SPEAKER_01 0:00

Okay, this person definitely has enough money to buy better clothes than what he's wearing, and that's because can we we can bleep, right? We can bleep. The fuck dresses like shit all the time, right? My guest today is Isabella's son. Isabella is the founder of Short Story, a wildly successful apparel brand for petite women. The reason I wanted to have Isabella on is because I've been noticing this narrative that exists in Silicon Valley, but kind of America more broadly. And the narrative is that as long as you're talented and hardworking, you can make it here, and the whole valley will rally behind you. But that narrative I find is only partially true. Yes, Silicon Valley is a meritocracy. It might even be the most meritocratic place in the world. But it was also made by a certain kind of person for a certain kind of person and for a certain kind of company. And I know from stories like mine and stories like Isabella's that if you don't fit that mold perfectly, you kind of have to go at it alone. Isabella is one of the most talented founders I know. And the company she's built is an absolute monster. But because she doesn't fit that tight mold of an AI B2B sass business, she's had to do this somewhat by herself. I found this conversation to be weirdly cathartic. It reminded me of the original thesis of the show. And I think you'll find, if you're the founder of a business like this that doesn't fit that tight mold, I think you'll find it to be cathartic too. With that, I bring you Isabella's son. Isabella, thank you for being on the podcast. Uh, I want to start with this. Can you tell me a little bit about um your early life? Tell me about how you grew up.

SPEAKER_02 1:55

Early life was growing up in Beijing. Um, fun fact the street that my family is from is next to uh what's called the forbidden city. And it is a very old um structure that as a kid, when you grow up there, you you don't think much of it, right? You're it's next door. And years later, as an adult, when I went back, I was like, whoa, this is some real history here.

SPEAKER_04 2:21

Yeah.

SPEAKER_02 2:21

Um, but yeah, uh growing up in Beijing is is very chaotic. It's very loud. Um, and that was quite formative because I I'm I'm um I'm a chaotic, loud person.

SPEAKER_01 2:33

I can relate to that. Uh I grew up in Delhi. And um uh wait, what year were you born?

SPEAKER_02 2:40

90.

SPEAKER_01 2:40

Okay, so we're around the same age. 90s in Delhi and Beijing, I think probably felt kind of similar. And uh I find that like as things get louder and more and hotter, uh-huh, I start to get in my zone.

SPEAKER_03 2:54

Uh-huh.

SPEAKER_01 2:55

And it's there's some sort of like childhood muscle that's still there. Uh-huh. I've just, I feel very comfortable in like a decibel level and a heat level that makes most people around me very uncomfortable. I I wonder if it's the same for you.

SPEAKER_02 3:06

Uh, it makes the two of us.

SPEAKER_01 3:07

Yeah.

SPEAKER_02 3:08

Um this this heat, yes, like this spiciness, I think is something that when you're when you grow up, you're in the environment and you you sort of like it is part of you. It is very you, and you take this heat, and then maybe later on it translates into intensity. Yeah. Maybe it's passion. Um, but yeah.

SPEAKER_01 3:26

It's before we started rolling, we were talking about our mutual obsession with spicy food. And I think it's more the same where you realize when you grow up in a place like that, eating food like that, where you're like, um, oh, it can't hurt you. It can only add interest to your life. It can only make things uh weirder and less predictable and more fun. It's not actually gonna hurt you, you know. Like, um, and I think that has kind of for me, even as a founder, sort of defines a lot of my relationship with risk and chaos. Is like, I think there's a type of person whose like default position towards risk. I wonder if you agree with this, like some type of person whose default position is no risk, no chaos. And I'm like, no, no, no, you that'll be an awful fucking life. Like, I want some, I want actually quite a bit of risk, and I want quite a bit of chaos. Let's it's what adds spice to life. Like, what the fuck's the point of anything? But um anyway, I want to, on that note, you come from uh, as I understand, a family of founders, right? Uh your ma'am, your your mom's a founder, your uncle's a founder. Uh, do you remember the first time that you kind of became aware of that as like a conscious choice that people make, that a choice that maybe you could make at some point in your life. That like, okay, there are people whose parents are have jobs, but that's not what your mom's doing. Your mom has is a business person. Did you were you aware of that difference at all as a kid?

SPEAKER_02 4:48

Well, first of all, I think that that makes it sound much better than like a family of founders, like, oh, you know, like it's it's not really that fancy. It's, you know, my mom is a she owns a business and she's been an entrepreneur for a long time, for you know, 20, 30 years. Um, and my dad is entrepreneurial. And I mean, my parents had done own businesses, run businesses, um, and they succeeded and failed many times. So I think for me growing up, it was watching the reality of like the founder. Oh, it sounds so fancy. But this is the reality of owning a business, administering a business, doing the taxes for the business. It's all these unglamorous things that I watched them do. And and and like at dinner, you know, my mom would get a call and we'd be in the middle. As my mom, my mom and I grew up, we grew up together. She raised me as a single mom and we grew up together, kind of. Um, and so she would like run off to take a take a call. And as a kid, that that moment for me was like, huh, that's interesting. Okay, it business never stops. Yeah, it's not something that has an hour, an opening hour and a closing hour.

SPEAKER_01 5:59

So did you ever think it was a cool thing to do when you were a kid?

SPEAKER_02 6:04

I thought it was what everybody did.

SPEAKER_01 6:08

You just said it was like the default choice.

SPEAKER_02 6:11

Sort of.

SPEAKER_01 6:12

Um how did things shape up for you? Like, do you remember the experience of leaving China? What was that? What was that like for you?

SPEAKER_02 6:18

I do, and I actually wonder what when did you did when did you move?

SPEAKER_01 6:22

I moved when I was 17.

SPEAKER_02 6:24

Oh, wow.

SPEAKER_01 6:24

How old were you?

SPEAKER_02 6:25

I was nine.

SPEAKER_01 6:26

Okay. Uh so yeah, that that that's old enough to have like conscious memories, right? It's uh what did that feel like?

SPEAKER_02 6:34

Um moving at nine was such an opening of the brain. I'm sure it was for you as well. Um, because you have this notion of what America is like. And in Chinese, it means the beautiful country.

SPEAKER_04 6:47

Yeah.

SPEAKER_02 6:48

So you are hearing about America and having all these notions about the country. And then you I went to Seattle and I arrived at Seattle Sea Tac airport. And I just looked at everyone around me and like, oh, okay. We also look like people. There are restaurants, there were signs. I mean, in English, but like it was quite normal. So I think I felt very comfortable from day one. I was very comfortable with new stuff, weird stuff. Um, I wasn't very um oddly looking back, I wasn't very afraid of doing anything.

SPEAKER_01 7:21

Hmm. What um in those kind of early years, what do you think your mom wanted for your life with with moving to America? What what do you think she was hoping would your life would become?

SPEAKER_02 7:33

This this is feeling like a therapy session. This is tapping deep into psychotherapy.

SPEAKER_00 7:40

So you bill after this.

SPEAKER_02 7:42

Um, what does she want me to become?

SPEAKER_01 7:45

Yeah. What what do you think her hope was with with moving to America and moving you to America? What do you think she was hoping would come of of your life?

SPEAKER_02 7:52

My mom is the ultimate untiger parent. She could not care less about grades or whatever. She was like, Isabella, I all I want you to be in life is happy.

SPEAKER_01 8:04

That's beautiful.

SPEAKER_02 8:05

Um, so I I I think the the the it it actually felt weird for me because I felt like, well, you need to give me some expectations, but there's this thing that uh I've seen a lot of like um brown parents do.

SPEAKER_01 8:22

No, um, I think especially immigrant brown parents will do this. I wonder if it was true at any level for you, where um, you know, you take these big risks in your life. Uh you're moving countries, starting businesses, right? And it's all at least at some level in the pursuit of like, well, my kids are gonna have a really good life. And there's this like expectation that I think a lot of brown parents have that my kids won't have to take the risks that I want to take. And very often that works out. And you see a lot of these sort of children of immigrants, right, that are incredibly like risk averse and they're very hunkered down and just want to succeed in like a straight line. And then very often, almost just as often, it totally fucking backfires because you just raised this little tiger at home that saw you like take risks all day, every day. And then it creates this like kind of like I know this happened with my parents. My dad also started a business the year I was born and was somehow confused when I wanted to start a business. Was because for him, it was like, well, no, but I already did all this. Like you should yeah, for you, like I I made all this money. I did all this so you wouldn't have to take these risks. And but I was like, oh, but that's not the lesson I got from your watching your life at all. The lesson I got from it was that like the biggest waste in life would be to not like go after something big, to not have risk, to not have spice, right? Was that your experience at all? That I it like um that your mom kind of took on a lot of these sort of big risks, and uh was she surprised at all when you wanted to go off and be a founder and do this like kind of more uncharted thing? Was that at all a moment?

SPEAKER_02 10:01

I I don't think she was surprised. Uh, I don't think she really dictated at any point in my life what I should be doing, what I should be thinking about, or how I should be approaching things. I will say one one um sort of uh anecdote that really stuck with me is my mom said, you know, I I came to the US with with one suitcase. And you know, she would go to um, it was I think it was KFC back in the day. She would stand outside the KFC store and look at the the the picture of the whatever, the the chicken bucket and be like, wow, that looks delicious, but like it's kind of pricey. And as a single mom immigrant, like you are those things are real luxuries. I remember going to Starbucks with my mom, and you know, she's trying to order a coffee, and the the the the barisa's like, What do you what would you like? And she's like, I I don't know. Whatever you like.

SPEAKER_03 10:57

Yeah.

SPEAKER_02 10:58

And then Barisa was so confused, but I felt in that moment, I I I did feel embarrassed. I was a young teenager. I felt embarrassed, but looking back, it was really this amazing opportunity to watch someone who's so close to me to be in uncomfortable situations. And that taught me a lesson about it's okay to be uncomfortable.

SPEAKER_03 11:19

Yeah.

SPEAKER_02 11:19

And I find myself nowadays often very uncomfortable.

SPEAKER_01 11:24

So yeah. That is a really beautiful idea that I hadn't thought about because I didn't um my parents never immigrated, right? My parents still live in India. And so um, but in fact, I feel like that's a thing that not enough children of immigrants talk about is watching the experience of watching your parents not know what's going on, right? Or you're watching your parents also be new to something. Um, to me, that that that's really beautiful. Um well, you come out of that, right? And you have this uh very successful, I would say, you know, and very traditionally successful career, right? You go, you go to school, you study, was it finance, right? Study finance, you go into you go work in finance, you're like on the trading floor, Bank of America. I'm sure I'm missing large chunks of your like details there, but I guess the one question I have about that like sort of pre-founder part of your life. Uh what did you want from your career at that time? Was it that this was all setting up economic security so you could go start a company eventually? Or was it like, no, this is what you wanted to do when the founder thing kind of came out of left field? Or was it somewhere in the middle?

SPEAKER_02 12:34

That's a good question. I'm I'm thinking back, I think um, you know, like you said, it's it's it's sort of a traditional path, right? It's the okay, you you go to school and then you go get a job, maybe you move to New York City and you work in banking. And it's it's uh, yeah, I remember walking to the one Brian Park uh the B of A headquarters on 42nd Street and thinking, wow, this building is massive. It's so tall. It's the tallest build, one of the tallest buildings in New York City. I'm like, I want to work here.

SPEAKER_03 13:05

Yeah.

SPEAKER_02 13:06

There wasn't really much consideration for like what does it actually mean? Um, which is so um when I meet people today and I try to recruit them to my company, it's a very different mindset. It's uh at that time, it was a mindset of like, I want to be at the pinnacle of whatever it is that I'm doing. Um, meaning if if it's if it's in sales and trading, I want to get really good at analyzing data. I want to get really good at um crunching numbers. And I I I I and I like that super high adrenaline fast paced. Um I always felt that it was an apprenticeship though, that it was never going to be you might have felt this way too. It was not something that I want to do for the next 50 years.

SPEAKER_01 13:56

Yeah. I have two sort of things off of that. Um one is um, do you find that that it I guess is is that something that you struggle with? Because I know I do. I can't suck at something. I can either try to be really good at it or I will not do it at all. Um I don't want to, and it prevents me from being able to take on a lot of new things. Because part of getting part of making something good is making something really shitty, right? And I struggle with that a little bit. So I'm curious about that. Maybe yeah, maybe I I'd like to hear the answer to that first. Is like, is that a struggle of yours at all? Uh to just be bad at something for a bit, or do you as soon as you see something, do you need to get good at it?

SPEAKER_02 14:41

I'm terrible at a great variety of things. Um, truly. Yeah. Um where where where to start? Um I don't think that I need to, I don't think I feel the need to be good at everything. It feels definitely painful when I when you realize how how much you suck at something.

SPEAKER_01 15:10

Um the other question I have off of that, right, is um so you find this like uh let's call it traditional, because I can't think of or maybe conventional is a better word, right? Um career path, and you excel at it, right? Like you you ring all the bells, you're you're like you're doing great in it. Was there any point at which either that career or I mean to make it very specific, sort of the fashion, the aesthetics of that profession, right? Um maybe even like the the culture around it at at large, did it ever feel like, well, I'm trying to get good at this thing or I'm in this thing, but this thing isn't made for me. It's not it's optimized for someone else as the core user. Um yeah, I'm I mean, of course, the obvious one I'm interested in is the fashion part of it, right? Um But yeah, did you ever feel like, okay, well, I'm doing really well at this thing and I'm like on paper doing all the stuff right and succeeding, but like it's not really this world isn't really made for me. Did you ever feel that way?

SPEAKER_02 16:14

Yes, I did. I did. I mean, I well to get back to your earlier question, I I I sucked at a number of things, and one of the things that I sucked at was um maybe it goes back to there's a little bit of immigrant mentality. I really had a hard time um speaking in front of groups. Uh and I could crush the numbers, but speaking, but giving a presentation, oh my god, like uh like my heart is palpitating. Like it's it's it's still now now, now no more. Okay. But but but but that was one of the things that I really sucked at. Um and so so so going back to your question, the trading floor environment is extremely high, high energy, is high adrenaline. It is very, very exciting. I mean, you imagine like you've got people who still have those old-fashioned turret um phone systems with like a million different buttons. Everybody has six screens. You need like four eyes or something to look at all the screens, and there's just constantly like phone calls and people to people swinging bats. And like this happened. We hit the circuit breaker and it was so exciting.

SPEAKER_03 17:23

Yeah.

SPEAKER_02 17:23

And it really like hit the spot for me, the chaos part. Um, and the spicy part. Um, the part that eventually grew a little bit more dull was what is the meaning of this? How long do I want to be doing this?

SPEAKER_04 17:39

Yeah.

SPEAKER_02 17:40

Um, and I'm super intellectually challenged, but again, like, how does this relate to the world? Um, so I think that in those moments is when I started to think, what could I be contributing to? What can I be solving?

SPEAKER_01 17:56

And um do you do you remember the first moment I felt like, okay, I'm I want to go do something else. This isn't this isn't it for me? Do you remember was there like a genesis to that?

SPEAKER_02 18:06

One fine uh evening in in New York City, I went to Uniqlo, it's a great store. Yes, um, to buy one of those puffer jackets. And so I was in the puffer jackets section looking at puffer jackets, realized none of them fit me. Uh I'm 5'1. Um, you're very tall. Also, you might have the opposite.

SPEAKER_01 18:29

Uh Unico doesn't fit me for the opposite reason. Yes.

SPEAKER_02 18:32

Okay.

SPEAKER_01 18:33

But I can relate, yes.

SPEAKER_02 18:34

So many of us have found at some point like this this issue with with fit. So I was trying to buy this puffer jacket, and then I ended up in the kids section, actually.

SPEAKER_04 18:44

Yeah.

SPEAKER_02 18:44

Um, and I ended up in the kids section, there was a lady there who said, Um, are you looking for something for your kid?

unknown 18:51

Yeah.

SPEAKER_02 18:52

And I was kind of embarrassed. I was like, Yeah.

SPEAKER_04 18:55

Yeah.

SPEAKER_02 18:56

But like that actually was one of the many moments where I felt just so frustrated that I could not find a simple jacket and I had to go to the kids section. But I'm a full grown adult woman. So can't there, there's this has got to be some massive error in the cosmos of why can we not make this happen?

SPEAKER_01 19:18

Yeah. Well, I I I read in one of the articles about you uh the stat that you mentioned that what is it, like about half of American women are under five foot four, but like four percent, is it right, of clothing is made for them? Is that am I getting that right?

SPEAKER_02 19:35

Yes, and now 2%.

SPEAKER_01 19:36

So it's um I've been thinking a lot about that because I've been thinking about how uh again, something that I think immigrants are uniquely sort of privy to, right? The ways in which you don't have to build active discrimination into the system for there to be discrimination in the system, right? That I I just been thinking about my wife is short, uh shorter than me. Uh she is five foot two. Um, and it creates this unique experience, right? Where uh everything in our house, like basically nothing exists on the top cabinet of our house. Um and I think about that a lot. Use Hongs. Exactly. But it's this kind of interesting um thing where nobody sat down and said, let's fuck over five foot two people, right? Uh I'm hoping they didn't. But at some point, somebody decided the cabinets need to be where I think it's like the standard cabinet is 84 inches, like that's the top of it, right? 84 inches is within my line of sight. Like, I mean, it's not I'm not eye-level with it, but I can see it, right? But my wife at what is that, 62 inches is a solid damn near two feet below the standard America, the top shelf of the standard American cabinet, right? And I just think about like that's one little example of like when a world is designed by one type of person for that type of person, right? You don't need to be actively thinking about discriminating against people to end up with that as the outcome, right? And I I mean like by extension of the story that like my wife and I lived in Europe for a little bit. She was living in Sweden, and I was, we were like, we were still dating at the time, and I was living in Germany, and I visited her, and it's the only time I've seen her like genuinely um having like an identity crisis about her like sort of sense of fashion because all every store she would go into, she wanted her needed to buy winter clothes. Every store she would go into is designed for people that are like five foot nine and above, or women that are five foot nine and above. And every jacket she I remember she was like actually furious about how every jacket made her look like an oompa loompa because every winter jacket was like to the full with her. And and again, it's like that's a really um it's a really painful feeling to live in a world that constantly feels like it wasn't not even that it's discriminating against you, that it wasn't designed for you with you in mind at any level, right? And I Like I do think that a lot of fashion can can kind of feel that way. Um, anyway, this is all just my ranting about my wife being short, but coming back to to you for a second, like um where do you think that bias kind of comes in from? Why why is it because to me that I read that, I'm like, oh, 2% versus half of all women, that's like a market failure. Why does that exist? Why has that not been fixed yet?

SPEAKER_02 22:25

You know, I I think to your point, it wasn't from ill intent. It's just from uh the way that things have become. Um so it's funny that you mentioned the the top shelf. Like I was literally at Suvla the other day, and in the bathroom, the mirror is so high up. Yeah, the only thing I could see when I wash my hands is the top of my forehead.

SPEAKER_00 22:50

Oh no.

SPEAKER_02 22:51

So is is that is that I mean, it's not systemic failure. It's just like somebody had to put a mirror up and they had to do it quick, and they did it that way. Um so I I I do think there's the sort of the uh historical evolution of Garmin making that is part of this. That's quite an interesting um history. Um, and so you you you would have these models are like um that form the basis of your pattern, and they're usually much taller, right? Five, eight, five, nine. And then you have this pattern, like literally a piece of fabric that's your pattern, and you use that to scale your clothes up and down size-wise. Um, it's a it it it is a very manual process, and is one that is used even today. I went to um a a place and I saw the pattern maker literally put blocks of fabric piled this high. It's not digital. We're in San Francisco, right? Yeah. I mean, next door there's agents writing themselves.

SPEAKER_03 23:56

Yeah.

SPEAKER_02 23:57

People who are still taking physical patterns and using giant scissors to cut patterns.

SPEAKER_00 24:04

Wow.

SPEAKER_02 24:05

So some of it comes from the fact that um the technology use hasn't caught up. Some of it comes from the makers, um, the pattern makers and the I mean, frankly, the apparel retail industry are aren't the types of people who are making data-driven decisions.

SPEAKER_03 24:27

Yeah.

SPEAKER_02 24:28

Um so it's a chicken and eye problem, right? It's a it's a it's actually a manufacturing problem. It's a where do you alloc as a retail as a clothing maker and retailer, where do you allocate your resources? And then what happens is you have substitutes that are very poor substitutes for people like your wife and myself. Um and that is a self-perpetuating chicken and egg problem. Yeah, then exacerbate over time, and then suddenly you have a whole segment of people who are one height and are not being served.

SPEAKER_01 25:06

Yeah. I um that that is so interesting to me. Uh, I think um you kind of see it all the time. Like once you start to notice this pattern, you sort of see it everywhere, right? Of um America s in in so many ways feels like it's uh optimized for um for people that are young, rich, and uh attractive in a very tightly defined sense, right? Um and if you are all three of those things, good for you. Congratulations. If you are two out of those three things, life's pretty fucking great. If you're one out of the three, yeah, you can still exist. But the more things that you don't have out of that like very narrowly defined set, if you're attractive, but just not in like a very standard kind of like Western American sense, right? If you are uh, or you know, keep uh going with the analogy, but then it feels more and more that American society, American consumerism, American capitalism marketing is not designed for you, right? Um, and I love businesses that sort of find the gaps in that, right? And can kind of build well for that. Like I'm still I'm not tall enough to need big and tall clothing. Okay, but I have friends where they're like, dude, I want to spend money. I want to, I want to own better clothes. Like after this, I'll uh we'll talk about a couple people with the cameras off. Like that we both know that I'm like, okay, this person definitely has enough money to buy better clothes than what he's wearing. And that's because can we we can bleep, right? We can bleep. Fucking dresses like shit all the time, right? And he definitely has the money to buy better clothes, but I know what options are available to him at his like uh size. That's all that's available to him. So anyway, but I I find those types of businesses to be really, really interesting that like lock into um uh into the fact that American society, I feel, is really designed for one type of person and can like these businesses find market opportunities in other types of you know, markets, other types of people. Um I want to bring this back, bring this back to you. I there's a story that I heard you tell about your mom uh when she's getting her MBA and she's like also working a job and she's also single parenting, and you saw her in the same pair of gray sweatpants all the time. And I think that to me is like sort of the other aspect of uh the company you end up starting, right? Tell me tell me a little bit about that, like the problem of women's work wear and how hard that is. Because it's obvious for obvious reasons a very foreign problem to me. Like, how does that how did you kind of become aware of that separate problem?

SPEAKER_02 27:48

I I think this is something that is really universal. Whether you're you know tall or on a shorter spectrum or uh uh woman, dude, whatever. It's like people, we are busy, we get dressed, and our confidence comes from feeling like uh the best version of ourselves and like the dressing with clothing is a huge part of that. Um, I do remember because my mom was so incredibly busy all the time, she I just still remember those gray sweatpants, and they had these like drawstring at the bottom before that was cool. Uh um, and she definitely did not have time to get dressed for for work uh with all the things that she had going on. And I remember taking, we went to New York City again, like we were on Fifth Ave, and I just felt this immense desire to give my mom a makeover. I really wanted to take her to a store, buy her a nice outfit, you know, get her hair done, get her makeup done. And it it's this very deep desire to help someone see themselves in the way that I see them because I looked up to her, I look up to her so much. And she didn't do her hair or anything, but she to me, she was super mom. She is super mom. And so I I I really felt a deep sense of gratification even later on as I became an adult and I made my own money. I was able to buy my mom things. I felt super, super satisfied. And that I think is now that I'm thinking about it, there might be a little bit of this gratification feeling from serving my customers today.

SPEAKER_03 29:28

Yeah.

SPEAKER_02 29:28

That I feel deeply happy when I see someone who's in a new outfit and they say, My God, these are like literally the best pair, like the only pair of jeans that have ever fit me.

SPEAKER_01 29:40

Yeah.

SPEAKER_02 29:40

I feel I feel tickled.

SPEAKER_01 29:43

Um, do you remember? This was not on my list of questions, but now I'm curious about it. Do you remember the first thing you bought your mom with your own money?

SPEAKER_02 29:50

I remember buying her stuff from Ann Taylor.

SPEAKER_01 29:55

That's a very mom brand.

SPEAKER_02 29:56

It's a very mom brand. Um, probably a dress of some sort, like a floral dress.

SPEAKER_01 30:03

Yeah. Was that the was that the first thing you bought? Was it first paycheck, or how far into making money was that?

SPEAKER_02 30:10

Um I think I started to do internships and stuff in high school. And that was when I started to make money. And that was probably, I don't remember exactly when or what, but I I I I do remember the feeling of like, hey mom, I I caught you this. And she was really excited.

SPEAKER_01 30:25

I am always that's very cute. I I am always surprised by how many people's first paycheck goes towards buying their mom something. I'm very like touched by that. I I did the same thing. My first I'm in college, I made a thousand dollars for doing some like, I don't know, marketing work for some startup. They gave me a thousand dollars and I did two things with it. I still remember. I spent uh$800 of that buying my mom earrings. Uh, and I spent$200 of that taking my then girlfriend, now wife, to Shea Panese for her birthday. Those are the two things that I did, and that was all that you can do with a thousand dollars. So it's earrings and chapanese, and maybe the worst uh speaking like really from like financial safety perspective, probably the worst way to spend money. But if I could go back, I wouldn't change a dime of that. That's exactly how I would spend it. Oh, I also bought my sister a bracelet, but that was that was separate. Um significantly less valuable. But that's very sweet. Um, but it's but it's so universal. Like, I mean you did the same thing. We all there is something I think very rewarding about taking your first paycheck in, like, you know, spending it on your mom, um bringing this back to to you and to your career, right? Um, so you have these sort of like parallel thoughts, right? You're you're in this aggressive, chaotic uh world of finance that you love in many ways, but you kind of know it's not it's not the end for you. Um, you know, you've like recognized this problem personally of like how much clothing is not fashion is not made for uh for women like you, uh, women your size. And then you have this kind of third thing of like, yeah, it's just really hard to dress well for work. Um at what point does that become like what was the first version of short story? What was the very first idea you came up with that eventually became the company?

SPEAKER_02 32:20

I think this ties in very much with the San Francisco story because I had at that point lived in New York for seven or eight years. And you know, I did the thing as a young person would do in New York City. You go to all the clubs and whatnot. And then uh I moved out here to San Francisco. And I wish uh initially I was very resistant because I'm not a palm trees girl. There's a lot of palm trees here.

SPEAKER_04 32:43

Yeah.

SPEAKER_02 32:44

So moving here, um, the vibe day one was just real different. Um, it wasn't so much about like, oh, Goldman Sachs or Morgan Stanley. It wasn't about that. It was like, what are you building? What are you working on? And that felt like a really exciting energy to me. Um, and at that point I had started to like kind of tinker with different ideas. This was pre, you know, nowadays you could build an app in three hours.

SPEAKER_04 33:10

Yeah.

SPEAKER_02 33:11

This was like several years ago where you had to really think through what you wanted to build. Um and but this I was still working at the time, uh uh and I still needed to look decent, like very decent and polished. But this problem was not going away. So the very first version of short story was literally I I went to go um um uh buy some stuff. And I I think the first very first few customers came through Reddit. Um, there's a community on there, and the idea was what if I shopped for you? Because over the years I had accumulated this knowledge of which brands are actually gonna work for someone who's shorter. Um, and so I would actually go buy the clothing myself um and then hack together the like a some kind of janky website back then. Um, and those were my first customers. Um, and I think for them, it must have felt very nascent, like there was no clear explanation of what the what does this thing even do? Yeah. They were like, okay, cool, I'm I'm down.

SPEAKER_03 34:23

Yeah.

SPEAKER_02 34:23

So I had this board on my um kitchen wall, and every time I got one more customer, I would pin like a little flower on on the board.

SPEAKER_01 34:33

That's beautiful. I I do think that there's some a lesson there for founders, right? Where the the shittier the version of your product that somebody will sign up for, the more you're solving a problem, right? Like it's I remember the first version of our thing was uh literally we didn't even put up an e-commerce website. We just were like, here's a Google voice number, text us what you want. And no way that started to just kind of like take off. And it was the same thing where like, no, we were solving a specific problem. So people will people didn't care that, or they were able to get over that that like hurdle of it, right? Um at what point does it become serious enough for you uh to want to quit your job over and to want to do this like full time?

SPEAKER_02 35:15

I always knew. I I don't know that there was a defining moment, but uh, and I don't actually frankly remember if there was like one day that I sat down and said, I'm doing it. It was it was just like you just know. I think as an entrepreneur, there is something very like gut instinct. And when you see someone respond in the way that they probably did to these essentials, you just knew there was something, and you you have felt this problem so deeply. And so you have just utter conviction that there has to be a better solve. And so that that the I I think I probably said, I mean, if I don't do this, who's gonna do this? Like, I gotta do this. Yeah. So um I mean, everything else was like kind of fell into place. I mean, we did YC and that was a whole experience. Um, but yeah, even back then, I I think I just knew.

SPEAKER_01 36:01

What was YC like for you?

SPEAKER_02 36:03

Getting our butt kicked every week.

SPEAKER_01 36:05

Yeah. Um can you for somebody that knows vaguely about it, right? Knows that YC is a cool thing and the founder should do it. Um, can you give them like a primer on just what like functionally what it's like? What what the experience of doing YC is like? Warm Intro is brought to you by Wii Funder. WeFunder created this thing called the community round that lets you raise money directly from your community. So instead of going to VCs and rich people, angel investors, you can go straight to your friends and your family and your customers. And, you know, this is not a traditional ad read. I used Wii Funder for my company three times. We ran three rounds in Wii Fund and we raised over a million dollars. And I found that it completely changed how everybody felt about our business. Our customers all of a sudden didn't feel like they were just customers. They felt like they were owners in the business. They shopped with us more, they told their friends about it. My team felt like what we were doing was important because our community had shown up to invest in it. I tell every founder I can find to go raise a WeFund around. Especially for companies that care about community, there is nothing greater you can do than letting that community invest. Go to WeFunder.com slash join to check it out.

SPEAKER_02 37:28

To me, YC was stripping down to the core of are you shipping or not? And I remember in our group, small group, um our partner is Kevin Hale, every week he'd be like, Did you ship? And we would have we would be like, Oh, well, this happened and that happened, and the and the the mailman, like the the postal service, whatever. And he'd be like, Did you ship or not?

SPEAKER_00 37:53

Yeah. I know I knowing Kevin, I know exactly what that sounds like. Yeah.

SPEAKER_02 37:58

And if he didn't ship, like at which point do I need to come over to your house to ship for you?

unknown 38:02

Yeah.

SPEAKER_02 38:03

Because this is you, it just didn't get done. So every week that like stripping down of all of the whatever scenarios this uses, it was really um brutal and I loved it.

SPEAKER_01 38:16

Yeah. I I'm struck by how much that's kind of my takeaway. That was my takeaway from YC too. Is it YC is I felt like, was it is it two months, three months? What is YC? Oh my gosh. What is I don't know. Some number of months of other founders, more accomplished founders, telling you that doesn't matter. This doesn't matter. Doesn't matter, doesn't matter, doesn't matter. And until, yeah, you're exactly right. It gets stripped down to like, did you ship product? Did you get customers? And if you did those two things, you can go to bed. And that's it. That's all you need to do is ship product and get customers. I like even down to I have you found that like YC founders all we all kind of sound a little bit similar, at least when we talk about our companies. Have you noticed this at all?

SPEAKER_02 38:59

But I say more.

SPEAKER_01 39:00

Okay. I think that this is uh also the advice I give people when they're reaching out about like how to get into YC. I'm I the only real advice I have. I mean, at this point it was so long ago for me. Like I'm coming up on 10 years of having done YC, and I'm like, just focus on clarity. Just when you explain your company in the interview or in the video, just strip it of any marketing speak, strip it of any like the world's first, the first time anybody like revolutionary disrupting. Take all of that out. All YC wants to see from you is do you understand your product well enough to be able to explain it in plain terms, right? Like they don't need you to pitch it to them. They're smart enough to like understand the market potential and all that stuff, right? They just want you to come in and say, we are going to be a stitch fix for petite women, right? Like that is an easy to understand thing. And that let's start from there. I think like so much of the experience of YC, even down to like aesthetically what YC does, right? Like I was struck by how bare YC is like. Did you do it in Mountain View or uh back in the day, yeah. Yeah. So the Mountain View office is so bare, right? So except for that like very orange room. But there's um when you walk in, because I remember the partners told us at the time, uh, I think Sam Altman was, yeah, Sam Sam was still running YC. Sam was the CEO when we went through it. And um uh I think it was him or somebody talking about how like this bus full of tourists had come to YC and they were doing a tour of Silicon Valley and they wanted to see YC. And they were so fucking disappointed because it's just gray walls and like one gray sofa with the tiniest possible photos. You you remember the the you know the main room, the room you walk into? And I thought that that was a very like interesting kind of symbolic story for what YC is like, right? Because everybody thinks it's some big like production. Everyone thinks there's all this like kind of fancy, glamorous stuff going on. But in reality, the core experience of YC is stripping down, right? Of just like, no, no, no, no, no. Focus, focus, focus, focus, focus. It's so bare. And I think like it's still every YC founder, that's the way that I think every YC founder still communicates. There's this extreme emphasis on clarity, making sure there's absolutely no waste in any sentence when you talk about your company. Um, making sure like you you become so aware of like vanity metrics versus like real metrics and all this stuff.

SPEAKER_02 41:25

But um anyway, on that note, I mean the other way to say is do not bullshit. Yes, right. I mean, it's something that um is is super relevant today. Um, just like what are you making? Whose pain are you solving? Do not bullshit. I mean, you I invest, you probably do as well. It's like it's got it's gotta be somebody's huge problem that you're solving versus some, you know, pretty words. Um and I I think this is something that I also say to my team as well. It's like, don't get fancy. Just uh whether it's um writing comms internally or writing um a an email to a customer, just speak as if you would to a friend, to a human. Yeah, not don't write like uh uh you know jargon.

SPEAKER_01 42:09

Yes. You are speaking my language so much. I it's the thing I tell my team constantly is like start with like don't like start typing uh thinking what would a marketer say. Like literally write it in the barest form possible first, and then you you can always dress it up, but start with like like I there's um I'm a big Bob Dylan fan, and something he would say about like he always believed that all along the watchtower was his best song, best written song. And he would always talk about how you couldn't poke a finger through it. There were no gaps in it, there was no there was no fat on the sentences. And I I that's what I think good writing should feel like. It's like it's just if you can be one thing, be clear, right? Um, but as I'm I relate to that very much. I I'm curious about this part of your YC experience because this was a big part of mine. We you're in this group, right? For for people that don't know uh the core part of YC is you are in these groups, right? I'm I think they're still doing this, right?

SPEAKER_03 43:09

I yeah, I think so.

SPEAKER_01 43:10

I hope so. Um, and you sit down every week and you talk with the other companies in your group and you have a group partner and you go around in a circle, everybody talks about the progress you make, right? In that last week. Uh and I found it very difficult because everybody else was doing software. And so it was to go from a hundred to two hundred users is uh, of course, it's a lot of work, but it it's it's lines of code, right? And we for us that meant literally 200 shipments as opposed to 100 shipments. And it was such we missed multiple group office hours because my co founder and I at the time were just shipping out orders. We would miss dinners because we were shipping out orders. Um, did that happen to you?

SPEAKER_02 43:50

It's triggering a lot of uh past life uh memories, yes.

SPEAKER_01 43:56

Absolutely. Because it's the types of companies this is gonna all build up to a bigger. But like the types of companies that we've started don't kind of did when we started them, but like now really don't fit the mold of like what a silicon valley company is supposed to be. Um yeah, would you did you were you aware of that when you were going through YC? You're like, no, my I have a different type of company than everybody else here.

SPEAKER_02 44:19

Very similar to you. I felt keenly aware of the fact that that my company was a different beast. And um while some of the advice that um that YC gave and some of the other things that the other founders were sharing are very applicable and um, you know, it totally uh applies to SaaS, uh, we operate in the real world. And there's weather, geography, uh things literally things that are happening in the real world that impact how we do our business. So um I I found that I was thirsting for advice on um how do you hire a warehouse manager?

SPEAKER_03 44:58

Yeah.

SPEAKER_02 44:59

I mean, they would, they would, that's not something that they would talk about. Um, how do you um manage a group of people who are packing on the assembly uh floor? Uh I had no clue how to do that. So, you know, a lot of this, and I'm sure this is true for you as well, was figuring out going from sitting on the trading floor to the real world. Um one minute you're talking about, you know, even ah, and the next minute you're you're you're literally showing someone how to pick an order. Um traversing that spectrum was so challenging and exciting every day. It's very hard.

SPEAKER_01 45:41

I um I want to hear more about like it being entrepreneurship not being as glamorous as people think. It seems like you, because of what your mom did, you kind of already knew that it wasn't gonna be glamorous, but were you surprised by how much your lifestyle had fallen from being this like hotshot, cool corporate finance person in New York to like tapes and cardboard? Like, were you surprised by this at all?

SPEAKER_02 46:10

In the moment, it was too real to think about because I remember when we moved into our first warehouse on the first day the pipes burns burst. So I looked at the pipe, I look at the ladder and I'm like, well, there is no one else here. Yeah. So I pulled the ladder over and I climbed up to the very top of this. You know, it was a very tall warehouse little squiggly ladder, and I put duct tape, literally duct tape, the pipe. We survived those moments. Yeah, but in the moment, you just, you're just you're just doing it. You don't think twice.

SPEAKER_01 46:48

I was surprised by how much rodents were a part of my life all of a sudden. Because we we started off as a food company. Right. And the first thing you find out when you start a food company or a food warehouse is that rodents run your life. Like my co-founder and I would spend uh like late nights at the warehouse. That was also our office. And the first night we were there, the lights would turn off, and we thought somebody had broken into our warehouse. Wow. You heard it was I heard these like loud, like thumping or things like going up the steps, and we freaked out. So we had turned all the lights on. We're trying to figure out what's going on. It took us a couple of days to realize that they're uh the fact that I know the breed of rat that exists, it called Norway rats. By the way, rats are I have no problems with spiders. I am good with even cockroaches. Like I'm like, I'm I don't like them, but I can I don't I don't get weirded out. Rats drive me up the wall. But all of a sudden now I'm on paper, this 22-year-old uh founder and CEO of a YC backed company. Uh, there are articles being written about us, but so much of my day was about killing rats and not having rats get anywhere near our warehouse. And like um I I think um every day I would get in my car. I had a 2003 BMW convertible, which I had bought for$5,000. And I used to use it like a pickup truck. So I would literally put the top down on the car and pile it up with boxes and then strap them down and I would drive them over to the UPS in the Bayview, which I know that, yeah.

SPEAKER_00 48:23

You know that UPS, yeah.

SPEAKER_01 48:25

Exactly. I would back my my tiny little convertible into unload boxes, yeah. And um it was, it seemed like we were always on the verge of missing the shipping time, and we missed it like every other day. And I remember like the moment I realized how much how stressed my I was was so we used to ship food, and so we had like dry ice in these boxes. And if it didn't ship out that day, we have to the whole thing would have to get repacked. And I remember one time the I pride myself on like not losing, I don't have much of a temper, and I pride myself on not losing my like temper very often. I I think it's a very like unbecoming quality in a person, but anyway, that I pride myself on this. And I remember I got a call. I'm all of 23 years old, spent all day, and packing boxes with dry ice is a painful process because dry ice is very cold and your fingers get very, very, very, very cold and it like hurts. Like you can actually like you get immobilized for for brief moments. And we I dropped out maybe like 50 boxes, and this is all doing YC, by the way. And I went back and I used to have the same routine. I would go back to the McDonald's and 16th Street, which by the way also got shut down because a man walked in there with a raccoon like a week after. Again, more rodents as part of my life. But I we used to go to the McDonald's, and my only relief for the day was eating my double quarter pounder with cheese after shipping out orders. And I parked my car and I got a call from a number I didn't recognize, and I pick up and the person said, Hey, is this you? You you just dropped out of these boxes? And I was like, Yeah. And he's like, Yeah, these can't ship out, they don't have the right uh dry ice marking on them. And he started to just kind of like go off, sort of like kind of a little bit yell at me. And I said things that I like genuinely I'm still kind of surprised. I was like, Hey, hey, hey, man, who the fuck do you think you're talking to? And I just like I immediately just like lost my mind. And then I went and like he was like, Okay, fine, man. Well, ship them out. And I remember like this conversation ends, and I'm looking at this like double quarter pounder in my lap, and it was being like, Who have I become? What the fuck? Did I just say who are you talking to? Like it was also, it was way too much for my little brain. Like it was just way too much, and I had no understanding of it, you know. Every week we were trying to ship out, it was unglamorous, which I didn't have a problem with. I like kind of sort of prided myself on it, but it was like sometimes physically painful and often gross and like very full contact, but I don't know. I'm telling you all of this as if you haven't felt it or felt all the same things a hundred times over.

SPEAKER_02 51:01

I I mean food isn't food is next level.

SPEAKER_01 51:03

Right, you gotta deal with returns and stuff.

SPEAKER_02 51:06

Yes, but I mean, food, I truly have respect for you because food is totally next level. And I mean, we I think what you're describing is is the reality that as founders, uh, some most days we are one thin line away from total meltdown. But somehow you you keep it together because number one, you keep it together for your team. Um I mean one thing as I've as our team has grown, I feel immensely responsible. Um I feel responsible for everyone's livelihoods, I feel responsible for their kids, um, their families. Um, and it's not it becomes less about like these moments of total meltdown, and you're like, I gotta pick myself back to together. I pick myself up. Um certain phone calls and meetings where at the end of the meeting, I'm sure you felt this. You sit there and you're like shit.

SPEAKER_03 52:02

Yeah.

SPEAKER_02 52:03

And then you gotta walk out of the meeting and go to your next one-on-one and be like, hey, let's talk about your you know, XYZ. And you're there to support that person because it's not about you anymore. That has been a big, big lesson for me growing up as an only child, growing up where um, frankly, I I was more of an individual contributor than a team player. Uh, and I think that's made me much more conscious of the greater community, my team, um, the team of customers or the community of customers that we built, and just like the overall, the the bigger, the bigger picture. Yeah. And that keeps the moments of like the HVAC, the toilets are bursting. The toilets are bursting. That's happening.

SPEAKER_00 52:47

Yes, it has. It's very much so. Yeah.

SPEAKER_02 52:50

Some toilet is always always bursting. That keeps those moments sort of like, yeah, okay, you know what happened. Let's fix it.

SPEAKER_01 52:59

Yeah. I obviously relate very hard to everything you're saying. I also found that to be true because you know, you start off this thing in your 20s, and it's this like weird mix of glamorous on the outside and painful on the inside, right? And the thing that sobers you and the thing that keeps you going, uh, I find is this like sense of responsibility on one hand towards everybody else, like your team, your investors, even to yourself. And then on the other side, like, yeah, this uh if you're lucky, you fall in love with the work, you know. Um, and if you're not lucky, then you do it purely out of responsibility. But I do think that like in the best case, that's what I've seen happen to my favorite founders. Uh, you know, you included in that list. Like I it it sobers you, it makes you an adult. It like now when I talk to founders now, um, it's how I imagine pilots must feel talking to each other. Where there's this level of, by the way, if if anyone's if you're ever at an airport and you see two pilots talking, like position yourself close to them. I love hearing pilots talk. It's the same as like hearing like chefs, like Michelin Star chefs talk. Um you have this like uh you you develop this like vernacular um of um describing stressful situations. Even like down to like pilots never call it, no, at least the few pilot conversations that I've been eavesdropping on. You they will rarely say plane, they'll call it like bird or they'll call it a bus or something, right? Where there's something about that where like even verbally, you're like slightly de-escalating the intensity of the situation, right? And I think I feel a similar kinship. I mean, like talking to you right now, that like hour and a half long phone call we had before this. Um I you just feel like, okay, this is a without knowing the specifics of what you've gone through since starting your company, I have a very strong instinct for how it must have felt, you know? And I think like that's um it it tinges um everything about a person. Like to go through something that like um intense, it it sort of it it marbles your personality, it makes you a certain kind of person.

SPEAKER_02 55:17

That's why I worry about Gen Z.

SPEAKER_01 55:19

Yeah. Expand on that. Tell me more about that.

SPEAKER_02 55:22

A vast array of weird and challenging experiences makes you sturdy. Um and today, you know, you know, we we have we have all people from all different walks of life, different generations on the team. And uh I like that they intermingle and um give each other energy. I I do think there's something very going back to the thing about just being like brutally honest and being like cut and strip things down to the core.

SPEAKER_04 55:52

Yeah.

SPEAKER_02 55:53

I I I I worry because this does this just makes me sound so old.

SPEAKER_01 55:58

Um don't worry. I um I consistently sound like I'm 80 years old and it's my best. Okay, that makes you a bus. Yes.

SPEAKER_02 56:06

It's not that I worry. I I I think it's a question it's a question of like today when you are growing up in a different environment and maybe you're more protected. Um, how do you get that experience?

SPEAKER_01 56:17

Yeah. I do think that there's some sort of fundamental misunderstanding about what makes life worth living, right? What makes life like I'm I'm not saying you have it, I'm saying like with this new generation. I do now I'm really gonna sound a thousand years old. But and um at some level, I don't know if it's a just if it's a generational difference or if it's just the young people always tend to believe this, right? Uh, and young people of every generation will believe this. But the avoidance of misery is not what gives life meaning. And it's not what gives you joy, right? It's uh the overcoming of like um amounts of misery that you did not think you could overcome. Like I even I think about the word trauma a lot. You know, I'm I'm fascinated by that word. Like, would you okay, here's a quick one. Do you describe the experience you've gone through as a founder? Do you describe that as traumatic ever?

SPEAKER_02 57:13

That's a very good question. I think it it would be described as traumatic by standard definition.

SPEAKER_01 57:20

Perfect answer. Okay. Perfect answer. Can I uh look? This is the way you described it, is exactly how I think about it, also. That I can think of a lot of people that would describe it as traumatic. I don't choose to describe it as that. I believe in the concept of trauma. I think it's great that we learned that uh in the last couple generations, that in this last generation we realized that it doesn't only apply to soldiers. Like I appreciate that. But I think that there's something about calling something traumatic, right? That you label it as a thing that you can't even deal with anymore, you know? And I think when you call something traumatic, you make a statement about your ability to do that kind of thing. Um, and so at that level, like I'm very reluctant to call things traumatic. Because I'm like, yeah, it was some hard, it's like tough, but also like there are coal miners. Uh it wasn't that bad. Like there are it's um, it was hard and it like it taught me a lot. And there are moments that I felt really, really bad about myself. Um I'm not sure I'm willing to call it traumatic, though. Um, do you do you share that at all?

SPEAKER_02 58:30

Uh I I I I think it's sort of like this whole spectrum of human emotions, the whole spectrum of human experience, which like is funny because living here in SF, everywhere you go, it's an AI conversation, right? Yeah. Um, but ever since I was a kid, I love I love writing. Uh I love writing short stories specifically. And um, I really appreciate like I I I want this human aspect of us to it, it saddens me in a way, but anyway, this is getting off tangent. Um back to your question of like the trauma. I I like to think of it as like flavor. It's just going back again to the flavor of the human experience. Like flavor depth, spicy, salty, sour. Let me taste it all. I want to know what it's like.

SPEAKER_03 59:16

Yeah.

SPEAKER_02 59:16

And so we sort of protect ourselves from the flavor, then like what what what what is there left?

SPEAKER_01 59:23

Oh man, you're I'm shocked by how much we think the same way about this stuff. Like uh yeah, to me, like the isn't the great tragedy in life, the great tragedy in life isn't feeling bad things. It's feeling nothing, right? The lack of spice is far more painful than too much spice. Um, but yeah, I this has veered so far off my list of questions. I God, this is gonna be a very forced transition back in. Um let's talk about actually what was for me as an e-commerce founder a particularly painful, spicy time, which was, and I'm sure it was for you too, the pandemic. Uh all of a sudden, supply chains are shut down, you can't operate warehouse, you can't be in person, which is really hard for an e-commerce company, obviously. And very relevant to you, people aren't people don't know you work where as much anymore. Uh how hard was that for you all? Like, was it how did you deal with the pandemic?

SPEAKER_02 1:00:24

Um, it's again one of those things that I um as you mature as a founder, you you're sort of like um things that will things will come, things will happen, and you just take it one day at a time. It wasn't so sort of like this like um, oh, we have this militaristic strategy of like Q1 to Q4, this is what we're gonna do, this is how we're gonna overcome it. It was like, okay, we're gonna come in tomorrow, we're gonna keep shipping. Um, and yeah, carry on.

SPEAKER_01 1:00:55

God. How many times during the pandemic, or maybe just in general since starting the company, have you looked at the bank account or just looked at some piece of data and been like, yeah, I don't think we're gonna make it?

SPEAKER_02 1:01:07

Countless times.

SPEAKER_01 1:01:08

Yes. Right? Isn't it like it's like every other week or something?

SPEAKER_02 1:01:11

Yeah. I mean, you you know, you just you're like, okay, all right, we got two weeks. I mean, and there's I put in my own money. I mean, you we've gone through all the emotional aspects of this. Yeah. It is something that I think as a I was talking to someone yesterday and he said, Well, what are what is it really like to be a founder? And I said, It's it's this, um, it is like parenting in that there's no, there's no break. You don't, you don't, you don't sign off when you when you when you end the day. You your mind doesn't, you don't stop thinking about your company. You don't stop thinking about your team. You don't stop thinking about how do I solve this problem for the customer. It's like once the choice is made, it's a constant commitment. Um, and um, and yeah, and and that's something that you carry. It's an enormous burden and a privilege.

SPEAKER_01 1:01:55

Yeah. Um yeah, I I I think about that a lot too, about how it's not the hours that you work, it's how you feel in the hours that you're not working that's different about being a founder versus being, right? That um I I've had weeks where I was work I worked close to a standard 40-hour week. Um, what I can promise you is that the other hours of the day did not feel how they would for a person working at nine to five, right? Um I like that, I like that definition a lot. Um have you found that you know coming out of the pandemic, I I feel like this is a very under-reported story. Um that like there's a lot of talk of how, you know, here I'm talking post-2022 or so, right? Uh there's a lot of talk about how there's so much funding in the space and all that. Um, but when you really like double click into it, you realize, oh no, it's all going towards one. It's again back to the the young, hot rich thing, right? Like it's going to a very particular type of company, right? And um sucks for you and I that we are not that type of company, right? Um, few questions there. One is have you felt in that kind of period since the pandemic that Silicon Valley is optimized for a type of company, uh, and a type of person, and you are not that company, you are not that person.

SPEAKER_02 1:03:19

I mean, that's the whole my whole life story. Um being the underdog is painful. And it makes you want to fight so much more, and it makes the fight so much more fun. Uh, you're not armed with$30 million that you could just deploy any way you want. You're like, how do I actually build this? And you're looking at the bank account and you're looking at you, you need to hire, you need to, you know, ship, you need to uh service your customers. Um, and day one, operating with scarcity, I think just builds you into a different person.

SPEAKER_01 1:04:01

I have a two-parter um off of what you just said. One, I'm fascinated by this. And for the same reason that I'm fascinated by chefs, right? I am fascinated by the founders of consumer companies, which you and I both are. Um and the the interesting thing to me about our lives is the dichotomy between the the delicate, beautiful experience we're trying to create for a customer versus like the sheer running around through like flames with your head cut off that it is to run the company. Like to me, the like the split screen of that is so fucking funny. Um what uh the first part of it is let's talk about a beautiful picture you painted.

SPEAKER_02 1:04:45

I've never thought about it that way, but that's precisely just like the oasis of calm in the front end.

SPEAKER_01 1:04:52

With like just an ocean of madness in the back, right? Like it's um, I think it reminds me of like when you watch Bear or something. I bear is hard for me to watch that show because it does remind me too much of being I have been locked inside a walk-in freezer before. So it's a it's not as fun to watch because we've a lot of my life was spent in walk-in fridges and walk-in freezers when I was running it as a food company. Um, but that that moment that uh exists in Bear and in every cooking show, right? Where like everybody's yelling at each other and like damn near hitting each other with pots and pans and like stabbing each other with like really nice chef's knives. And then the person walks out of the kitchen, the doors fling open, and it's like perfect calm and beautiful music. And just like that, I think is a very beautiful thing for me. But I want to talk about the delicate part of that for for you for a second. Um tell me about like the journey that when a woman such as yourself, having lived the same kind of consumer experiences that you lived that led to you starting this company, when a woman signs up for short story, which rather I also love the name, but she signs up for short story and she goes through that experience, starting with a quiz and then on down to Like getting the box and opening it up. What are you hoping she feels at sort of every stage of that journey? What do you hope that being a short story customer makes her feel like?

SPEAKER_02 1:06:10

The number one thing is to be understood. I I want her to feel like we deeply understand the not just the obvious things that you know your pants are too long or whatever, but somehow the feeling that you're feeling a little less put together. You're feeling maybe a little frumpy. You're not feeling good about what's going on here. And if if the the understanding that like something that looks good in a photo could look disastrous on your body, like that is another level of understanding. So we we shoot all our uh clothing on actually petite models for this reason. Um, because so many times, you know, you would go to Zara, you would go to like what whatever, you would see something, and then you would put it on, you'd be like, This is a joke, right? Like this has gotta be a joke. Uh I mean, it's just ridiculous. Um, so the understanding of okay, like actually, actually, we do get it. Um, and then the second thing is um competence. Uh competence as in we've done the work, we've done the research, we have graded the pattern ourselves. Um, we have a technical designer who looks at every centimeter of you know, this the saddle, we call the saddle on a denim, um, and graded it accordingly, because that is what it takes for a proper fit. Um so the the the understanding and the competence, and and then leads to um the third piece, which is like like a like a like a relationship. It's a human voice. And I know that today you can go on Google shopping and you can like upload your photo and it can generate like the AI stuff. Yes, it's it's wonderful. I still think my theory is end of the day, there's nothing that replaces you and I sitting here, yeah, having this conversation. I I get to know you, you guys know me. It just feels it's very personal.

SPEAKER_01 1:08:10

Um I can't overstate how valuable that just one little part of what you said even is, right? The experience of seeing a model that has your body, looks like you, right? That I uh, you know, I had this experience kind of somewhat late in life. I'm not I've never been that focused on my appearance. I was lucky that my parents didn't raise me with too much of I like design, I like like putting together clothes, all that, but I never was that focused on my appearance. It just wasn't an important part of my self-conception.

SPEAKER_02 1:08:42

I I feel like there's an aesthetic, but like a strong aesthetic coming through.

SPEAKER_01 1:08:46

Yes. But to me, I make the distinction between design and and um and appearance I get or aesthetics where I care a lot about design and I love designing a silhouette uh for the clothes that I'm wearing. I like designing anything in my life. Like I think designing your life is very like you know, um fulfilling thing, right? Yeah. Um but I there was something about the experience recently of watching Mamdanny in New York become, yeah, get elected, whatever you think of his policy, to like some, don't like some. I don't care about any of that. Um but the experience of him becoming like a hot person, that people were like, yeah, I think he's hot. But it was like the idea that he was desirable. Like I've I've I have known Indian men to be considered hot in America. That's not that unique. But the fact that he's like uh he looks like a cousin, I would have. He looks from certain angles like me. Like we deal with the same type of like jowl fat problems, the same type of like belly fat problems with the same way our facial hair comes out. And there was something really beautiful to me about seeing all these like cool young people be like, uh, oh yeah, no, the the hottest person in America right now is Zoran Mamdani, which I and again, a fully recognized people aren't like it's because he's successful and he's good at other things, whatever. But I thought that was a very like um, I remember we had to shoot an episode the day after his inauguration, and I wasn't feeling good about my left camera angle. And I remember watching him, I'm like, oh, he's got the same angle. Like he's got the same angle problems, and it made me feel so much better. Like it's the same day about the uh about the episode. But I think that's a really powerful uh idea you're talking about of like being seeing yourself in a model, right? Like seeing seeing yourself represented even at the level of marketing now. So that's the beautiful part. Uh let's switch over to the other side of what your day looks like today. Um, I'll give you three emotions. Uh tell me like what share of your day is sort of driven by each of these emotions, right? You can throw in more if you want.

SPEAKER_03 1:10:59

Okay.

SPEAKER_01 1:11:00

But uh three three emotions I have for you are dread, ambition, and joy. How much are each of those feelings a part of your day?

SPEAKER_02 1:11:11

So we so we know there's type one fun and type two fun.

SPEAKER_01 1:11:16

I'm I'm not familiar with this concept. What is this?

SPEAKER_02 1:11:18

So sort of like type one fun is when you're having fun in the moment.

SPEAKER_01 1:11:21

Okay.

SPEAKER_02 1:11:21

Type two fun is when you look back and it you felt it was fun. But in the moment it did not feel fun.

SPEAKER_03 1:11:28

Yeah.

SPEAKER_02 1:11:28

I I think for I'll I'll say this and then I'll answer your question. Yes. Um for me today, a lot of it is, you know, we're past this the initial zero to one stage. Now it's about scaling and is more type two fun. Meaning in the moment when I'm building a scale out plan, isn't is it's it's exciting. But is this something that I'm like, oh my god, this is something I want to do every single day, is figure out head count. Not not not particularly.

SPEAKER_04 1:11:57

Yeah.

SPEAKER_02 1:11:58

Um but I think when you zoom out and see ah, we went went from here to here to here, that's that's very rewarding. And that's the joy part. I think for dread, I I I I still dread um having certain meetings. Yeah, this is a reality of founders, right? Um you're looking at your day at 9 a.m., you're like, damn, the whole day is meetings. That's when I feel dread. Not because I don't like the people who I'm meeting with, but it's like I need time to think. I enjoy thinking. That's probably why you started a company, is you wanted to think and solve problems. Um what was the third one?

SPEAKER_01 1:12:37

Ambition.

SPEAKER_02 1:12:37

Ambition. Oh, uh uh ambition. I don't think it's an active feeling that I feel.

SPEAKER_01 1:12:42

Yeah. Responsibility? Is that in there?

SPEAKER_02 1:12:45

Ambition in the sense that I want us to become a great brand. I want us to become a great company, but less so that I think it's more long-term nowadays. I still obsess about revenue. I look at our our daily revenue chart every day, which I'm sure you do too. I'm like, oh, here, here, here. But but again, it's like zooming out. It's ambition at this stage for me is about building a great brand that people respect, that people want want to work at this company. It's less about this week's revenue.

SPEAKER_01 1:13:18

Um, yeah, I can I can really relate to to all of that. You know, I I have to say that I think um what is it for you? Um, oh I I I think less so now, but there was a good solid period where dread was a really big part of my day. And for me, it was it would start off early in the morning. I would wake up with a feeling of dread, and I would kind of spend the whole day living that down. I think I used ambition to numb out some of the the dread I felt, because it was it's easy to abstract. I see, especially a lot of men do this, young men. Um you take how you're feeling, which is a you feel not seen, you feel uh overlooked, you feel small, you feel, you know, whatever you feel. You feel these like bad emotions that are common for any young person, but especially for a young founder. And then you sort of put, you take yourself out of it by thinking about how big of a deal you're gonna be one day. Uh it's the cheapest form of cope, but by God, does it work? Like it does really get you through a lot. I don't recommend it. And I think I ended up spinning my wheels uh in place for way too long because I had these like I was putting myself to bed with these lofty ideas of what I was doing, these lofty stories, like so sort of self-glamorizing what I was doing. Um, so I would say I had a lot of dread, and the more dread that I had, the more ambition I kind of developed as a sort of a like a numbing mechanism, as a coping mechanism. Um joy wasn't really a part of my life at all in the middle there. I think what has been really beautiful in the last few years has been I have allowed uh joy to be a bigger and bigger, and especially creative joy, the the joy of taking on something new and like really falling in love with it. I try to give that as much space as I can. And the more I do that, the more dread and ambition sort of get chased up in the best possible way. Like the reality is I'm reflexively ambitious, as are you, right? Like, otherwise, you don't do shit like this. Like it's we all want to build a really big company, we all want to make money, we all want to do all that stuff. I don't need to remind myself of my ambition.

SPEAKER_02 1:15:31

Like, I just don't need to remember yes, exactly.

SPEAKER_01 1:15:33

I will I'm reflexively ambitious. I just try to, I want my day to be dictated by as much joy as I possibly can get. And that could be both type one and type two joy, right? Um but so that's that's kind of the answer for me. Um but anyway, people people hear about me a lot on this fucking podcast. Coming coming back to you.

SPEAKER_02 1:15:53

That's really interesting.

SPEAKER_01 1:15:55

Um you know, it to me, you are like I truly mean this. I'm not just like gassing you up. Like I really do feel this way. Um to me, you and their handful of founders like this, the founders of mostly uh consumer companies and e-commerce companies are like uh you're like the platonic ideal of a founder. To me, this is what uh we are all supposed to be. We're all supposed to be able to put up with ridiculous amounts of stress and stupid shit and put out beautiful products day over day, week over week, year over year, continuously grow, like have both the vision of this like bigger thing you're trying to build and then the chops to run what how big is the team now? Well, I know at one point it was 120 people, right? So like it's I don't know, but like the being able to manage both the vision and also like the complexity and the minutia of running a team. To me, like what you have pulled off since 2019 or uh 2018 is like it truly is the platonic ideal of like what it means to be a founder. Um and Silicon Valley, I think, pays a lot of lip service to that by like we're about founders, we are a firm, we are a VC firm by founders for founders, we're a podcast about founders. Like, shut the fuck up. You make content for AI B2B SaaS founders, okay? They're founders, but they don't represent all founders, right? And I think like that's a lot of what Silicon Valley like pays lip service to, but isn't actually about so I guess the first part of this is me like, I guess, giving your flowers if you haven't gotten them. Receive, receive bootcase. Cool. But then the other part is like, is there any frustration that you feel? Again, it's similar to it's all comes back to like, yeah, it's designed for someone else idea, right? Like, is there any part of you that feels frustrated that you're like, I'm as good as, if not better, than any founder out there? And this shit is being made unnecessarily difficult for me. Um, because and I'm being overlooked.

SPEAKER_02 1:18:03

You know, I I've never minded being an underdog. Again, like we go back to that concept. Um I I know there's a lot money sloshing around. And who doesn't want to get giant piles of money thrown at you, right? And we all that's great. Um, I never had that. And I'm not gonna make it a pretty picture like, oh, I didn't want that, and like, oh, I was too good for that. Of course I wanted um, you know, when we were raising our seed to to to have the same long line at demo day that some other companies enjoyed, which I did not have. Um, but I truly I don't mind it today. I think it's it's always hard. It's it's every it's hard for everybody, just in different ways. So if you can sort of like find like the mental image I have is like in the, you know, the deep um volcanic ashes, there's a sword being forged. Like it's every day is being sharpened by the the forces of gravity. Like that's the image that I have. Like I'm I'm under a lot of pressure, tremendous pressure as founder. You're under a lot of pressure every day. And that can we turn that pressure into something useful? Um, and in some ways, I kind of shut out the rest of the world. Like so and so they raise whatever. I don't give a damn. Yeah, good for them. I really am happy for them. Great, but it's not us. It's not our path, and we weren't gonna be on our own path. So the The Hobbit is one of my favorite movies. Um I just I have the the Hobbits, uh, you know, they're they're they're they're small creatures, uh, not a lot of height, but a lot of adventure and a lot of um fight.

SPEAKER_01 1:19:43

So um I have this like thing I've been kind of dealing with that I've been trying to just kind of been meditating on this concept for a bit. And I really want to get your I think you're the perfect person to ask about this. Um it starts with sort of like a meta debate uh about America, but then it I kind of see it everywhere and see it's about Silicon Valley, see it even about like the fashion thing that we're talking about, the world of fashion, um, which is, you know, there's this notion about America that it is a creedle nation, right? That we are uh the thing that sets America apart, this is what pe proponents of this will say, and I'm very partial to this. The thing that sets America apart is that you can't just move to China, you can't just move to India and become Indian, you can't move to Germany. This is Ronald Reagan in his farewell speech, right? You can't move to Germany and become German, but you can move to America and become American. That's on one side, right? And then on the other side, um, I don't know, I was hearing big jump. You know Hasan Menaj, uh the comedian. Of course. So it was an episode recently where he had Kumel Nangiani on from also a comedian, and they're discussing if they've ever felt American. And uh Kumil says, I've never felt American, even though he's been a citizen for a decade plus. And he says, I do think that membership in a group is at some level dependent on other members of the group accepting you as one of their own. And I've been thinking a lot about that in particular because of the political moment we're living through. Like um, I know a lot of my identity is a little bit different than I think the children of immigrants very often, right? Um, you and I are the same, and like we immigrated slightly different ages, but we both actually went through the process of immigrating, right?

SPEAKER_02 1:21:29

I think we're called the 1.5 generation or something like that.

SPEAKER_01 1:21:32

Yeah, perfect. So we're, you know, as like 1.5 generation immigrants, right? Like, I find I'm like really wrestling with that idea a lot of um there's this kind of lofty vision of Silicon Valley as like a place that dreamers come and can start whatever. Uh, or if America is a place where anyone can build the the dream and become American. And on the other side, there's this reality of like, well, can you really become American if half the country will never see you as truly America? Uh, can you really be part of the Silicon Valley experience if much of the valley, or at least the gatekeepers, don't see you as part of the club? Um how do you think about that? How important is it for you? I guess just that's the main question is like, does it even matter if um like my wife, who's a first generation American, her parents immigrated, she has a very different uh uh answer to this than I do. But to her, it's like, yeah, I don't give a fuck. Like, you don't you don't have to see me as American? I don't care. I'm American, I feel American. But I I moved here as you know, almost an adult. Um, how do you think about that? Where where do you land on like to what degree is your membership of a group contingent on other members of the group seeing you as part of it?

SPEAKER_02 1:22:54

This is a very interesting question. Um, I think I've been very lucky in the sense that I I'm I'm dull in some ways. I'm not sensitive. I'm not very sensitive. And I just go like it's like when you go to a party and you you have people who you don't know. And you know, for me, it's like I just I start, you know, grabbing a drink. Hey, what how's it going? Like, nice to meet you. And I just sort of go right into it without thinking too much about it. And so I think I've been first of all very lucky in that I can't coming to this country, going to ESL class. I don't know if you've ever did that. Uh no. Okay. Yeah. I took ESL class and just very quickly um learned that I think the bottom, the ethos is it is still a very accepting place. Because I've lived in places that aren't that even today, in spite of all the craziness. So I I I feel fortunate, I think, um, on the whole.

SPEAKER_01 1:23:48

And you feel the same way about Silicon Valley, did you say?

SPEAKER_02 1:23:51

Last weekend I went to Hackathon. Um, there were like a hundred people there. There were engineers, non-technical people, designers, and it was just like everybody in a room and let's build. I don't doesn't matter your experience, how much money you raise, are you a founder? Let it was just a group of people building and then looking at each other's work. And I really like that environment. It just does not matter your title or anything. It's just again the question, what are you working on?

SPEAKER_01 1:24:17

Yeah. Yeah. You're I had I went to a YC event after years recently, and I had that exact feeling where I was like, oh man, I forgot. My dumbass thought that Silicon Valley was lives on Sand Hill Road. Um, no, no, no. Silicon Valley lives in these rooms. Silicon Valley lives in this conversation, right? Um, you invest now also.

SPEAKER_02 1:24:40

Um I do think there should be a short ETF for all the startups that are blowing smoke.

SPEAKER_01 1:24:45

Yes, 100%. There should be some way to short all of them. Um, but you know, so actually that that brings me to to you know one of my final questions here, which is uh you invest now, right? And um what do you uh forget the company for a second? Like, what are you looking for in a founder when you talk to them? Um, when you're deciding whether or not to invest in someone.

SPEAKER_02 1:25:08

I find that I'm really drawn to people who are tinkers.

SPEAKER_04 1:25:13

Yeah.

SPEAKER_02 1:25:13

They tinker around something on their own time. They are not the the first moment that they pitch something to you is not the first moment they've thought about this. They've been thinking about this thing for years, for decades. This is something that annoys them or something they've been struggling with, and they just can't help themselves but think about this all day long. I love seeing that, and that really gets me lit up when I see the deep uh the the deep drilling very deep for a long time on some kind of problem. And then I'm like, you really do know this stuff. Yeah, and you could talk about this for like 12 hours. I can see that. That that makes me very excited.

SPEAKER_01 1:26:01

Um yeah, I uh I I bet you'd be really good at this. I have found with e-commerce founders, uh you ever hear the thing that like um uh you can figure out how many uh if an animal is a predator or prey, you're not figure out like it's very strongly correlated with being a predator or prey, how many shades of green they see. Because like they're animals that need for their survival one way or the other to be able to see the difference between different shades of green in the wild to be able to. I feel like with e-commerce founders, it's shades of gray with like that you put in the background. I can spot F5, F5, F5 from like a mile away. And I can spot E E1, E1, E1. Like these are RGB codes for people who are very keen to reaching out. No, I'm such a dork about e-commerce. Like, I think to me, those are very different choices about the brand you're really. And I just I I love the the the way that you're describing that's also my sort of like favorite type of founder is just uh yeah, because you're letting your curiosity drive, and then you're building the grit needed to keep working on the thing you're curious about, right?

SPEAKER_02 1:27:04

Actually, my co-founder is such a person. Uh, there's this game called Factorial. And basically, like you build you build a where like an assembly line. And so we'll work like a 12-hour day, and you know, he will go home and he will play this game for another six hours. And I'm like, what is wrong with you? You literally want to do this for six more hours?

SPEAKER_01 1:27:22

It's like Dwight in the office, uh, is playing Second Life, but in a second, like his Second Life is literally just his actual life. Yeah, it's he is still called Dwight Shrewd and he double. Yeah, that's really funny.

SPEAKER_02 1:27:34

Same mode, never changes.

SPEAKER_01 1:27:36

Um, let me flip this on to you for a second, which is what do you think has made you so successful as a founder? And how have you how are you finding yourself changing at this point in your career as a founder? How are you finding yourself um uh yeah, shaping up shaping up differently from maybe how you expected you would? Like uh are you finding yourself becoming more sensitive to the These things less sensitive? Are you finding yourself becoming more focused, less focused? How how have you sort of mapped your own development?

SPEAKER_02 1:28:09

I think the biggest thing that's changed about me is I have learned to shut up.

SPEAKER_01 1:28:14

I have not learned that yet.

SPEAKER_02 1:28:15

It's very, very, very difficult when you see when you have a gut reaction to a business problem and you're like, I know exactly what we should do in this moment. And to not say that thing and to let someone on your team say, I think we should do this or whatever is very difficult. But I have to force myself to stop and say, What do you think?

SPEAKER_01 1:28:37

Okay. Final question. Um years from now, people look back at the story of your career. Um, what do you hope firstly? I guess who do you hope hears your story? And what do you hope that person gets, feels from hearing your story?

SPEAKER_02 1:28:57

I think that being an underdog is a great advantage. I feel they I hope they it it it you ever read the book The Hard Things About Hard Things?

SPEAKER_03 1:29:06

Many times.

SPEAKER_02 1:29:07

And the flip side is like many things are easy. I mean, it's it's it's great, it's great when things are easy. But there's something very, very joyful, very deeply satisfying when you've done a hard thing and you continue to do it again and again and again and just see what you're capable of. That's very powerful.

SPEAKER_01 1:29:27

That is very powerful. I think it's a great place to end. Isabel Sun, thank you so much for bringing on a podcast.

SPEAKER_02 1:29:32

Thank you for having me.

SPEAKER_01 1:29:37

Warm intro is produced and edited by J Wan Moon and Alex Aiko. Hosted by me, Chai Mishro.