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Ruby. Max Siegelman was in Miami, Florida with his fiance when he got a text out of the blue. It was a hairstylist he knew.
B
She's like, you won't believe it. And I'm like, what? And she's like, you didn't see the pictures of Kendall? And I'm like, in Paris. And she's like, yeah, she wore your hat.
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Max is the owner of Siegelman Stable, a luxury apparel brand in New York. And the Kendall in question was. Yes, Kendall Jenner at Paris Fashion Week.
B
She was on her way to the off white show, so there was a lot of camera on her, but her hair color. And she ended up wearing a hat that I never wanted to produce. It was a black and tan, two tone, five panel hat with black embroidery.
A
And why was it such a big deal that Kendall was wearing a hat? She just dyed her hair red for the Prada show that she was walking in later that week. This was huge news, apparently, and so kept under wraps that Kendall took special care to conceal her hair for as long as possible. Suddenly, everyone had to what was that hat?
B
It just kept saying Kendall Jenner in a hat or whatever.
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The opportunity of a lifetime that would launch his business into the stratosphere just came knocking. Max had to get the word out and fast, before his 15 minutes of fame were up. Welcome to the Unshakables from Chase for Business and Ruby Studio from iHeartMedia. I'm Ben Walter, CEO of Chase for Business. There's nothing small about the impact small businesses have on our country. Every day, I hear from owners who are not only fueling our economy, but also shaping the character of our community. Yet, too often, you tell us about the hurdles you face. Regulatory red tape, access to capital, and the constant challenge of finding resources to grow. These aren't just headlines. They're your stories, and they matter deeply to us. We don't use the unshakeables typically to talk about us. This podcast is about you. But it's important that we also bring to you important resources that may help. And in this case, I'd like to talk about JPMorgan Chase's recent American Dream initiative, which is designed to help put the American dream back within reach for small business owners everywhere. Through expanded capital and coaching, advocating for smart policies that matter to small businesses, and continuing to innovate around services that help small businesses run and grow. We plan to support 10 million small businesses over the next several years. To learn more about the American Dream initiative, go to jpmorganchase.com Communities America. Kathleen, welcome back. It's good to have you again.
C
So good to be here. I think our team really took this Year of the Horse in the Zodiac calendar assignment seriously. We have a literal horse brand here today.
A
You worked hard on that one, didn't you?
C
Listen, honest to God, I've been all about this year. Last year was Year of the Snake. It was awful. Shedding, shedding, shedding. And we're ready to, like, gallop. This is once every 12 years. I'm very excited and I know that's woo woo and you hate it, but here we are.
A
But I genuinely hope you're right. I am in. Let me tell you, on today's episode, Siegelman Stable from New York City. To start, Kathleen is right. This episode is about horses. It's also about hats. But first, it's about the Siegelmans. Max's dad started his own stable, Siegelman stable, in the 1980s to train harness racing horses. This was cool to Max's classmates on career day, but just daily life to him.
B
When I was growing up, I didn't look at him as an entrepreneur. I looked at him as like, oh, he trains racehorses for a living. Which is very different than most parents in the town I grew up in.
A
The normalization of a unique job may have been what pushed Max into starting his own company, even though he considers himself risk averse.
B
I think anytime you're starting something new and you start working with someone and you're like, oh, I can also do this and create something for myself. I think that's when the light bulb goes off and you're like, let me just try and do it on my own.
A
He started his first company right after college. It was called Raoz Social, which was a social media platform that aggregated celebrities social media pages. It let fans follow along in one
B
spot, was able to get LL Cool J as a partner and a founder on it.
A
Rao's social didn't last, but the work got him connected to all the right people. From there, he used those connections to
B
start a creative agency running marketing ads for athletes and music artists. Anything from an Instagram collab post with a brand and negotiating what that creative ordeal looked like to an album release concept for a music artist.
A
He got so good at that, out of the box thinking that the Billboard company out front wanted Max to help take them into the digital age.
B
I started their social department, was head of social, like, kind of moved into what is the best made up title of all time as head of cultural relevance. And that was my title.
A
When I left, that's a very millennial slash Gen Z title, I gotta say.
B
Yeah. And I give a lot of credit to the cmo, who is not millennial or Gen Z, who actually came up with that title. It was pretty amazing.
A
And if you're thinking, what on earth is the head of cultural relevance? I had the same question.
B
It was a combination of really having this, I guess call it creative agency on the side of this social media job and continuing to bring OutFront into the fold of cool projects with people who typically wouldn't be like, ooh, let me call out front media and buy a billboard or a Subway ad. And this moment in culture that combined what was thought to be a old school dying industry and bring some pop culture and coolness to it.
A
So you were connecting dots across the landscape.
B
Yeah.
A
Which is exactly what Max does best.
B
I always had this knack of finding the right thing or connecting the right people or projects to create a moment in culture or some noise around certain things with certain people or brands.
A
He connected dots for out front for seven years. That tenure overlapped with the pandemic, where he suddenly found himself with a lot of downtime. And he started making clothes for fun.
B
Making hats and sweatshirts with my dad's racing stable logo on it that my mom made for him in the 80s.
A
The hand drawn logo was put onto hats and jackets for staff at the horse stable to wear. A few extra items made their way home. And after all these years, Max still loved the logo.
B
The logo my mom drew for my dad, it's very imperfect. It's like up and then straight down, and there's a lot of weird things within the horse and the cart and the number and all that stuff.
A
He knew he wanted to use that same logo on the new clothing, but he didn't have the original drawing, just some old hats with it on it. The logo would also have to be digitized if he wanted to use it today.
B
And it was so detailed embroidery that I was like, I'm so. I'll never be able to remake that file. I don't have that skill to make any file.
A
But he did have a graphic designer at out front who had the skill to make that file. The designer tried to correct the initial mistakes in the drawing.
B
I was very annoying. I wanted to keep it imperfect on the hat. To me, that was the cool part about it, like simplifying it and just making it a simple flat embroidery wasn't cool enough for me to want to do anything with.
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Once he got the logo, he spent $300 on hats and sweatshirts. He gave them out to his family and friends. He also sent a few out to people he'd worked with in the past.
B
Music artists, athletes, et cetera.
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They actually wore the hats and posted about them online. Max would repost photos of people wearing the gear on Instagram, and then more artists and athletes would reach out like,
B
yo, I need one.
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He spent another $300 on more hats and sent them out. They found the right audience.
B
Gunna and Future, two hip hop artists, had worn it. Gunna posted it on Instagram. Future ended up wearing the hat in a music video. And that was the moment. I was like, damn, maybe there's really something here. People either identify with the logo or just think it's cool or it's aspirational or whatever their feeling is towards that logo. It's making some type of connection and they want it. I didn't go out and be like, oh, I want to start a fashion brand. That was never the intention. The intention was, I'm going to use these logos that I have for my dad's racing stable and make some hats and sweatshirts because it's cool.
A
Just to get on the same page about these hats. They're baseball caps, and the logo embroidered on it is of a driver in a cart being pulled by horses. Think chariot racing, but a bit sportier. I was wondering why Max decided to do hats originally. Why not just sweatshirts or tote bags or anything else easy to order?
B
It's a good question that probably not enough people ask. I was working at Out Front, which is mostly known as a billboard company. And so at the time, I was like, there's no better billboard than the front of a hat that you can brand because it's just people walking around and people looking at it all the time. The other reason was I always enjoyed wearing hats. And so I'm like, if I'm going to make something with my family name and brand name on it, I'd prefer it be a hat so I could wear it all the time.
A
And the logo, of course, was already in the family, but the Horse and country living aesthetic was really speaking to
B
people in 2020, throughout the pandemic, when people were leaving cities and going to more of a country lifestyle and people like loving the outdoors more and the westernness and horses and all that stuff. And so I think all of those things played a role in us creating this at the right time, with the right aesthetic and storytelling.
A
Max made a website and started making hats regularly, but still in smallish quantities. The first six Months of Siegelman stable went like this. Max would make a few hats, announce a drop on Friday afternoon. They'd sell out immediately. If you're familiar with streetwear brands, especially sneaker drops, you'll know the playbook.
B
I knew Eric Emmanuel in Supreme and New York Sunshine and Off White. I got to work around Virgil for the last couple years of his life.
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That's Virgil Abloh, fashion icon and luxury streetwear visionary who founded Off White and later was the artistic director of menswear at Louis Vuitton. He passed away in 2021.
B
And so that's the world I knew. I knew how to create something cool that was appealing to people, whether it was relatable or aspirational, where you make a limited amount and you promote that. You have a limited amount, and if you know, you know. And then it sells out in 30 seconds. That's how we originally built it. In the first iteration, I was only making like 72 hats and like 72 sweatshirts at first, but I was making it feel a lot bigger. And people were like, pissed off. They couldn't get it. But then all of a sudden, the hats would start to go on resale websites and they would sell for 2x to 30x the price.
A
The hats were 46 bucks, which is expensive for a hat, but cheap for a luxury streetwear brand.
B
The price point is always a very interesting conversation. The big challenge is bring those people over to be your $46 hat customer, to a $76 hat customer, to a $468 jacket customer.
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Which is exactly where Max wanted to be. If he wanted to reach the $468 jacket customer, he had to grow the awareness and reputation of Siegelman Stable. He decided a low and slow approach was best.
B
I actually remember the point where I'm on a road trip for my full time corporate job in, like, Tampa, Florida, and I'm on the phone with a friend and I'm like, we're either going to build a brand that lasts for a super long time, or at least try to and it's going to be really, really hard, or we're going to try and sell this $46 hat a million times over, and I'll figure it out and move on to the next thing in 18 months when everyone's sick of us. That would have been the easy route, though. That sounds crazy to say that that would have been the easy route. So we chose the hard route, which was to grow a brand to evolve over time from that $46 hat into what we are now
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to grow into the brand Max wanted to be. He knew he needed more eyes on the hats. He also needed the cultural approval from tastemakers. He shipped out more product.
B
I had a friend who would go unnamed who was in the NBA, and I was like, I'll try and get you a couple pieces before you go to the NBA bubble.
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Max wasn't able to ship the product out in time, AKA he really wanted the mailing address to the bubble.
B
So once I got the address, I was like, oh, if you change the player name and the team name, it must be the same for everyone, all the players. And so it ended up being that that was the case.
A
Wow. You just took a shot and sent him off to the NBA bubble.
B
That was it. I risked half of my $300 investment to send to 10, 15 guys. And I was lucky enough it worked. And that's where it started to get some awareness on League Fit's Instagram or a Bleacher report or a hypebeast and a complex. And that was kind of like the first part where I was like, all right, there's really, really something here. When you own your own business, you own every decision. Catch the red eye or take the 6am, make a new hire or promote internally.
A
Celebrate a win with the toast at the gate or unwind at the lounge.
B
Big props to this team.
A
Some decisions are a win win, like earning eight times points on Chase Travel. Chase Sapphire reserved for business. The business card that gives back all you put in. Visit chase.com ReserveBusiness to learn more. Cards issued by JPMorgan Chase Bank. Any member FDIC subject to credit approval terms apply. Okay, Kathleen. It's the year of the horse, so so far so good, especially for Max. Even at the beginning of this company, he had a clear vision for the brand. And I really want your view on this idea of scale versus scarcity, because I think that's fascinating in the context of consumer brands. I know their goal is just to sell as much as they can, as fast as they can. It's all about volume. And he took a very different approach
C
on so many different levels, right? Like how he thought about revenue, how he thought about financing, marketing, inventory management, networking. I'm very unfamiliar with founder stories where they're saying, you know, we're going to withhold inventory so that we can create scarcity and demand, and it's usually not something that you're honestly able to do. I've seen it used as a marketing ploy, right.
A
When you're already scaling and you do it with one special limited edition run or something.
C
Yeah, sold out. But this felt really unusual to be doing it so soon. And it was neat to hear that there's a market for reselling this sort of thing.
A
If I think about luxury fashion as a particular ecosystem. Right. It's very celebrity driven. Even the large quantity numbers aren't what you would think of as anywhere close to large quantity for mass brands. How you define scale in the luxury space is just fundamentally different than how you define scale elsewhere. Some of those numbers sound really small. But overall luxury is high price point, low volume. So in relative terms, I think that's true. I don't know a lot of examples of brands that started that way.
C
Yeah, I think that's the distinction. It's usually further down the line. And he kind of did it out of the gate.
A
I think he understood something from his agency days that ran very deep, which is here's how you create buzz and excitement and story around something. Yes, it helped that he had a giant Rolodex of NBA players, but it's clear to me that he understood the power of creating that sort of buzz in energy and scarcity all at the same time.
C
Speaking of Rolodex. So it's not the average story to hear. You're getting DMs from future to wear your gear. For those that don't have access to a celebrity network. Because I hear this a lot, how do I get at someone? Right. One of the most effective ways to do it is to look at who someone is surrounded by. So who is their crew? Like it's the stylist, it's the glam team, it's the personal trainer, this trusted circle. And then trying to find a way through social media, through DMs to directly access these sorts of folks can be a really nice way to kind of have arbitrage into a celebrity if you're looking to gain access. So it's takes time, it takes research. You've got to stalk who they're tagging and following. But I think that's something that the everyday listener who's listening to the story and saying, well, I don't have that sort of network can think about trying to perhaps build their network knowing that celebrity and influencer is really powerful in scaling your business in this day and age.
A
Yeah, I have nothing to add to that other than cool. Back to max. Take us to the next chapter. Because you now say, okay, there's more than nothing. Yeah, right. I was doing some charitable stuff and I was making some hats for Some friends. And now I found a sea of opportunity here. Like, what's going on?
B
I don't think I knew what I was doing at the time. I did not have a credit card. Didn't have a credit card for probably the first two years. I was paying straight up cash or
A
debit card even personally. That was it.
B
Yeah.
A
Wow.
B
I paid cash for hats. And I'm talking about like thousands and thousands and thousands of hats. And it wasn't even just hats. It was other stuff. But, like, from a quantity perspective, hats was it. And so I'm like, I'm so dumb for that. Like, where are all your points?
A
So you would just take the money and plow it back in and buy more inventory?
B
Yeah, I mean, I never took any money out of the business.
A
As Max learned E commerce, he was also learning how the fashion industry worked.
B
If you're not in the fashion business and you don't understand the different layers of creating, I had no clue. I would send blank T shirts early on, before we were doing cut and sewing blank T shirts or sweatshirts to embroidery and print shop in Brooklyn. And they'd email me and be like, how big do you want the logo? Where do you want the logo? And my response would just be like, put it where everyone puts it. That was literally my response. Just put it where everyone puts it. And then the next thing you know, Justin Bieber is wearing a T shirt with a logo where everyone puts it. And so, like, I don't know. And then you start to learn and figure it out.
A
Justin Bieber wore that Siegelman stable shirt in 2022, by the way. And as soon as he was photographed in it, people started ordering. In the process of trying to fulfill the orders for that shirt, Max learned another valuable lesson for large corporations producing in big quantities. This happens at a fulfillment center or third party logistics partner, also called A3PL. Max was told he needed a fulfillment center to start fielding orders.
B
It was way too early for us. We weren't set up for it internally infrastructure wise in terms of barcoding and on Shopify on the back end. And like, this is just stuff you don't know. Know if you've never done it before. And the first two or three releases in the three PL were disaster. We had Justin Bieber wear a white T shirt with a red print on it and everyone who ordered got a size small. But the best moment ever was we felt like we had control back when that 3 PL dropped 3 pallets of boxes full of clothes and shipping materials and all that in front of our office in Brooklyn and just left it there, and I carried it up eight flights of stairs by myself.
A
Now, while Justin Bieber did inspire a good chunk of shirt sales, that endorsement alone didn't suddenly put Siegelman Stable on the map.
B
I think the general public thinks that just because you're on person X, you'll all of a sudden sell a hundred thousand units of something. We don't have enough time to even talk about how it's so far from the truth. There's like 10 people in this world who can change your business forever.
A
Max did manage to get one of his hats on just one of those 10 people.
B
Kendall Jenner.
A
It was Paris Fashion Week 2022. Kendall was walking to attend one of the fashion shows, but she dyed her hair red for her appearance in Prada's upcoming show.
B
So there was like a lot of camera on her, but her hair color.
A
And on top of Kendall's head on that fresh new red hair was a Siegelman stable hat.
B
It was a black and tan two tone, five panel hat with black embroidery that I never intended to make and sell because I didn't like it after I saw five samples of it.
A
Max didn't like the samples, so he didn't order any more. He just sent the samples to friends and forgot about it.
B
I'm in Miami in a coffee shop at like 8am and I get a text from her hairstylist, and she's like, you won't believe it. And I'm like, what? And she's like, you didn't see the pictures of Kendall? And I'm like, in Paris? And she's like, yeah, she wore your hat. I'm like, googling. Refresh, refresh, refresh. We need to get back to the hotel room. We need to figure out how to get a picture of this hat or a mock up, and we need to get it online.
A
This was the frenzy Max needed. The brand was now forever endorsed by one of the biggest celebrities in the world. And even better, the hat was rare. There were only six of them. People went crazy trying to get their hands on one.
B
I had to, like, call the manufacturer and find out how many they had available. How quickly get them. Call the factory. How quick can we embroider them? And I didn't even have a picture of it. I didn't have a product page for it. Nothing. I don't even know how many of these hats I can get, how fast I can get them. I'm calling the hat manufacturer. Sure. I'm, like, trying to figure that all out, like all happened within like 20 minutes.
A
And during that time, the photos of Kendall Jenner were spreading fast. Then Max ran into another issue. He was the only person who knew she was in a Siegelman stable hat.
B
It just kept saying Kendall Jenner in a hat or whatever. I was like, all right, I need to email Vogue and say it's the Siegelman stable hat and link it out. Or email GQ as a Siegelman stable hat and link it out. That's how I spent my entire day. That day. It was a moment in this business that I will never forget. I mean, I know where I was sitting, I know how many hats, I know what revenue looked like that day. And it was just like a pretty crazy thing. In the history of our short lifespan as a brand,
A
Where are you trying to take it as big as we
B
can, but without sprinting and making a lot of mistakes along the way?
A
How do you think about as big as we can when the way you've described the whole brand to me, it's based on exclusivity and rarity. Those two things sort of feel like they're a little bit in at least tension, if not conflict.
B
There was a point throughout the last two years that we made that decision where there is certain product that is always on. Because if you're only making all your revenue on Friday between 1 and 1:30, it's not great to grow a business. And so we have a bunch of different revenue models for ourselves. So it's our dtc, which is sometimes always on product. We also have our exclusive capsules that are those limited runs that there's a lot of hype built up around it. We have our collaborations that we do with the New York Knicks, New York Rangers, the Mets, the Yankees, all of those pro sports. And we'll continue to build even outside of New York.
A
Have you gone global yet?
B
Yeah, we sell global. We did a pop up in Oslo, Norway early on. We did a project with Kygo DJ as part of Palm Tree Crew and he was headlining a show there. And we are in talks of doing a pop up in London maybe this fall. And so, yeah, as we continue to scale and be able to infiltrate new markets with new projects and new partners, we'll continue to look global.
A
Do you travel a lot?
B
We do travel a lot. I traveled a ton in my past job. I travel a ton now. I think a part of being a brand that sits at the center of culture, you have to show up at these big tentpole moments.
A
Are you building a business or a Legacy or both?
B
Both.
A
So I think I figured out the business you're building. Tell me about the legacy you're trying to build.
B
The business and the legacy definitely overlap. In the beginning, it wasn't necessarily about, I want to build a legacy and keep my family name continuing to evolve and building something cool. Once we decided to sell stuff and start making money, I said that we would always stick true to my dad's story. So by telling his story with harness racing, through our clothes and through our content and storytelling, but also the equine therapy pit. So we still donate to this day a portion of proceeds to equine therapy programs.
A
Okay. What does your father think of it?
B
He thinks it's all crazy. Continues to, I think, like, he was one of the first doubters, like, who's gonna wear a Siegelman stable hat?
A
Fair question.
B
I mean, yeah, for sure. He now calls himself the CEO, the Chief Equine Officer. But to his credit, anytime we need a horse for a photo shoot, he's the guy, and he typically will pull it off.
C
So, Ben, now I've heard two titles I want someday. Head of Cultural relevance and Chief Equine Officer.
A
Yeah, Some unique titles in this one.
C
One thing that I think is worth touching on is how Max is traveling both internationally and domestically to promote his business. So from the beginning, he's coming out of the gate focused on international. He's got Kendall Jenner wearing his product in Paris. He's traveling overseas for these pop ups, and then domestically, he's rooted in New York, as we know, but then he's flying down to Miami. He's on the scene in different places. This helps him not only as a founder, inspire his creativity, but it's relationship building, it's networking, it's allowing him to get deals done in other Geos. And ultimately, the biggest benefit is that it lets him flex bigger than he is, bigger than his brand is, which is something that, with a simple plane ticket, other founders can do too.
A
Look, travel is something that, broadly speaking, is an inspiration category writ large. Whether it's inspiration for the creative side of your business, if your business has a creative side, if it's inspiration for what products you could launch next or where you could launch them, or if it's inspiration for the kind of people and ecosystems that you want to sort of mesh with your brand. Travel is just an inspiration category. Always has been, always will be. There's a sex appeal to it.
C
Yeah. And I think it's also, you know, beyond the inspiration, all that. It's a founder flex like we're seeing founders that are moving from city to city and on the circuit and showing up at industry events and speaking and posting about it. And that becomes also a way to signal like, my brand is doing well. I'm doing well.
A
Yeah.
C
Here I am in the south of France in August and here I am in Austin, Texas for South by Southwest. Like those are things that I think have also become very much part of the brand building game.
A
I think that's right.
C
It's a game of perception.
A
I would say partially, Kathleen. It is partially a game of perception, but it's also in the digital world we live in the power of these in person events when they happen. I think it's made it so that there are fewer but more important and more climactic in person events throughout the year. So, you know, south by Southwest, I'm from Texas. It used to be sort of a small thing and now it's gotten huge or whatever the event, Lions, can Lions. It doesn't matter what it is. Like they were always there, but the cultural focus on them has amped up. And I think people's desire to be a part of in person events, particularly post pandemic and post social media generation, is quite high.
C
That's right. And if you leave face to face having made one new connection, you know, higher order connection within your network, one new deal, I mean, it's worth its weight in gold. And a lot of times you can get in rooms with people you wouldn't normally be able to get in a room with.
A
The other thing I loved about the story, Kathleen, you know, we have to talk about the credit card. I mean, I do work for Chase starting a business in cash. Only cash. That's amazing to me. I have to be honest. I love when I hear about a business that basically just bootstrapped it all the way up with their own cash. You know, you hear a lot of stories about, well, I emptied my savings account and got it going. He got this thing going for 300 bucks and then he probably sold that stuff for 600 bucks and then plowed back in 600 bucks. And then maybe he sold that for 1500 and he plowed back in 50. I'm making up the numbers. But, you know, and he was fine with that. He was fine with that. And it took him longer for sure than it would have taken otherwise. He could have scaled that business much faster if he had a bunch of NBA players wearing his stuff in the bubble and he'd gone out and he'd either borrowed money or taken an investor or whatever, he could have scaled that much quicker. It wouldn't have had the staying power, most likely, and it certainly wouldn't have had the exclusivity. But he could have. I kind of like that he bootstrapped it. And what I would have said is he probably should have had credit, at least if it was personal credit ready in case he needed it. That's something that I think he would probably even admit could be done differently now that he knows what he knows credit is.
C
Or a line of credit, which I didn't know about until I started my own business, is their primary financing tool to scale their business. Can you talk a little bit about that? Like for someone who doesn't want to use their own money and wants to kind of rely on credit to get going. And it can be such a helpful tool.
A
I always tell people in the very early days of a business, when you are a startup, you should think about if you want to use credit. That's great. It is your credit. So you can get a personal card or a business card, but it's going to be backed by your personal credit. So when someone says, I want to get started, but I don't want to take any personal risk, I just look at them and say, no such thing.
C
This is really good. Yeah. Even if you're using your business credit card, it's gonna impact you personally a hundred percent. No one ever told me that. But that's. Wow.
A
Nobody's gonna give you a startup business card that is only backed by your business that doesn't exist. Because that's called equity.
B
Right.
A
The whole point is it has to be backed by something. So some people say, I'm gonna take a home equity loan. Fine, but you are guaranteeing it with your house. Some people say, I wanna do it on a credit card, whether it's personal or business. While you're betting your personal credit against that. As you grow as a business and when you get to a certain size and profitability, you can start to take out either a line of credit or credit cards that are based on where it is we are lending to the entity as opposed to you as an individual. But that doesn't happen till a lot bigger than people think. I mean, that's not really for sort of a two, $3 million business. That's for a 15, 20, $30 million top line business. Before you're starting to think about that kind of underwriting. Because when you're smaller than that, you are betting on yourself. Now if you don't want to bet on yourself. You shouldn't start a business because that's what starting a business is. So I'm not taking that lightly. I'm taking that quite seriously. But I tell people all the time, if you believe in your idea enough, you have to believe it enough to bet on it with your own personal assets, whether that comes in the form of savings, credit, score, home equity. Pick what you want to put on the line. You're putting something on the line.
C
I think that's really helpful for people. And there are other options out there, which is good.
A
Yeah. Over time, you can start to finance with your revenue streams. You can finance with other assets. There are things you can do as you grow. But to really get started, I mean, I can't tell you how many people come up to me and say, how do I get a loan to start my business? And I say, well, do you mean how do you get an investor? No, no, no. I just want a loan. Well, right, but you want a loan with no consequences, right? No, that doesn't exist because a loan with no consequences is called equity.
C
You heard it here, folks.
B
There you go.
A
Kathleen, so good to see you again. I'm glad we got to do this one together.
C
Always a delight and a pleasure. Look forward to seeing you next time.
A
So, last question I want to ask you, and we ask this of all of our guests. If you had to give one piece of advice, what would it be?
B
Question everything, which is a Virgil Abloh quote. Question everything. Because I've learned over time that just because someone has more money or more years of experience or thinks they may know because they're older, you should question it. Have they done it before? Did it work out? And they may be right? And it's not to like, pooh, pooh their input or what they have to say about something. It just makes you really think about what they're saying and digest it and fully understand it before you maybe step foot and do what they say. And so question everything and also just go and do it.
A
Thanks so much for listening to this episode of the Unshakeables. If you liked this episode, please rate and review it. And next time we're talking about an entrepreneur who I'm not sure sleeps, to be honest. He's a hustler in the best sense of the word. He's opened seven businesses over the last decade and he's just getting started.
B
As an entrepreneur, you learn that there's always something better, but you can't just jump to it. You can't just jump to a $10 million development without building up your cash. The bank won't just give it to you.
A
No, we won't. I'm Ben Walter and this is the Unshakables from Chase for Business and Ruby Studio from iHeartMedia. We'll see you back here soon.
May 19, 2026 | iHeartPodcasts
Host: Ben Walter, CEO of Chase for Business
Co-host: Kathleen Griffith
Guest: Max Siegelman, Founder of Siegelman Stable
This episode of The Unshakeables spotlights Max Siegelman, founder of the luxury apparel brand Siegelman Stable. It traces his journey from a pandemic side project rooted in family heritage to the breakthrough moment when Kendall Jenner wore one of his hats at Paris Fashion Week—an event that catapulted the brand into the global conversation. The discussion delves into scarcity-driven branding, the role of celebrity influence, lessons in business infrastructure, and blending legacy with commerce.
Family Roots:
Max’s father started Siegelman Stable for harness racing in the 1980s.
The original hand-drawn logo, made by Max's mother, became the iconic insignia for the brand's hats and sweatshirts.
Starting Out:
Max began his entrepreneurial path with Raoz Social, followed by founding a creative agency, and eventually worked as "Head of Cultural Relevance" at Out Front, a billboard company.