#009: Max Siegelman - Facing Your Fears, Engineered Virality, and Building Confidence

When you think about the word successful, who do you think about?

People that are happy. Could be anyone. I'm sure there's a lot of wealthy people that are happy, but the majority of wealthy people I think are pretty unhappy. I think it's what your journey is along the way to get to what you consider success that will either make you happy and successful when you reach that quote unquote success.

You always hear people talk about like, I wanted, you know, this exit or I wanted this amount of money and then you get it and it's like, now what?

I thought that was going to wherever that is. I don't think the end goal is success. I think to get to that point is succeeding. So I guess succeeding is a better word than success.

Max Siegelman is the co-founder and CEO of Siegelman Stable, a racing and luxury sports fashion brand based in New York. Previously, he served as head of cultural relevance at Outfront Media. In this episode, we cover how Max and his partner built Siegelman Stable from scratch with a focus on organic virality and high-quality goods. How to build confidence through repetition, and why more people need to focus and face down their fears. Welcome back to episode 9 of the Turning Pro Podcast. We have Max Siegelman from Siegelman Stable joining us today. Thanks for joining, Max.

Thanks, Benjamin.

So Maxwell has become a good friend of mine over the last couple months. Um, I would like to say he's a man of few words. He's like everywhere but nowhere at the same time. Like, you just, you see him, you see him in all the scene, but yet he's like, he doesn't want to be in the scene. And I just He's someone who I've continued to try and figure out over the last couple of months because he's, he's kind of cryptic in a lot of ways. And I think a lot of people have the same intrigue. The place, the place I want to start this, I want to know, like, what, what drives you? The good and the bad, the dark and the ugly. I want to know, like, what, what drives you to do the things you're doing right now?

That's a tough question. You got to start with a tough one, huh?

That's a heavy question up front.

Yeah.

I've been so curious for so long.

What drives me? I guess the people around me, for one, is what drives me, whether it's like family, friends, Caroline, and then wanting to do things that are meaningful versus just do things to do things. And I think that now in just like things being so accessible to everyone, people could just do things to do things because they can. And I think that that hopefully is a difference maker in the things that I'm doing versus what other people are doing.

So being able to do the things that other people can't do.

I don't think I said that. I think you put—

no, no, no, I'm at— it's like figure— it's like figuring out how to do the things that other people kind of dream about on your own, but in your own way.

And I think some people have the access to do it because they may have an existing audience or followers or whatever already. So being able to do it like strategically and fun and using like marketing experience or networking connections to do it in a different way and like a unique way. I think is partially what drives me also. And like, to prove someone wrong always is a good driver.

Who are you? Do you have like some chip on your shoulder that's driving what you're doing, at least right now?

Uh, I don't think so. I think it's a combination of like, uh, I fell into it a bit, and maybe in the beginning people questioned it, like, who's gonna wear a Siegelman Stable hat or something like that? And I think that is like a small driver, but I think those are things that people always get when they first start stuff. Um, but I don't think it's like a chip on my shoulder, like no one believed in me ever, um, or I didn't believe in myself that I could do something. But now it's like cool to try and prove that you can do something the way you want to do it versus surrounding voices, because there's definitely more and more surrounding voices as you continue to grow in a successful path.

Yeah, the first, uh, your first response to that question, I feel like a lot of people would have answered what drives you as like, my customers, my investors, the pull from the market, um, like, you know, the team. And you were immediate, just family, friends, Caroline.

Yeah, man, well, those are three of the most important things in my life. Uh, I was just speaking in general. I wasn't really speaking for just Siegelman Stable. I think those things that you listed are important if we're speaking specifically to Siegelman Stable, but I think the three things that I said are probably a part of that before those people anyway. So yeah, yeah.

But Max is also someone who, like, I think the reason we got along when we first met too is because he's someone who tries to like push himself to limits in ways that like most people don't understand. And when we met each other and we're like, wait, you're also like— I'm pretty sure like one of our first conversations was at Soho House having dinner, and I was like, oh, have you ever heard of this gym Tone House? And he's like, yeah, you go? I was like, yeah. He's like, you want to go tomorrow, 6 AM? I was like, yeah, let's do it. And we haven't missed like I mean, when we're traveling, yeah, but we've been going like every Wednesday and Friday.

I pick up Ben at 5:30 in the morning or 5:00, 5:40 in the morning and look at each other at 6:15 and we're like, what the fuck are we doing here? And it's the same thing. We just keep doing it. I've never been with the hardest workout of all time. It's like the hardest workout class, not even just in New York City. I think anywhere you go and it just like pushes you to the limit. I think both because we have both athletic backgrounds and Ben played hockey and I played soccer, and I think that's probably part of it. But I also thought for sure he was gonna vomit, and I couldn't wait to see it the first time. But he was better than I thought.

Do you play soccer in college? Yeah, I played club soccer.

Nice. Oniata State School, upstate.

Very cool. Yeah, D1, D2, uh, D3.

I went from 1 to 3 my freshman year.

What position?

Goalie.

No way.

Psychopath. Short goalie.

Well, when you start to peel back the layers of the onion, you're like, okay, I mean Things start to make sense. Yeah, who signs up for goalie? But hold on, so like, I don't want to lose this thought though because I didn't sign up for goalie. But yeah, anyway, or continued to play goalie. Uh, but Tone House, as he said, is like one of the hardest gyms I've ever been to. And it's like every single time we go, it's miserable, yet like every time we want to go again. I think that mindset is something that carries with all of us across anything we do. It's like if you're going to do something like push the limits to actually see yourself grow But the thing that I love about Max is that he does it in like such a quiet and like calm way. I think there's so— one of the things I think from watching him intimately build Seaman Stable, because there's a— he has a huge following of people are watching it from the outside. But when I see it from the inside, he's just like very quiet about it. Like he goes about it in a way where he knows how to navigate certain landmines and like keep relationships warm all the time. But he's not like in your face yelling about it. And I just think it's like a phenomenon. Like the first time I saw a hat out of New York, I was like, okay, that's a coincidence. Now it's like every airport I go to, every— people are like, oh, you were— you know, I always now ask, do you know Max? And they're like, no. And I'm like, okay, that's when I know it's actually like a—

but it's still like, it's still like, uh, I hate to say like, if you know, you know thing, but like people always say that, but it's become like a, like a networking thing almost where it makes you like approachable if you're wearing the hat or wearing a piece that says Seagull and Stable on it because people will start like, oh, do you know Max? Or if it's two people who don't know me who are wearing it, it's like kind of even cooler. But I've, I've gotten off a plane before with Caroline and the first person we saw was wearing a Seagull and Stable hat and he was like, yo, nice hat, bro.

And I He said that to you?

Yeah, I was like, yeah, dude, nice. This is kind of awkward. I didn't know what to do. I started sweating, but like, we got through it.

Uh, it's cool. But I think I do want to talk a little bit about like the story of it. Um, but before we get into the actual Siegelman Stable story, I think a huge piece of it is the relationships that you've been cultivating for the last decade. I would love to dig a little deeper into how you think about relationships because it's something that you do better than probably 99% of people in my life.

Uh, yeah, I mean, for me it's always been about— it's not like the corny lines, like, it's who you know, uh, versus what you know, but it like kind of is. Um, and to me, like, all the people I've met in the last 8 to 10 years after school, um, has been— the majority of people I'm still close with are people that I've done stuff with either for free to have that relationship or gain a relationship and not necessarily always about work when you first meet them or for the first 3 years that you meet them, but at some point down the line can turn into something that could be both mutually beneficial. So even if someone came to me and was like, hey, can I get introduced to this person? It's not like I would ever ask for like an intro fee or like, how can I get involved? I was just like, do it, knowing that hopefully somewhere down the line I had something to offer or get involved because I could offer something that would help. Uh, I think also 99% of my relationships were built through fitness for probably the better half, probably, probably up until I started Seagull and Stable. Now it's like coming from a lot of different places, but before that, 99% of them were all through fitness. Even like my first co-founder on a company that I started my senior year of school was LL Cool J, and that was through his boxing trainer that I happen to see in the gym at like 5 AM when I would go before I started working. So it's like kind of interesting that I guess we have that relationship. I guess I'll have to know you forever now, but that's kind of how it started.

I also think there's something about, uh, a lot of high performers being involved in fitness. I think this notion of like if you're building a company, it's also impossible to exercise, yet like a lot of the most successful people in the world prioritize that fitness piece. And so I think it's really freaking cool where you can be in a community of people who also have aspirations and live busy lives, yet like fitness will always take priority. And I think one of the things I learned from like watching you navigate in that realm is that you always make time for the things that are important to you.

Yeah, well, I think it's like when I first moved to this city, I think like fitness was a big piece of just my life personally, because you're going from playing soccer in college and like having that time allotted to always practice, play, whatever. And then you get into like the real world and you're like, I kind of want to keep that same schedule so I like have the right mind to do other things. Uh, and it was like right when like going out to like steak dinners and drinks with coworkers or with potential business deals and stuff like that was like transitioning to like you didn't have to do that to get stuff done or to like network. And like group fitness became like a networking opportunity for for a lot of people. And I think that's kind of where I put a lot of eggs in my basket, and like, that's where I went heavy to get a lot of those relationships. So, um, for me, it's just what worked.

What if— I feel like a lot of kids right out of college, or even 5, 6 years out, um, try to—

I'm deep out. I wish I wasn't as deep out.

I have my 5-year reunion in like a month.

I wish I had my 5-year reunion.

Um, there was a—

we're saying Yeah, but it took me a little longer to get through school because of hockey.

Took Ben some time.

Yeah, I can't wait for my 5-year reunion.

I can't believe you blame it on hockey, but whatever.

Can't believe what?

You blame it on hockey.

No, yeah, I mean, whatever, it's an easy cop-out.

Yeah, it's a fair reason. I forgot what question. Oh, okay. Um, yeah, I feel like a lot of people, myself included, right out you're trying to like force some deal or force some sale or force something to happen. Is that Is that something you just understood intimately? Like, hey, that's not the way to do this. I want to see if I actually vibe with this person and then hopefully down the road something will happen. Or even thinking about down the road.

Yeah, I'm not the in-your-face person, but like, probably goes back to what we were talking about before. I think we started recording and like Ben loving confrontation and me not. I think it's like not too different in business where it's like the way you approach someone. It's like, are you all over them? And like they get annoyed. Like there's a fine line between that. And I was just like, all right, if you don't want to do it, you don't want to do it. I'll figure it out another way. And that was just kind of always been my mentality. So I haven't never been like someone to like be on top of someone to just get an answer, whether it was the one you wanted or not. Um, and that for me has worked, but for other people being on top of someone always works.

So, but he has the discipline about it too, because I've heard there's definitely been like 540 car rides where he's like, this fucking person like hasn't answered me or is like taking me for a ride on this thing or the other, but he can keep his composure. Because you'll never compromise your own character and like the public's perception of you because you want to maintain that because it's clearly working for you.

Yeah, I mean, I think not that you should always care about public perception, but you never want anything to come back to you. Like, I'm sure I've said things that aren't nice behind closed doors about some people, and that's not right either, but try and be a little bit quiet about it.

Yeah, totally. Uh, so the name of the podcast is Turning Pro, and the The essence of that name is around like these moments in your life where you decided to like take things to the next level, or these realizations where you were taking things serious, sacrificing certain things to become a pro. What are some of those moments that happened in your life, both personally and professionally?

Uh, I thought it was because you and I couldn't make it in our pro sports, but so we just decided now we just call ourselves—

now we're here.

Uh, say that question again. That's a tough question too. Damn.

I could have played a pro sport. I just want to make sure you know that. It's the same, for the record, if I was 6 foot. Make sure it's on record. Um, no, the purpose— the, the name of the podcast is around those moments in your life where you essentially became a pro, where you decided to like get up from one table and move to the next with, you know, the people in the next phase of where you're trying to get to. Like, what were the moments in your life where you're like, this is, you know, a realization moment for me where I'm, I'm taking this to the next level?

Yeah, I mean, I think I was lucky to learn early enough, like after school and having like my own startup and then working at a media agency, but also still having like my own like creative agency on the side was like, no one fucking knows anything. And like, if you're confident enough in what you're saying, like someone either believe you or think that that's correct. And I think that that's a big piece of like overcoming worrying about what everyone else is thinking. Not that I don't always or sometimes worry about what other people think when you do stuff, but I think it's a big piece in just like professional world is like no one knows anything. And if you're going to do something the same way someone else does it, then it's fine. Like you could work a 9 to 5 job and do the things that people can sit at a computer all day and do. But if you're trying to do something different and you're trying to build your own thing or anything like that, I think it's super important to understand that like no one knows anything. And if you want to do something the way you want to do something, and you're successful doing it, then that's the right way to do it.

And what was the moment with Seagull and Stable where you're like, okay, this isn't just, you know, my girlfriend and I sitting in my apartment making hats. Like, this is a real business and it's time to, time to man up and, you know, take a big swing at this thing. Was there like one moment that happened where you're like, fuck?

I don't know if there was one moment. There's definitely been a few moments that have, have helped the trajectory of what Siegelman Stable is now. Like, when I first started this, it was just me. It was before I met Caroline. And we wouldn't be where we are now if Caroline didn't get involved. When she did get involved, though, I asked, can you please not get involved because I don't want it to hurt our relationship? That's— we can go there after. But, uh, Ben's smiling. He's like, yeah, I'm ready for that. Uh, so I think like the, the first biggest one for me, I guess, was, uh, having some NBA players wear it like walking into the tunnel. I had gifted like a handful of dresses that I got my hand on, hands on, and, and was lucky enough for one or two of them to wear it and got some like pretty good attention, mostly through like horse racing people, but also just like through my own social media channels and friends. No fashion publication picked it up or anything like that. And then fast forward maybe like 8 months or so, Kendall Jenner wore a hat Paris Fashion Week. She had like just dyed her hair for a Prada show and it was all about her hair and she was wearing the hat. So obviously it was a, was a big step for us. So then there's been a few moments along the way that's, that's increased our trajectory of where we're at now. And then obviously when Caroline got involved 3 weeks after we started dating, when I asked her not to, like, I think just made it more real. Not because there was just more than one person doing stuff, but, uh, it was definitely like the, the way that we were doing stuff changed the, the trajectory of like what we wanted to build versus just like making hats and making t-shirts. And like what we still don't even have fully out yet, but behind the scenes have been working on, uh, has just gone in a much bigger way than I could have imagined if I was just selling hats out of my apartment, as you put it.

How have you, how have you had to change the way you operate? Either do things you didn't do before or stop doing things now versus, as you mentioned, like, I guess, 3 weeks before you met when you were doing it alone?

Uh, yeah, I mean, operationally, I don't know if positive or negatively, not much has changed versus like we're not running it out of our apartment. We have an office. We don't have any other employees full-time. We have some other employees that either help us with fulfillment or operational stuff and manufacturing stuff. So I think it's been a super smart, strategic, slow growth, and that's kind of what we wanted. But there's a ton going on behind the scenes over the last few months and now, and I think a lot will be continuing to follow that trajectory over the next few months or year.

Tell us more about that.

Um, I mean, just looking at, uh, making our own cut and sew pieces versus using blanks, uh, I think is obviously a next huge step for us that we've already started, uh, to like really embed ourselves in fashion more than just, uh, fast fashion or hypebeast type fashion. Uh, I think that's where I wanted— that's what I wanted when I initially started this, right? Like I wanted to follow like a drop model, look at like Supreme or Eric Emanuel and do it that way. And we still follow that drop model, but you, you get to a point where you're going to want to have always-on product. You're going to want to have nicer, more upscale things. And I think for the things that we envision Siegelman Stable to be in the next 2 to 5 years, uh, we're putting a lot of effort and work behind the scenes. And by we, I mean Caroline is on it.

Is there anything that you— there's obviously like some brands you can model off of, as you mentioned, like Supreme. Like, hey, I like this model, or I like the way they do business or their long-term approach. But what are the things that you can say, okay, I like what they're doing, but also this is what we're uniquely doing and we're not going to do that. We're going to do it this way. What are those things?

Yeah, I mean, I think so when I first started, like I said, it's like the Supreme Eric Emanuel model and Supreme model now has changed too. Like you can walk into Supreme and you can get maybe not almost anything, but you can get a lot. Eric still does an amazing model of— I mean, I'm sure he's up his quantities at this point and now he's selling kid shorts and beyond just shorts. and does his drops at Friday at 12 o'clock basically every week with a different colorway or a different product. Uh, and I think for him that that has been super successful and I think it's super smart and he's done an amazing job and I'm sure we'll continue to do that. And that's how I wanted to start it because it felt like the right opportunity to create that scarcity. So we've spent $0 on marketing. So to do what we've done spending $0 on marketing is to build brand equity with scarcity and demand. Uh, if you go on Grailed now, there's probably 50+ pieces for resale from 3x to 30x, and it's nuts. Uh, I still want to play that game a bit, but also understanding we need to grow our business in terms of revenue and customer base, and toying with making customers happy. And if they miss 4 drops in a row, they're Is that a lost customer? How can you make sure that that loyal customer gets an opportunity before a bot? Like, that's a real thing now for us too, is like looking at bots checking out before loyal customers can get hats and colors that they're trying to get. So, um, all of these things are like learnings for us. Neither of us have ever done it before. Uh, I've been aware of it. I have awareness of brands and in fashion and in streetwear and have seen what people have built, what's worked and what's not. Uh, and like you said, we're trying to like pick things that we think make sense for our brand that we can take from other brands and do new and creative stuff ourselves as well.

What do you foresee as the biggest challenges to scale, like, cool?

To scale cool? Yeah, uh, to cross the threshold of not being cool. Uh, and I guess to explain that, it's like if 1,000 people want your hat, you shouldn't sell 1,000 pieces because that's not cool, and you shouldn't sell 5,000 because then you're definitely not cool. Uh, I think it depends the situation. I think it's, uh, like we've been approached by department stores to have stuff up, and I just, I don't want to have clothes hanging. That's not the business model as it is now. Uh, I think in the future, sure, maybe we can get there for certain items. Uh, but I think you get to a certain point and things change too when you have potential investors or investors and money in the bank and how you see revenue now versus how we see it in a year or two. Um, so I think it's a fine line between still being cool, uh, and doing too much.

Do you think it's just a sheer quantity game as you grow, or like, what are like other qualitative things that need to be top of mind for you as you think about like building a global brand that always feels, you know, scarce for people talking about it, but you're actually able to scale it from a numbers perspective, which inherently means you're probably selling more product.

Definitely. Yeah. No, and I, I think, well, I think there'll be a point that we have always on product, and I think that would be just kind of like our single and stable basics. But I think anytime we do a collaboration or a smaller collection, like, those will be more limited, and those will be the things that you might end up seeing on resale. or that will sell out in 20 seconds. Um, so I think having a balance of both of those, having your always-on products and having the more scarce products and limited editions of stuff is an important thing to build towards.

As you navigate some of these decisions, which it seems like are happening faster and faster from the sense I get, um, which of them are you excited about? All of them? Or do some of them like scare the shit out of you? Like, how are you thinking about them?

I'm just stressed 24/7.

That's why he just works out all the time. He's like, I'm just going to go run 10 miles and get it off my mind.

Uh, I think which scares me the most, I don't even know. Um, I think being able to, to have these like cut and sew pieces that we're working on and have our own production, and we do all of our production in New York and New Jersey, I guess a little bit in LA, but all in the US. That's a piece of our brand. Like, it's a heritage brand at the end of the day, whether we're a new brand in terms of fashion or we're an existing brand or legacy brand or heritage brand, whatever you want to call it, because it's an actual racing stable. It started in the '80s. I think it's still important that it's a piece of the story is that we make everything here. I mean, there's issues every day. I got it. Everything scares me.

How do you stay like even when all that shit is happening?

Caroline and fitness. That's it. I mean, it's two simple things. Fitness with Ben or not. And yeah, I mean, I could do a lot better with it. I definitely don't handle it well a lot of the time.

What could you do better? What are you working on right now?

Myself. Myself. I should be working more on myself. And I say I will a lot, and I don't necessarily always do. Um, but yeah, I mean, just the way you handle certain things, uh, certain situations, uh, I think the more times that you get put in those situations, you learn how to handle it better. And we're still so young as a brand that there's new situations every day or every week. Uh, so I think a lot of it is, is how you handle it.

Do you think part of it is like letting go of certain parts of your responsibility within the business, like so you can work on the business instead of in the business as you think about scaling?

Yeah, I think it'll happen eventually. I think we're working towards that. Uh, I think it's good that we're both in the weeds on everything now because you know what's right and what's not, uh, and be able to be a real boss for future employees. And like, you've done it before, so you know, uh, they may come in and have more experience in that space and know it better, so you should be open to understanding that. And open to taking their direction on it. But I think for now, for now, it could be a day or two, I don't know, or week, is it's good that we have our hands in everything. I mean, it's two of us. Literally, our hands are in everything.

At what point— Go ahead.

Is there a— is there like a collab that you haven't done yet or someone that you haven't been able to get in touch with that's like the dream or wish?

Well, uh, from a collab standpoint, it's all of it's been so organic. Like, we— it's not like we've reached out to anyone. It's all been in like through networking, um, or we've been hit up by a team or a brand, or we met the right person and it's kind of just happened. Uh, so I can't say if there's like one. I think like, I think, I think to me personally, if we were able to do something with another like bigger brand that helps elevate and align us with the right thing, I think it would be great, right? And I think like the thing for me, anytime we say yes to doing a collab or working on a project with, with someone else or another brand, it's like, where do they sit in the world? Like, are we aligning with the right things? Because I think brand alignment is 100% of everything when you're building a brand from scratch. People to, to wear it. I mean, I don't know, I guess like some soccer players.

Just, there's got to be, there's got to be a name on the tip of your tongue that's like the one person where you're like, if this person has it on, like, I, uh, no, I mean like Bella Hadid and Gigi Hadid have never worn it and they're both like horse girls, so like that could be cool.

But like I always set out from the beginning, I was like, I want this brand to be for anyone and everyone. Like I want, uh white female farmer in Idaho to want to wear the same hat as Future, who's from Atlanta, a rapper. And like, that's what I want. And that's what it's been so far. So to me, that's one success in the bag. So I don't, I don't think I could pinpoint one person, but it's fun when you see a random picture of, of someone wearing it for the first time. It's like pretty cool to see.

Was there, was there a moment from you actually— I want to hear the story because I haven't heard— I think you've heard like origin story, but from idea to like first hat that you made to I actually want to turn this into a business and I want to work on this together.

Yeah, I mean, when I first started this, I didn't intend to do it as a business. I like my— so my dad is a racehorse trainer. He started his own racing stable in the '80s, um, but he always had the extra element of like opening up his stable to different equine therapy programs, whether it's like inner city youth kids or veterans or special needs kids. And when I first started this, none of that was in my head. It was all about like, I want to recreate this like one hat that I had that my— I think my grandpa made for my dad in the '80s. And this one jacket that I had that had like my grandfather's name embroidered on the front. And I literally was just like, I'm going to make 3 hats that look like this in 3 different colors and 3 sweatshirts that had the logo from the jacket on the back and the front in 3 different colors. And I spent like $300 and made like 20 of each or something. And I gave it to my brother, gave it to my dad, my mom, maybe like some extended family and some friends. And I started posting on Instagram and a ton of people started hitting me up and I was like, yeah, whatever. And continuously people were hitting me up about it and decided to put another like $300, $400 into it and make it, create a Shopify. Sold out in like 2 seconds, not 2 seconds, like 20 minutes. No one really knew about it. It was like family and friends, but they were buying it. So I just kept reinvesting the money, buying the same amounts of product and did that maybe like 5, 6 times. And then I was like, all right, maybe this— there's something to this. So I took all the money, put it back in, did the same 6 SKUs, and then gifted a handful of hip-hop artists and basketball players. A few months went by. Gunna ended up wearing the sweatshirt. and then Future wore the black and gold hat in a music video. And that was like stepping stone one. I was like, all right, maybe this is real. Put all the money just right back into it. Did the same 6 pieces again, uh, gifted it to some NBA guys. Tim Hardaway wore it. It was on like League Fits on Instagram. And that was like another stepping stone of like, okay, let's do it again. Um, but when I really started to sell it, I was like, the only way I'm going to do this if there's like a real brand purpose. So we donate a portion of proceeds to different equine therapy programs to like stick true to like my dad's story and the Siegelman Stable like heritage story. Um, and that's kind of how it started.

The, the first thing that you mentioned was casually of like, hey, I want to do these shirts, and yes, I just made them. The amount of people— I had no idea what I was doing, but it could be a brand, it could be a software company, it could be an agency, whatever. 99% of people, that's not obvious to them of like, oh, this cool idea, yeah, I'm gonna go actually do this.

I think it goes back to the networking thing. It was like, I know that I can get this in some of the right people's hands who could, who would wear it and post it. And like, maybe I can get some visibility on it and let's just see what it, what happens. And that's kind of how it happened.

What's the best advice your father ever taught you?

The best advice my father ever taught me. Probably a lot of advice. Uh, one of his famous ones is whoever takes the most vacations wins.

You leverage.

That's it. It's like whoever takes the most vacations wins. It's like, what's the purpose of life? There's like, go on vacations with the people you love. Like, whoever takes the most vacations wins. Like, wins the game of life.

My interpretation of it was that— and this is probably so wrong— my interpretation of that is like, when you're doing the things you love, everything like feels like a vacation.

Maybe that's it. That could be your interpretation though. I like that. You should live by that.

That's your new slogan.

What? I don't even— I don't even know what the slogan—

I guess the other one was like, live close to where you work, because he would commute from Long Island to where Siegelman Stable was in like South Jersey. And now I work from home. So, well, we have an office, but work from home.

There's a lot of, um, we've talked about this before, that like a lot of founders or creators that I'm friends with, everyone thinks— I don't know if it's like public perception or Instagram or something, but everyone thinks they're like constantly traveling on trips on like cool shoots. Most founders that I know are up at like 6 AM stressed and literally just work all day. And so walk me, I'm curious, just day-to-day, what does your routine look like? Walk me through wake up to the day.

Monday, Tuesday, Thursday, I wake up at 6:00 and have coffee in bed with Caroline and then go to the gym and start the day. Being that we live together and work together, our workday is 7:00 AM to 11:00 PM. Wednesdays and Fridays, I pick up Bennett 5:40 and work out and then get to it. Um, yeah, I mean, there's no such thing as like— like, we sometimes box fulfillment, or we do fulfillment on Saturdays and Sundays. Like, uh, I mean, we travel a good amount, but we look like we travel a lot more than we do, probably. Like, we have, uh, we have stuff being— whether it's like people wearing our stuff somewhere or our stuff being given a VIP, some like whatever. Like it looks like we're in a lot of places. Um, I mean, in May we're not here at all, so we are traveling a bunch. But, uh, but yeah, I mean, it's always on. Like my phone's on do not disturb, is giving me anxiety right now.

So Max, I would say, probably spends more time on his phone. And I spend a lot of time on my phone. I think he's far and away one of the most addicted people to his phone out of anyone I know, but that's because his work is literally his phone?

I talk to like 200 people a day.

On what, like DMs?

Doesn't matter, text, call, email, DMs, whatever.

I can't function on my phone.

Dude, have you looked at your average screen time? You probably know it, don't you?

No idea. 18 hours.

When's the last time you like put away your phone for like a day?

This is the longest it's been in a while right now. How long have we been talking?

Sweating.

Yeah, I am sweating, by the way.

Um, is there— I'm, I'm curious to know, have you and Caroline had like explicit conversations around finding ways to try and like delineate between like your relationship and work? Or like whether it be activities or moments or like rules? I know like the coffee in bed is a staple for you. I've heard this a million times. Um, are there other things that you try to do so that it doesn't just consume every other part of your relationship?

Uh, yeah, I mean, we, we try and— I mean, there's no balance, but like, and what is balance, I guess? But like, we It's tough. It's a tough response because it's like we both love it so much, but we also understand that there are times where it's like too overwhelming. It's like all we're doing. But I think it probably goes back to what we were talking about before, like what motivates you. I think we both want what we built from the ground up to be successful. Um, so I think it's like enjoying those grounding moments that we do have. And then understanding that like no one else is gonna fucking do it if we don't do it. So at least we get to do it together. I think we talk about a lot is like pre-pandemic or now or whatever, it's like most of the time people don't see their significant others ever. Like you go to work 9 to 5, you go to the gym after, you go to dinner, like you see them on the weekends, but you probably have stuff to do on the weekends. Like we, we kind of feel lucky that we get to do all this stuff together. We get to travel for work together, we get to come here and do this podcast together. We get to spend the rest of the day together because we work together. So it's like the balance for us is like we get to do all this stuff together, whether it's work or not. So it's like to be thankful for that, which I think she points out to me more so I can understand that. But I think that's kind of how we look at it. It's like we're lucky that we get to do all this stuff together.

Yeah. When you think of— I think this is Tim Ferriss' question. When you think about the word successful or like who is successful in your mind, who do you think about? Not just in brands and fashion, anyone.

People that are happy.

Like who specifically in mind? Are you like—

could be anyone. Go outside, it could be a homeless guy. If he's happy, he's happy. That's successful. But like, I don't know, I'm sure there's a lot of wealthy people that are happy, but the majority of wealthy people I think are pretty unhappy. I think it's like what your journey is along the way to get to what you consider success that will either make you happy and successful when you reach that quote-unquote success. Um, it's like my parents are like two of the happiest people I know, and they're like— I would consider them successful. But I think it's like, it's a— it's tough to define that.

Do you think it becomes a rat race though when you quantify success as like a future state versus like the success of what you get to do every single day when you wake up? Like, so you're not endlessly chasing something because you always hear people talk about like, I wanted, you know, this exit or I wanted this amount of money and then you get it and it's like, now what? I thought that was going to be the thing that fixed me and then I got in, I realized it wasn't. So just around like the success of your freedom day to day versus like this thing that you're constantly chasing that drives you.

Yeah. And I probably don't realize as much. And again, like Caroline pointed out to me, it's like the success for us is one that we get to work together. Two is like we can drop stuff at any time we want and we know what we're gonna end up with, uh, and being able to work for yourself. Like, being able to work for yourself I think is, is a huge success. I don't think it's the end-all be-all, but I think it's a huge success. I never want to have to take orders or like be told— not be told what to do, what not to do, because you need that sometimes, but like sit at a desk all day and do work. I couldn't do it anymore. So I think like it's like a corny line, but a lot of people say it now, like success is the journey to wherever that is. I don't think they're— I don't think the end goal is success. I think like to get to that point is like succeeding. So I guess succeeding is a better word than success.

Yeah, I like that. The success is like an end state.

He's making so many shirts after this versus succeeding. Whoever takes the most vacations win. Successful is not success without successing.

No, it's succeeding, not the amount of logos for—

we should have some slogans every episode, a main slogan for the show.

I also think we could just put them up there, just endless ones. Vacation one's a good one.

I like that.

You, uh, you mentioned like overwhelm. I feel like most of my day is either deeply fulfilled and excited or stressed and overwhelmed, but I can't have one without the other. How do you think about that?

Seems like we should both go to therapy together.

Group therapy.

All our girlfriends send us to therapy.

Yeah, mine's been trying. Um, yeah, I mean, I think I have the highest of highs and I think I have the lowest of lows, and you probably don't want to be around me at the lowest of lows. So it's like, it's where self-work comes in. I haven't done the work to get there yet, so I'm currently in a good space but in an hour, if something happens or a few things happen, it could trigger me and I could be in the worst space. But I, I'm aware of that, which maybe is the first step.

You've been around a lot of like high performers across business, entertainment, sports. Like, is that something you think about in terms of— or I've talked to these people about like how they handle that, because I think you need to have some like it factor that allows you to even get to that place to begin with, but I'm sure you've probably had some interesting conversations around that topic with some of these people that you know.

Yeah. I mean, I think a lot of them, a lot of them don't do it. And I think a lot of them end up in a place that they don't want to be. And I think the people who do do it, you see success. If they're an athlete after their athletic career is over, you see success in other verticals or other things that they're doing. So yeah, I mean, I think you can learn from watching what other people do. And especially if they're doing the work for themselves and pays off.

What would you say are the most common top 3 traits you see in high performers?

Ben's killer with these.

Good question.

The top 3 traits in high performers. Very good question. You're going to have to cut this podcast for me to answer these questions. I think one is like understanding what the important things in your life are and if they're the right things that you prioritize. I think that probably covers one and two, right? I think if you prioritized not going out and partying and your social life and like, I never was one to like prioritize my social life over the journey of success to where I thought I would want to be and do. Um, so I think prioritization is one. Um, understanding like what— that if you do something, if you're confident in the way that you do something versus in the way that you see everyone else doing things and it's starting to work for you and you continue that, I think that's also— so that's not like a one word, that's a long two. And the third one, maybe just like being self-aware and like being realistic with yourself, like what's actually possible versus like what is a total dream scenario that you're so far away from. And also, I guess the fourth would be, which I always mention, I feel like, is like knowing what you're good at, what you're not, and being able to delegate the things you're not good at. I think that's something that Caroline and I both are really self-aware about, is like what we are both very good at and what we are both either not good at or not interested in, that we can balance each other to alternate tasks or alternate things that need to get done.

Someone said something to me along those lines. I was like a freshman in college or something, and that was the first time it resonated with me when someone said, make your A's, A pluses, and find someone else to do your C's for you.

Yeah.

Because I think there are a lot— like, David Goggins is the epitome of the person who's like, find the things you suck at and like become good at them and like callous your mind and face your fears and the things you're not good at.

He says it.

Yeah, he's all about like— that's why his whole thing is like chasing the things that scare you, which is why he operates like the way that he does.

I think it could work for some people. Like, it works for him, right? But like, at the end of the day— and I love Goggins. Like his thing is that.

No, I know, but no, I was— the end, my end of my thought was that like I don't think that's like a common thing. I think the more common path is just like lean into what you're good at and again like fill in the holes around you, and then when you can delegate those things, that's when you actually start to elevate and level up. But, um, to your point about like the high performers, the reason I asked that is because I think the, the thing that I've started to realize, for better or for worse, is I think the fear of failure and like an insecurity about not doing enough or being good enough at whatever the thing is has been like a commonality of people around me that I've seen that have become so successful because they're just never satisfied and they don't want to fail.

Yeah, I mean, I have thoughts of like, okay, like I think if it's a longer answer, but I guess it's like if you know, if you could plan for what's next, then I think you have a lot less space for failure. So like I could easily sit here and worry about like, I don't know what's next for Seagull and Stable. And if I fail at this point, it sucks because there is such an opportunity and like we are doing such amazing, cool things. So like I could sit here and think that, but also knowing that like what we've been working on, what's coming up and like planning for what's next, you don't really have time to think about the failure piece of it. So I think that is also an important piece.

However, how have the goalposts moved since you started Siegelman Stable?

Uh, I don't think there was a goalpost in the beginning. I think it was like, I'm just gonna do this and wing it and figure it out.

Like, sell 10 hats.

A little bit more than that, but like, yeah, like, that was number one. Yeah, like, for sure. It's like, get the right people to wear it and sell them to whoever your customer is. Like, you don't know who your customer is until you start selling. And I think we still try and figure out who our customer is, because if you think your customer is someone and you're making these things to sell to that customer that you think it is, and then you're wrong, you just invest a lot of money into something that's not working. Um, so I think the goal— there's clearly goalposts now, and I think there's multiple of them. Uh, and I think understanding the, the right moves you need to make to, to get to each of those is difficult, but you can figure it out if you plan for it. And I think the, the goalpost in the beginning of this was like, okay, I want to sell X amount of hats, and then at some point and I want to create scarcity and see how it's on resale. That was like goal 1 after understanding I was going to start selling it. And then goal 2 started to be like, I really want to tell the brand story more. And I think that's what resonated with people and the give back to Equine Therapy piece. And then now it's like, how do we continue both of those things, like the, the heritage brand and telling that brand story? How do we make ourselves a face of harness racing? How do we bring attention to that? In a super positive way? How do we continue to give back to equine therapy in an even bigger way? And how do we really make a play into fashion? And what are those moves and what do we look like and what are we doing together? So I think there's a ton of goalposts to target.

I think the part about the goalposts for me within culture is that like it changes all the time and it's kind of like adapt or die, right? Like when you're building a software company, it's a little bit more clear of like, this is the pain point that I'm solving. And like, you can quantify what needs to happen in order to do that. But with you, the thing you've been able to do is continue to evolve. Like, every time you do a drop, the person it is, the thing it is that you're selling. And I feel like that will forever be a moving goalpost because of the point that you're not relevant anymore. Like, people forget about you and the brand dies.

Yeah, I think that's right. And then you have to— you do have to adapt. But I also think at the same time you need to balance to stay true. So I think you need to stay true to the brand story, the heritage piece, the what you— what do you look like in on someone? Like, are you selling a piece because it's what's hot now, or are you creating a piece because that's what fits your brand and fits your aesthetic and what you really want to do? But you need to figure out what that balance looks like.

Yeah, I think whether you're running a brand or you have Platter, like a software company, staying true to mission and your people, your customers, and quality, if that's at the core, I think moving goalposts are a good thing. I feel like growing up, you're told, like, be careful of those moving goalposts. It's always going to happen. It'll get you. I think that's a positive thing.

Yeah, I think stagnation is the worst thing ever because shit's just going to pass you by in a lot of different directions. That can be personally, professionally. But I think that's part of, again, going back to why I think we get along is that we continue to push ourselves to limits that other people I find really strange, honestly, more than anything else. But I think for me, a lot of that, it comes from that like fear of failure, always wanted to like challenge. Like it's a game with myself of like just trying to be better than what I was previously. Um, and then translating that into professional is very easy to do because there's a lot of overlap.

Yeah, I agree. I'm curious, do you have a, do you have like a clear division between work and life, or is it a clear vision between clear division? Or is it just one in the same?

Shut up. This podcast with my girlfriend, this is like another meeting for us. Uh, I mean, at this point it's two. It's like Siegelman Stable is a family brand. Like, it's my last name, so there's no division. Like, I am not— my dad says I am Siegelman Stable, but like, I am Siegelman Stable, right? So it's like, you walk outside, you're Siegelman Stable. If you kick some random person on the street you're Siegelman Stable, your brand's over, right? So it's like there's no division in that piece of it. And then obviously Caroline and I are the only two who run this brand, the zero division. Uh, so I think again though, I think you need to look at it— perspective is everything on that. I think you need to look at it as like we're fortunate to be able to do that. Like I don't, I don't have a, a brand name tag that says, hello, I'm Max, I'm XYZ employee at whatever company, and like you have a clear division, you leave the office at 5:30, and it's like most of the time you don't enjoy that. Um, so I think you have to have the perspective of like, I'm happy that there's no division, like I'm just living my life now.

That's an interesting, uh, insight though, just the notion of building something literally tied to your name. Uh, even a lot more responsibility, but you know, but even for me as like a founder of a company, it's very different than and you, where like part of your brand is your name, and mine couldn't be further from that. So I actually think it's— now that we're just like talking about in real time, it's almost impossible for you to like have a division between like personal and work. The closest you can get to it is like going on a vacation and like not wearing—

oh, I'm out today. Like, no.

Yeah. Oh no, but it's like not wearing a piece, but like that's also just like, then you're like, I'm not marketing myself.

I won't wear the black on black hat because you can't see the embroidery on the hat. Yeah. Of course.

I feel like it's a— again, I have a separate like business name versus my name. It's still scary because your reputation's on the line, but it's different. I mean, is it, is it a blessing and a curse, or is it just a blessing?

For now, it's just a blessing. I think it's, uh, I think it comes with a lot of responsibility. Um, I don't take responsibility for anyone in the world with the last name Siegelman, but for my direct— me and my family, I do. Um, but I think it's a blessing. I don't think it's a curse to this point.

Have you had to— how have you had to take more responsibility? Like, how have you changed how you operated at all?

I've never had like a— I don't have any bad background. So like, so far so good.

Yeah.

Um, I don't think I've changed that much. Like, I really don't think anything's changed other than I wear my name every day. Like, I always used to like walk into conferences and someone hands you a name tag and I'm like, I'm not gonna wear this fucking name tag. Like, what is this? Like, I'm not. And now I just— I wear it by choice.

I think it's really just like answering the bell when things are there, and you're probably making more decisions and taking on more responsibility, but it was kind of just this seamless transition where you pretty much exhausted your other job to a point where you're like, I just have to like move to this. But it was a normal transition for you because you were already more or less doing it before you decided to like make that jump full-time into it?

Yeah, I mean, I think like, I think I personally always like doing consulting work for athletes or rappers or whoever. Like, you still are kind of your own brand in essence, but not selling your name on items that other people are wearing, right? And you can't take responsibility for everyone who wears your stuff. It's just things will happen eventually. But, um, I think it's kind of like I didn't change in any which way, uh, and I don't foresee that happening either.

So how do you think you've like grown personally over the past year, 2 years even?

Uh, good question.

I love anything like— I think anything that like a therapist would ask him, like self-talk type, he like— he's like, I don't want it. I don't want to answer this question.

My back's in a full sweat, by the way. I just want to make that clear. This couch is 150 degrees.

I'm sorry.

It's okay. I'm just gonna take a shirt from your closet after, um, shirtless podcast. Uh, what's— how have I changed in the last year? Grown, grown. Um, past 6 months. 6 months, I probably haven't grown. The last, last 2 years, uh, that's not true. Last 6 months, we probably had, I think, together, like, one of our biggest lessons in terms— not personal relationship, but work. Like, we thought we were doing something right and it was super wrong, um, and it cost us a little bit of money and time, but I think it was the best lesson that we could have ever got, uh. So it was a, it was a quick tuition, uh, but a quick education, um. And I think that that was, that's a, that was a— what did you say before, a blessing or a curse? That was both. I think personally, like, in the last 2 and a half years, I think my life probably changed when Siegelman Stable started. It started ramping up and Caroline and I started dating and she started doing Siegelman Stable with me for the better in every positive way possible. So I think that's probably number one. But I think it's changed in, in a very positive way. I think being able to have your own business, do things the way you want to do, uh, not listen to outside noises, which I think took me a while to, to understand that, like, if someone's telling you to do something because they think it's right, like, question it. Like, have they done it in the past and was it successful? And if it hasn't, then you probably should just continue doing things the way you're doing if it's going right. Um, so I think I'm growing in a ton of ways. I don't know how to describe them, but I have. Caroline hates them.

Something's definitely happened.

Yeah, something's definitely happened.

I'm curious, how do you, um, how do you ensure that something has definitely happened? I don't know, I can't put my finger on it, but something— I don't know what it is, but I'm different now.

Yeah, I still sweat a lot, so.

All right, we're gonna end there. How much time do we have?

Uh, I literally need a new— Um, like, this cushion needs to be washed.

That's okay, you're doing great.

Thanks.

Um, question I have for you: if Siegelman Stable fails, yeah, why?

It won't, because it's already successful in my eyes. I think we're continuing to be successful, um, and I don't think it will fail. I think even if Siegelman Stable ended Immediately after this podcast because I went outside and did something stupid is probably the only way that would be a failure. I think the things that we've been able to accomplish are things that 99% of people will never accomplish in their life. And that's not saying it in a conceited way and cocky way. It's like, I actually don't think most people would be able to do what we've done so far, especially with $0 spent. No money raised and starting this with $300 and using your network that you built yourself over a certain amount of time. So to me, Sequoia Stable is not a failure ever, even if we quote unquote fail at some point.

When are you at your best? Who are you around? What are you working on? Where are you?

Family, friends, at home. Uh, I don't know what a vacation is, but probably on a vacation. Um, yeah, I mean, I think like the— to the first question, it's like when you're around the people that bring you up versus like drag you around or ask for things all the time or whatever it is, I think that's when you're at your best. I'm at my best at 6:30 in the morning drinking coffee with Caroline talking about what we're gonna do today because we don't have any lines between relationship and work. Uh, but I think that's like when my head's the most clear. Um, I could write press releases on the treadmill. I'm pretty good at that at this point. So I guess that's probably another place I'm pretty good. Um, but I think it's about the people you surround yourself, um, whether it's family, friends, or just the right advisors or people.

Max is so good at like—

he—

Max has so many friends and so many people, yet he has the smallest circle. I don't know if that makes sense in my own head when I say it.

I have a lot— I feel like I have a lot of different friend groups.

Like, you have a lot of different friends that offer different things, but like your core core group is like very small.

Yeah, I keep this— I keep a tight circle.

Keep it tight.

Yeah. Why is that important?

I don't necessarily think it's important. I just think those, like, those are the people that help bring you up or make you more confident to do the things that you should be doing or benefit you in some type of way. Uh, I'm sure the majority of the people I'm friends with talk to their parents once a week. I talk to my parents once a day. Caroline's like, no, he talks to them 5 times a day. But like, that to me, like, those are the important people in my life, and that those are the people who have gotten me here so far. Um, it goes beyond that to different friends and stuff like that, but I keep it tight.

Have you had to outgrow any friends?

Uh, not by choice. I think, I think, and then you just outgrow people organically or naturally because you don't have the same things in common. Or like, I'm still super close with like my 15 guy friends from high school, and 90% of them live in New York City, and I'll see them maybe a few times every other month or like we still have so much in common. We may live all such different lives. Like they might be doctors or work in real estate or lawyers. Like that's just different world than I'm in. But I think like what I just said to Ben is like I have groups of friends that have interests in such different things that like if I know I need something at that point, like I can hang out with that group of friends. Um, so I don't think that's an issue. I think it's just— but my core group of people that I see on a weekly basis is tight.

What are the commonalities of that core, core group?

Um, I don't know if there are commonalities, just like love and positivity.

I don't like— I don't think—

I don't think there's like— yeah, I guess those are two commonalities. Um, like, family is definitely like number one for me. Like, we moved to where we live now the day my nephew— our nephew was born. And like, we're like, oh, we'll live there for a year, and then we're on 2 years now, which will end very soon by someone's choice. Um, but, uh, but like, those are the things that are important, and those are the things that I think as you continue to do things that you want and are, are on a road to successful journeys, then I think those are important people to keep around. Siegelman Stable is a fashion brand that donates a portion of proceeds to different equine therapy programs around the world. You can find us on Instagram @siegelmanstable or siegelmanstable.com. Uh, you can find me on Instagram @max_siegelman.

Thanks for joining us today, Max.

Yeah, thanks for coming on.

Thank you both.