a compromise. It turned out to be the best thing ever.

Kara Goldin 19:09
When you look back on the years since you’ve started and that you’ve grown to be I’m sure there, there’s been some mistakes that have been made, whether it’s on certain products or I’ll never forget that the founder of Bowlin branch told me that his mistake was that he grew up in a house where he always had bed skirts on every bed, so he assumed that he needed to buy Lots of bed skirts, and you actually don’t change the bed skirt very often. And so he said, I have so many bed skirts that I should have. Are there any bedskirt kind of stories from TIBI where you thought everyone needs to have this and and, boy, were you wrong, or you still have them. It was,

Amy Smilovic 20:01
you know, I remember, it was my very one of my very first shipment of dresses that I sent out, and I had fit everything on me. And the factory, also, I was, you know, producing in Hong Kong, and they had this vision, though, of what an American woman was supposed to be. And so they were fitting it on me, but they were like, but the American woman is So, you know, in their mind, they’re like, the American woman’s huge. Yeah, you Americans, you guys are huge. So they went back and, like, kind of reformulated everything on their own. And my mom was the one who was shipping out all of our first deliveries while she was also working as the high school principal at the time. And I remember she called me in the middle of the night, and she’s like, Amy, I’m getting all these calls from these stores, and they’re saying that all of your dresses have cone boobs on them and and I just, I went to the factory, and they had just altered everything to fit what they thought was this American boob that was this very sharp Madonna cone boob, if you can imagine Madonna singing in the late 90s. And I wish I had a good story of what those cone boob dresses got to be used for. We we donated them. I don’t even want to think about where this place was that we donated them, and all these women running around in these comb boob dresses, but, but those were the things that you know when you’re starting out again. I was saying a lot of people don’t have the benefit of starting out small. I think it was about 150 cone boob dresses. And, you know, I got to learn a big lesson from it. Hire a technical designer, you know, really stay on top of that part of the business, but, but you also learn, like you know, what you were, what you had to do in order to keep your business afloat, how you have to take things back. You have to make sure that you are doing right by the customer and and it was, it was that was painful. I wish I could say it had led into, like this whole cone boob, fabulous trend moment, but it did not

Kara Goldin 22:19
so interesting. And on the flip side of this, what was the the item that maybe you just weren’t sure was really going to take off? And boy, did it take off.

Amy Smilovic 22:30
It was, oh god. It was, I mean, there’s a very specific story around that. So I had created a skirt that was a hand drawn print that it was one of my mother in law’s prints, and I’d redrawn it, and I had it hanging up at a showroom at this place called the coterie, which is where you went to go sell everything to the stores. And a woman who was her name was Janine Braden, and she was one of the founders of Fred Siegel in LA, and Fred Siegel was like the it store at the time in LA, and she looked at the skirt, and she said, I love the idea of this. And if you took this idea and made it in a bunch of prints, I’m all in. So I thought about it, and the next day, I was staying at this shitty little, tiny little apartment off of McDougall street that I had rented for like $100 a night for when I came in town from Hong Kong, and there was a vintage store, and they had this pile of souvenir scarf prints from Paris, from Japan, from London, the kind that you would buy off of like Rue de Rivoli in Paris that would just be, like $1 you know, hanging in a gift shop. And I bought a bunch of these very, very tacky, brightly colored scarf print skirts, and I brought them back to Hong Kong, took them out to Benny and Ivan my factory. And I was like, How can we create prints based on these? And I want to turn them, though. I want to put them onto the richest, richest silk, this 40 mommy four ply silk, and I want to do them in these beautiful bias cut skirts. And we did it. And I remember, on my way back to New York, I stopped off in Paris. I stayed with a friend in Paris, and she was like, those are the tackiest skirts I’ve ever seen. No one will ever wear those skirts. And I thought, but don’t you think they’re so tacky that they’re great? And she was like, that’s not a thing. And it scared the hell out of me. And so I got to the coterie, and I hung my little skirts up. And I kid you not, I think we I did over $300,000 in sales on that skirt, at wholesale, at the coterie, and then months later, I was in New York, and I opened up the New York Times, and Bill Cunningham had dedicated the entire Sunday section to. That skirt. And he called it this trend that he had been seeing in New York, but it was all my skirt on different fashion editors and customers. And it was, I mean, it was, wow, it took off. But then it became, it locked me in at the same time, I became the boldly bright colored printed person, and that I had, I spent years and years unwinding after that. So the good comes with the bad. Sometimes, if you don’t know how to navigate, it

Kara Goldin 25:31
so interesting. So success has has grown on you, and compared to what 1997 when you were first starting out, how do you define success today, and how is it different from when you were first starting

Amy Smilovic 25:55
success for me, today is waking up every day with a sense of control. And you know the I mean, the world is crazy, right? You never know what’s going to be handed at you each day. And so when I say a sense of control, I just mean that I’ve got the right people in the bunker with me to tackle any problem that comes our way. And you know, crappy things are going to happen, really good things are going to happen. And you just want the people around you who can help you weather the storm and enjoy, you know, the sun when it comes out as well. And then, you know the clouds are going to come again and and that’s just part of life. But, you know, I grew up with these parents who left everything, you know, in Chicago when they were in their early 20s, with my sister and I, and we moved to this small island off the coast of Georgia and drove around in a tiny little Jeep and sane for shrimp and and life was really good. And so I’m like, you know, I just don’t place a tremendous amount of value on things and money and location as long as you have your your family and the people that you love around you.

Kara Goldin 27:18
No, I love that. Well, such. You’re so inspiring. I’m so happy that I got chance to meet you. And Almost Reckless is a must for everyone to put on their list, whether you’re a founder or not, or whether you are familiar with TIBI. I always think knowing the story behind any brand is incredible, but you have just really shown what just to go do it and have the resilience be able to pivot all of those things are just very, very spelled out in everything, hopefully in this interview, but for people, but also in Almost Reckless so thank you so much, and for everyone listening, be sure to check out TIBI, check out Almost Reckless and Amy, thank you so much. Again, you are just a total rock star.

Amy Smilovic 28:11
Thank you so much. I love this. Thank you very much.

Kara Goldin 28:14
Thank you. Thanks again for listening to the Kara Goldin show. If you would please give us a review, and feel free to share this podcast with others who would benefit. And of course, feel free to subscribe so you don’t miss a single episode of our podcast, just a reminder that I can be found on all platforms. At Kara Goldin, I would love to hear from you too. So feel free to DM me, and if you want to hear more about my journey, I hope you will have a listen or pick up a copy of my Wall Street Journal, best selling book, undaunted, where I share more about my journey, including founding and building. Hint, we are here every Monday, Wednesday and Friday. Thanks for listening and goodbye for now.

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