The Exchanges

Q Can I ask, you mentioned there about kind of utilizing inventory in a very smart way to preserve kind of the valuable cash that you had in the early days. Can you unpack that? How did you do that from a mechanics perspective in terms of cash preservation aligned to the inventory?

A Well, I mean, it's, it's simple, you know, you buy inventory up front, and then you pay your vendors at a certain time, but if you can actually extend your payment terms so that you're collecting cash From your customers before you're paying your vendors, then, you know, then you have like, you have a cash cycle that works. And so, you know, what we, we turn the inventory very fast. I mean, even today, we turn our inventory over six times a year, where, you know, a lot of traditional retail turns at something more like four. So if you're turning your inventory six times a year, and then you can have your payment terms such that, you know, you're like, just as a very simple example, if you're buying something at a 50% margin, like you just have to sell through half of your inventory before Before you pay your vendor in order to be able to not use cash to buy inventory. And so that's a good example, you know, on the marketing front, the product market fit of this, you know, of this concept was so strong that we grew in a really viral way for the first many years. And, you know, and this was viral, not necessarily in like a tricky, you know, kind of digital way. Like this was genuine, just like people telling other people real word of mouth. And, you know, when you're able to grow your business that way with very little upfront marketing, then that also promotes Cash and capital e…

AI assessment note: “extend your payment terms so that you're collecting cash From your customers before you're paying”

Q Which angels done? I always love kind of shining a light on amazing angels. Which angel did the most to help the company, and how so?

A Oh, I mean, I've been so lucky to have just incredibly supportive investors. I really only had two angels, if I'm honest, and so the first to Kinderson Cassidy, I mean, she gets credit for, frankly, like, being the catalyst for everything. I mean, she was the first person who committed money to Stitch Fix, and she actually was a critical connection to Steve Anderson, who ended up being our kind of substantial angel from, um, from a financial perspective, and Steve is actually a Still on our board, you know, he's been so supportive, and he's, I don't know, he's been, like, both emotionally, like, an emotional support help for me, but also, you know, helping with recruiting, and so, you know, both of our only angels were incredibly important in the, kind of, success of the company.

AI assessment note: “both of our only angels were incredibly important in the, kind of, success”

Q it was really in the realization that you went from nought to a billion in five years, and you raised just forty-two million by the time of the IPO, which, especially, like, today in today's fundraising market, was just kind of staggering for me, and so my first question around that is, like, on reflection, are you happy that you were forced to be so capital efficient so early on?

A I mean, you know, it's, it's near impossible to turn back time, and it's just, like, hard to turn back the decision to And imagine what could have been, You know, I can look back now and say, there's so much that we learned by being capital efficient. Like, you know, we, we are forced to be capital efficient. And so we really had to understand how to turn our inventory in a way that we didn't have to use valuable cash to fuel our growth in the inventory front. We had to really understand the customer journey and understand, you know, when we spend money to acquire customers, what does that payback period look like? You know, there is so much really good hygiene around really understanding the business and really understanding the economics of the business that was forced. Through capital efficiency that I am grateful for now, but you know, the flip side is like, you know, you think about, you know, we, there's just, you know, raising hundreds of millions of dollars, like it's such a huge advantage. And like, I think it was really hard to watch a lot of, you know, like mostly male founders, many who are bombastic and, you know, have these big visions. And I felt like my vision was big too. And, you know, and to be able to raise so much money when I really struggled to raise the little money that I did. And, you know, when you raise that much money, like you can, Hire amazing peo…

AI assessment note: “yeah, I feel really, really grateful for it, but I also”

Q kind of preserving the cash there. I guess my question to you is like, with that kind of hindsight that you have, how do you think about weighing the two different levers of growth versus profitability? I always kind of think through it in my head. Kind of flip-flop back and forth, as we were saying. How do you think about kind of weighing the levers of growth versus profitability?

A Well, I mean, I think first and foremost, there's a baseline. There's like a hurdle before you're even, before you're thinking about trade-offs. There's a hurdle of just like, is, does the math work? Like, does the unit economics of the customer journey work? And that, so assuming that that is true, then I think it's always growth. Like, I think especially in those early days, you know, growth is the accelerant. Like, growth is what gives you momentum. And most are looking at market opportunities that are huge. They're in the billions of dollars. In our case, it's four hundred billion dollars. Like when you're looking at a market opportunity of four hundred billion dollars, you know, growing at 20% year over year on a twenty million dollar run rate, like that's not going to get you even close to kind of making the most of that market opportunity. And so, you know, I do think growth is almost always going to be most important, predicated on the fact that, you know, this is a healthy business and one where the math works.

AI assessment note: “assuming that that is true, then I think it's always growth”

Q yours before, and I want to start a little bit before Stitch Facebook. Because you mentioned before about working in Banana Republic, and as a lifeguard, and I always feel that, kind of, these experiences are so formative to how we think today, and big lessons in that, your first jobs. What do you think were your biggest learnings from those first few roles, and how it impacted your mindset?

A I mean, there are so many things. I mean, one thing was just, like, both in those jobs, in the Banana Republic job, and in the lifeguard job, like, so much of what I loved about the job was the people that I worked with, and I think that really persisted of just, like, you know, we are all human, like, Like, we all have a limited number of waking hours, and we spend a lot of those waking hours at work, and so really thinking about what is it that makes work rewarding? What is it that people enjoy about those roles, and how can I make sure that those are part of the culture, I think, is something that really persisted, and, you know, I just also think, and I think every entrepreneur kind of knows this because you start by building these basic building blocks, and everybody has done everything, but, you know, I do think it also just, like, the humility of the frontline work is Super important. Like, it's just remembering that every single process and, you know, new thing that we're doing and that everything we're doing is really impacting the work, you know, from packing the fixes all the way to, you know, the technology that's allocating fixes to warehouses, like all of this is really interconnected. And, and so I think just like it, you know, having all of the different jobs really gives you a deep appreciation of the hard work that goes into business. And also, you know, the k…

AI assessment note: “the humility of the frontline work is Super important”

Q I love that in terms of kind of bringing the vulnerability to the table. A question I have to ask is, like, absolutely, it works in the early days. How does that change when you're a public company? Can you have that vulnerability To be so open about the challenges and the struggles when one is a public company CEO.

A Yeah. I mean, the sphere of what you talk about changes a little bit, like, you know, obviously we're not talking about business results, you know, in between quarters and, but like, you know, at a high level, like the business results within quarters are not actually the hard things. I mean, you know, the last nine months have been the hardest like time of my leadership period. I mean, between COVID and, and between the racial injustices that have, you know, come that we've been seeing so clearly, um, between this, You know, this very tumultuous presidential election. I mean, all of this has been just, you know, some of the most challenging times of my leadership. And also, I know these have been some of the most challenging times and frankly, of everybody's experience in the last few months. And so, you know, I think being able to talk about some of those things and the impact that it's had on me and how challenging it's been, like a lot of people can empathize with that. Like we are all going through this together. And I think, you know, maybe there is a 20, 30 year ago version of leadership where we thought that people making decisions were in ivory towers and knew everything and You know, more and more, I think we're realizing that, you know, we are all human, and we are all trying to do the best that we can with the information that we have, and to be able to build that t…

AI assessment note: “the sphere of what you talk about changes a little bit, like, you know, obviously”

Q it was really in the realization that you went from nought to a billion in five years, and you raised just forty-two million by the time of the IPO, which, especially, like, today in today's fundraising market, was just kind of staggering for me, and so my first question around that is, like, on reflection, are you happy that you were forced to be so capital efficient so early on?

A I mean, you know, it's, it's near impossible to turn back time, and it's just, like, hard to turn back the decision to And imagine what could have been, You know, I can look back now and say, there's so much that we learned by being capital efficient. Like, you know, we, we are forced to be capital efficient. And so we really had to understand how to turn our inventory in a way that we didn't have to use valuable cash to fuel our growth in the inventory front. We had to really understand the customer journey and understand, you know, when we spend money to acquire customers, what does that payback period look like? You know, there is so much really good hygiene around really understanding the business and really understanding the economics of the business that was forced. Through capital efficiency that I am grateful for now, but you know, the flip side is like, you know, you think about, you know, we, there's just, you know, raising hundreds of millions of dollars, like it's such a huge advantage. And like, I think it was really hard to watch a lot of, you know, like mostly male founders, many who are bombastic and, you know, have these big visions. And I felt like my vision was big too. And, you know, and to be able to raise so much money when I really struggled to raise the little money that I did. And, you know, when you raise that much money, like you can, Hire amazing peo…

AI assessment note: “there is so much really good hygiene... that I am grateful for now”

Q I love that in terms of kind of bringing the vulnerability to the table. A question I have to ask is, like, absolutely, it works in the early days. How does that change when you're a public company? Can you have that vulnerability To be so open about the challenges and the struggles when one is a public company CEO.

A Yeah. I mean, the sphere of what you talk about changes a little bit, like, you know, obviously we're not talking about business results, you know, in between quarters and, but like, you know, at a high level, like the business results within quarters are not actually the hard things. I mean, you know, the last nine months have been the hardest like time of my leadership period. I mean, between COVID and, and between the racial injustices that have, you know, come that we've been seeing so clearly, um, between this, You know, this very tumultuous presidential election. I mean, all of this has been just, you know, some of the most challenging times of my leadership. And also, I know these have been some of the most challenging times and frankly, of everybody's experience in the last few months. And so, you know, I think being able to talk about some of those things and the impact that it's had on me and how challenging it's been, like a lot of people can empathize with that. Like we are all going through this together. And I think, you know, maybe there is a 20, 30 year ago version of leadership where we thought that people making decisions were in ivory towers and knew everything and You know, more and more, I think we're realizing that, you know, we are all human, and we are all trying to do the best that we can with the information that we have, and to be able to build that t…

AI assessment note: “the sphere of what you talk about changes a little bit”

Q Not at all. I've been excited for this one for a long time, so I would love to start with some context. How did you make your way into the world of startups, and how did you come to change the world of fashion, really, with Stitch Fix?

A You know, I was definitely not, like, a born entrepreneur. I didn't have, like, a lemonade stand growing up, but, but, you know, I became really passionate about the The space of like really understanding the problem of there is so much fashion out there. There's so much apparel. There's so many brilliant designers. And yet the process of figuring out what are the best things for me is so broken. And, you know, the store's world is broken for obvious reasons of just putting every single skew on the floor and expecting people to sift through it. But what was interesting was just, you know, kind of e-commerce and online and all of the kind of new technology to me still didn't solve the problem. And so I became really, really fascinated with this What is buying apparel going to look like 20 years from now, and how can I be part of that future? And it was a little bit of a wandering path, but, you know, candidly, I would have been perfectly happy working at Stitch Fix, but when I spent a lot of time in the landscape and understanding what are companies doing, and, like, who is at the forefront of what's going to be the future of shopping, I really didn't see any kind of opportunity that I felt like represented that future, and so, you know, I kind of, by, I guess, process of elimination, really, arrived at the The conclusion that if I wanted to be part of that future, that I could …

AI assessment note: “arrived at the conclusion that if I wanted to be part of that future”

Q Can I ask, you mentioned there about kind of utilizing inventory in a very smart way to preserve kind of the valuable cash that you had in the early days. Can you unpack that? How did you do that from a mechanics perspective in terms of cash preservation aligned to the inventory?

A Well, I mean, it's, it's simple, you know, you buy inventory up front, and then you pay your vendors at a certain time, but if you can actually extend your payment terms so that you're collecting cash From your customers before you're paying your vendors, then, you know, then you have like, you have a cash cycle that works. And so, you know, what we, we turn the inventory very fast. I mean, even today, we turn our inventory over six times a year, where, you know, a lot of traditional retail turns at something more like four. So if you're turning your inventory six times a year, and then you can have your payment terms such that, you know, you're like, just as a very simple example, if you're buying something at a 50% margin, like you just have to sell through half of your inventory before Before you pay your vendor in order to be able to not use cash to buy inventory. And so that's a good example, you know, on the marketing front, the product market fit of this, you know, of this concept was so strong that we grew in a really viral way for the first many years. And, you know, and this was viral, not necessarily in like a tricky, you know, kind of digital way. Like this was genuine, just like people telling other people real word of mouth. And, you know, when you're able to grow your business that way with very little upfront marketing, then that also promotes Cash and capital e…

AI assessment note: “extend your payment terms so that you're collecting cash From your customers before you're paying”

Q six billion sight unseen. It's kind of scales of success that it's difficult to think through in the early days, and so I guess my question is, how important do you think vision is, and do you think actually it's very difficult to have vision, because it can be limiting, because you can kind of accept it when actually that's only a percent or so of what you can achieve?

A I mean, I think the notion of having this, like, bold aspiration is critically important. I think having this North Star, having this, like, you know, this is the crazy thing that we're doing that nobody else is doing, like, that's such an important I'm part of an entrepreneur and a company, really, of really having that connection to what that broad, like, aspirational vision is. I think where you have to be a little bit flexible is the how you get there, and I mean, that part's super interesting of just, like, even, like, the kind of transformation that we're going through now at Stitch Fix of, like, we sold six billion dollars to close on site unseen. That means we have this incredible capability that we've built around apparel recommendations. How do we now take that kind of capability and expand Expand from fixes and into other ways of buying from us. And that in and of itself is, is a pretty big change. And I think like being able to be agnostic to how you achieve the vision and being able to allow that kind of how we get there to evolve over time. Like there's a little bit of humility to that. Like used to always, I mean, I feel like we've all been absorbed in politics of late, but you know, like in politics, it always drove me crazy that people would, would talk about flip-flopping as though it was a bad thing of just like, I used to believe this and now I believe that.…

AI assessment note: “the notion of having this, like, bold aspiration is critically important.”

Q Which angels done? I always love kind of shining a light on amazing angels. Which angel did the most to help the company, and how so?

A Oh, I mean, I've been so lucky to have just incredibly supportive investors. I really only had two angels, if I'm honest, and so the first to Kinderson Cassidy, I mean, she gets credit for, frankly, like, being the catalyst for everything. I mean, she was the first person who committed money to Stitch Fix, and she actually was a critical connection to Steve Anderson, who ended up being our kind of substantial angel from, um, from a financial perspective, and Steve is actually a Still on our board, you know, he's been so supportive, and he's, I don't know, he's been, like, both emotionally, like, an emotional support help for me, but also, you know, helping with recruiting, and so, you know, both of our only angels were incredibly important in the, kind of, success of the company.

AI assessment note: “she was the first person who committed money to Stitch Fix, and she actually was a critical connection”

Q yours before, and I want to start a little bit before Stitch Facebook. Because you mentioned before about working in Banana Republic, and as a lifeguard, and I always feel that, kind of, these experiences are so formative to how we think today, and big lessons in that, your first jobs. What do you think were your biggest learnings from those first few roles, and how it impacted your mindset?

A I mean, there are so many things. I mean, one thing was just, like, both in those jobs, in the Banana Republic job, and in the lifeguard job, like, so much of what I loved about the job was the people that I worked with, and I think that really persisted of just, like, you know, we are all human, like, Like, we all have a limited number of waking hours, and we spend a lot of those waking hours at work, and so really thinking about what is it that makes work rewarding? What is it that people enjoy about those roles, and how can I make sure that those are part of the culture, I think, is something that really persisted, and, you know, I just also think, and I think every entrepreneur kind of knows this because you start by building these basic building blocks, and everybody has done everything, but, you know, I do think it also just, like, the humility of the frontline work is Super important. Like, it's just remembering that every single process and, you know, new thing that we're doing and that everything we're doing is really impacting the work, you know, from packing the fixes all the way to, you know, the technology that's allocating fixes to warehouses, like all of this is really interconnected. And, and so I think just like it, you know, having all of the different jobs really gives you a deep appreciation of the hard work that goes into business. And also, you know, the k…

AI assessment note: “humility of frontline work is Super important. Like, it's just remembering”

Q with you. I'm a total people person. The challenge I have when I interview a lot of leaders is they all say to me, Harry, the thing that I've learned is that people don't scale with the business. And then I think about the people that I love to work with, the morale, the camaraderie. Do you agree with that? People don't scale with the business and inevitable management churn?

A Oh, I think there is inevitable change and churn and evolution of the team, and it's a natural part of growing a business. And, you know, the reality of having, you know, I've been in a very, like, you know, fortunate position of being really supported by having a Team that really has actually done a lot to mentor and coach me to help me to be able to scale. But the notion of going from zero to a billion plus in revenue is like, I mean, it's a crazy steep learning curve. And, you know, not only I think is this, is it a capability question, but I think there's also like a desire question. Like, you know, you even hear from founders of like, oh, I'm more of an early stage person. And, you know, and I feel like I've just been really lucky that like, I think it's been a really challenging intellectual journey throughout. Like, I really do love this stage. Like I love this stage and And in the same way, I mean, a very different way, I guess, but in the same purity of loving it as I love the early stages of the company. And I do think that a lot of that is because of the team that I've had around me and that team has been evolving. And, you know, I think it's not, you know, it's not necessarily a bad thing if there's somebody who is going to be amazing for one stage of the business and that, you know, the next stage of the business, it might not be right for them and it might not be …

AI assessment note: “I think there is inevitable change and churn and evolution of the team”

Q with you. I'm a total people person. The challenge I have when I interview a lot of leaders is they all say to me, Harry, the thing that I've learned is that people don't scale with the business. And then I think about the people that I love to work with, the morale, the camaraderie. Do you agree with that? People don't scale with the business and inevitable management churn?

A Oh, I think there is inevitable change and churn and evolution of the team, and it's a natural part of growing a business. And, you know, the reality of having, you know, I've been in a very, like, you know, fortunate position of being really supported by having a Team that really has actually done a lot to mentor and coach me to help me to be able to scale. But the notion of going from zero to a billion plus in revenue is like, I mean, it's a crazy steep learning curve. And, you know, not only I think is this, is it a capability question, but I think there's also like a desire question. Like, you know, you even hear from founders of like, oh, I'm more of an early stage person. And, you know, and I feel like I've just been really lucky that like, I think it's been a really challenging intellectual journey throughout. Like, I really do love this stage. Like I love this stage and And in the same way, I mean, a very different way, I guess, but in the same purity of loving it as I love the early stages of the company. And I do think that a lot of that is because of the team that I've had around me and that team has been evolving. And, you know, I think it's not, you know, it's not necessarily a bad thing if there's somebody who is going to be amazing for one stage of the business and that, you know, the next stage of the business, it might not be right for them and it might not be …

AI assessment note: “I think there is inevitable change and churn and evolution of the team”

Q I think it's such a fascinating perspective to, to see kind of the board from the other side there being a board member at Grubhub and also at Glossier. How has being a board member for someone else changed your perspective on board management, I guess, and what have you brought back to Stitch Fix from those experiences?

A So much, um, I mean, I love being on those boards, and for, actually, for quite different reasons, I would say, and, but I learn a ton from both of them, and, you know, Grubhub, I think, was at first, it was the obvious of, like, I really knew nothing about, you know, board management or, you Managing a public company or, I mean, really, like, I mean, anything in that sphere. And so I learned so much. And Matt, who's the entrepreneur and CEO, I mean, he's an incredible leader to learn from. And there's CFO, Adam, CFO and president. He's phenomenal also. There are general counsel, Maggie. I mean, you know, there's so many people on that team that I've learned so much from. And then there, you know, I think an intangible thing too is just like, you know, that stock price definitely bounced around a lot. And I think just like the, the thick Skin of like being comfortable with that, the conviction that you can have in the longterm while also being, you know, uncomfortable in the short term. Like, you know, those, those were things that I can't say that I totally learned that, but the exposure certainly helped from, you know, being able to see that and then experiencing it on our own later. And then Glossier is like, I mean, you know, I think that's, I've learned so much on that board too. I mean, Emily is an incredible entrepreneur. She is a real visionary. And, and, you know, I th…

AI assessment note: “a lot of that I bring back to Stitch Fix”

Q I think it's such a fascinating perspective to, to see kind of the board from the other side there being a board member at Grubhub and also at Glossier. How has being a board member for someone else changed your perspective on board management, I guess, and what have you brought back to Stitch Fix from those experiences?

A So much, um, I mean, I love being on those boards, and for, actually, for quite different reasons, I would say, and, but I learn a ton from both of them, and, you know, Grubhub, I think, was at first, it was the obvious of, like, I really knew nothing about, you know, board management or, you Managing a public company or, I mean, really, like, I mean, anything in that sphere. And so I learned so much. And Matt, who's the entrepreneur and CEO, I mean, he's an incredible leader to learn from. And there's CFO, Adam, CFO and president. He's phenomenal also. There are general counsel, Maggie. I mean, you know, there's so many people on that team that I've learned so much from. And then there, you know, I think an intangible thing too is just like, you know, that stock price definitely bounced around a lot. And I think just like the, the thick Skin of like being comfortable with that, the conviction that you can have in the longterm while also being, you know, uncomfortable in the short term. Like, you know, those, those were things that I can't say that I totally learned that, but the exposure certainly helped from, you know, being able to see that and then experiencing it on our own later. And then Glossier is like, I mean, you know, I think that's, I've learned so much on that board too. I mean, Emily is an incredible entrepreneur. She is a real visionary. And, and, you know, I th…

AI assessment note: “the conviction that you can have in the longterm while also being, you know, uncomfortable”

Q Not at all. I've been excited for this one for a long time, so I would love to start with some context. How did you make your way into the world of startups, and how did you come to change the world of fashion, really, with Stitch Fix?

A You know, I was definitely not, like, a born entrepreneur. I didn't have, like, a lemonade stand growing up, but, but, you know, I became really passionate about the The space of like really understanding the problem of there is so much fashion out there. There's so much apparel. There's so many brilliant designers. And yet the process of figuring out what are the best things for me is so broken. And, you know, the store's world is broken for obvious reasons of just putting every single skew on the floor and expecting people to sift through it. But what was interesting was just, you know, kind of e-commerce and online and all of the kind of new technology to me still didn't solve the problem. And so I became really, really fascinated with this What is buying apparel going to look like 20 years from now, and how can I be part of that future? And it was a little bit of a wandering path, but, you know, candidly, I would have been perfectly happy working at Stitch Fix, but when I spent a lot of time in the landscape and understanding what are companies doing, and, like, who is at the forefront of what's going to be the future of shopping, I really didn't see any kind of opportunity that I felt like represented that future, and so, you know, I kind of, by, I guess, process of elimination, really, arrived at the The conclusion that if I wanted to be part of that future, that I could …

AI assessment note: “arrived at the conclusion that if I wanted to be part of that future”

Q Willingness to be open, I guess. One place where it's often quite difficult is on boards. I said, I spoke to Bill before the show, and he mentioned your great talent when it comes to board management, he said. And so, when it comes to board management, what does great board management really mean to you? And I guess, how's, how's your style of board management changed over the years?

A Yeah, I mean, it's a good question. I think, you know, to me, what I've really loved about our board is actually getting a range of perspectives, and I ache a conflict. Like, I love being able to have a difference of opinions on the board. I think, you know, with our management team, with our company, like, we have A clear vision. We're all very aligned. We all, you know, we certainly will disagree about things, but I would say by and large, we see, you know, we see the world kind of in a similar way through, you know, kind of through the shared experiences that we have. And the board is such an amazing thing that has, you know, some intimate experience of the company, but actually largely has an outside perspective. You know, I really think that what I get from the board is to be able to have these outside perspectives, to be able to get challenge, to be able to hear challenges. I think, you know, it's being able to have a healthy challenge on like why it You know, why wouldn't you do it this way? Or do you think that this is important? Just that kind of that challenge is a really kind of valuable part of the board. And so I think Bill's been an incredible, incredible board member. I mean, he's added so much value to our board. There's so many instances where I look back and I'm like, Bill saw the future, you know, years before I saw it. And so, but I think that's also part of…

AI assessment note: “what I've really loved about our board is actually getting a range of perspectives”

Q hard truths, no matter how hard they are, is, uh, Bill Gurley, who I, I spoke to before the show, and he said to me, there's one thing I'd love you to ask Katrina, and it's specifically around vision. He said, how far are you along in implementing your vision? Is it 90%? Is it 10%? And what are the core blockers in your mind to date that you face?

A I mean, it's a great question, and I don't even know that we're 10%. I mean, this is Such a huge industry, and the way that we are approaching it is so radical. I mean, Stitch Fix to date, we have sold six billion dollars of clothes sight unseen. Like, this is a model where we are, like, the aspiration that we have is that we would like to be better at picking clothes for people than, than they themselves would be. Like, that is a bold, radical aspiration, and the idea that we can be best in the world at recommending apparel and matchmaking between people and apparel products, and potentially other products as well, is massive. And so, you know, it's really hard to even feel like we're 10% there. I think what's been so intellectually exciting and rewarding about this space that we operate in is that, like, nobody had really thought about this as, like, a math recommendations problem of, like, trying to figure out, like, who are the people on the planet, and what are the things on the planet, and how do we matchmake between them? And so we are in this incredible position where I think we are best in the world at recommendations for apparel, and I think we are farthest along, and at the same time, like, every day, I think we know what else is next. Because we know how we can be better, and I mean, just the, you know, to be able to feel like we've come really far, and we've done a…

AI assessment note: “I don't even know that we're 10%.”

Q Willingness to be open, I guess. One place where it's often quite difficult is on boards. I said, I spoke to Bill before the show, and he mentioned your great talent when it comes to board management, he said. And so, when it comes to board management, what does great board management really mean to you? And I guess, how's, how's your style of board management changed over the years?

A Yeah, I mean, it's a good question. I think, you know, to me, what I've really loved about our board is actually getting a range of perspectives, and I ache a conflict. Like, I love being able to have a difference of opinions on the board. I think, you know, with our management team, with our company, like, we have A clear vision. We're all very aligned. We all, you know, we certainly will disagree about things, but I would say by and large, we see, you know, we see the world kind of in a similar way through, you know, kind of through the shared experiences that we have. And the board is such an amazing thing that has, you know, some intimate experience of the company, but actually largely has an outside perspective. You know, I really think that what I get from the board is to be able to have these outside perspectives, to be able to get challenge, to be able to hear challenges. I think, you know, it's being able to have a healthy challenge on like why it You know, why wouldn't you do it this way? Or do you think that this is important? Just that kind of that challenge is a really kind of valuable part of the board. And so I think Bill's been an incredible, incredible board member. I mean, he's added so much value to our board. There's so many instances where I look back and I'm like, Bill saw the future, you know, years before I saw it. And so, but I think that's also part of…

AI assessment note: “what I've really loved about our board is actually getting a range of perspectives”

Q of self-doubt, especially when I joined boards, especially for the first time, so much self-doubt and imposter syndrome. I guess my question was, like, in terms of, like, the self-doubt, did you ever have self-doubt? Because when I listen to your interviews now, and I watch you on many news channels, it's this incredible leadership figure. Did you ever have self-doubt? And I guess, how did you deal with that?

A Yeah, I think, I mean, this notion of self-doubt and imposter syndrome, just, like, I totally empathize with it, and at the same time, like, as I think about the root of it, it really is around just, You know, kind of authenticity and, like, this notion of, like, how do we actually create environments where, like, many different people can feel like they can succeed, and I think, you know, part of the reason we're talking about imposter syndrome, especially in some place like tech, is because that we, we've been historically in an industry where so many people have felt excluded, and so many people feel like there are not people like them to aspire to be like, and, like, those things just have to change, and, like, I feel like historically people have talked about imposter syndrome as being Something that individuals deal with, like that you or I are wrangling with, but actually this is something that like the environment is creating. Like the technology ecosystem is, is excluding people in a way that makes it so that people feel like they're imposters when they're here. And like that, you know, that's a broader challenge that we really need to be thinking about. How do we actually create more inclusive environments and ones where we see greater representation so that more people feel like they belong? I mean, ultimately that's really what imposter syndrome is. And, you know, f…

AI assessment note: “historically people have talked about imposter syndrome as being Something that individuals deal with”

Q of self-doubt, especially when I joined boards, especially for the first time, so much self-doubt and imposter syndrome. I guess my question was, like, in terms of, like, the self-doubt, did you ever have self-doubt? Because when I listen to your interviews now, and I watch you on many news channels, it's this incredible leadership figure. Did you ever have self-doubt? And I guess, how did you deal with that?

A Yeah, I think, I mean, this notion of self-doubt and imposter syndrome, just, like, I totally empathize with it, and at the same time, like, as I think about the root of it, it really is around just, You know, kind of authenticity and, like, this notion of, like, how do we actually create environments where, like, many different people can feel like they can succeed, and I think, you know, part of the reason we're talking about imposter syndrome, especially in some place like tech, is because that we, we've been historically in an industry where so many people have felt excluded, and so many people feel like there are not people like them to aspire to be like, and, like, those things just have to change, and, like, I feel like historically people have talked about imposter syndrome as being Something that individuals deal with, like that you or I are wrangling with, but actually this is something that like the environment is creating. Like the technology ecosystem is, is excluding people in a way that makes it so that people feel like they're imposters when they're here. And like that, you know, that's a broader challenge that we really need to be thinking about. How do we actually create more inclusive environments and ones where we see greater representation so that more people feel like they belong? I mean, ultimately that's really what imposter syndrome is. And, you know, f…

AI assessment note: “historically people have talked about imposter syndrome as being Something that individuals deal with, but actually”

Q Can I ask, I love that in terms of kind of creating that environment of safety. Like, how do you think about, like, what does it take specifically to create that environment of safety, and is there any things you think can be done to really engender that more directly?

A I mean, this idea of just, like, creating more inclusive environments is super, super important, and I mean, I find myself super aware of it. Like, I can be in meetings and Feel like this person is trying to talk over me or this person, you know, made me feel dumb. Like there are things that all people do, um, on purpose or not on purpose that can have impact on others of how people feel in those moments. And so, you know, I do think that like just creating these environments where people feel safe to be able to speak their mind, where it's not just that, you know, their voices are, are kind of like where voices are welcomed, where we're trying to deliberately and Include the voices of people is really important. And then, you know, statistics, we talk a lot about authenticity of just, I think being able to, I think one just really important leadership, it was the only leadership tool that I had because I didn't have all the experience that I didn't have, you know, the prior history of success. Like the only tool I really had was this authenticity and vulnerability to be able to bring people along and being able to be vulnerable about like, these are the things that are hard and these are the things that are happening and helping people to feel like that we're all part of this journey together. You know, I think that That was really the only leadership tool that I had, and now …

AI assessment note: “the only tool I really had was this authenticity and vulnerability to be able to”

Q Totally with you there. I do want to ask the final one, and probably the most exciting of all. What do the next five years hold for you and for Stitch Fix? Can you paint a little bit of that roadmap for me?

A Oh gosh, I mean, five years feels like such an enormous period of time. This is, I truly believe this, this is the most exciting time in the history of Stitch Fix. Like, we have this incredible capability, and now we have the opportunity to take these amazing recommendations and productize them in many ways. And so, you know, I see, like, you know, kind of innovation, redefining, like, expanding, like, these are some of the words that come to mind for me. But I think, you know, being able to transform the way that people find what they love in a much, Broader way and to have a much bigger impact in the world of apparel is all what's super exciting. Um, and I think also just, you know, I think in now we're 10 years in, I think we've now finally been able to really clearly define some of the things that we want to do around sustainability and DEI, and so I think that will be a greater focus as well for the next five years.

AI assessment note: “sustainability and DEI, and so I think that will be a greater focus”

Q founders say, and they say, you know, but if we retain the user and they come back, For 12 orders, then we start to see, you know, the curve look attractive, and then our payback really starts to kick in. Do you think, like, payback has to be on, like, first order for the unit econ to work in your mind, and how did you think about that more granularly?

A Yeah, I mean, I think it really does depend on the space in the industry, and, you know, I mean, does it have to be first order, or does it not? So, I mean, I think there's a lot, it depends a lot on the business and the industry, and, and how consumers behave, so I don't know, there's one dogmatic way to look at it, but I do think that, like, the notion of, like, I, I do, Like you, I see a lot of models that are like, you know, assuming people spend, nobody ever leaves the business and, you know, has pretty aggressive assumptions around, you know, what people will do. But I think like at the end of the day, like really focusing on what is the lifetime value of a customer and what are all the ways that you can increase and improve that? Like, I think that is, I mean, it's just the best North star. And so when you're looking at lifetime value, you, it means you can also achieve that by trying to reduce your customer acquisition costs. It means that you can achieve that by trying to make sure that your customers come back You know, there's a lot of ways, assuming that people are calculating that in a rational, real way, there's a lot of ways to be able to continue to, there's a lot of lever that you can use to try to improve that LTV, but that's really, I think, and especially as we're, I mean, to be honest, I think if people could have thought about that, thought about LTV in a …

AI assessment note: “I think it really does depend on the space in the industry”