The Exchanges

Q And then in terms of kind of implementing it from the first steps, what did that look like?

A Well, I found my first engineer by posting an ad on Craigslist and And saying, I'm stealth company seeks engineer to build first version of product for equity, only no money. And believe it or not, that actually resulted in a fantastic engineer from Google who had made a bunch of money and didn't really want to work anymore, but he didn't want to get bored. So he became my first engineer. I had a designer friend who designed the first version of the site. And so we had a prototype up and running and that allowed me to go out and Find my technical co-founder, Dan. And then from there, we bootstrapped and, you know, spent our lives building the product.

AI assessment note: “Well, I found my first engineer by posting an ad on Craigslist”

Q What was the moment of transition there in terms of realizing the need to transition from a doer to a manager?

A It's when you have someone else who can do it better than I was doing all the CS tickets and I was actually working with the designer on every little piece of every single design that went out and writing all the copy, et cetera. And then as you start to get bigger, whether you're raising money or you're turning on revenue, et cetera, you have the ability to hire people that are way better at those things than you are. And then your goal goes from doing it or micromanaging them to empowering them to do it. And you have to figure out constantly, or I had to figure out constantly, how do I upgrade my own operating system so that I can make this shift and And it is extremely jarring. It is psychologically confusing. You know, people talk about it a lot, that Harvard Business School. Oh, this is, you know, how you evolve a company. But like when you're in the trenches doing it, it is a real challenge. And it took me a while to figure that out.

AI assessment note: “It's when you have someone else who can do it better than I was”

Q And then in terms of kind of implementing it from the first steps, what did that look like?

A Well, I found my first engineer by posting an ad on Craigslist and And saying, I'm stealth company seeks engineer to build first version of product for equity, only no money. And believe it or not, that actually resulted in a fantastic engineer from Google who had made a bunch of money and didn't really want to work anymore, but he didn't want to get bored. So he became my first engineer. I had a designer friend who designed the first version of the site. And so we had a prototype up and running and that allowed me to go out and Find my technical co-founder, Dan. And then from there, we bootstrapped and, you know, spent our lives building the product.

AI assessment note: “I found my first engineer by posting an ad on Craigslist”

Q Absolutely. No, I agree. I always say constraint enforces creativity. Um, so yes, I do agree. But, but then when you decided to take the funding, then how were the funding rounds in terms of the raises and how did they differ?

A Oh, well, our first seed round, my very first, well, my first two advisors and angel investors were Garrett Camp and Travis Kalanick. So I was very lucky. They were just my two best friends basically at the time. And they were sort of, I mean, their, their position was, we have no idea how the beauty industry works. This sounds crazy to us, but Melody, you're totally nuts, and we will help you get more angel investment from other people, because we know Cause you're totally crazy. And so it was, it was like them investing in me and in the opportunity that we were going after. Our series A and series B were much more of, it wasn't imagine a world where it was, uh, here's the opportunity, here's the math, and here's how we've grown and here's scale. So it was very much more on the numbers and the fact that we had grown so quickly, purely organically, and that we were tapping into something because our customers were so passionate about the product and that we were figuring out how to grow.

AI assessment note: “Our series A and series B were much more of... here's the math”

Q So you said that about the six years and it being unusual. Absolutely it is. In terms of that, what do you think is the key then to such a successful long tenure that you've experienced and had? Are there kind of core fundamentals that have allowed it to continue and thrive with time?

A I think it really comes down to two things for me. The first thing is Resiliency. So you have to love having shit thrown in your face every single day. And by that, I mean, people are going to have meltdowns. You're going to realize your executive team isn't working out. You're going to realize that you are, you know, now that your company is at the next level, like you're not driving the value that you need to drive. So you need to hurry up and go get your skills. You're going to get your ass handed to you by your investors sometimes, right? Or by your board. You're going to realize that the products used to have market fit and there've been some changes in the market. Now you need to go out and get that again. And so those constant challenges you have to love, because if you don't love that super frenetic pace, it's gonna, gonna kill you because it's incredibly, incredibly intense. And then the second thing is for me really about constantly asking myself, how can I drive the most value and being really honest with myself and saying, all right, even though you love that, you have to give that to someone else because you suck at it or, you know, something that was working before now isn't working. And we are constantly Constantly evolving, whether it's the org structure or what people are doing or how we report or, uh, you know, the dashboards and the numbers that we show or th…

AI assessment note: “I think it really comes down to two things for me. The first thing is Resiliency.”

Q What is the mental perspective that you gain from that kind of fiscal tightness?

A It means that every single dollar, you never know if you're ever going to see it again. I mean, when we raised the, our first amount of capital, I had only ever been in debt my whole life. I'd always worked. I'd always had one or several jobs. I worked full time in addition to, you know, my last year of school. I commuted to San Francisco two and a half hours each way every day. Like I have had to work extremely hard my whole life. And I think what bootstrapping teaches you is you may never see this dollar again, so you better spend Every hour, every day, getting, you know, to product market fit as fast as possible because time is running out. And I think it allowed us to be super effective with capital, with our time, with being iterative in those early days. And, you know, that has carried me through the rest of my company. I remember those days and I don't take that for granted. And so, you know, again, like when founders don't go through that discipline, you just think about things very differently. Like a dollar is here, it's there, you're not worried. And I just think that that you run a Totally different ship that way.

AI assessment note: “you may never see this dollar again, so you better spend Every hour”

Q And then let's finish today on the next five years for you and for Starseed. What have we got in store?

A Oh my goodness. Well, let's see. Last year we did about 1.6 billion in bookings across the platform. So we had a great year. This year we started to turn on revenue to a higher degree. And so we're going, we're focusing on that as our next big push. And we're also going to be focused on growth. We've never had to market ourselves. So we're going to start to learn how to do that, which I'm excited about. And I think, you know, we're going to be profitable in the next year. So for me, beyond profitability, it's how can we drive the most return for our customers? How can we make as much money as possible along the way? And how I just want to make sure that as we're doing these things, I'm still loving it. My team's still loving it. Our community's happy. So that's how I think about it.

AI assessment note: “we're focusing on that as our next big push. And we're also going to be focused on growth.”

Q move through stages because some people are very much an advocate of the suggestion that actually people are very much destined for certain stages of company development and But particularly in the kind of the exec management level, and then they churn out, and it's kind of a continuing cycle where people are meant for certain stages. Do you agree with this, or do you think there is the flexibility?

A I think it's very rare to see that flexibility. I, it is that rare bird to find the person who can work at the public style company, or the company that's on that smooth paved road that is scaling, that can also go do the early stage stuff, or that gravelly road. I just haven't met many of those people in my experience. You either are thrilled by this is Very consistent and very predictable business model. We have product market fit. I can see where we are now, and I'm very thrilled about the mostly HR and business structure or structure type of challenges to bring this company public. Or you love the chaotic shits being flung across the wall, back and forth, up and down, meltdowns, like learning every single day and rolling up your sleeves and doing the actual work and thriving in that chaos. I just haven't met very many people that like Those two things. So, I mean, the job is a hundred percent different job. It's like, it's two different industries.

AI assessment note: “I think it's very rare to see that flexibility.”

Q that I've all listened to, obviously, in preparation for this. Yeah. But in terms of the immense success, and it's easy to look and think CEOs have all the answers, but you very humbly stated before that that's maybe not the case. So with that in mind, what were the answers that maybe you didn't have and what were the most challenging elements that you didn't know the answer to?

A Well, it's interesting because when I first started the company, I had had product positions before. I'd worked with software engineers building product for a couple of years, but what people may not realize is that as a first time founder, you have no idea what you're doing. You're probably And so for the first year or two of starting a company, it's really about, okay, now I need to find an accountant. Now I need to find a lawyer. Now I need to figure out, you know, who my customer personas are. I've never done that before. Now I need to figure out what my MVP is. How do I find a designer? Like there are so many things and there's such a wide breadth of things outside of big stuff like funding that you have to figure out. And what's interesting is that in the first year or two, you're basically like, just give me a problem and I'll solve it. And so you get into this mode of, give me a problem. I'll solve it. I'll figure out the answer. You got to make a decision quickly. And so you do it and you move on. But after that first year or two, you have to take a completely different type of approach to running and building your business, which is not having all the answers and not being the person to go do it. You turn from a doer to someone who needs to empower the rest of your team to do. And that was a huge shift for me. And I think one of my biggest lessons as a Poorly for a wh…

AI assessment note: “as a first time founder, you have no idea what you're doing.”

Q Absolutely. No, I agree. I always say constraint enforces creativity. Um, so yes, I do agree. But, but then when you decided to take the funding, then how were the funding rounds in terms of the raises and how did they differ?

A Oh, well, our first seed round, my very first, well, my first two advisors and angel investors were Garrett Camp and Travis Kalanick. So I was very lucky. They were just my two best friends basically at the time. And they were sort of, I mean, their, their position was, we have no idea how the beauty industry works. This sounds crazy to us, but Melody, you're totally nuts, and we will help you get more angel investment from other people, because we know Cause you're totally crazy. And so it was, it was like them investing in me and in the opportunity that we were going after. Our series A and series B were much more of, it wasn't imagine a world where it was, uh, here's the opportunity, here's the math, and here's how we've grown and here's scale. So it was very much more on the numbers and the fact that we had grown so quickly, purely organically, and that we were tapping into something because our customers were so passionate about the product and that we were figuring out how to grow.

AI assessment note: “here's the opportunity, here's the math, and here's how we've grown”

Q So you said that about the six years and it being unusual. Absolutely it is. In terms of that, what do you think is the key then to such a successful long tenure that you've experienced and had? Are there kind of core fundamentals that have allowed it to continue and thrive with time?

A I think it really comes down to two things for me. The first thing is Resiliency. So you have to love having shit thrown in your face every single day. And by that, I mean, people are going to have meltdowns. You're going to realize your executive team isn't working out. You're going to realize that you are, you know, now that your company is at the next level, like you're not driving the value that you need to drive. So you need to hurry up and go get your skills. You're going to get your ass handed to you by your investors sometimes, right? Or by your board. You're going to realize that the products used to have market fit and there've been some changes in the market. Now you need to go out and get that again. And so those constant challenges you have to love, because if you don't love that super frenetic pace, it's gonna, gonna kill you because it's incredibly, incredibly intense. And then the second thing is for me really about constantly asking myself, how can I drive the most value and being really honest with myself and saying, all right, even though you love that, you have to give that to someone else because you suck at it or, you know, something that was working before now isn't working. And we are constantly Constantly evolving, whether it's the org structure or what people are doing or how we report or, uh, you know, the dashboards and the numbers that we show or th…

AI assessment note: “I think it really comes down to two things for me. The first thing is Resiliency.”

Q move through stages because some people are very much an advocate of the suggestion that actually people are very much destined for certain stages of company development and But particularly in the kind of the exec management level, and then they churn out, and it's kind of a continuing cycle where people are meant for certain stages. Do you agree with this, or do you think there is the flexibility?

A I think it's very rare to see that flexibility. I, it is that rare bird to find the person who can work at the public style company, or the company that's on that smooth paved road that is scaling, that can also go do the early stage stuff, or that gravelly road. I just haven't met many of those people in my experience. You either are thrilled by this is Very consistent and very predictable business model. We have product market fit. I can see where we are now, and I'm very thrilled about the mostly HR and business structure or structure type of challenges to bring this company public. Or you love the chaotic shits being flung across the wall, back and forth, up and down, meltdowns, like learning every single day and rolling up your sleeves and doing the actual work and thriving in that chaos. I just haven't met very many people that like Those two things. So, I mean, the job is a hundred percent different job. It's like, it's two different industries.

AI assessment note: “I think it's very rare to see that flexibility.”

Q What is the mental perspective that you gain from that kind of fiscal tightness?

A It means that every single dollar, you never know if you're ever going to see it again. I mean, when we raised the, our first amount of capital, I had only ever been in debt my whole life. I'd always worked. I'd always had one or several jobs. I worked full time in addition to, you know, my last year of school. I commuted to San Francisco two and a half hours each way every day. Like I have had to work extremely hard my whole life. And I think what bootstrapping teaches you is you may never see this dollar again, so you better spend Every hour, every day, getting, you know, to product market fit as fast as possible because time is running out. And I think it allowed us to be super effective with capital, with our time, with being iterative in those early days. And, you know, that has carried me through the rest of my company. I remember those days and I don't take that for granted. And so, you know, again, like when founders don't go through that discipline, you just think about things very differently. Like a dollar is here, it's there, you're not worried. And I just think that that you run a Totally different ship that way.

AI assessment note: “every single dollar, you never know if you're ever going to see it again”

Q You said also about transparency. I'm always intrigued. Are there any elements where maybe transparency is potentially detrimental? Maybe in terms of funding rounds, should you be so open in terms of how the funding round is going in terms of salaries, in terms of compensation? What are the thoughts around kind of complete transparency? Are there any things that maybe shouldn't be transparent?

A That's a great question. I mean, it can be challenging for When, I mean, the biggest challenge is when you are, let's say you're in the A stage of, of raising money, and you don't have a lot of runway, and as a startup, you need to try and keep as much of the power in that negotiation process as you can, while also, you know, you've got a couple months left, and so if employees are out there telling, telling the world that you've got a couple months left, then VCs, if they hear that information, right, they're going to leverage that against you, and that can have a significantly detrimental effect On the terms of the round. I mean, there are some things like just privacy things and, you know, that you can't really share with your team, but you know, and I've struggled with this. I really have struggled with this because in the past we've had executive teams that were really great with sharing information and fantastic with setting the right context. And then we've had folks that haven't been great at that. And so I'm not going to say that I'm, I'm really amazing at it, but we are extremely transparent right now as an organization. We're always trying to get better.

AI assessment note: “can have a significantly detrimental effect On the terms of the round”

Q What was the moment of transition there in terms of realizing the need to transition from a doer to a manager?

A It's when you have someone else who can do it better than I was doing all the CS tickets and I was actually working with the designer on every little piece of every single design that went out and writing all the copy, et cetera. And then as you start to get bigger, whether you're raising money or you're turning on revenue, et cetera, you have the ability to hire people that are way better at those things than you are. And then your goal goes from doing it or micromanaging them to empowering them to do it. And you have to figure out constantly, or I had to figure out constantly, how do I upgrade my own operating system so that I can make this shift and And it is extremely jarring. It is psychologically confusing. You know, people talk about it a lot, that Harvard Business School. Oh, this is, you know, how you evolve a company. But like when you're in the trenches doing it, it is a real challenge. And it took me a while to figure that out.

AI assessment note: “It's when you have someone else who can do it better than I was doing”

Q You said also about transparency. I'm always intrigued. Are there any elements where maybe transparency is potentially detrimental? Maybe in terms of funding rounds, should you be so open in terms of how the funding round is going in terms of salaries, in terms of compensation? What are the thoughts around kind of complete transparency? Are there any things that maybe shouldn't be transparent?

A That's a great question. I mean, it can be challenging for When, I mean, the biggest challenge is when you are, let's say you're in the A stage of, of raising money, and you don't have a lot of runway, and as a startup, you need to try and keep as much of the power in that negotiation process as you can, while also, you know, you've got a couple months left, and so if employees are out there telling, telling the world that you've got a couple months left, then VCs, if they hear that information, right, they're going to leverage that against you, and that can have a significantly detrimental effect On the terms of the round. I mean, there are some things like just privacy things and, you know, that you can't really share with your team, but you know, and I've struggled with this. I really have struggled with this because in the past we've had executive teams that were really great with sharing information and fantastic with setting the right context. And then we've had folks that haven't been great at that. And so I'm not going to say that I'm, I'm really amazing at it, but we are extremely transparent right now as an organization. We're always trying to get better.

AI assessment note: “they're going to leverage that against you, and that can have a significantly detrimental effect”

Q Can I ask, how do you look to ease that then? Is that with kind of experienced and wise counselors and investors and mentors? Is that with kind of insane operational research? What does that look like then to kind of educationally onboard?

A Honestly, I think it's a bit of everything. You know, it's a bit of your team saying you're micromanaging me back off. You're like, okay, well, all right. How do I empower you and help you, but also let you not fuck up? Cause I don't think you're doing a great job right now. You know, it's learning how to teach them how to do it in the way I did a ton of research on HBR, you know, best practices for a manager. How do you evolve? How do you make that transition as a manager? And a lot of it is just talking to founders. This is also something that I have done to varying degrees of success over the years, but something I really rely on now, which is all of my founder friends and operator friends who have gone through this asking them, you know, Hey, here's a huge challenge that I'm having. I'm micromanaging my team and I'm having trouble Getting to the next level, whatever problems you have, you have to ask people and you have to ask a ton of people. You can ignore their advice, right? But just getting that information in those data points on this is how other really successful businesses have done it and made this transition. You can survive and you can adapt your skills, you know, cause I've been running this company for a long time.

AI assessment note: “Honestly, I think it's a bit of everything.”

Q Can I ask, how do you look to ease that then? Is that with kind of experienced and wise counselors and investors and mentors? Is that with kind of insane operational research? What does that look like then to kind of educationally onboard?

A Honestly, I think it's a bit of everything. You know, it's a bit of your team saying you're micromanaging me back off. You're like, okay, well, all right. How do I empower you and help you, but also let you not fuck up? Cause I don't think you're doing a great job right now. You know, it's learning how to teach them how to do it in the way I did a ton of research on HBR, you know, best practices for a manager. How do you evolve? How do you make that transition as a manager? And a lot of it is just talking to founders. This is also something that I have done to varying degrees of success over the years, but something I really rely on now, which is all of my founder friends and operator friends who have gone through this asking them, you know, Hey, here's a huge challenge that I'm having. I'm micromanaging my team and I'm having trouble Getting to the next level, whatever problems you have, you have to ask people and you have to ask a ton of people. You can ignore their advice, right? But just getting that information in those data points on this is how other really successful businesses have done it and made this transition. You can survive and you can adapt your skills, you know, cause I've been running this company for a long time.

AI assessment note: “Honestly, I think it's a bit of everything.”

Q You have an exec coach too, you mentioned. What are the benefits of that externally to the board?

A You know, they teach you, I was really specific in what I wanted with an Processing conversations, and I hate that stuff. What I want when I speak to an executive coach is specific skill sets. I have specific goals of how I want to grow and learn as a CEO. Those change as the business needs change, and I want case studies. I want people that I can talk to who've done this well, and I want the advice of someone who understands the fundamentals of the skills that I need to learn. So we'll talk about things like Board dynamics and what's the appropriate ways to work with a board so that they have the information that they need, but that you're also holding them accountable for the decisions that they need to make and sort of their obligation to the business. That's been something that I have been learning a lot more about. I'm very fascinated about. So for me, it's really about what are fundamentals, business fundamentals of being a CEO. I've never done this before. This was my first time, right? And so you have to just be really hungry to learn and to grow and And a coach is a great way in combination with the other ways for me to do that.

AI assessment note: “So we'll talk about things like Board dynamics and what's the appropriate ways”

Q that I've all listened to, obviously, in preparation for this. Yeah. But in terms of the immense success, and it's easy to look and think CEOs have all the answers, but you very humbly stated before that that's maybe not the case. So with that in mind, what were the answers that maybe you didn't have and what were the most challenging elements that you didn't know the answer to?

A Well, it's interesting because when I first started the company, I had had product positions before. I'd worked with software engineers building product for a couple of years, but what people may not realize is that as a first time founder, you have no idea what you're doing. You're probably And so for the first year or two of starting a company, it's really about, okay, now I need to find an accountant. Now I need to find a lawyer. Now I need to figure out, you know, who my customer personas are. I've never done that before. Now I need to figure out what my MVP is. How do I find a designer? Like there are so many things and there's such a wide breadth of things outside of big stuff like funding that you have to figure out. And what's interesting is that in the first year or two, you're basically like, just give me a problem and I'll solve it. And so you get into this mode of, give me a problem. I'll solve it. I'll figure out the answer. You got to make a decision quickly. And so you do it and you move on. But after that first year or two, you have to take a completely different type of approach to running and building your business, which is not having all the answers and not being the person to go do it. You turn from a doer to someone who needs to empower the rest of your team to do. And that was a huge shift for me. And I think one of my biggest lessons as a Poorly for a wh…

AI assessment note: “now I need to find an accountant. Now I need to find a lawyer.”

Q You have an exec coach too, you mentioned. What are the benefits of that externally to the board?

A You know, they teach you, I was really specific in what I wanted with an Processing conversations, and I hate that stuff. What I want when I speak to an executive coach is specific skill sets. I have specific goals of how I want to grow and learn as a CEO. Those change as the business needs change, and I want case studies. I want people that I can talk to who've done this well, and I want the advice of someone who understands the fundamentals of the skills that I need to learn. So we'll talk about things like Board dynamics and what's the appropriate ways to work with a board so that they have the information that they need, but that you're also holding them accountable for the decisions that they need to make and sort of their obligation to the business. That's been something that I have been learning a lot more about. I'm very fascinated about. So for me, it's really about what are fundamentals, business fundamentals of being a CEO. I've never done this before. This was my first time, right? And so you have to just be really hungry to learn and to grow and And a coach is a great way in combination with the other ways for me to do that.

AI assessment note: “what's the appropriate ways to work with a board so that they have the information”

Q Final question before we move into the quickfire, and it's a question on board management. You mentioned board once earlier. I'm intrigued to kind of managing the board. How's that changed and evolved over time as you've increased the size of the board with different funding rounds and kind of the board management aspect for you as the CEO and founder?

A What I've found is that you need different expertise at different stages of the business. I will say that the thing, one of the big lessons that I've learned around what makes a good board member is having as much operation experience as you can, because investors can sort of say, well, here's what we've seen other companies do. Here are some trends and here's some data. And an operator can say, well, I did it. I did it three times. Here's Here's the real way it worked, and the pros and the cons, and here's six people that you can talk to that led it at my last three companies, and here's one person you can talk to that did it poorly, and it's just a different type of support. I think it's, it's good to have as much operating experience as you possibly can at companies. That's been my experience.

AI assessment note: “you need different expertise at different stages of the business.”

Q Final question before we move into the quickfire, and it's a question on board management. You mentioned board once earlier. I'm intrigued to kind of managing the board. How's that changed and evolved over time as you've increased the size of the board with different funding rounds and kind of the board management aspect for you as the CEO and founder?

A What I've found is that you need different expertise at different stages of the business. I will say that the thing, one of the big lessons that I've learned around what makes a good board member is having as much operation experience as you can, because investors can sort of say, well, here's what we've seen other companies do. Here are some trends and here's some data. And an operator can say, well, I did it. I did it three times. Here's Here's the real way it worked, and the pros and the cons, and here's six people that you can talk to that led it at my last three companies, and here's one person you can talk to that did it poorly, and it's just a different type of support. I think it's, it's good to have as much operating experience as you possibly can at companies. That's been my experience.

AI assessment note: “one of the big lessons that I've learned around what makes a good board member”