From Retail Collapse to Amazon Growth: How Shy Iland Rebuilt Through Handbags | Emily Blumenthal & Shy Iland

What happens when the retail world you built no longer works? In this episode, Shy Iland, founder of Daisy Rose and former owner of the indie-boutique chain Big Drop, shares how the 2008 financial crisis reshaped his entire approach to fashion. After watching handbags outperform most retail categories during the downturn, Shy pivoted from brick-and-mortar retail into handbag manufacturing, sourcing, and private label production. He opens up about the realities of running multi-store retail before ecommerce, the pressure of inventory, rent, and shrinking margins, and the difficult decision to walk away from a family business. From traveling to China’s Canton Fair to building factory relationships and eventually launching Daisy Rose, Shy breaks down how Amazon FBA, influencer momentum, and disciplined sourcing helped transform his next chapter into a scalable business.

Key Takeaways:

• Accessories survive downturns — Handbags often outperform trend-driven categories during economic shifts.
 • Manufacturing is relationship-driven — Strong factory partnerships matter more than chasing the lowest price.
 • Scale requires adaptation — Moving from retail to sourcing to Amazon selling demanded constant reinvention.

🎧 Listen now for a candid look at retail survival, handbag manufacturing, and building a modern accessories business from the ground up.

Our Guest:
 Shy Iland is the founder of Daisy Rose and former co-owner of Big Drop, a pioneering New York boutique chain known for discovering emerging designers before the ecommerce era. With decades of experience spanning retail, sourcing, manufacturing, and Amazon-driven growth, Shy has built a business rooted in adaptability, product instinct, and strategic scaling.

Host Emily Blumenthal is a handbag industry expert, author of Handbag Designer 101, and founder of The Handbag Awards. Known as the “Handbag Fairy Godmother,” Emily also teaches entrepreneurship at the Fashion Institute of Technology. She is dedicated to celebrating creativity, craftsmanship, and the art of building iconic handbag brands.

Find Handbag Designer 101 Merch, HBD101 Masterclass, one-on-one sessions, and opportunities to book Emily Blumenthal as a speaker at emilyblumenthal.com. 

Transcript

Handbags That Survive A Recession

SPEAKER_02 0:00

When I was handling the buying part of the business, I think the one category that I didn't have any any output was handbags. That was all the buyers. But what I noticed during 2008, 2009, when the financial crackdown happened, meltdown happened, I've noticed that while all categories in the store went down by 20, 30, 50, 60%, the only category maintained the same and even went up a little bit was handbags, handbags and accessories, which was very interesting at the time.

SPEAKER_01 0:37

Hi, and welcome to Handbag Designer 101 the podcast with your host, Emily Blumenthal, handbag industry expert, and uh handbag fairy godmother. Each week we uncover the stories behind the handbags we love from the iconic brands and top designers to creativity, craftsmanship, and culture that define the handbag world. Whether you're a designer, collector, or simply passionate about handbags, this is your front row seat to it all. Welcome,

Daisy Rose Name And Early Roots

SPEAKER_01 1:11

Shy Island of Daisy Rose to Handbag Designer101, the podcast. Welcome, welcome.

SPEAKER_02 1:19

Thank you, Emily. Thank you very much for having me.

SPEAKER_01 1:22

Yeah, so we were just discussing, you and I connected on LinkedIn, which as I tell my students, that's where the old people hang out. So that's where the humble brags happen. Like, oh, I'm pleased to let everybody know that I'm amazing and had a promotion and blah, blah, blah. So I'm happy I was able to find it, or we were able to connect there. Your company is called Daisy Rose, and you were just telling me the origin of the name.

SPEAKER_02 1:52

Yes. When I was looking for the right name, I came up with the Daisy Rose, which Daisy was the name of my late grandmother, and Rose is the name of my mother. So Daisy Rose, it is.

SPEAKER_01 2:07

Was your family initially in handbags?

SPEAKER_02 2:10

No, not at all, actually. I'm originally from Israel. I moved to New York many years ago, before 2000, and I started working in uh random work, random jobs, and then my relative he owned one boutique store called Big Drop.

SPEAKER_01 2:30

And right, right, right, right. I forgot. Yes, you almost made me spit my water out. Yes, Big Drop was the place for independent designers, literally one of the hardest stores to get picked up in. I remember.

SPEAKER_02 2:45

Yes. Um, so so I joined him along the way when we intended to expand and open more stores. I was the one who found and opened the big drop in uh West Broadway and then Upper East Side, Madison. We even expanded into uh to Miami, South Beach. I remember at the time the Gensworth Hotel, today is the one hotel, and uh yeah, those were good the good old days, early 2000s.

SPEAKER_01 3:13

That was the heyday I discovered like Rebecca Meinkov, Monica Bakir, Grayson. I gotta go through my book to look at all the names of all the boats at that time, like that's where they were all. It was like it was Burr and Big Drop. That was it.

SPEAKER_02 3:30

Yeah, see those two stores.

The Big Drop Boutique Era

SPEAKER_02 3:33

It was pre-e-commerce. So when you wanted to see what the eat bag is or what the hottest denim are, you have to actually walk into the store and see what they have. You couldn't compare, you couldn't browse, you just had to go and see what you have. Like you said, everybody wanted to be in the stores. We specialize in uh we specialized in contemporary designers. We basically were willing to meet anybody that wanted to show their designs, what they have, and we were very picky about who we brought in, and we really liked finding up-and-coming designers where who looked for, you know, the first place to basically display their goods.

SPEAKER_01 4:15

Yeah, no, you guys, I I sorry for interrupting, you guys were truly pioneers. I mean, the the independent designer boutique, like that's that was the heyday, like that was the time where if you were a new designer, like getting into Barney's was almost as important as getting into Big Drop. It was like they were both aligned with the same value and carried the same weight.

SPEAKER_02 4:43

Yes, we felt it too. I mean, around uh, for example, Fashion Week, where everybody came to New York either for buying or for the trade shows. We saw everybody in the stores. Everybody visited to see what's in there, what big drop carried at the time. And all the designers they wanted to be there so they can also drop name and say, hey, we're at Big Drop. Those were the good old days. We worked hard, you know, to build um a buying office that was second to none. Team of buyers, assistant buyers, analysts, uh, budget. We visited all showrooms, all trade shows, domestic and and international. We accepted appointments from everybody. You know, we were ahead of the game at the time.

SPEAKER_01 5:27

I always say to be a pioneer is expensive because to take on new things, you know, you run the risk of things not working out, and especially dealing with newer designers. You run into so many headaches from delivery issues to quality issues to them not showing up to, you know, and then you're the one who has to like almost train all these new people on protocol to be in a boutique.

SPEAKER_02 5:58

Yes, yes, it's very challenging. You have to manage a lot of things, and at the end of the day, you're in between employees. When you have so many bo so many stores, you you have to make sure that you bring the right people, and then you you have the buying team and you have to to handle all the buying and seeing everybody. Very complicated rents, you know, dealing with landlords and real estate and trade shows and traveling. There's a lot of things going on, uh running a boutique uh chain as well, you know. Because fashion is you know, you buy four, five, six months in advance. The good thing about it is you know in May what's going to be sold in wintertime in September, October. So you're you're ahead of the game. And you know, it's it gives you a benefit to know the trends, know what's coming, but also to recognize voids in the market. And I think we we're really good at that.

E-Commerce Hits And 2008 Fallout

SPEAKER_01 6:58

So that probably took you, if I remember, till like 2007, 2008, that whole like rush of everything. And then by the time like 2008, 2009 hit, and then when the market dropped, like things absolutely took I don't like saying took a turn for the worse, but things started to change because I remember back in the day when I was selling my bags to boutiques and I put my website on my hang tag, and that's such chaos. Like, no, you can't do that. And then if you got press, like you had to be very specific with which like which channels of distribution. So you couldn't list your website, you had to list two stores, and there was no guarantee if they list the stores, and then it made things located. And then with the advent of social media, like it's it didn't make the boutique irrelevant, it made the boutique have to work 10 times harder to keep.

SPEAKER_02 8:00

Yes, I think the the introduction of e-commerce, uh, you know, the early days took a big toll on retail because you had competition, but it it was an unfair competition because the amount of traffic that they can get is not the amount of traffic you can get. I mean, we're we're in New York, you get uh you know good amount of traffic, but imagine you know, boutiques in in Ohio or Texas, it's tough, it's tough, and you can compare, you you can see if it's on sale or it's not. So, retail, you had to actually go into e-commerce, but it's totally different business. So it's like running two separate businesses at the same time. Those were, yeah, though I think that together with uh the economy at 2008-2009, those were the difficult years for boutiques, especially for us as well. We I think at the time our revenue dropped within six months by 60 to 70 percent. We had to shut down stores, oh my god, let employees go. Yeah, it was brutal.

SPEAKER_01 9:07

So at which point you're running this business with a cousin? Yes, second cousin. And at which point who who called it? Who was like, Oh yeah, it's always the cousin. At which point, who called it? Who was like, that's it, we're done? Or were you like, That's it, I'm going home? When did you who called it and then who was the first one to go?

SPEAKER_02 9:28

I think I felt burnt throughout that process because I had to deal with all the vendors. I had to basically, you know, it's people that you had a relationship with, brands and and and stealth people that you had to call and say, hey, you know, the that order that I placed uh three, four months ago, I'm gonna have to cancel it because our budget shows that we can't bring in any more goods in your category. So you had to go and burn personal relationships and you had to file let go of employees, you have to have negotiations with landlords about rents and shut down stores. It was a very difficult period at the time that at some point I just came to him and I said, Listen, I can't do this anymore. I think I'm gonna stay until the ship is stable, until you can keep going, whatever it takes. But once it's done, I'm out.

SPEAKER_00 10:20

Exactly.

SPEAKER_02 10:20

I'm I'm done. I'm done with retail. I don't want to do retail anymore. And it took about a year or so. I think end of 2009, we closed two stores, we had a huge office showroom and warehouse that we shut down. We moved into a much smaller office at the sub-basement of our Sprint Street location, which is the most famous one. Once that was done, I said thank you, and that's it for me. And

Leaving A Family Business Cleanly

SPEAKER_02 10:53

when I was thinking about what would be my next move, I said that will be something that I'm not gonna be tied down to a certain location. I'll be able to do it from anywhere in the world.

SPEAKER_01 11:05

Was it complicated? Because I've had a lot of people like on the podcast and designers I know that have gone into business with family members, with siblings, with mothers, and with fathers. I mean, the stories I've heard that my father and I didn't speak for years because my father made me third and I had holidays together, and we didn't even acknowledge each other, and we had to fake it for our kids so my kids could have cousins, like the stories. So, how did it end up with your cousin and second cousin, still a cousin? But how did you leave things saying, Okay, I'm out, I'm done, and I'm I'm gonna start something new, and you're probably not gonna be involved.

SPEAKER_02 11:54

Yes, we were when we started, we were very close. We did everything together, and yeah, throughout the years, I mean it became more business than personal, and towards the end, it was unpleasant. It's tough. I mean, it I always say that selecting a partner is like selecting uh a spouse, you know. You have to know who you're going into partnership with, and it's tough to to let go. And he he I I think at the time he he got uh hurt that I'm leaving, leaving him with everything behind. But I did my part, and you know, I I I stayed as long as uh you know everything was uh stable and he could keep running the business, but you know, it was something that I just had to do for myself. So yeah.

SPEAKER_01 12:45

That is so hard, you know, it's like you feel this like emotional, moral responsibility, but then it's like I'm gonna crack. I will physically break if I stay. I don't even want to be here, I can't even like go there anymore. New beginning because you know, you went there is just something to do, and you accidentally stayed significantly longer. So, you know, to go through being your home for so long and say, Oh shit, now what I'm supposed to do.

SPEAKER_02 13:17

Yes, you're you're 100% correct. I mean, this is exactly what it was. You feel obligated, and at the end of the day, that is your baby, that is the business that you put sweat and tears into. When you have a business, you don't go home at 7 or 8 or 8 p.m. and say, That's it. You keep working or you go to business meeting or you think about the next day, and what you're gonna do, it never ends. And it's 24-7 all year round, and and the the decision to let go and leave this thing is is a very difficult decision, which you know came after uh you know significant consideration, but at the end of the day, it was the right thing for me to do at the time to move on and you know start fresh with new energy and find something that I'm passionate about and start building it from scratch.

SPEAKER_01 14:10

How

Betting On Handbags Without Experience

SPEAKER_01 14:11

in the world did you come up with handbags after running such a powerful boutique and seeing the business and seeing the drama and seeing the nightmares that handbag designers go through, what made you be like, hey, that looks fun? If you ever wanted to start a handbag brand and didn't know where to start, this is for you. If you had dreams of becoming a handbag designer but aren't trained in design, this is for you. If you have a handbag brand and need strategy and direction, this is for you. I'm Emily Blumenthal, handbag designer expert and handbag fairy godmother, and this is the handbag designer 101 masterclass. Over the next 10 classes, I will break down everything you need to know to make, manufacture, and market a handbag brand, broken down to ensure that you will not only skip steps in the handbag building process, but also to save money to avoid the learning curve of costly mistakes. For the past 20 years, I've been teaching at the top fashion universities in New York City, wrote the handbag designer Bible, founded the handbag awards, and created the only handbag designer podcast. I'm going to show you like I have countless brands to create in this in-depth course from sketch to sample to sale. Whether you're just starting out and don't even know where to start or begin, or if you've had a brand and need some strategic direction, the handbag designer 101 Masterclass is just for you. So let's get started, and you'll be the creator of the next it bag. Join me, Emily Blumenthal, in the Handbag Designer 101 Masterclass. So be sure to sign up at Emily Blumenthal.com slash masterclass and type in the code oncast to get 10% off your masterclass today.

SPEAKER_02 16:34

And even went up a little bit was handbags, handbags and accessories, which was very interesting at the time. But I think what it was is that you can carry a handbag multiple times versus a blouse that you wore you were once, twice, three times until everybody saw you with, and that's done. So I think I think that was what it was at the time that made me think handbags. I think it was that and the fact that there are no sizes and fit to handbags. It's a handbag. And that was what made me say, okay, I think this is gonna be my direction.

Canton Fair And Factory Vetting

SPEAKER_02 17:17

And I thought about you know, the the idea was to create a company where you can come to help you produce bags in uh high quality while maintaining low costs, and that was the idea. But there were basically three issues. One, I didn't have any factories, two, I didn't know anything about handbags, and three, I had no customers looking for handbags. So that was at the time, right? But I had a lot of uh people I knew from my past, and I found out that there's uh a big trade show in China twice a year where all manufacturers basically not all, but uh a lot of manufacturers show their uh uh manufacturing capabilities. So I flew to the trade show, I took a notebook with me, and I passed booth by booth, and I found out you know, different manufacturers, each one specializing in a different uh category or different material or have other abilities, and it just created a network of factors that I can at least start with. I picked up the ones I thought were good or had what I was looking for. I developed a range of sample, different categories, different materials, and went back to the US and started uh showing them and talk to people, and that's how it started basically.

SPEAKER_01 18:43

I have so many questions. Okay, because and I got this, I got this very uh sage advice a hundred years ago when I was an intern at an ad agency, where someone from ESPN said to me, because I was so eager to be on the sales side, because the sales side so glamorous, right? Because those are the ones who go out, they go door to door, they're the ones who to be the one who's selling. He said, You would never open up a clothing store if you didn't know how to shop. And if until you understand the mind of a buyer, then you have no business creating anything to sell. So I'm so curious. What was the trade show? Because I know my listeners will want to know. How did you and also, you know, this is just you. So what was a trade show? How did you determine the aesthetic? How did you know that that aesthetic would still be on trend? And how did you really hone in on who your customer really was? Because necessarily the person in Miami and isn't the same person in Cincinnati. So, how did you hit all that from the start? Sorry, it's a lot.

SPEAKER_02 20:00

Um yeah, it's it's there's a lot of aspect into this, but you know, running a uh buying office for so many years and seeing so many designers and brands coming and going, see who survived and who didn't, see what sold and what didn't, what price point, what material. The advantage that I had at the time was I saw I had the retail retail mind going into manufacturing. So I had an advantage because when I was looking into it, I was looking at it as a buyer. So and and doing it again for so many seasons, you know ahead what's coming, you know what the cycle is because fashion is a cycle, you know, the same same trends come every few years, they're coming back like fringe. It can be hot today, and in three, four years hot again. This is how fashion works. So going into that trade show in China at the time, I was actually looking for uh manufacturing abilities for what I've known. Who can I think the thing in China and you know, especially is you can always find cheaper. It's much harder to find quality manufacturers, quality materials. It's much more difficult. And trying to recognize who can do things that I've seen before and other designers doing, or a certain bag that solved really well for us. Who can who who from all these people would be able to produce something like it? And I think that was my guideline at the time. Who my customer would be was it wasn't very clear because I didn't know if it'll be uh, you know, if I have a customer looking for PU bag for seven, eight dollars or a leather bag for fifty, sixty dollars. So I I've created a range of samples from. That end and to that end. And I I was just whoever looking for a customer, whoever's gonna bite on something, just give it to them. It's very similar to buying retail. You buy when you go when you look at a collection, you buy a few pieces from that collection and from that group and from this group. And when you see what the customer buys, that's where you go deep and you buy more of that or bring them more.

SPEAKER_01 22:27

How did you determine your DNA with having seen so many designers and saying, okay, I'm not gonna be the person who put something out there that someone else did, right? As someone who wants to remain authentic, wants to remain, you know, develop your own brand that people will say, okay, I know that this would go back to Daisy Rose. How are you able to say this is our look that isn't necessarily what someone else did?

SPEAKER_02 23:00

At the time, Daisy Rose, the idea of Daisy Rose was manufacturing, wasn't the brand. And I think it's different. Two years later, I've created private label Daisy Rose, which is sold online. That's when I think from my experience, any business, the DNA is determined, it's a process. Because when you start with an idea, it doesn't mean that necessarily that's gonna be the brand or the company. It gravitates, it changes, it depends what your customer wants. And that's when you you focus towards that direction. For example, you know, if you think you you'll be selling a lot of uh leather bags, and suddenly you have more customers looking for wallets, then you're gonna shift into wallet at the time. So the idea that I have creating a wide range of products from leather to PU bags, from leather wallets to PU wallets or fashion accessories, keychains, back, uh computer sleeves, a wide range of items. So when a customer gravitates towards something, I'm able to give them the solution and help them develop.

SPEAKER_01 24:19

Wow. This is so so is Daisy Rose started off as private label and then you've evolved into being your own brand.

SPEAKER_02 24:27

It started as a production company that uh helped other brands and department stores produce private label. That's who that's how it started. It's you know, the core of the business. Few years later, I and that's a that's an interesting story. Around 2017-2018,

Amazon FBA And Influencer Sellouts

SPEAKER_02 24:50

I said, you know, I'm producing so many things. I think I I can combine you know my buying and manufacturing and create a brand and start selling on Amazon. And you know, at the time it wasn't as saturated as it is today. One of my factories called me, I was selling some items, and one of my uh factories called me and said, Listen, a customer ordered 10,000 wallets with certain print, and I'm stuck with it. Do you have a customer that can sell them? And I said, you know what? Uh why don't you send me uh 500 pieces and I'll I'll check with my customers. And I checked, there wasn't a lot of interest in it, and I said, you know, I have, I think at the time around 300 pieces of it. I'll just gonna send it to uh Amazon FBA and see what happened, and started selling little by little, and then one morning I woke up and it was sold out. I was like, wow, from selling five, six pieces a day into uh 200 pieces overnight. I produced 500 pieces, tipped them again, sold five, six a day, and then one morning I wake up, all sold out again. I I didn't realize what hit me, I didn't know what happened. And a few days later, I received a we received a message from a customer saying, Hey, I saw that wallet that such and such influencer posted. Do we have more of it? And we asked her, who is this person, who is this Instagram account? And she sent us this account, and we found out that that influencer bought one wallet and she posted it, and every time she posted it, it was just sold out. So that's how the private label kicked out, and we just produced more and more items and grow it into the brand that it is today. We sold on Amazon, Walmart, and our own Shopify, uh Daisy Rose.com.

SPEAKER_01 26:47

Wow, wow. This is like the coolest evolution story. I think it's really inspirational. And what was the trade show you went to in China? Just so everybody knows what it's called.

SPEAKER_02 27:01

It's uh the Canton Fair. It's the biggest trade show in China. It's twice a year, it's uh end of April and end of October. There are three phases. The phase for bags and fashion is the third phase, which is the first week of May and the first week of November. Okay, it's huge. It's huge. If anybody goes there, it's five days, it goes it goes five days. There's no way you can finish uh walking all of it in five days. It's huge.

SPEAKER_01 27:33

Oh my god, it's huge.

SPEAKER_02 27:35

Oh my god. Think uh coterie or uh in key at the time, multiplied by by 30 or 40 or 50.

SPEAKER_01 27:44

Oh my god. So

Sourcing Lessons And Where To Buy

SPEAKER_01 27:46

I think there's so many lessons to take away from this that I think that it is possible to actually create a brand and reverse engineer and take your time into developing something and testing the waters and really seeing if there's traction, momentum, interest, and then finding a good manufacturing partner who is open to working with you. But I think these factories, as I've spoken many times, they will be more inclined to work with you if you know how to work with them. But if you go to them not knowing how factories work, what they're looking for, what terms are, all of that stuff, you will be treated a much different way. You will be charged a much different way. Your samples will cost you significantly different because they know they're dealing with someone green and new. So I would, I think this is such an educational episode that we're having together because it really speaks to without all that buying experience, there's absolutely no way you would have known how to design into something that has the opportunity to sell and more importantly, to sell at mass, especially with all the tariff issues and all that nonsense, that there's always a workaround. You just have to figure out the right way to do it.

SPEAKER_02 29:13

Absolutely. I think uh most manufacturers don't understand brands, and most brands don't understand manufacturing. You know, I I think I sit in the middle, I'm basically the bridge between the idea and the execution. And you know, it's a big part of what I learned in the process. I think that you know, most people, most people think that, you know, uh, hey, I have a great idea, I'll make a sample and and I'll start selling it. Where, you know, in reality, it's wrong material, wrong color, wrong pricing, wrong factory, delays, quality issues, frustration, and then it's not selling. There's so much going into it that when when you start, you need you need somebody experienced, somebody that knows what they're doing, and you have to do your research. It's not as simple as it used to be. I think the the market is saturated, everybody's done almost everything. You have to be really good or really special to make it out there today, in in today's environment.

SPEAKER_01 30:19

Yes. How can people find more about Daisy Rose? Find you, follow you, and get their hands on your products before an influencer does and it sells out.

SPEAKER_02 30:33

Well, um uh our our items are sold on daisy rose.com, on Amazon, and on Walmart under Daisy Rose Bags. Uh Instagram is Daisy Rose Bag. And we also have for our manufacturing capabilities, we have DaisyRoseFactory.com, which showcased our factory and our capabilities, manufacturing capabilities in China.

SPEAKER_01 30:58

That's amazing. This is so helpful. I know people that are obsessed with bags and people who want to make bags will really enjoy this episode. Thank you so, so much for joining us, Jai.

SPEAKER_02 31:11

Thank you, Emily. I really appreciate it.

SPEAKER_01 31:13

Thanks for listening. Don't forget to rate and review and follow us on every single platform at GameBag Designer. Thanks so much. See you next time.